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Sample records for chalcone

  1. Heterocyclic chalcone analogues as potential anticancer agents.

    Science.gov (United States)

    Sharma, Vikas; Kumar, Vipin; Kumar, Pradeep

    2013-03-01

    Chalcones, aromatic ketones and enones acting as the precursor for flavonoids such as Quercetin, are known for their anticancer effects. Although, parent chalcones consist of two aromatic rings joined by a three-carbon α,β-unsaturated carbonyl system, various synthetic compounds possessing heterocyclic rings like pyrazole, indole etc. are well known and proved to be effective anticancer agents. In addition to their use as anticancer agents in cancer cell lines, heterocyclic analogues are reported to be effective even against resistant cell lines. In this connection, we hereby highlight the potential of various heterocyclic chalcone analogues as anticancer agents with a brief summary about therapeutic potential of chalcones, mechanism of anticancer action of various chalcone analogues, and current and future prospects related to the chalcones-derived anticancer research. Furthermore, some key points regarding chalcone analogues have been reviewed by analyzing their medicinal properties. PMID:22721390

  2. Solvent-Free Synthesis of Chalcones

    Science.gov (United States)

    Palleros, Daniel R.

    2004-01-01

    The synthesis of twenty different chalcones in the absence of solvent is presented. The results indicated that out of the twenty different chalcones investigated seventeen can be obtained in a matter of minutes by mixing the corresponding benzaldehyde and acetophenone in the presence of solid NaOH in a mortar with pestle.

  3. Chalcones: compounds possessing a diversity in applications

    OpenAIRE

    Urmila Berar

    2012-01-01

    Chalcones are a class of α, β- unsaturated carbonyl compounds that form the central core for a variety of naturally occurring biologically active compounds. They exhibit tremendous potential to act as a pharmacological agent. Besides their various pharmacological activities, chalcones have been explored for different optical applications including second harmonic generation materials in non- linear optics, fluorescent probe for sensing different molecules.

  4. SYNTHESIS AND CHARACTERIZATION OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

    OpenAIRE

    Ramesh Dhani; P. Sudheer Kumar; C.A. Abhilash; CH. Jahnavi

    2012-01-01

    Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The name chalcones was given by Kostanecki and Tambor. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of novel heterocyclics with good pharmaceutical profile can be designed. Chalcones have been considered as a magic moiety possessing myriad spectrum of medicinal...

  5. Dietary chalcones with chemopreventive and chemotherapeutic potential.

    Science.gov (United States)

    Orlikova, Barbora; Tasdemir, Deniz; Golais, Frantisek; Dicato, Mario; Diederich, Marc

    2011-05-01

    Chalcones are absorbed in the daily diet and appear to be promising cancer chemopreventive agents. Chalcones represent an important group of the polyphenolic family, which includes a large number of naturally occurring molecules. This family possesses an interesting spectrum of biological activities, including antioxidative, antibacterial, anti-inflammatory, anticancer, cytotoxic, and immunosuppressive potential. Compounds of this family have been shown to interfere with each step of carcinogenesis, including initiation, promotion and progression. Moreover, numerous compounds from the family of dietary chalcones appear to show activity against cancer cells, suggesting that these molecules or their derivatives may be considered as potential anticancer drugs. This review will focus primarily on prominent members of the chalcone family with an 1,3-diphenyl-2-propenon core structure. Specifically, the inhibitory effects of these compounds on the different steps of carcinogenesis that reveal interesting chemopreventive and chemotherapeutic potential will be discussed. PMID:21484163

  6. A New Geranylated Chalcone from Andrographis lobelioides.

    Science.gov (United States)

    Sumalatha, Manne; Rammohan, Aluru; Gunasekar, Duvvuru; Deville, Alexandre; Bodo, Bernard

    2016-01-01

    A new O-geranylated chalcone, 2'-hydroxy-2-methoxy-4'-O-[(E)-3,7-dimethyl-2,6-octadienyl] chalcone (1), together with three known flavones, 5-hydroxy-7,2'-dimethoxyflavone (2), skullcapflavone I (3) and echioidin (4), were isolated from the leaves of Andrographis lobelioides. The structure of 1 and the known compounds (2-4) were achieved by extensive 1D and 2D NMR spectral and chemical studies. PMID:26996025

  7. Structural Antitumoral Activity Relationships of Synthetic Chalcones

    OpenAIRE

    Cesar Echeverria; Juan Francisco Santibañez; Oscar Donoso-Tauda; Escobar, Carlos A.; Rodrigo Ramirez-Tagle

    2009-01-01

    Relationships between the structural characteristic of synthetic chalcones and their antitumoral activity were studied. Treatment of HepG2 cells for 24 h with synthetic 2’-hydroxychalcones resulted in apoptosis induction and dose-dependent inhibition of cell proliferation. The calculated reactivity indexes and the adiabatic electron affinities using the DFT method including solvent effects, suggest a structure-activity relationship between the Chalcones structure and the apoptosis in Hep...

  8. Monoamine oxidase inhibitory activities of heterocyclic chalcones.

    Science.gov (United States)

    Minders, Corné; Petzer, Jacobus P; Petzer, Anél; Lourens, Anna C U

    2015-11-15

    Studies have shown that natural and synthetic chalcones (1,3-diphenyl-2-propen-1-ones) possess monoamine oxidase (MAO) inhibition activities. Of particular importance to the present study is a report that a series of furanochalcones acts as MAO-B selective inhibitors. Since the effect of heterocyclic substitution, other than furan (and more recently thiophene, piperidine and quinoline) on the MAO inhibitory properties of the chalcone scaffold remains unexplored, the aim of this study was to synthesise and evaluate further heterocyclic chalcone analogues as inhibitors of the human MAOs. For this purpose, heterocyclic chalcone analogues that incorporate pyrrole, 5-methylthiophene, 5-chlorothiophene and 6-methoxypyridine substitution were examined. Seven of the nine synthesised compounds exhibited IC50 values heterocyclic chalcones are reversible and competitive MAO inhibitors. 4h, however, may exhibit tight-binding to MAO-B, a property linked to its thiophene moiety. We conclude that high potency chalcones such as 4h represent suitable leads for the development of MAO-B inhibitors for the treatment of Parkinson's disease and possibly other neurodegenerative disorders. PMID:26432037

  9. SYNTHESIS AND CHARACTERIZATION OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Ramesh Dhani

    2012-12-01

    Full Text Available Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The name chalcones was given by Kostanecki and Tambor. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of novel heterocyclics with good pharmaceutical profile can be designed. Chalcones have been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. By using different synthetic methods new chalcone derivatives were synthesized and characterized by physicochemical analysis. Chalcone is a lead nucleus for future developments to get effective compounds.

  10. Chalcone derivatives as potential antifungal agents: Synthesis, and antifungal activity

    OpenAIRE

    Deepa Gupta; Jain, D. K.

    2015-01-01

    Much research has been carried out with the aim to discover the therapeutic values of chalcone derivatives. Chalcones possess wide range of pharmacological activity such as antibacterial, antimalarial, antiprotozoal, antitubercular, anticancer, and antifungal agents etc. The presence of reactive α,β-unsaturated keto group in chalcones is found to be responsible for their biological activity. The rapid developments of resistance to antifungal agents, led to design, and synthesize the new antif...

  11. CHALCONE AS A VERSATILE MOIETY FOR DIVERSE PHARMACOLOGICAL ACTIVITIES

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    Hatish Prashar*, Anshul Chawla, Anil Kumar Sharma and Rajeev Kharb

    2012-07-01

    Full Text Available Chalcones are 1, 3-diphenyl-2-propene-1-one, consist of two aromatic rings linked by a three carbon α, β-unsaturated carbonyl system. The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been focused on the synthesis and biodynamic activities of chalcones. These are considered to be precursors of flavonoids and isoflavonoids. The aim of this review is to summarize chalcones and their diverse pharmacological activities like anticancer, antimicrobial, analgesic and antiviral activities etc.

  12. Five new prenylated chalcones from Desmodium renifolium.

    Science.gov (United States)

    Li, Yan-Ping; Yang, Yu-Chun; Li, Yin-Ke; Jiang, Zhi-Yong; Huang, Xiang-Zhong; Wang, Wei-Guang; Gao, Xue-Mei; Hu, Qiu-Fen

    2014-06-01

    Five unusual new prenylated chalcones, renifolins D-H (1-5), were isolated from whole Desmodium renifolium plants. All of their structures were determined by spectroscopic methods including 1D and 2D NMR. All of the isolates were evaluated for cytotoxicity using five tumor cell lines. Compounds 2 and 3 exhibited cytotoxicity against A549 cells, with IC50 values of 2.8 and 2.2 μM, respectively. PMID:24704553

  13. Chalcone derivatives as potential antifungal agents: Synthesis, and antifungal activity

    Directory of Open Access Journals (Sweden)

    Deepa Gupta

    2015-01-01

    Full Text Available Much research has been carried out with the aim to discover the therapeutic values of chalcone derivatives. Chalcones possess wide range of pharmacological activity such as antibacterial, antimalarial, antiprotozoal, antitubercular, anticancer, and antifungal agents etc. The presence of reactive α,β-unsaturated keto group in chalcones is found to be responsible for their biological activity. The rapid developments of resistance to antifungal agents, led to design, and synthesize the new antifungal agents. The derivatives of chalcones were prepared using Claisen-Schmidt condensation scheme with appropriate tetralone and aldehyde derivatives. Ten derivatives were synthesized and were biologically screened for antifungal activity. The newly synthesized derivatives of chalcone showed antifungal activity against fungal species, Microsporum gypseum. The results so obtained were superior or comparable to ketoconazole. It was observed that none of the compounds tested showed positive results for fungi Candida albicans nor against fungi Aspergillus niger. Chalcone derivatives showed inhibitory effect against M. gypseum species of fungus. It was found that among the chalcone derivatives so synthesized, two of them, that is, 4-chloro derivative, and unsubstituted derivative of chalcone showed antifungal activity superior to ketoconazole. Thus, these can be the potential new molecule as antifungal agent.

  14. Chalcone derivatives as potential antifungal agents: Synthesis, and antifungal activity.

    Science.gov (United States)

    Gupta, Deepa; Jain, D K

    2015-01-01

    Much research has been carried out with the aim to discover the therapeutic values of chalcone derivatives. Chalcones possess wide range of pharmacological activity such as antibacterial, antimalarial, antiprotozoal, antitubercular, anticancer, and antifungal agents etc. The presence of reactive α,β-unsaturated keto group in chalcones is found to be responsible for their biological activity. The rapid developments of resistance to antifungal agents, led to design, and synthesize the new antifungal agents. The derivatives of chalcones were prepared using Claisen-Schmidt condensation scheme with appropriate tetralone and aldehyde derivatives. Ten derivatives were synthesized and were biologically screened for antifungal activity. The newly synthesized derivatives of chalcone showed antifungal activity against fungal species, Microsporum gypseum. The results so obtained were superior or comparable to ketoconazole. It was observed that none of the compounds tested showed positive results for fungi Candida albicans nor against fungi Aspergillus niger. Chalcone derivatives showed inhibitory effect against M. gypseum species of fungus. It was found that among the chalcone derivatives so synthesized, two of them, that is, 4-chloro derivative, and unsubstituted derivative of chalcone showed antifungal activity superior to ketoconazole. Thus, these can be the potential new molecule as antifungal agent. PMID:26317075

  15. An antileishmanial chalcone from Chinese licorice roots

    DEFF Research Database (Denmark)

    Christensen, S B; Ming, C; Andersen, L;

    1994-01-01

    A bioassay guided fractionation of an extract of Chinese licorice roots led to the isolation of (E)-1-[2,4-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-[4- hydroxy-3-(3-methyl-2-butenyl]phenyl-2-propen-1-one, which in vitro showed potent antileishmanial activity. In addition, the novel chalcone (E)-1......-[2,4-dihydroxy-3-(3-methyl-2- butenyl)phenyl]-3-(2,2-dimethyl-8-hydroxy-2H-benzopyran-6-yl)-2-prope n-1-one was isolated from the roots. The latter compound only showed antileishmanial activity at high concentrations....

  16. ANTIMICROBIAL SCREENING OF SOME NOVEL SUBSTITUTED CHALCONE DERIVATIVES

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    Ramesh Dhani

    2012-10-01

    Full Text Available Chalcone is an aromatic ketone that forms the central core for the variety of important biological compounds, which are collectively known as chalcones. The derivatives of chalcones with an annular nitrogen atom in the phenyl ring were reported to have a wide range of biologically activities, such as antibacterial, anti-tuberculostatic and anti- inflammatory. The chalcones, two aromatic rings are linked by an aliphatic three carbon chain which bears a very good synthon so that variety of novel heterocyclics with good pharmaceutical profile can be designed. Chalcones have been considered as a magic moiety possessing myriad spectrum of medicinal activities. Diversity of biological response profile has attracted considerable interest of several researchers across the globe to explore this skeleton for its assorted therapeutic significance. The synthesized chalcone derivatives were screened for antimicrobial activity by comparing with the standard drug of ciprofloxacin on two gram positive and two gram negative strains, the synthesized compounds, by using Disc-diffusion method. Chalcone is a lead nucleus for future developments to get effective compounds.

  17. Syntheses and properties of chalcone derivatives. Chalcone yudotai no gosei to seishitsu

    Energy Technology Data Exchange (ETDEWEB)

    Noguchi, A.; Kato, Y.; Yasui, S. (Nippon Kanko Shikiso Kenkyusho Co. Ltd., Okayama (Japan))

    1991-11-20

    Photoresist is used as a protective film in the photo-etching during manufacturing semiconductor devices. A technique of mixing light absorbers is proposed to prevent reduction in its resolution because of halation. As the light absorbing materials, mono-azo and polymethine coloring agents of certain kinds have been proposed. This paper describes syntheses of eleven chalcone derivatives for the purpose of developing ultraviolet light absorbers for the photoresist, and discussions on various characteristics required for the primary evaluation, such as absorption spectrum characteristics, solubility, light resistance, and heat resistance. As a result, it was found that the chalcone derivatives with weak donors, such as alkoxyl and hydroxyl groups are useful as absorbers for i-line (365 nm) of mercury vapor lamps. Especially those with hydroxyl groups are promising for the positive type photoresist because they are soluble in alkaline aqueous solution. 8 refs., 3 figs., 3 tabs.

  18. [Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents].

    Science.gov (United States)

    Opletalová, V; Sedivý, D

    1999-11-01

    Chalcones and their heterocyclic analogues show various biological effects, e.g. anti-inflammatory, antitumour, antibacterial, antituberculous, antiviral, antiprotozoal, gastroprotective, and others. The present review discusses in greater detail the fungistatic and fungicide properties of these compounds and presents also their chemical structures. The mechanism of antifungal effects of chalcones and their analogues has not been investigated in greater detail. Due to the presence of a reactive ketovinyl moiety in the molecule the compounds of this type are able to react with the thiol groups of enzymes. It cannot be excluded that chalcones interfere with the normal function of the membranes of fungi and moulds. Further investigation of chemical, physical, and biological properties of chalcones and their analogues could lead to the elucidation of the mechanism of their action and finding of effective fungicidal and fungistatic agents in this group of organic substances. PMID:10748740

  19. Exploring pharmacological significance of chalcone scaffold: a review.

    Science.gov (United States)

    Sahu, N K; Balbhadra, S S; Choudhary, J; Kohli, D V

    2012-01-01

    Chalcones (1,3-diaryl-2-propen-1-ones) and their heterocyclic analogues, belong to the flavonoid family, which possess a number of interesting biological properties such as antioxidant, cytotoxic, anticancer, antimicrobial, antiprotozoal, antiulcer, antihistaminic and anti-inflammatory activities. Several pure chalcones have been approved for clinical use or tested in humans. Clinical trials have shown that these compounds reached reasonable plasma concentration and are well-tolerated. For this reason they are an object of continuously growing interest amongst the scientists. However, much of the pharmacological potential of chalcones is still not utilized. The purpose of this review is to provide an overview of the pharmacological activity of naturally occurring and synthetic chalcones. This review highlights more recent pharmacological screening of these compounds, their mechanisms of action and relevant structure-activity relationships. PMID:22320299

  20. Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives

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    Essam Mohamed Sharshira

    2011-03-01

    Full Text Available Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities.

  1. Synthesis and Antimicrobial Evaluation of Some Heterocyclic Chalcone Derivatives

    OpenAIRE

    Essam Mohamed Sharshira; Nagwa Mohamed Mahrous Hamada

    2011-01-01

    Some new heterocyclic compounds containing isoxazole, pyrazole and oxadiazole ring systems were prepared from various chalcones. The synthesized compounds have been characterized by elemental analysis and spectral methods. These compounds were screened for their antimicrobial activities.

  2. Chalcones and flavonoids as anti-tuberculosis agents.

    Science.gov (United States)

    Lin, Yuh-Meei; Zhou, Yasheen; Flavin, Michael T; Zhou, Li-Ming; Nie, Weiguo; Chen, Fa-Ching

    2002-08-01

    A series of flavonoids, chalcones and chalcone-like compounds were evaluated for inhibitory activity against Mycobacterium tuberculosis H37Rv. Among them, eight compounds exhibited >90% inhibition on the growth of the bacteria at a concentration of 12.5 microg/mL. Chalcones 1-(2-hydroxyphenyl)-3-(3-chlorophenyl)-2-propen-1-one (22) and 1-(2-hydroxyphenyl)-3-(3-iodophenyl)-2-propen-1-one (37) demonstrated 90 and 92% inhibition, respectively. Chalcone-like compounds (heterocyclic ring-substituted 2-propen-1-one) 1-(4-fluorophenyl)-3-(pyridin-3-yl)-2-propen-1-one (48), 1-(3-hydroxyphenyl)-3-(phenanthren-9-yl)-2-propen-1-one (49), 1-(pyridin-3-yl)-3-(phenanthen-9-yl)-2-propen-1-one (50) and 1-(furan-2-yl)-3-phenyl-2-propen-1-one (51) exhibited 98, 97, 96 and 96% inhibition, respectively. The actual minimum inhibitory concentrations (MIC), defined as the lowest concentration inhibiting 99% of the inoculum, for 22, 37, 48, 49, 50 and 51 were 20.3, 31.5, 48.3, >35.7, 6.8 and 19.2, respectively. A hydrophobic substituent on one aromatic ring, and a hydrogen-bonding group on the other aromatic ring resulted in increased anti-TB activity of the chalcones and chalcone-like compounds. Flavones and flavanones are more geometrically constrained than the corresponding chalcone analogues. The decreased activity of the flavones with respect to the chalcones may be due to the confinement of the terminal aromatic rings to the same plane. PMID:12057669

  3. Synthesis and anticonvulsant activity of certain chalcone based pyrazoline compounds

    OpenAIRE

    Sudhakara Rao Gerapati; Kalaichelvan V K; Ganguri Sudhakara Rao

    2015-01-01

    Convulsions are involuntary, violent, spasmodic and prolonged contractions of skeletal muscles. That means a patient may have epilepsy without convulsions and vice versa. Epilepsy is a common neurological abnormality affecting about 1% of the world population. The primary objectives of these synthesized compounds are to suppress seizures and provide neuroprotection by minimizing the effects from seizure attacks. Here some of the chalcones and chalcone based various pyrazolines were evaluated ...

  4. Design and synthesis of chalcone-based macrocyclic polyethers

    OpenAIRE

    Subrata Jana

    2015-01-01

    A series of chalcone-based macrocyclic ethers have been synthesized. These macrocyclic ethers contain polyether as well as extended conjugation to the benzene ring to function as fluorescent sensor for cations. The modeling studies show that the chalcone part of the receptors remains partially out of plane from the polyether part and the keto moiety of the receptors always directed outwardly in the receptor itself. This may be changed during the recognition of metal ions. The tendency of the ...

  5. Synthesis and Characterisation of Biologically Potent Novel Chalcone Moieties

    OpenAIRE

    Mahammadali Khanusiya; Z. M Gadhawala

    2016-01-01

    As displaying a dominant biological interest of some amino chalcone derivatives which were synthesized by claisen-schmidt condensation reaction of amino acetophenone with aromatic aldehyde in presence of sodium hydroxide. These chalcones were screened for antifungal activity against candida albicans strain and also for antibacterial activity against staphylococcus epidermidis (G positive) and pseudomonas aeruginosa (G negative) strain by NCCLS method. The synthesized compounds were characteri...

  6. Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones

    OpenAIRE

    COŞKUN, Demet; Tekin, Suat; SANDAL, Süleyman; Coşkun, Mehmet Fatih

    2016-01-01

    Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl)-2-propanones propenones (3a–f), were designed, synthesized, and characterized. In vitro antitu...

  7. Solvent Free Synthesis of Chalcones and their Antibacterial Activities

    OpenAIRE

    K. Rajendra K. Saini; S. Amit Choudhary; Joshi, Yogesh C.; Joshi, P.

    2005-01-01

    The solvent free synthesis of six chalcones was carried out by grinding the piperanal and the acetophenone (unsubstituted, 4-methyl, 4-methoxy, 4-bromo, 4-nitro, 3-chloro) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yield and high purity. Minor quantities of Ketol and Michael addition product were easily removed by recrystallization. The result indicates a correlation between the success of the solvent-free synthesis and ...

  8. Synthesis, SAR and antibacterial studies on novel chalcone oxazolidinone hybrids.

    Science.gov (United States)

    Selvakumar, N; Kumar, G Sunil; Azhagan, A Malar; Rajulu, G Govinda; Sharma, Shikha; Kumar, M Sitaram; Das, Jagattaran; Iqbal, Javed; Trehan, Sanjay

    2007-04-01

    With an intention to synergise the antibacterial activity of chalcones and oxazolidinones, several hybrid compounds possessing both chalcone and oxazolidinone moieties were synthesized and tested for antibacterial activity. The hybrid molecules containing heterocycles instead of aromatic ring were found to be active. A SAR study with various heterocycles resulted in a lead molecule 20, which was converted to one of the potent antibacterial compounds 27. PMID:17150281

  9. Synthesis and Characterisation of Biologically Potent Novel Chalcone Moieties

    Directory of Open Access Journals (Sweden)

    Mahammadali Khanusiya

    2016-05-01

    Full Text Available As displaying a dominant biological interest of some amino chalcone derivatives which were synthesized by claisen-schmidt condensation reaction of amino acetophenone with aromatic aldehyde in presence of sodium hydroxide. These chalcones were screened for antifungal activity against candida albicans strain and also for antibacterial activity against staphylococcus epidermidis (G positive and pseudomonas aeruginosa (G negative strain by NCCLS method. The synthesized compounds were characterized by means of their FT-IR and 1HNMR spectral study.[14

  10. SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF SOME NOVEL ARYL AND HETROARYL CHALCONE ANALOGUES

    OpenAIRE

    Tribhuvan Singh; R Lavanya; Srikanth Merugu; P.Sudhakar; Syeda Sana Yasmeen

    2012-01-01

    A new series of Heterocyclic chalcones showed diversified biological activities. In view of potential biological activities of Heterocyclic chalcones derivative were prepared by claisen-Schmidt condensation technique. The compound were screened for anti-inflammatory and antibacterial activity.

  11. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    OpenAIRE

    P. M. Rachmale

    2012-01-01

    In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spect...

  12. The antileishmanial activity of novel oxygenated chalcones and their mechanism of action

    DEFF Research Database (Denmark)

    Zhai, L; Chen, M; Blom, J;

    1999-01-01

    Our previous studies have shown that licochalcone A, an oxygenated chalcone, has antileishmanial and antimalarial activities, and alters the ultrastructure and function of the mitochondria of Leishmania spp. parasites. The present study was designed to investigate the antileishmanial activity...... and the mechanism of action of a group of new oxygenated chalcones. The tested oxygenated chalcones inhibited the in-vitro growth of Leishmania major promastigotes and Leishmania donovani amastigotes. Treatment of hamsters infected with L. donovani with intraperitoneal administration of two oxygenated chalcones...

  13. Synthesis and Biological Evaluation of Retinoid-Chalcones as Inhibitors of Colon Cancer Cell Growth

    Science.gov (United States)

    Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids were designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer ce...

  14. Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones

    Directory of Open Access Journals (Sweden)

    Demet Coşkun

    2016-01-01

    Full Text Available Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl-2-propanones propenones (3a–f, were designed, synthesized, and characterized. In vitro antitumor activities of the newly synthesized (3a–f and previously synthesized (3g–j chalcone compounds were determined by using human breast (MCF-7 and prostate (PC-3 cancer cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide (MTT assay. Cell viability assay for the tested chalcone compounds was performed and the log⁡IC50 values of the compounds were calculated after 24-hour treatment. Our results indicate that the tested chalcone compounds show antitumor activity against MCF-7 and PC-3 cell lines (p<0.05.

  15. Second harmonic generation and crystal growth of new chalcone derivatives

    Science.gov (United States)

    Patil, P. S.; Dharmaprakash, S. M.; Ramakrishna, K.; Fun, Hoong-Kun; Sai Santosh Kumar, R.; Narayana Rao, D.

    2007-05-01

    We report on the synthesis, crystal structure and optical characterization of chalcone derivatives developed for second-order nonlinear optics. The investigation of a series of five chalcone derivatives with the second harmonic generation powder test according to Kurtz and Perry revealed that these chalcones show efficient second-order nonlinear activity. Among them, high-quality single crystals of 3-Br-4'-methoxychalcone (3BMC) were grown by solvent evaporation solution growth technique. Grown crystals were characterized by X-ray powder diffraction (XRD), laser damage threshold, UV-vis-NIR and refractive index measurement studies. Infrared spectroscopy, thermogravimetric analysis and differential thermal analysis measurements were performed to study the molecular vibration and thermal behavior of 3BMC crystal. Thermal analysis does not show any structural phase transition.

  16. Synthesis of Novel Chalcones as Acetylcholinesterase Inhibitors

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    Thanh-Dao Tran

    2016-07-01

    Full Text Available A new series of benzylaminochalcone derivatives with different substituents on ring B were synthesized and evaluated as inhibitors of acetylcholinesterase. The study is aimed at identification of novel benzylaminochalcones capable of blocking acetylcholinesterase activity for further development of an approach to Alzheimer’s disease treatment. These compounds were produced in moderate to good yields via Claisen-Schmidt condensation and subjected to an in vitro acetylcholinesterase inhibition assay, using Ellman’s method. The in silico docking procedure was also employed to identify molecular interactions between the chalcone compounds and the enzyme. Compounds with ring B bearing pyridin-4-yl, 4-nitrophenyl, 4-chlorophenyl and 3,4-dimethoxyphenyl moieties were discovered to exhibit significant inhibitory activities against acetylcholinesterase, with IC50 values ranging from 23 to 39 µM. The molecular modeling studies are consistent with the hypothesis that benzylaminochalcones could exert their effects as dual-binding-site acetylcholinesterase inhibitors, which might simultaneously enhance cholinergic neurotransmission and inhibit β-amyloid aggregation through binding to both catalytic and peripheral sites of the enzyme. These derivatives could be further developed to provide novel leads for the discovery of new anti-Alzheimer drugs in the future.

  17. Synthesis of Chalcones with Anticancer Activities

    Directory of Open Access Journals (Sweden)

    Syam Mohan

    2012-05-01

    Full Text Available Several chalcones were synthesized and their in vitro cytotoxicity against various human cell lines, including human breast adenocarcinoma cell line MCF-7, human lung adenocarcinoma cell line A549, human prostate cancer cell line PC3, human adenocarcinoma cell line HT-29 (colorectal cancer and human normal liver cell line WRL-68 was evaluated. Most of the compounds being active cytotoxic agents, four of them with minimal IC50 values were chosen and studied in detail with MCF-7 cells. The compounds 1, 5, 23, and 25 were capable in eliciting apoptosis in MCF-7 cells as shown by multiparameter cytotoxicity assay and caspase-3/7, -8, and -9 activities (p < 0.05. The ROS level showed 1.3-fold increase (p < 0.05 at the low concentrations used and thus it was concluded that the compounds increased the ROS level eventually leading to apoptosis in MCF-7 cells through intrinsic as well as extrinsic pathways.

  18. Design and synthesis of chalcone-based macrocyclic polyethers

    Directory of Open Access Journals (Sweden)

    Subrata Jana

    2015-12-01

    Full Text Available A series of chalcone-based macrocyclic ethers have been synthesized. These macrocyclic ethers contain polyether as well as extended conjugation to the benzene ring to function as fluorescent sensor for cations. The modeling studies show that the chalcone part of the receptors remains partially out of plane from the polyether part and the keto moiety of the receptors always directed outwardly in the receptor itself. This may be changed during the recognition of metal ions. The tendency of the fluorophore, to be out of plane, increases with increasing the ring size.

  19. Synthesis and Biological Evaluation of Chalcone Derivatives Linked Triazoles

    OpenAIRE

    Ashvin D. Panchal; Prashant D. Kunjadia; Patel, Pravinkumar M.

    2011-01-01

    In this work, an attempt was made to synthesize chalcone 3-(Substitutedphenyl)-N-(4H-1, 2, 4-triazol-4-yl)acrylamide by condensation of substitutedbenzaldehyde with N-(4H-1,2,4-triazol-4-yl)acetamide under basic conditions. A simple condensation reaction of substitutedbenzaldehyde and N-(4H-1, 2, 4-triazol-4-yl)acetamide using Sodium hydroxide as a base was carried out for the study. The synthesized chalcone derivative was characterized by FTIR, 1H-NMR & 13C-NMR and studied for their Antimicr...

  20. Ultrastructural and morphological changes in Leishmania (Viannia) braziliensis treated with synthetic chalcones.

    Science.gov (United States)

    de Mello, Tatiane F P; Cardoso, Bruna M; Bitencourt, Heriberto R; Donatti, Lucélia; Aristides, Sandra M A; Lonardoni, Maria V C; Silveira, Thais G V

    2016-01-01

    Cutaneous leishmaniasis has an estimated incidence of 1.5 million new cases per year and the treatment options available are old, expensive, toxic, and difficult to administer. Chalcones have shown good activity against several species of Leishmania. However few studies have discussed the mechanisms of action and drug target of this group of compounds in Leishmania. The synthetic chalcones that were evaluated in the present study were previously shown to exhibit activity against Leishmania (Viannia) braziliensis. The objective of the present study was to identify ultrastructural and morphological changes in L. (V.) braziliensis after treatment with three synthetic chalcones (1-3). Promastigotes were treated with chalcones 1-3 and evaluated by transmission and scanning electron microscopy. Cellular and nuclear morphology of the parasites, changes in membrane permeability, and DNA fragmentation in agarose electrophoresis gel were also investigated after exposure to synthetic chalcones. All three synthetic chalcones (1-3) induced ultrastructural alterations in mitochondria, intense vacuolization, two nuclei with rounding of parasites, and cellular and nuclear shrinkage. Chalcones 1-3 also induced no changes in membrane permeability, and presence of nucleosome-sized DNA fragments. Synthetic chalcones 1-3 induced ultrastructural and morphological changes, suggesting that chalcones 1-3 induce apoptosis-like cell death. Further studies should be conducted to elucidate other aspects of the action of these chalcones against Leishmania spp. and their use for the treatment of cutaneous leishmaniasis. PMID:26632504

  1. A new chalcone from the aerial roots of Ficus microcarpa

    Institute of Scientific and Technical Information of China (English)

    Hui Xu; Xiang Min Wang; Xing Wei; Jing Yuan Li; Ke Liu

    2009-01-01

    A new flavonoid with chalcone skeleton was isolated from the dried aerial roots of Ficus microcarpa.The structure of the compound was elucidated on the basis of spectral methods including ID and 2D NMR.The new compound showed weak inhibitory effect on nitric oxide production and cytotoxicity against K562 and PC3 ceils.

  2. Synthesis and Characterization of a-Bromo Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    BUDAK Yakup; CEYLAN Mustafa

    2009-01-01

    a-Bromo chalcones containing 2-thiene ring were prepared in good yields by the condensation of 1-(thien-3-yl)ethanone with aromatic aldehydes,followed by bromination with bromine and selective dehydrobromination with triethyl amine at room temperature.

  3. ANDROECHIN, A NEW CHALCONE GLUCOSIDE FROM ANDROGRAPHIS ECHIOIDES

    Institute of Scientific and Technical Information of China (English)

    B.JAYAPRAKASAM; D.GUNASEKAR; K.V.RAO; A.BLOND; B.BODO

    2001-01-01

    A new chalcone glucoside, androechin, and a known flavone glucoside, echioidinin 5-O-gluco side, were isolated from the whole plant of Andrographis echioides. Androechin was character ized as 2,2',6'-trihydroxy-4'-methoxychalcone 2'-O-,β-D-glucopyranoside by spectral and chemical studies.

  4. Inhibition of sortase A by chalcone prevents Listeria monocytogenes infection.

    Science.gov (United States)

    Li, Hongen; Chen, Yutao; Zhang, Bing; Niu, Xiaodi; Song, Meng; Luo, Zhaoqing; Lu, Gejin; Liu, Bowen; Zhao, Xiaoran; Wang, Jianfeng; Deng, Xuming

    2016-04-15

    The critical role of sortase A in gram-positive bacterial pathogenicity makes this protein a good potential target for antimicrobial therapy. In this study, we report for the first time the crystal structure of Listeria monocytogenes sortase A and identify the active sites that mediate its transpeptidase activity. We also used a sortase A (SrtA) enzyme activity inhibition assay, simulation, and isothermal titration calorimetry analysis to discover that chalcone, an agent with little anti-L. monocytogenes activity, could significantly inhibit sortase A activity with an IC50 of 28.41±5.34μM by occupying the active site of SrtA. The addition of chalcone to a co-culture of L. monocytogenes and Caco-2 cells significantly inhibited bacterial entry into the cells and L. monocytogenes-mediated cytotoxicity. Additionally, chalcone treatment decreased the mortality of infected mice, the bacterial burden in target organs, and the pathological damage to L. monocytogenes-infected mice. In conclusion, these findings suggest that chalcone is a promising candidate for the development of treatment against L. monocytogenes infection. PMID:26826492

  5. Synthesis of Urea based Chalcone Derivatives and Evaluate its Biological Activity

    OpenAIRE

    Arpita Desai; Vyas, K. B.; Rajarshi N. Patel; K. S. Nimavat

    2016-01-01

    Chalcones have been the center of attraction for researchers from several decades due to nits innumerous therapeutic application, Efforts have been done in my research to synthesized chalcones and their derivatives that further reacts with various substituted aldehyde to give corresponding substituted chalcone derivatives. Now these derivatives on condensation with Guanidine nitrate gives the vast range of phenyl pyrimidine amine Derivatives. Structure elucidation of synthesized compound had ...

  6. IN VITRO SOLUBLE EPOXIDE HYDROLASE ENZYME INHIBITORY ACTIVITY OF SOME NOVEL CHALCONE DERIVATIVES

    OpenAIRE

    Kuppusamy Asokkumar; Lokeswari Prathyusha Tangella; Muthusamy Umamaheshwari; Thirumalaisamy Shivashanmugam; Varadharajan Subhadradevi; Puliyath Jagannath; Arumugam Madeswaran

    2012-01-01

    Objective Soluble epoxide hydrolase (sEH) belongs to the α/β -hydrolase superfamily, a subclass of α/β proteins. Chalcones are chemical compounds that show hopeful obliging efficacy in controlling numerous diseases. The main objective of the study is to evaluate the sEH inhibitory activity of some synthesized chalcone derivatives and identification of its mode of inhibition. Methods Four different chalcone derivatives (PC-1 to PC-4) were selected for synthesis by Claisen-Schmidt method. The i...

  7. Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience

    Science.gov (United States)

    Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr.

    2002-09-01

    A guided inquiry experiment involving the synthesis and characterization of substituted benzalacetophenones (chalcones) is described. The chalcones are produced in the aldol condensation of substituted benzaldehydes with substituted acetophenones. Each student is assigned a different target chalcone and conducts online and printed literature searches on the target. After completing the synthesis and purification of their product, the students compare their data with those found in the literature.

  8. Synthesis of novel chalcone derivatives and their stabilization effect of spiropyran in PMMA films

    Institute of Scientific and Technical Information of China (English)

    Zheng Kai Si; Qing Zhang; Min Zhao Xue; Yuan Yuan Zhu; Liang Ming; Qiao Rong Sheng; Yan Gang Liu

    2011-01-01

    Three novel bis-chalcone derivatives with different alkyldioxy spacers were synthesized and dispersed into polymethyl methacrylate (PMMA) chloroform solution with 6-nitro-1'-ethyl-3',3'-dimethylspiro-2H-1-benzopyran-2,2'-indoline (ESP) to prepare photochromic PMMA films in a facile way. After irradiation with 365 nm UV light, the photocrosslinking reaction between chalcone units was proved to retard the decolorization of merocyanine form of the photochromic spiropyran effectively, as results of the steric hindrance produced by photocycloaddition of chalcone groups. It has been found that the bis-chalcone molecule with the shortest spacer has the most effective stabilizing effect on retardation of decoloration of spiropyran.

  9. Synthesis, spectral correlation and insect antifeedant activities of some 2-benzimidazole chalcones

    Directory of Open Access Journals (Sweden)

    P. Janaki

    2016-01-01

    Full Text Available Some substituted styryl 2-benzimidazole ketones have been synthesised by fly-ash:H2SO4 catalysed aldol condensation of 2-benzimidazole methyl ketone and various substituted benzaldehydes in microwave oven. The yields of these chalcones are more than 70%. The purities of synthesised benzimidazole chalcones were checked by their physical constants and spectral data earlier published in the literature. The spectral frequencies of these chalcones have been correlated with Hammett substituent constants, F and R parameters. From the results of statistical analyses the effects of substituent on the group frequencies were discussed. The insect antifeedant activities of these chalcones have been studied using Dethler’s method.

  10. Synthesis, characterization and evaluation of antioxidant activities of some novel chalcones analogues

    OpenAIRE

    Lahsasni, Siham Abdelrahmane; Al Korbi, Faeza Hamad; Aljaber, Nabilah Abdel-Aziz

    2014-01-01

    Background Chalcone, an important intermediate of flavonoid synthetic pathway, has been shown to exhibit diverse biological and pharmacological activities such as anti- cancer, antioxidant, anti-inflammatory, etc. Results In this study, a novel series of chalcones fatty acid esters 5b-e and 6b-e have been synthesized via the reaction of the respective chalcones with either palmitic or stearic acid. Another related class of compounds comprising 2,3-disubstituted chalcones 7b-d and 8b(b’)-d as ...

  11. Catalytic Hydrogenation Reaction of Naringin-Chalcone. Study of the Electrochemical Reaction

    OpenAIRE

    B. A. López de Mishima; H. T. Mishima; A. N. Giannuzzo; M. A. Nazareno

    2000-01-01

    The electrocatalytic hydrogenation reaction of naringin derivated chalcone is studied. The reaction is carried out with different catalysts in order to compare with the classic catalytic hydrogenation.

  12. SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME CHALCONE DERIVATIVES AND THEIR COPPERCOMPLEXES

    Directory of Open Access Journals (Sweden)

    P. M. Rachmale

    2012-03-01

    Full Text Available In the present investigation, 4-chloro acetophenone on condensation with 2-nitro benzaldehydes in methanolic NaOH solution yielded the corresponding chalcone. These chalcone were further reacted with Isonicotyl hydrazide and semicarbazide in ethanol which led to the formation of chalcone Isonicotyl hydrazone and chalcone semicarbazone derivatives respectively. The newly synthesized derivatives and there copper complexes were characterized on the basis of their chemical properties and spectroscopic data such as IR, NMR and UV. All newly synthesized compounds were evaluated for their antibacterial activities against E. coli and S. aureus also for antifungal activities against P. notatum.

  13. Spectroscopic studies on the interaction between chalcone and bovine serum albumin

    International Nuclear Information System (INIS)

    The interaction between chalcone and bovine serum albumin (BSA) has been studied by spectroscopic techniques under physiological condition. By the analysis of fluorescence spectrum and fluorescence intensity, it was observed that the chalcone has a strong ability to quench the intrinsic fluorescence with BSA through a static quenching procedure and non-radiation energy transfer were the main reasons for the fluorescence quenching. The association constants of chalcone with BSA were determined at different temperatures based on fluorescence quenching results. The positive entropy change and enthalpy change indicated that the interaction of chalcone and BSA was driven mainly by hydrophobic forces. The process of binding was a spontaneous process in which Gibbs free energy change was negative. The distance, r, between donor (BSA) and acceptor (chalcone) was obtained according to the Forster's theory of non-radiation energy transfer. The UV–vis, CD, FT-IR, synchronous and 3-D spectral results revealed the changes in the secondary structure of BSA upon interaction with chalcone. The effects of some common metal ions on binding of BSA–chalcone complex were also investigated. -- Highlights: • We explored the interaction between chalcone and BSA by fluorescence spectroscopy. • The fluorescence quenching mechanism was static quenching. • The binding constants and thermodynamic parameters were calculated. • The interaction is driven mainly by hydrophobic force. • The binding of chalcone to BSA induced changes in the secondary structure of BSA

  14. Synthesis and Cytotoxicity of Chalcones and 5-Deoxyflavonoids

    Directory of Open Access Journals (Sweden)

    Jing Zhang

    2013-01-01

    Full Text Available Chalcones 1~8 and 5-deoxyflavonoids 9~22 were synthesized in good yields by aldol condensation, Algar-Flynn-Oyamada reaction, glycosidation, and deacetylation reaction, respectively, starting from 2-acetyl phenols substituted by methoxy or methoxymethoxy group and appropriately benzaldehydes substituted by methoxy, methoxymethoxy group, or chlorine. Among them, 13 and 17~22 are new compounds. The cytotoxicity bioassays of these chalcones and 5-deoxyflavonoids were screened using the sulforhodamine B (SRB protein staining method, and the results showed that compounds 2, 4, 5, 6, 10, 15, and 19 exhibited moderate cytotoxicity against the cancer cell line of MDA-MB-231, U251, BGC-823, and B16 in comparison with control drugs (HCPT, Vincristine, and Taxol.

  15. Synthesis and Biological Evaluation of Chalcone Derivatives Linked Triazoles

    Directory of Open Access Journals (Sweden)

    Ashvin D. Panchal

    2011-10-01

    Full Text Available In this work, an attempt was made to synthesize chalcone 3-(Substitutedphenyl-N-(4H-1, 2, 4-triazol-4-ylacrylamide by condensation of substitutedbenzaldehyde with N-(4H-1,2,4-triazol-4-ylacetamide under basic conditions. A simple condensation reaction of substitutedbenzaldehyde and N-(4H-1, 2, 4-triazol-4-ylacetamide using Sodium hydroxide as a base was carried out for the study. The synthesized chalcone derivative was characterized by FTIR, 1H-NMR & 13C-NMR and studied for their Antimicrobial and Antifungal activities and compared with the standard drugs, some compound of the series exhibited promising anti-microbial and anti-fungal activity compared to standard drugs.

  16. Anti-inflammatory cyclohexenyl chalcone derivatives in Boesenbergia pandurata.

    Science.gov (United States)

    Tuchinda, Patoomratana; Reutrakul, Vichai; Claeson, Per; Pongprayoon, Ubonwan; Sematong, Tuanta; Santisuk, Thawatchai; Taylor, Walter C

    2002-01-01

    The cyclohexenyl chalcone derivative [(-)-hydroxypanduratin A], together with the previously known panduratin A, sakuranetin, pinostrobin, pinocembrin, and dihydro-5,6-dehydrokawain were isolated from the chloroform extract of the red rhizome variety of Boesenbergia pandurata (Robx.) Schltr. [currently known as Boesenbergia rotunda (L.) Mansf., Kulturpfl.]. Their structures were assigned on the basis of their spectroscopic data. (-)-Hydroxypanduratin A and (-)-panduratin A showed significant topical anti-inflammatory activity in the assay of TPA-induced ear edema in rats. PMID:11809452

  17. Growth, characterization and nonlinear optical property of chalcone derivative

    Science.gov (United States)

    Indira, J.; Karat, P. Prakash; Sarojini, B. K.

    2002-07-01

    The synthesis of chalcone derivative compound is reported. The compound showed second harmonic generation conversion efficiency in powder form. Solubility of 1-(4-methoxyphenyl)-3-(phenyl)-2-propen-1-one in acetone was studied. Single crystals of the same compound was grown by slow evaporation technique using acetone as the solvent. Large crystal of size 55×33×5 mm 3 was obtained. The microhardness of the crystal was measured by Vickers hardness method.

  18. Synthesis and Antimicrobial Activity of Some Chalcone Derivatives

    OpenAIRE

    Prasad, Y. Rajendra; Rao, A. Lakshmana; Rambabu, R.

    2008-01-01

    In an effort to develop antimicrobial agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with appropriate aromatic aldehydes in the presence of aqueous solution of potassium hydroxide and ethanol at room temperature. The synthesized compounds were characterized by means of their IR, 1H-NMR spectral data and elemental analysis. All the compounds were tested for their antibacterial and antifungal activities by the cup plate method.

  19. Accumulation of the chalcone isosalipurposide in primary leaves of barley flavonoid mutants indicates a defective chalcone isomerase

    International Nuclear Information System (INIS)

    Mutants defective in flavonoid biosynthesis have become increasingly useful in elucidating the potential functions of these compounds in plants. To define the role of flavonoids as UV-B protectants in barley, we have screened part of the collection of proanthocyanidin-free barley mutants at the Carlsberg Research Laboratory, Copenhagen, Denmark. The four mutants ant 30–245, ant 30–272, ant 30–287 and ant 30–310 showed drastically reduced flavonoid levels in the primary leaf as compared to their corresponding parent varieties, and in addition accumulated a new mutant-specific phenolic compound which was identified as the chalcone glucoside isosalipurposide. Results from diallelic crosses indicate that all four mutants belong to the same new complementation group, which is designated as the Ant 30 locus. This gene has not earlier been described in barley. The data presented suggest a defective chalcone isomerase gene for the observed flavonoid pattern in leaves of ant 30 mutants. (author)

  20. Comparative study of Chalcone synthase promoters across plant families

    Directory of Open Access Journals (Sweden)

    Francisco Buitrago

    2009-10-01

    Full Text Available Estudio comparativo de promotores de la Chalcón Sintasa en diferentes familias de plantas In the post – genomic era the understanding of gene regulation has become a challenge and a research priority. In this research, we performed a comparative study of the regulator sequences of the chalcone synthase gene across plant families. Twenty-two sequences of chalcone synthase promoters were compared considering three regulator Cis elements: G-Box, H-Box and TATA Box. Our results show that these Cis elements are conserved among species and even at the family level. However, in some species all of the Cis elements were not found, showing that the expression and regulation of these promoters via the Cis elements can be variable. Additionally, a comparison between promoters from a species with a chalcone synthase multigene family showed that the duplicate genes are variable in the composition of the Cis elements, suggesting that these genes could be expressing in different ways. Key Words: Promoter; Chalcone synthase; Cis elements; Floral expression. Resumen En la era post-genómica, el entendimiento de la regulación génica se ha convertido en un reto y una prioridad de investigación. En este trabajo realizamos un estudio comparativo de las secuencias reguladoras del gen de la chalcón sintetasa de varias familias botánicas. Veintidós secuencias de promotores de Chalcone Synthase fueron comparados teniendo en cuenta tres elementos Cis reguladores: Caja-G, Caja-H y Caja-TATA, que podrían estar actuando como una sola unidad cooperativa. Nuestra comparación muestra que estos elementos puede que se conserven en algunas especies e inclusive que se conserven a nivel de familia. Sin embargo, en algunas especies no todos los elementos Cis fueron encontrados, mostrando que no todas las especies se regulan bajo los mismos parámetros. Adicionalmente, una comparación entre promotores de una misma especie con una familia de multigenes Chs, mostró que los

  1. Solvent-dependent regioselective oxidation of trans-chalcones using aqueous hydrogen peroxide

    Energy Technology Data Exchange (ETDEWEB)

    Peng, Wang; Jiabin, Yang; Lushen, Li, E-mail: jimin@seu.edu.cn [Southeast University, Nanjing (China). School of Biological Science and Medical Engineering; Jin, Cai; Chunlong, Sun; Min, Ji [Southeast University, Nanjing (China). School of Chemistry and Chemical Engineering

    2013-03-15

    A novel method for regioselective oxidation of trans-chalcones with hydrogen peroxide in acetonitrile to afford cinnamic acids is reported. Only trans-b-arylacrylic acids were observed. A wide range of functionalized products can be effectively produced from various chalcones in good to excellent yields. (author)

  2. Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents

    Directory of Open Access Journals (Sweden)

    Bahram letafat

    2013-11-01

    We described synthesis and cytotoxic activity of poly-functionalized 3-benzylidenechroman-4-ones as new chalcone-like agents. These compounds can be considered as conformationally constrained congeners of chalcones to tolerate the poly-functionalization on the core structures for further optimization.

  3. Synthesis of Chiral Chalcone Derivatives Catalyzed by the Chiral Cinchona Alkaloid Squaramide

    Directory of Open Access Journals (Sweden)

    Dandan Xie

    2014-11-01

    Full Text Available An effective method has been developed for the preparation of novel chiral chalcone derivatives under mild conditions from the easily accessible starting materials nitromethane and chalcone derivatives 2. The corresponding products were obtained in moderate yields with excellent enantioselectivities (up to 99%.

  4. SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY OF SOME NOVEL ARYL AND HETROARYL CHALCONE ANALOGUES

    Directory of Open Access Journals (Sweden)

    Tribhuvan Singh

    2012-07-01

    Full Text Available A new series of Heterocyclic chalcones showed diversified biological activities. In view of potential biological activities of Heterocyclic chalcones derivative were prepared by claisen-Schmidt condensation technique. The compound were screened for anti-inflammatory and antibacterial activity.

  5. SYNTHESIS AND GREEN BROMINATION OF SOME CHALCONES AND THEIR ANTIMICROBIAL SCREENING

    OpenAIRE

    Mayur R. Adokar

    2013-01-01

    Chalcones are the versatile molecules having the structural flexibility which permits structural transformations into flavonoids, flavanones, pyrazoles, oxazoles, pyrimidines etc. Changes in their structure have offered the development of new medicinal agents having improved pharmacological potency. Their derivatives have attracts increasing attention due to numerous pharmacological potential. In the present communication we report the synthesis of chalcones from various acetophenone derivat...

  6. SYNTHESIS AND IR, NMR CARACTERISATION OF NEW P-(N,N-DIPHENYLAMINO) CHALCONES

    OpenAIRE

    Sîrbu Dumitru; Marin Ion

    2011-01-01

    This article reports on the high yield synthesis and novel chalcones with isothiocyanate and imidazol groups. The synthesis was started from N,N-diphenilamine and finished with 4-(N,N-diphenylamino)-4’-(2-thioxo-imidazolidin-4-one)-chalcone, where the cheap and accessible reagents were used.

  7. Synthesis of Chiral Chalcone Derivatives Catalyzed by the Chiral Cinchona Alkaloid Squaramide

    OpenAIRE

    Dandan Xie; Ying Xie; Yan Ding; Jian Wu; Deyu Hu

    2014-01-01

    An effective method has been developed for the preparation of novel chiral chalcone derivatives under mild conditions from the easily accessible starting materials nitromethane and chalcone derivatives 2. The corresponding products were obtained in moderate yields with excellent enantioselectivities (up to 99%).

  8. Discovery and structure activity relationships of 2-pyrazolines derived from chalcones from a pest management perspective

    Science.gov (United States)

    Synthesis of chalcones and 2-pyrazoline derivatives has been an active field of research due to the established pharmacological effects of these compounds. In this study, a series of chalcone (1a-i), 2-pyrazoline-1-carbothioamides (2a-i) and 2-pyrazoline-1-carboxamide derivatives (3a-g) were synthes...

  9. Green synthesis of chalcones derivatives as intermediate of flavones and their antibacterial activities

    Science.gov (United States)

    VH, Elfi Susanti; Matsjeh, Sabirin; Wahyuningsih, Tutik Dwi; Mustofa, Redjeki, Tri

    2016-02-01

    Four chalcones derivatives have been synthesized from 3,4-dimethoxybenzaldehyde and acetophenone derivatives (2-hydroxy acetophenone, 2,4-dihydroxy acetophenone, 2,5-dihydroxy acetophenone and 2,6-dihydroxy acetophenone). The synthesis of these chalcones were conducted by Claisen-Schmidt condensation using grinding techniques at room temperature in the absence of solvents. The chalcones were prepared by grinding together equivalent amount of the approriate hydroxyacetophenone and 3,4-dimethoxybenzaldehyde in the presence of solid sodium hydroxide. Grinding techniques for synthesis of the chalcones derivatives is simple, efficient and environmentally benign compared to conventional methods. Then, the four chalcones derivatives undergo cyclization reactions to produce four flavones after reacted with iodine. The synthesized compounds were characterized by spectrometry (IR, 1H-NMR, 13C-NMR and MS).

  10. Green synthesis of chalcones derivatives as intermediate of flavones and their antibacterial activities

    International Nuclear Information System (INIS)

    Four chalcones derivatives have been synthesized from 3,4-dimethoxybenzaldehyde and acetophenone derivatives (2-hydroxy acetophenone, 2,4-dihydroxy acetophenone, 2,5-dihydroxy acetophenone and 2,6-dihydroxy acetophenone). The synthesis of these chalcones were conducted by Claisen-Schmidt condensation using grinding techniques at room temperature in the absence of solvents. The chalcones were prepared by grinding together equivalent amount of the approriate hydroxyacetophenone and 3,4-dimethoxybenzaldehyde in the presence of solid sodium hydroxide. Grinding techniques for synthesis of the chalcones derivatives is simple, efficient and environmentally benign compared to conventional methods. Then, the four chalcones derivatives undergo cyclization reactions to produce four flavones after reacted with iodine. The synthesized compounds were characterized by spectrometry (IR, 1H-NMR, 13C-NMR and MS)

  11. Green synthesis of chalcones derivatives as intermediate of flavones and their antibacterial activities

    Energy Technology Data Exchange (ETDEWEB)

    VH, Elfi Susanti, E-mail: elsantivh@yahoo.com; Redjeki, Tri, E-mail: tri-redjeki@yahoo.com [Universitas Sebelas Maret, Ir Sutami 36A Surakarta Indonesia, 57126 (Indonesia); Matsjeh, Sabirin, E-mail: sabirin-mara@yahoo.com; Wahyuningsih, Tutik Dwi, E-mail: mustofajogya@yahoo.co.id [Department of Chemistry FMJPA Universitas Gadjah Mada, Jl Sekip Utara, Yogyakarta Indonesia 55281 (Indonesia); Mustofa, E-mail: tutikdw@hotmail.com [Faculty of Medicine, Universitas Gadjah Mada, Yogyakarta Jl. Sekip Utara Yogyakarta Indonesia, 55281 (Indonesia)

    2016-02-08

    Four chalcones derivatives have been synthesized from 3,4-dimethoxybenzaldehyde and acetophenone derivatives (2-hydroxy acetophenone, 2,4-dihydroxy acetophenone, 2,5-dihydroxy acetophenone and 2,6-dihydroxy acetophenone). The synthesis of these chalcones were conducted by Claisen-Schmidt condensation using grinding techniques at room temperature in the absence of solvents. The chalcones were prepared by grinding together equivalent amount of the approriate hydroxyacetophenone and 3,4-dimethoxybenzaldehyde in the presence of solid sodium hydroxide. Grinding techniques for synthesis of the chalcones derivatives is simple, efficient and environmentally benign compared to conventional methods. Then, the four chalcones derivatives undergo cyclization reactions to produce four flavones after reacted with iodine. The synthesized compounds were characterized by spectrometry (IR, {sup 1}H-NMR, {sup 13}C-NMR and MS)

  12. Synthesis and Phase Transition Behaviours of New Chalcone Derivatives

    OpenAIRE

    S. T. Ha; Low, Y. W.

    2013-01-01

    A series of new chalcone derivatives with a general formula of C11H27COOC6H4COCH=CHC6H4X where X=F, Cl, Br, and NO2 were well synthesized and crystallized from organic solution. The physical properties as well as the chemical formulations of these compounds were determined by spectroscopic techniques (FTIR, and 1H and 13C NMR). Differential scanning calorimetry (DSC) and polarizing optical microscopy (POM) techniques were employed to study their transition temperatures and mesophase character...

  13. The Preparation of Some Novel Indazole Derivatives by Using Chalcones

    Institute of Scientific and Technical Information of China (English)

    Javad Safaei-Ghomi; Zohreh Alishahi

    2005-01-01

    @@ 1Introduction Indazole and its derivatives have little biological significance and have not been found in natural products due to the difficulty for living organisms to construct an N - N bond. Indazole derivatives exhibit variety of pharmacological properties such as anti-inflammatory, antidepressant, antitumor, antiarthritic and analgesic activities[1]. Different synthetic pathways generate these compounds. For instance, ring closure of pyrazole moiety, addition of hydrazine derivatives to carbonyl compounds[2] and cycloaddition reaction[3]. Herein, we report the synthesis of some new indazole derivatives by using chalcones as starting materials.

  14. Synthesis and bioevaluation of substituted chalcones, coumaranones and other flavonoids as anti-HIV agents.

    Science.gov (United States)

    Cole, Amy L; Hossain, Sandra; Cole, Alex M; Phanstiel, Otto

    2016-06-15

    A series of chalcone, flavone, coumaranone and other flavonoid compounds were screened for their anti HIV-1 activity in two cell culture models using TZM-bl and PM1 cells. Within the systems evaluated, the most promising compounds contained either an α- or β-hydroxy-carbonyl motif within their structure (e.g., 8 and 9). Efficacious substituents were identified and used to design new HIV inhibitors with increased potency and lower cytotoxicity. Of the scaffolds evaluated, specific chalcones were found to provide the best balance between anti-HIV potency and low host cell toxicity. Chalcone 8l was shown to inhibit different clinical isolates of HIV in a dose-dependent manner (e.g., IC50 typically⩽5μM). Inhibition of HIV infection experiments using TZM-bl cells demonstrated that chalcone 8l and flavonol 9c had IC50 values of 4.7μM and 10.4μM, respectively. These insights were used to design new chalcones 8o and 8p. Rewardingly, chalcones 8o and 8p (at 10μM) each gave >92% inhibition of viral propagation without impacting PM1 host cell viability. Inhibition of viral propagation significantly increased (60-90%) when PM1 cells were pre-incubated with chalcone 8o, but not with the related flavonol 9c. These results suggested that chalcone 8o may be of value as both a HIV prophylactic and therapy. In summary, O-benzyl-substituted chalcones were identified as promising anti-HIV agents for future investigation. PMID:27161874

  15. Stability of photochromism in new bifunctional copolymers containing spiropyran and chalcone moiety in the side chain

    Energy Technology Data Exchange (ETDEWEB)

    Choi, Dong Hoon; Ban, Si Young; Kim, Jae Hong [Kyunghee Univ., Suwon (Korea, Republic of)

    2003-04-01

    We synthesized three copolymers bearing photochromic spiropyran dye and chalcone moiety in the side chain for studying the dynamic properties of their photochromism. They contain methacrylate-spiropyran (MA-spiropyran) and methacrylate-chalcone) (MA-chalcone) with the different concentration. The photosensitivity of the newly synthesized copolymers was investigated by using UV-Vis absorption spectroscopy. We absorbed photodimerization and phtochromic behavior under UV irradiation at the same time. The effect of photocrosslink on the rate and stability of photochromism in three copolymers was considered in this study. This study might be helpful to design photochromic materials for irreversible optical memory by virtue of photocrosslinking reaction.

  16. Stability of photochromism in new bifunctional copolymers containing spiropyran and chalcone moiety in the side chain

    International Nuclear Information System (INIS)

    We synthesized three copolymers bearing photochromic spiropyran dye and chalcone moiety in the side chain for studying the dynamic properties of their photochromism. They contain methacrylate-spiropyran (MA-spiropyran) and methacrylate-chalcone) (MA-chalcone) with the different concentration. The photosensitivity of the newly synthesized copolymers was investigated by using UV-Vis absorption spectroscopy. We absorbed photodimerization and phtochromic behavior under UV irradiation at the same time. The effect of photocrosslink on the rate and stability of photochromism in three copolymers was considered in this study. This study might be helpful to design photochromic materials for irreversible optical memory by virtue of photocrosslinking reaction

  17. Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth

    OpenAIRE

    Mizuno, Cassia S.; Paul, Shiby; Suh, Nanjoo; Rimando, Agnes M.

    2010-01-01

    Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-t...

  18. Synthesis of Urea based Chalcone Derivatives and Evaluate its Biological Activity

    Directory of Open Access Journals (Sweden)

    Arpita Desai

    2016-05-01

    Full Text Available Chalcones have been the center of attraction for researchers from several decades due to nits innumerous therapeutic application, Efforts have been done in my research to synthesized chalcones and their derivatives that further reacts with various substituted aldehyde to give corresponding substituted chalcone derivatives. Now these derivatives on condensation with Guanidine nitrate gives the vast range of phenyl pyrimidine amine Derivatives. Structure elucidation of synthesized compound had been made on the basis of element analysis, 1H NMR Spectra studies. The microbial activity of the synthesized compounds has been studied against the species bacillus subtillis, staphylococcus aureus, Escherichia coli, and salmonella typhi.

  19. Chalcones from Chinese liquorice inhibit proliferation of T cells and production of cytokines

    DEFF Research Database (Denmark)

    Barfod, Lea; Kemp, Kåre; Hansen, Majbritt;

    2002-01-01

    Licochalcone A (LicA), an oxygenated chalcone, has been shown to inhibit the growth of both parasites and bacteria. In this study, we investigated the effect of LicA and four synthetic analogues on the activity of human peripheral blood mononuclear cell proliferation and cytokine production. Four...... out of five chalcones tested inhibited the proliferation of lymphocytes measured by thymidine incorporation and by flow cytometry. The production of pro- and anti-inflammatory cytokines from monocytes and T cells was also inhibited by four of five chalcones. Furthermore, intracellular detection of...

  20. Molecular modeling based synthesis and evaluation of in vitro anticancer activity of indolyl chalcones.

    Science.gov (United States)

    Gaur, Rashmi; Yadav, Dharmendra K; Kumar, Shiv; Darokar, Mahendra P; Khan, Feroz; Bhakuni, Rajendra Singh

    2015-01-01

    A series of twenty one chalcone derivatives having indole moiety were synthesized and were evaluated against four human cancer cell lines. Indolyl chalcones 1a, 1b, 1d, 1f-1j, 2c, 2e, 2i showed good anticancer activity. Chalcones 1b and 1d were the most active and selective anticancer agents with IC50 values <1μg/ml and 1.51μg/ml, against WRL-68 cell line, respectively. Molecular mechanism was explored through in silico docking & ADMET studies. PMID:25860176

  1. SYNTHESIS AND GREEN BROMINATION OF SOME CHALCONES AND THEIR ANTIMICROBIAL SCREENING

    Directory of Open Access Journals (Sweden)

    Mayur R. Adokar

    2013-04-01

    Full Text Available Chalcones are the versatile molecules having the structural flexibility which permits structural transformations into flavonoids, flavanones, pyrazoles, oxazoles, pyrimidines etc. Changes in their structure have offered the development of new medicinal agents having improved pharmacological potency. Their derivatives have attracts increasing attention due to numerous pharmacological potential. In the present communication we report the synthesis of chalcones from various acetophenone derivatives with different aromatic aldehydes and green chemistry approach to their bromination with the help of Tetrabutylammonium Tribromide (TBATB. All the synthesized chalcone dibromides were screened for their antimicrobial activity against Aspergillus flavus, Rhizopus sp., Fusarium solani and Aspergillus niger.

  2. Development of fluorescent FeIII sensor based on chalcone

    Energy Technology Data Exchange (ETDEWEB)

    Wei Yanli, E-mail: weiyanli@sxu.edu.cn [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China); Qin Guojie [Institute of Horticulture, Shanxi Academy of Agriculture Science, Taiyuan 030031 (China); Wang Wenyan; Bian Wei; Shuang Shaomin [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China); Dong Chuan, E-mail: dc@sxu.edu.cn [Research Center of Environmental Science and Engineering, Shanxi University, Taiyuan 030006 (China)

    2011-08-15

    In this paper, 4-dimethylamino 2,5-dihydroxy chalcone (DMADHC), which exhibits excited state intramolecular charge transfer (ICT) characteristics, was synthesized and characterized. A sensitive optochemical sensor for Fe{sup 3+} ion was developed using DMADHC as fluorescence receptor. The fluorescence of DMADHC was gradually quenched with the addition of Fe{sup 3+} ion, which attributed to the formation of 1:1 complex between DMADHC and Fe{sup 3+} ion. The sensor exhibited excellent selectivity for Fe{sup 3+} ion over a large number of cation ions such as alkali, alkaline earth and transitional metal ions with a linear range of 3.984x10{sup -7}-1.135x10{sup -5} and a limit of detection of 8.223x10{sup -8} mol/L. On this basis, the sensor was preliminary applied to the determination of the content of iron ions in multi-vitamin tablet with satisfied results and the recoveries were in the 95-100% interval, and precision (n=5) was better than 5%. - Highlights: > A fluorescence receptor, 4-dimethylamino 2,5-dihydroxy chalcone was synthesis by one-step reaction. > Its intramolecular charge transfer fluorescence characteristics could be blocked by Fe{sup 3+} ion. > Based on this, an optochemical sensor for Fe{sup 3+} ion was developed. > Importantly, our proposed method is particularly useful for determination of Fe{sup 3+} ion in real sample.

  3. Synthesis and anticonvulsant activity of certain chalcone based pyrazoline compounds

    Directory of Open Access Journals (Sweden)

    Sudhakara Rao Gerapati

    2015-09-01

    Full Text Available Convulsions are involuntary, violent, spasmodic and prolonged contractions of skeletal muscles. That means a patient may have epilepsy without convulsions and vice versa. Epilepsy is a common neurological abnormality affecting about 1% of the world population. The primary objectives of these synthesized compounds are to suppress seizures and provide neuroprotection by minimizing the effects from seizure attacks. Here some of the chalcones and chalcone based various pyrazolines were evaluated for anticonvulsant activity. Their structures have been elucidated on the basis of elemental analyses and spectroscopic studies (IR, 1H-NMR & Mass spectroscopy. A preliminary evaluation of the prepared compounds has indicated that some of them exhibit moderate to significant anticonvulsant activity compared to a diazepam standard1-3.  All compounds were tested for their anticonvulsant activity using maximal electroshock induced convulsions (MES in mice at a dose level of 4 mg/kg.b.w. The compounds  Ph1, Ph2 , Py2 ,Py3 and Py4 have shown  to  good anticonvulsant activity when doses are administered as 25mg/ kg.b.w  , reduced the phases of seizures severity and  found to be active and also  increased survival rate. Remaining compounds are less efficacious.

  4. Combinatorial synthesis and antibacterial evaluation of an indexed chalcone library.

    Science.gov (United States)

    Ansari, Farzana Latif; Nazir, Samina; Noureen, Humaira; Mirza, Bushra

    2005-12-01

    A 120-membered chalcone library has been designed and prepared from six differently substituted acetophenones (A1-A6) and 20 benzaldehydes (B1-B20). The library was subjected to biological studies targeted against six bacterial strains. For the identification of the most-active member(s) of the library, the so-called indexed or positional-scanning method was applied. Six out of 26 sub-libraries, i.e., AL1-AL6, were synthesized by keeping the acetophenone moiety A fixed and using equimolar quantities of the 20 different benzaldehydes. The remaining 20 sub-libraries BL1-BL20 were prepared by keeping the benzaldehyde B component fixed and varying the six acetophenones (Table 1). The bactericidal activities of the resulting sub-libraries were tested and used as indices to the rows or columns of a two-dimensional matrix. Finally, parallel synthesis of 24 specific members with the highest-expected antibacterial activities, present in two sub-libraries, was carried out. These chalcones were screened again, and the results were exploited for establishing the structure-activity relationship (SAR) and the identification of the lead compound, which turned out to be 1,3-bis(2-hydroxyphenyl)prop-2-en-1-one (A2B2) in terms of activity towards Staphylococcus aureus and Bacillus subtilis (Tables 5-7). PMID:17191962

  5. Synthesis, crystal growth and studies on non-linear optical property of new chalcones

    Science.gov (United States)

    Sarojini, B. K.; Narayana, B.; Ashalatha, B. V.; Indira, J.; Lobo, K. G.

    2006-09-01

    The synthesis, crystal growth and non-linear optical (NLO) property of new chalcone derivatives are reported. 4-Propyloxy and 4-butoxy benzaldehydes were made to under go Claisen-Schmidt condensation with 4-methoxy, 4-nitro and 4-phenoxy acetophenones to form corresponding chalcones. The newly synthesized compounds were characterized by analytical and spectral data. The Second harmonic generation (SHG) efficiency of these compounds was measured by powder technique using Nd:YAG laser. Among tested compounds three chalcones showed NLO property. The chalcone 1-(4-methoxyphenyl)-3-(4-propyloxy phenyl)-2-propen-1-one exhibited SHG conversion efficiency 2.7 times that of urea. The bulk crystal of 1-(4-methoxyphenyl)-3-(4-butoxyphenyl)-2-propen-1-one (crystal size 65×28×15 mm 3) was grown by slow-evaporation technique from acetone. Microhardness of the crystal was tested by Vicker's microhardness method.

  6. Catalytic Hydrogenation Reaction of Naringin-Chalcone. Study of the Electrochemical Reaction

    Directory of Open Access Journals (Sweden)

    B. A. López de Mishima

    2000-03-01

    Full Text Available The electrocatalytic hydrogenation reaction of naringin derivated chalcone is studied. The reaction is carried out with different catalysts in order to compare with the classic catalytic hydrogenation.

  7. Evolution of the Chalcone Isomerase Fold from Fatty Acid-Binding to Stereospecific Enzyme

    OpenAIRE

    Ngaki, Micheline N.; Louie, Gordon V.; Philippe, Ryan N.; Manning, Gerard; Pojer, Florence; Bowman, Marianne E.; Li, Ling; Larsen, Elise; Wurtele, Eve Syrkin; Noel, Joseph P.

    2012-01-01

    Specialized metabolic enzymes biosynthesize chemicals of ecological importance, often sharing a pedigree with primary metabolic enzymes 1 . However, the lineage of the enzyme chalcone isomerase (CHI) remained a quandary. In vascular plants, CHI-catalyzed conversion of chalcones to chiral (S)-flavanones is a committed step in the production of plant flavonoids, compounds that contribute to attraction, defense 2 , and development 3 . CHI operates near the diffusion limit with stereospecific con...

  8. Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

    Energy Technology Data Exchange (ETDEWEB)

    Silva, Wender A.; Andrade, Carlos Kleber Z.; Napolitano, Hamilton B., E-mail: wender@unb.br, E-mail: ckleber@unb.br [Universidade de Brasilia (LaQMOS/UnB), DF (Brazil). Inst. de Quimica; Vencato, Ivo; Castro, Miriam R.C. de; Camargo, Ademir J. [Universidade Estadual de Goias (UEG), Anapolis, GO (Brazil). Ciencias Exatas e Tecnologicas; Lariucci, Carlito [Universidade Estadual de Goias (UEG), Goiania, GO (Brazil). Inst. de Fisica

    2013-01-15

    The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structure activity relationship. (author)

  9. New indolizine-chalcones as potent inhibitors of human farnesyltransferase: Design, synthesis and biological evaluation.

    Science.gov (United States)

    Moise, Iuliana-Monica; Ghinet, Alina; Belei, Dalila; Dubois, Joëlle; Farce, Amaury; Bîcu, Elena

    2016-08-01

    A new family of indolizine-chalcones was designed, synthesized and screened for the inhibitory potential on human farnesyltransferase in vitro to identify potent antitumor agents. The most active compound was phenothiazine 2a, exhibiting an IC50 value in the low nanomolar range, similar to that of known FTI-276, highly potent farnesyltransferase inhibitor. The newly synthesized indolizine-chalcones 2a-d constitute the most efficient inhibitors of farnesyltransferase bearing a phenothiazine unit known to date. PMID:27282741

  10. Synthesis, in vitro antimalarial activity and cytotoxicity of novel 4-aminoquinolinyl-chalcone amides

    OpenAIRE

    Smit, Frans J; N'Da, David D.

    2014-01-01

    A series of 4-aminoquinolinyl-chalcone amides 11–19 were synthesized through condensation of carboxylic acid-functionalized chalcone with aminoquinolines, using 1,10-carbonyldiimidazole as coupling agent. These compounds were screened against the chloroquine sensitive (3D7) and chloroquine resistant (W2) strains of Plasmodium falciparum. Their cytotoxicity towards the WI-38 cell line of normal human fetal lung fibroblast was determined. All compounds were found active, with IC50 v...

  11. Enzymatic Properties and Mutational Studies of Chalcone Synthase from Physcomitrella patens

    OpenAIRE

    Mahiran Basri; Raja Noor Zaliha Raja Abdul Rahman; Abu Bakar Salleh; Iffah Izzati Zakaria

    2012-01-01

    PpCHS is a member of the type III polyketide synthase family and catalyses the synthesis of the flavonoid precursor naringenin chalcone from p-coumaroyl-CoA. Recent research reports the production of pyrone derivatives using either hexanoyl-CoA or butyryl-CoA as starter molecule. The Cys-His-Asn catalytic triad found in other plant chalcone synthase predicted polypeptides is conserved in PpCHS. Site directed mutagenesis involving ...

  12. Synthesis and Antibacterial Activity of Some Heterocyclic Chalcone Analogues Alone and in Combination with Antibiotics

    OpenAIRE

    Tuong-Ha Do; Thi-Ngoc-Phuong Huynh; Khac-Minh Thai; Cat-Dong Tran; Thanh-Dao Tran; Thi-Thao-Nhu Nguyen

    2012-01-01

    A series of simple heterocyclic chalcone analogues have been synthesized by Claisen Schmidt condensation reactions between substituted benzaldehydes and heteroaryl methyl ketones and evaluated for their antibacterial activity. The structures of the synthesized chalcones were established by IR and 1H-NMR analysis. The biological data shows that compounds p5, f6 and <...

  13. Synthesis and In Vitro Cytotoxic Activity of Novel Chalcone-Like Agents

    OpenAIRE

    Bahram letafat; Raheleh Shakeri; Saeed Emami; Saeedeh Noushini; Negar Mohammadhosseini; Nayyereh Shirkavand; Sussan Kabudanian Ardestani; Maliheh Safavi; Marjaneh Samadizadeh; Aida Letafat; Abbas Shafiee; Alireza Foroumadi

    2013-01-01

      Objective(s): Chalcones and their rigid analogues represent an important class of small molecules having anticancer activities. Therefore, in this study the synthesis and cytotoxic activity of new 3-benzylidenchroman-4-ones were described as rigid chalcone analogues.   Materials and Methods: The reaction of resorcinol with 3-chloropropionic acid in the presence of CF3SO3H was afforded corresponding propiophenone. It was cyclized using 2M NaOH to give 7-hydroxy-4-chroman...

  14. Biochemical complementation of chalcone synthase mutants defines a role for flavonols in functional pollen.

    OpenAIRE

    Mo, Y; Nagel, C.; Taylor, L P

    1992-01-01

    Chalcone synthase catalyzes the initial step of that branch of the phenylpropanoid pathway that leads to flavonoids. A lack of chalcone synthase activity has a pleiotropic effect in maize and petunia mutants: pollen fertility as well as flavonoid synthesis is disrupted. Both maize and petunia mutants are self-sterile due to a failure to produce a functional pollen tube. The finding that the mutant pollen is partially functional on wild-type stigmas led to the isolation and identification of k...

  15. Biochemical, immunological, and immunocytochemical evidence for the association of chalcone synthase with endoplasmic reticulum membranes.

    OpenAIRE

    Hrazdina, G; Zobel, A M; Hoch, H. C.

    1987-01-01

    Chalcone synthase [naringenin-chalcone synthase; malonyl-CoA:4-coumaroyl-CoA malonyltransferase (cyclizing), E.C. 2.3.1.74], the key enzyme of flavonoid pathways that was believed to be soluble, has been localized on ribosome-bearing endoplasmic reticulum membranes in the epidermis of buckwheat (Fagopyrum esculentum M.) hypocotyls. Enzyme activity measurement and immunoblots of buckwheat hypocotyl homogenates that were fractionated on linear sucrose density gradients and developed with a spec...

  16. Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

    International Nuclear Information System (INIS)

    The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structure activity relationship. (author)

  17. Chalcone-Induced Apoptosis through Caspase-Dependent Intrinsic Pathways in Human Hepatocellular Carcinoma Cells

    Science.gov (United States)

    Ramirez-Tagle, Rodrigo; Escobar, Carlos A.; Romero, Valentina; Montorfano, Ignacio; Armisén, Ricardo; Borgna, Vincenzo; Jeldes, Emanuel; Pizarro, Luis; Simon, Felipe; Echeverria, Cesar

    2016-01-01

    Hepatocellular carcinoma (HCC) is one of the most commonly diagnosed cancers worldwide. Chemoprevention of HCC can be achieved through the use of natural or synthetic compounds that reverse, suppress or prevent the development of cancer progression. In this study, we investigated the antiproliferative effects and the mechanism of action of two compounds, 2,3,4′-trimethoxy-2′-hydroxy-chalcone (CH1) and 3′-bromo-3,4-dimethoxy-chalcone (CH2), over human hepatoma cells (HepG2 and Huh-7) and cultured mouse hepatocytes (HepM). Cytotoxic effects were observed over the HepG2 and Huh-7, and no effects were observed over the HepM. For HepG2 cells, treated separately with each chalcone, typical apoptotic laddering and nuclear condensation were observed. Additionally, the caspases and Bcl-2 family proteins activation by using Western blotting and immunocytochemistry were studied. Caspase-8 was not activated, but caspase-3 and -9 were both activated by chalcones in HepG2 cells. Chalcones also induced reactive oxygen species (ROS) accumulation after 4, 8 and 24 h of treatment in HepG2 cells. These results suggest that apoptosis in HepG2 was induced through: (i) a caspase-dependent intrinsic pathway; and (ii) by alterations in the cellular levels of Bcl-2 family proteins, and also, that the chalcone moiety could be a potent candidate as novel anticancer agents acting on human hepatomas. PMID:26907262

  18. Solvent-free Michael addition reaction of fluorene with chalcon

    Institute of Scientific and Technical Information of China (English)

    Fu Feng

    2011-01-01

    A series of novel Michael addition products of fluorene to chalcone were obtained in the presence of sodium hydroxide under solvent-free condition. The advantages of this procedure were mild reaction conditions, simple protocol, and high yields. The structures of the products were characterized by IR, 1H NMR, MS and X-ray diffraction. The crystal of the new compound 3 h is y= 64.2440(10)°, V = 2.4137(3) nm3, Z= 4, Dc=1.220 g/cm3, μ = 0.286 mm-1, F(000) = 920, R = 0.0656 and wR = 0.1554 for 5664 observed reflection with I > 2σ(I).

  19. Second harmonic chalcone crystal: Synthesis, growth and characterization

    Energy Technology Data Exchange (ETDEWEB)

    D' Silva, E.D., E-mail: deepak.dsilva@gmail.co [Department of studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199 (India); Narayan Rao, D. [School of Physics, University of Hyderabad, Hyderabad 500046 (India); Philip, Reji [Light and Matter Physics Group, Raman Research Institute, Bangalore 560080 (India); Butcher, Ray J. [Department of Chemistry, Howard University, Washington, DC 20059 (United States); Rajnikant [Department of Physics and Electronics, University of Jammu, Jammu Tawi 180006 (India); Dharmaprakash, S.M. [Department of studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574199 (India)

    2011-05-15

    The novel nonlinear optical chalcone derivative (2E)-3-[4-(methylsulfanyl)phenyl]-1-(3-bromophenyl)prop-2-en-1-one (3Br4MSP) crystals have been grown by slow evaporation technique at ambient temperature. The crystal was subjected to different types of characterization method in order to study its possible application in nonlinear optics. The structure determination of the grown crystal was done by single crystal X-ray diffraction study. The morphology of the crystal is studied. The crystal was subjected to thermal analysis to find its thermal stability. The grown crystals were characterized for their optical transmission and mechanical hardness. The second harmonic generation (SHG) efficiency of the crystal is obtained by classical powdered technique. The laser damage threshold for 3Br4MSP crystal was determined using Q-switched Nd:YAG laser.

  20. Second harmonic chalcone crystal: Synthesis, growth and characterization

    Science.gov (United States)

    D'silva, E. D.; Narayan Rao, D.; Philip, Reji; Butcher, Ray J.; Rajnikant; Dharmaprakash, S. M.

    2011-05-01

    The novel nonlinear optical chalcone derivative (2 E)-3-[4-(methylsulfanyl)phenyl]-1-(3-bromophenyl)prop-2-en-1-one (3Br4MSP) crystals have been grown by slow evaporation technique at ambient temperature. The crystal was subjected to different types of characterization method in order to study its possible application in nonlinear optics. The structure determination of the grown crystal was done by single crystal X-ray diffraction study. The morphology of the crystal is studied. The crystal was subjected to thermal analysis to find its thermal stability. The grown crystals were characterized for their optical transmission and mechanical hardness. The second harmonic generation (SHG) efficiency of the crystal is obtained by classical powdered technique. The laser damage threshold for 3Br4MSP crystal was determined using Q-switched Nd:YAG laser.

  1. Cationic chalcone antibiotics. Design, synthesis, and mechanism of action.

    Science.gov (United States)

    Nielsen, Simon F; Larsen, Mogens; Boesen, Thomas; Schønning, Kristian; Kromann, Hasse

    2005-04-01

    This paper describes how the introduction of "cationic" aliphatic amino groups in the chalcone scaffold results in potent antibacterial compounds. It is shown that the most favorable position for the aliphatic amino group is the 2-position of the B-ring, in particular in combination with a lipophilic substituent in the 5-position of the B-ring. We demonstrate that the compounds act by unselective disruption of cell membranes. Introduction of an additional aliphatic amino group in the A-ring results in compounds that are selective for bacterial membranes combined with a high antibacterial activity against both Gram-positive and -negative pathogens. The most potent compound in this study (78) has an MIC value of 2 muM against methicillin resistant Staphylococus aureus. PMID:15801857

  2. In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

    KAUST Repository

    Zenger, Katharina

    2015-07-19

    Xanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurally-related chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones.

  3. In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

    International Nuclear Information System (INIS)

    Xanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurally-related chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones

  4. Synthesis, growth, structure determination and optical properties of chalcone derivative single crystal

    Science.gov (United States)

    Karthi, S.; Girija, E. K.

    2014-04-01

    Acquiring large nonlinear optical (NLO) efficient organic material is essential for the development of optoelectronics and photonic devices. Chalcone is the donor - Π - acceptor - Π - donor (D-Π-A-Π-D) type conjugated molecule with appreciable hyperpolarizability of potential interest in NLO applications. The addition of vinyl and electron donor groups in the chalcone molecule may enhance the second harmonic generation (SHG) efficiency. Here we report the synthesis, crystal growth and characterization of a chalcone derivative 1-(4-methylphenyl)-5-(4-methoxyphenyl)-penta-2,4-dien-1-one (MPMPP). The MPMPP crystal was grown by slow evaporation solution growth technique from acetone. The grown crystal structure was studied by single crystal X-ray diffraction. The SHG efficiency of the grown crystal was determined by Kurtz and Perry method.

  5. Synthesis, growth, structure determination and optical properties of chalcone derivative single crystal

    Energy Technology Data Exchange (ETDEWEB)

    Karthi, S., E-mail: girijaeaswaradas@gmail.com; Girija, E. K., E-mail: girijaeaswaradas@gmail.com [Department of Physics, Periyar University, Salem - 636011 (India)

    2014-04-24

    Acquiring large nonlinear optical (NLO) efficient organic material is essential for the development of optoelectronics and photonic devices. Chalcone is the donor - Π - acceptor - Π - donor (D-Π-A-Π-D) type conjugated molecule with appreciable hyperpolarizability of potential interest in NLO applications. The addition of vinyl and electron donor groups in the chalcone molecule may enhance the second harmonic generation (SHG) efficiency. Here we report the synthesis, crystal growth and characterization of a chalcone derivative 1-(4-methylphenyl)-5-(4-methoxyphenyl)-penta-2,4-dien-1-one (MPMPP). The MPMPP crystal was grown by slow evaporation solution growth technique from acetone. The grown crystal structure was studied by single crystal X-ray diffraction. The SHG efficiency of the grown crystal was determined by Kurtz and Perry method.

  6. Synthesis and antibacterial and antifungal evaluation of some chalcone based sulfones and bisulfones.

    Science.gov (United States)

    Konduru, Naveen Kumar; Dey, Sunita; Sajid, Mohammad; Owais, Mohammad; Ahmed, Naseem

    2013-01-01

    Two series of chalcone based sulfone and bisulfone derivatives were synthesized using chalcone, thiophenol and sodium metal at room temperature, followed by oxidation of chalcone sulfides with m-CPBA at 0 °C in a novel method. Both sulfones and bisulfones were evaluated for their antimicrobial activities against Aspergillus niger and Candida albicans (yeast), Bacillus subtilis and Staphylococcus aureus (Gram (+) bacteria) and Pseudomonas aeruginosa and Salmonella typhimurium (Gram (-) bacteria) strains. Among them, compounds 2c, 3c, 6c, 7c, 8c and 9c have shown high antifungal activity against C. albicans compare to reference drugs viz. Amphotericin-B and Nystatin. Compound 1c has shown slightly better antibacterial activity against B. subtilis and compounds 5c, 6c and 7c have shown excellent antibacterial activity against S. typhimurium in compare to reference drugs Ampicillin and Kanamycin. PMID:23202847

  7. Antibacterial, antifungal and antimycobacterial activities of some pyrazoline, hydrazone and chalcone derivatives.

    Science.gov (United States)

    Evranos-Aksöz, Begüm; Onurdağ, Fatma Kaynak; Özgacar, Selda Özgen

    2015-07-01

    Twenty-seven previously reported chalcones and their pyrazoline and hydrazone derivatives as well as two further chalcones have been screened for their antimicrobial, antifungal and antimycobacterial activities against standard microbial strains and drug resistant isolates. The minimum inhibitory concentration (MIC) value of each compound was determined by a two-fold serial microdilution technique. The compounds were found to possess a broad spectrum of antimicrobial activities with MIC values of 8-128 μg/mL. One compound [(E)-1-(4-hydroxyphenyl)-3-p-tolylprop-2-en-1-one] had equal activity with gentamycin (8 μg/mL) against Enterococcus faecalis. Chalcones were found to be more active than their hydrazone and 2-pyrazoline derivatives against Staphylococcus aureus ATCC 29213 and E. faecalis ATCC 29212. PMID:26372110

  8. Inhibition of fumarate reductase in Leishmania major and L. donovani by chalcones

    DEFF Research Database (Denmark)

    Chen, M; Zhai, L; Christensen, S B;

    2001-01-01

    Our previous studies have shown that chalcones exhibit potent antileishmanial and antimalarial activities in vitro and in vivo. Preliminary studies showed that these compounds destroyed the ultrastructure of Leishmania parasite mitochondria and inhibited the respiration and the activity of mitoch......Our previous studies have shown that chalcones exhibit potent antileishmanial and antimalarial activities in vitro and in vivo. Preliminary studies showed that these compounds destroyed the ultrastructure of Leishmania parasite mitochondria and inhibited the respiration and the activity...... of mitochondrial dehydrogenases of Leishmania parasites. The present study was designed to further investigate the mechanism of action of chalcones, focusing on the parasite respiratory chain. The data show that licochalcone A inhibited the activity of fumarate reductase (FRD) in the permeabilized Leishmania major....... Since FRD exists in the Leishmania parasite and does not exist in mammalian cells, it could be an excellent target for antiprotozoal drugs....

  9. Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media

    Energy Technology Data Exchange (ETDEWEB)

    Marwani, Hadi M., E-mail: hmarwani@kau.edu.sa [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Asiri, Abdullah M. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Center of Excellence for Advanced Materials Research, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia); Khan, Salman A. [Department of Chemistry, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah 21589 (Saudi Arabia)

    2013-04-15

    The main focus of this study was to investigate spectroscopic properties, stoichiometric ratios, physicochemical parameters, polarity and photostability behaviors of newly synthesized chalcone dye in organized media. The chalcone dye, 1-(2,5-Dimethyl-thiophen-3-yl)-3-(9-etnyl-9H-carbazol-3-yl)-propenone (DTEP), was prepared by the reaction of carbazole aldehyde with 3-acetyl-2,5-dimethythiophene. Data obtained from FT-IR, {sup 1}H-–NMR, {sup 13}C-NMR and elemental analysis were consistent with chemical structure of newly prepared DTEP. Increases in fluorescence intensities of DTEP with cetyltrimethyl ammonium bromide (CTAB) were observed. In comparison of fluorescence intensities for DTEP with CTAB, reductions in fluorescence intensities for DTEP with sodium dodecyl sulfate (SDS) were noticed under the same experimental and instrumental conditions. Additionally, Benesi–Hildebrand method was applied to determine stoichiometric ratios and association constants of DTEP with CTAB and SDS. Stern–Volmer plot was used in order to further confirm the stoichiometric ratio and association constant of DTEP with SDS. Physicochemical parameters such as singlet absorption, molar absorptivity, oscillator strength, dipole moment and fluorescence quantum yield of DTEP were also determined. Fluorescence polarity study displayed that DTEP was sensitive to the polarity of the microenvironment provided by different solvents. Finally, fluorescence steady-state measurements revealed that DTEP has high photostability against photobleaching. -- Highlights: ► Mechanistic understanding of molecular structure of newly synthesized chalcone dye. ► Exploring spectral behaviors and physicochemical parameters of chalcone dye. ► Determination of stoichiometric ratios and association constants of chalcone dye. ► Determination of fluorescence quantum yield in different solvents. ► High photostability against photobleaching of chalcone dye was observed.

  10. Study on third-order nonlinear optical properties of 4-methylsulfanyl chalcone derivatives using picosecond pulses

    International Nuclear Information System (INIS)

    Graphical abstract: Photograph and schematic representation of Z-scan experimental setup used to investigate third order nonlinear properties of the chalcone materials. Highlights: ► Br and NO2 substituted chalcone derivatives were exposed to picosecond laser pulses. ► Third-order nonlinear optical (NLO) properties were investigated. ► Compounds show promising third-order and optical limiting properties. ► These materials found suitable for electrical and optical applications. -- Abstract: In this paper we present results from the experimental study of third-order nonlinear optical (NLO) properties of three molecules of Br and NO2 substituted chalcone derivatives namely (2E)-1-(4-bromophenyl)-3-[4(methylsulfanyl)phenyl]prop-2-en-1-one (4Br4MSP), (2E)-1-(3-bromophenyl)-3-[4-(methylsulfanyl) phenyl]prop-2-en-1-one (3Br4MSP) and (2E)-3[4(methylsulfanyl) phenyl]-1-(4-nitrophenyl)prop-2-en-1-one (4N4MSP). The NLO properties have been investigated by Z-scan technique using 2 ps laser pulses at 800 nm. The nonlinear refractive indices, nonlinear absorption coefficient, and the magnitude of third-order susceptibility have been determined. The values obtained are of the order of 10−7 cm2/GW, 10−3 cm/GW and 10−14 esu respectively. The molecular second hyperpolarizability for the chalcone derivatives is of the order of 10−32 esu. The coupling factor, excited state cross section, ground state cross section etc. were determined. The optical limiting (OL) property was studied. The results suggest that the nonlinear properties investigated for present chalcones are comparable with some of the reported chalcone derivatives and can be desirable for NLO applications.

  11. Synthesis and antibacterial activity of some heterocyclic chalcone analogues alone and in combination with antibiotics.

    Science.gov (United States)

    Tran, Thanh-Dao; Nguyen, Thi-Thao-Nhu; Do, Tuong-Ha; Huynh, Thi-Ngoc-Phuong; Tran, Cat-Dong; Thai, Khac-Minh

    2012-01-01

    A series of simple heterocyclic chalcone analogues have been synthesized by Claisen Schmidt condensation reactions between substituted benzaldehydes and heteroaryl methyl ketones and evaluated for their antibacterial activity. The structures of the synthesized chalcones were established by IR and ¹H-NMR analysis. The biological data shows that compounds p₅, f₆ and t₅ had strong activities against both susceptible and resistant Staphylococcus aureus strains, but not activity against a vancomycin and methicillin resistant Staphylococcus aureus isolated from a human sample. The structure and activity relationships confirmed that compounds f₅, f₆ and t₅ are potential candidates for future drug discovery and development. PMID:22728362

  12. Biotransformation of chalcones by the endophytic fungus Aspergillus flavus isolated from Paspalum maritimum trin

    Energy Technology Data Exchange (ETDEWEB)

    Correa, Marivaldo J.C.; Nunes, Fatima M.; Bitencourt, Heriberto R.; Borges, Fabio C.; Guilhon, Giselle M.S.P.; Arruda, Mara S.P.; Marinho, Andrey M. R.; Santos, Alberdan S.; Alves, Claudio N.; Santos, Lourivaldo S., E-mail: lss@ufpa.b [Universidade Federal do Para (IQ/FEQ/UFPA), Belem, PA (Brazil). Inst. de Tecnologia. Faculdade de Engenharia Quimica; Brasil, Davi S.B. [Universidade Federal do Para (PPGQ/IQ/UFPA), Belem, PA (Brazil). Inst. de Quimica. Programa de Pos-Graduacao em Quimica

    2011-07-01

    The fungus Aspergillus flavus isolated as endophytic of the plant Paspalum maritimum Trin. was evaluated for its potential application in biotransformation reactions. The compounds chalcone (1), 3,4,5-trimethoxychalcone (2) and 2,3,4,4'-tetramethoxy chalcone (3) were biotransformed, respectively, in dihydrochalcone (4), 3,4,5-trimethoxydihydrochalcone (5) and 2,3,4,4'-tetramethoxydihydrochalcone (6). The structures were elucidated by spectroscopic methods including 1D and 2D NMR techniques, and MS analysis. The dihydrochalcones 5 and 6 are new compounds. (author)

  13. Studies on the chalcone synthase gene of two higher plants: petroselinum hortense and matthiola incana

    Energy Technology Data Exchange (ETDEWEB)

    Hemleben, V.; Frey, M.; Rall, S.; Koch, M.; Kittel, M.; Kreuzaler, F.; Ragg, H.; Fautz, E.; Hahlbrock, K.

    1982-01-01

    Two higher plant systems are presented which allow to study coordinated gene expression of the light-induced metabolic pathway of flavonoid biosynthesis: tissue culture cells of Petroselinum hortense (Apiaceae) and different developmental stages of various genotypes of Matthiola incana (Brassicaceae). The gene structure of the chalcone synthase is mainly studied. A cDNA clone (pLF56) of parsley has been constructed and characterized conferring the chalcone synthase gene sequence. Strong cross hybridization between the parsley cDNA and Matthiola DNA allowed to identify a HindIII fragment (6000 bp) identical in size for parsley and different Matthiola wild type lines and a mutant line.

  14. Antileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis

    DEFF Research Database (Denmark)

    Nielsen, S F; Christensen, S B; Cruciani, G;

    1998-01-01

    of high quality (lymphocyte-suppressing model, R2 = 0. 90, Q2 = 0.80; antileishmanial model, R2 = 0.73, Q2 = 0.63). The coefficient plots indicate that steric interactions between the chalcones and the target are of major importance for the potencies of the compounds. A comparison of the coefficient plots...... for the antileishmanial effect and the lymphocyte-suppressing activity discloses significant differences which should make it possible to design chalcones having a high antileishmanial activity without suppressing the proliferation of lymphocytes....

  15. Synthesis of apoptotic chalcone analogues in HepG2 human hepatocellular carcinoma cells.

    Science.gov (United States)

    Park, Cheon-Soo; Ahn, Yongchel; Lee, Dahae; Moon, Sung Won; Kim, Ki Hyun; Yamabe, Noriko; Hwang, Gwi Seo; Jang, Hyuk Jai; Lee, Heesu; Kang, Ki Sung; Lee, Jae Wook

    2015-12-15

    Eight chalcone analogues were prepared and evaluated for their cytotoxic effects in human hepatoma HepG2 cells. Compound 5 had a potent cytotoxic effect. The percentage of apoptotic cells was significantly higher in compound 5-treated cells than in control cells. Exposure to compound 5 for 24h induced cleavage of caspase-8 and -3, and poly (ADP-ribose) polymerase (PARP). Our findings suggest that compound 5 is the active chalcone analogue that contributes to cell death in HepG2 cells via the extrinsic apoptotic pathway. PMID:26564263

  16. The Synthesis and Biological Evaluation of some Phloroglucinol-based Chalcones and Chromanones

    OpenAIRE

    2003-01-01

    A novel series of 2’,4’,6’-trimethoxychalcone derivatives were prepared using one-step Claisen-Schmidt condensations of aldehydes with methyl ketones. The compounds were evaluated for effects against malaria, 15-lipoxygenase and radical scavenging activity. Of the twenty-five chalcone derivatives, only one exhibited significant scavenging of DPPH radical: E-1-(2,4,6-trimethoxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-one (44). Almost all chalcone compounds showed potent inhibition of 15-lipo...

  17. Studies on Synthesis of Some New Chalcone and Pyrimidines and their Antibacterial Activity

    OpenAIRE

    Ketan Mistry; K. R. Desai

    2005-01-01

    Pyrimidine-2-one derivatives, 2-[2-{1ʹ-(p-nitrophenyl)-6ʹ-(substituted-phenyl)-pyrimidine-2ʹ-one-4ʹ-yl}-hydrazinomethyl]-3-(p-methoxy phenyl)-quina-zoline-4(3H)-one [4a-j] have been synthesised by the condensation of p-nitro phenylurea and various chalcones, 2-(substituted phenylchalconylhydrazinomethyl)-3-(p-methoxyphenyl)-quinazoline-4(3H)-one [3a-j] in the presence of catalytic amount of conc. HCl. And this series of chalcones have been synthesised by the reaction of 2-acetylhydrazinomethy...

  18. UV-induction of chalcone synthase mRNA in cell suspension cultures of Petroselinum hortense

    OpenAIRE

    Kreuzaler, Fritz; Ragg, Hermann; Fautz, Erich; David N Kuhn; Hahlbrock, Klaus

    1983-01-01

    DNAs complementary to poly(A)+ mRNAs from UV-irradiated cell suspension cultures of parsley (Petroselinum hortense) were inserted into pBR322 and used to transform Escherichia coli strain RR1. A clone containing a DNA complementary to chalcone synthase mRNA was identified by hybrid-selected and hybrid-arrested translation. Large and rapid changes in the amount of chalcone synthase mRNA in response to irradiation of the cells was detected by RNA blot hybridization experiments. The pattern of c...

  19. Design and synthesis of novel chalcones as potent selective monoamine oxidase-B inhibitors.

    Science.gov (United States)

    Hammuda, Arwa; Shalaby, Raed; Rovida, Stefano; Edmondson, Dale E; Binda, Claudia; Khalil, Ashraf

    2016-05-23

    A novel series of substituted chalcones were designed and synthesized to be evaluated as selective human MAO-B inhibitors. A combination of either methylsulfonyl or trifluoromethyl substituents on the aromatic ketone moiety with a benzodioxol ring on the other end of the chalcone scaffold was investigated. The compounds were tested for their inhibitory activities on both human MAO-A and B. All compounds appeared to be selective MAO-B inhibitors with Ki values in the micromolar to submicromolar range. Molecular modeling studies have been performed to get insight into the binding mode of the synthesized compounds to human MAO-B active site. PMID:26974383

  20. Synthesis and Antimicrobial Screening of New Pyrazolines Derived From Chalcones of Vanillin Analog

    Directory of Open Access Journals (Sweden)

    Krushnkumar Karangiya

    2016-03-01

    Full Text Available In present study the new series of 3-(Aryl-5-[4-(2, 4-Dichlorophenylmethoxy-3-methoxyphenyl]-4, 5-dihydro pyrazoline (2a-k and 3-(Aryl-5-[4-(2, 4-Dichlorophenylmethoxy-3-methoxyphenyl]-4, 5-dihydroacetyl pyrazoline (3a-k derivatives were synthesized from various substituted 3-Methoxy-4-(2, 4-Dichlorophenyl methoxy chalcones (1a-k. The new chalcones were synthesized using various acetophenones with newly synthesized aldehyde of vanillin analog by Claisen-Schmidt condensation. Characterization of pyrazoline derivatives have been established on the basis of IR, NMR, Mass and elemental analyses. The derivatives were screened for their in vitro antimicrobial Screening.

  1. Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone, flavone, and isoflavone

    International Nuclear Information System (INIS)

    Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan - silibin - have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed

  2. A Solid Phase Synthesis of Chalcones by Claisen-Schmidt Condensations

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    In order to accelerate the development of relatively inexpensive antimalarials that are effective against chloroquine-resistant strains of Plasmodium falclparum, a methodology for the solid phase synthesis of chalcone (l, 3-diphenyl-2-propen-l-one) analogues in reasonably high yields has been developed.

  3. Virtual Screening and Docking Studies of Synthesized Chalcones: Potent Anti-Malarial Drug

    Directory of Open Access Journals (Sweden)

    Prashant Singh

    2016-03-01

    Full Text Available A novel series of Chalcones were synthesized targets asexual blood stages of Plasmodium falciparum has been analyzed by utilizing a combination of molecular modeling techniques. Statistically significant structure-based quantitative structure activity relationships models were generated and validated through acceptable predictive ability to support internal and external set of compounds. Screening of most valuable drug among of pre-synthesized drug on the basis of binding efficiency to target receptor was carried out by docking view. Prior this pre-computed Mean IC50 and MIC value were also taken in consideration. The most effective compound on the basis all consideration was found. Previous studies have suggested that Ca2+-ATPase (PfATP6 of P. falciparum is the target of many anti-malarial drugs. However, the mechanism of inhibition of Ca2+- ATPase (PfATP6 is not known. Here we address this issue using bioinformatics tools. We generated a molecular model of Ca2+-ATPase (PfATP6 of P. falciparum and performed molecular docking of all chalcones. Molecular docking programme Glide iGEMDock was used to determine binding feasibility of 52 analogues of chalcones. The comparison of docking parameters showed, more than 5 analogues are better ligands of PfATP6. The binding of chalocones to PFATP6 is mediated by both hydrogen bonding, hydrophobic and polar interactions. Our results suggest that chalcones analogues are promising lead compounds for the development of anti-malarial drugs

  4. Chemistry of isoflavone heteroanalogs. 11. Benzodioxane analogs of chalcone, flavone, and isoflavone

    Energy Technology Data Exchange (ETDEWEB)

    Khilya, V.P.; Aitmambetov, A.; Turov, A.V.; Kornilov, A.M.; Litkei, D.; Patonai, T.

    1986-08-01

    Benzodioxane analogs of chalcones and their epoxides have been prepared. Different types of analogs of natural flavonolignan - silibin - have been synthesized from these compounds. The PMR spectra of the new compounds and the results of the preliminary biological testings are reported and discussed.

  5. Crystal structure determination from powder diffraction data of the coumarin vanillin chalcone

    Czech Academy of Sciences Publication Activity Database

    Ghouili, A.; Rohlíček, Jan; Ayed, T.B.; Hassen, R.B.

    2014-01-01

    Roč. 29, č. 4 (2014), s. 361-365. ISSN 0885-7156 Grant ostatní: AV ČR(CZ) Praemium Academiae Institutional support: RVO:68378271 Keywords : chalcone * absorption spectra * powder diffraction * crystal structure determination * coumarin derivatives Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 0.636, year: 2014

  6. Overexpression of petunia chalcone isomerase in tomato results in fruit containing increased levels of flavonols

    NARCIS (Netherlands)

    Muir, S.R.; Collins, G.J.; Robinson, S.; Hughes, S.G.; Bovy, A.G.; Vos, de C.H.R.; Tunen, van A.J.; Verhoeven, M.E.

    2001-01-01

    Tomatoes are an excellent source of the carotenoid lycopene, a compound that is thought to be protective against prostate cancer. They also contain small amounts of flavonoids in their peel (|[sim]|5–10 mg/kg fresh weight), mainly naringenin chalcone and the flavonol rutin, a quercetin glycoside. Fl

  7. Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups

    Science.gov (United States)

    Görgülü, Ahmet Orhan; Koran, Kenan; Özen, Furkan; Tekin, Suat; Sandal, Süleyman

    2015-05-01

    2,2-Dichloro-4,4,6,6-bis[spiro(2‧,2″-dioxy-1‧,1″-biphenylyl]cyclotriphosphazene (2) was synthesized from hexachlorocyclotriphosphazene (HCCP) and 2,2‧-dihydroxybiphenyl. The mixed substituent chalcone/dioxybiphenyl cyclophosphazenes (2a-h) were obtained from the reactions of (2) with hydroxy chalcone compounds in K2CO3/acetone system. The chalcone-cyclophosphazene compounds were characterized by elemental analysis, FT-IR, 1H, 13C, 31P NMR techniques. In vitro anti-carcinogenic activities of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Anti-carcinogenic activity of the compounds (2a-h) against androgen-dependent (LNCaP) and independent (PC-3) human prostate cancer cell lines were investigated. Our results indicate that the chalcone-phosphazene compounds (2a-h) have anti-carcinogenic activity on PC-3 and LNCaP cell lines (p < 0.05). The effective dose of the compounds was determined as 100 μM.

  8. Synthesis and Hydrogenation of Disubstituted Chalcones: A Guided-Inquiry Organic Chemistry Project

    Science.gov (United States)

    Mohrig, Jerry R.; Hammond, Christina Noring; Schatz, Paul F.; Davidson, Tammy A.

    2009-01-01

    Guided-inquiry experiments offer the same opportunities to participate in the process of science as classical organic qualitative analysis used to do. This three-week guided-inquiry project involves an aldol-dehydration synthesis of a chalcone chosen from a set of nine, followed by a catalytic transfer hydrogenation reaction using ammonium formate…

  9. In situ localization of chalcone synthase mRNA in pea root nodule development.

    NARCIS (Netherlands)

    Yang, W.C.; Canter Cremers, H.C.J.; Hogendijk, P.; Katinakis, P.; Wijffelman, C.A.; Franssen, H.J.; Kammen, van A.; Bisseling, T.

    1992-01-01

    In this paper studies on the role of flavonoids in pea root nodule development are reported. Flavonoid synthesis was followed by localizing chalcone synthase (CHS) mRNA in infected pea roots and in root nodules. In a nodule primordium, CHS mRNA is present in all cells of the primordium. Therefore it

  10. Chalcones isolated from Angelica keiskei inhibit cysteine proteases of SARS-CoV.

    Science.gov (United States)

    Park, Ji-Young; Ko, Jin-A; Kim, Dae Wook; Kim, Young Min; Kwon, Hyung-Jun; Jeong, Hyung Jae; Kim, Cha Young; Park, Ki Hun; Lee, Woo Song; Ryu, Young Bae

    2016-01-01

    Two viral proteases of severe acute respiratory syndrome coronavirus (SARS-CoV), a chymotrypsin-like protease (3CL(pro)) and a papain-like protease (PL(pro)) are attractive targets for the development of anti-SARS drugs. In this study, nine alkylated chalcones (1-9) and four coumarins (10-13) were isolated from Angelica keiskei, and the inhibitory activities of these constituents against SARS-CoV proteases (3CL(pro) and PL(pro)) were determined (cell-free/based). Of the isolated alkylated chalcones, chalcone 6, containing the perhydroxyl group, exhibited the most potent 3CL(pro) and PL(pro) inhibitory activity with IC50 values of 11.4 and 1.2 µM. Our detailed protein-inhibitor mechanistic analysis of these species indicated that the chalcones exhibited competitive inhibition characteristics to the SARS-CoV 3CL(pro), whereas noncompetitive inhibition was observed with the SARS-CoV PL(pro). PMID:25683083

  11. A new member of the chalcone synthase (CHS family in sugarcane

    Directory of Open Access Journals (Sweden)

    Miriam G.G. Contessotto

    2001-12-01

    Full Text Available Sequences from the sugarcane expressed sequence tag (SUCEST database were analyzed based on their identities to genes encoding chalcone-synthase-like enzymes. The sorghum (Sorghum bicolor chalcone-synthase (CHS, EC 2.3.1.74 protein sequence (gi|12229613 was used to search the SUCEST database for clusters of sequencing reads that were most similar to chalcone synthase. We found 121 reads with homology to sorghum chalcone synthase, which we were then able to sort into 14 clusters which themselves were divided into two groups (group 1 and group 2 based on the similarity of their deduced amino acid sequences. Clusters in group 1 were more similar to the sorghum enzyme than those in group 2, having the consensus sequence of the active site of chalcone and stilbene synthase. Analysis of gene expression (based on the number of reads from a specific library present in each group indicated that most of the group 1 reads were from sugarcane flower and root libraries. Group 2 clusters were more similar to the amino acid sequence of an uncharacterized pathogen-induced protein (PI1, gi|9855801 from the S. bicolor expressed sequence tag (EST database. The group 2 clusters sequences and PI1 proteins are 90% identical, having two amino acid changes at the chalcone and stilbene synthase consensi but conserving the cysteine residue at the active site. The PI1 EST has not been previously associated with chalcone synthase and has a different consensus sequence from the previously described chalcone synthase of sorghum. Most of the group 2 reads were from libraries prepared from sugarcane roots and plants infected with Herbaspirillum rubrisubalbicans and Gluconacetobacter diazotroficans. Our results indicate that we have identified a sugarcane chalcone synthase similar to the pathogen-induced PI1 protein found in the sorghum cDNA libraries, and it appears that both proteins represent new members of the chalcone and stilbene synthase super-family.Seqüências do

  12. Cytoprotective effects of chalcones from Zuccagnia punctata and melatonin on the gastroduodenal tract in rats.

    Science.gov (United States)

    de la Rocha, N; María, A O M; Gianello, J C; Pelzer, L

    2003-07-01

    The effects of 2',4'-dihydroxychalcone and 2',4'-dihydroxy-3'-methoxychalcone from Zuccagnia punctata Cav. (Fabaceae) and melatonin administration on ethanol-induced gastroduodenal injury were investigated in rats. Both chalcones showed significant preventive effects in treatment with melatonin previous to the necrotising agent. These effects could be due, in part, to the radical scavenging activity of the melatonin. PMID:12770521

  13. 2-Methoxy-2',4'-dichloro chalcone as an antimicrofoulant against marine bacterial biofilm.

    Science.gov (United States)

    Sivakumar, P M; Prabhawathi, V; Doble, Mukesh

    2010-12-01

    Marine paint mixed with 2-methoxy-2',4'-dichloro chalcone is able to considerably reduce the formation of biofilm by Vibrio natriegens, a marine bacterium, on polycarbonate (PC), polymethylmethacrylate (PMMA) and glass fiber reinforced plastic (GFRP). These polymers have been selected for the study, since they have wide marine applications. Surfaces coated with dichloro chalcone containing marine paint had the lowest number of colony forming units (CFU) (1-5×10(6)), proteins (20-30 μg/cm2) and carbohydrates (5-10 μg/cm2) attached to them after 28 days of exposure to the organism when compared to surfaces coated with CuSO4 mixed paint (20-40×10(6) CFU/ml, proteins of 50-60 μg/cm2 and carbohydrates of 40-50 μg/cm2) or plain marine paint (30-40×10(6) CFU/ml, proteins of 120-150 μg/cm2 and carbohydrates of 40-60 μg/cm2). At the end of the study period, the biofilm on PMMA was 7, 10 and 12 μm thick on chalcone, copper and plain paint coated surfaces, respectively. The first two paints increased the surface roughness but decreased the surface hydrophobicity when compared to the plain paint. Large number of dead cells was found on the chalcone mixed and predominantly live cells were found on plain paint coated surfaces. 15% of dichloro chalcone had leached out of PMMA surface after 28 days. The low amount of biofilm formed in the presence of dichlorochalcone can be associated to its antibacterial and slimicidal activity and also its ability to reduce the hydrophobicity of the surface. This dichlorochalcone appears to be a novel agent for decreasing the formation of marine biofilm. PMID:20708908

  14. IN VITRO SOLUBLE EPOXIDE HYDROLASE ENZYME INHIBITORY ACTIVITY OF SOME NOVEL CHALCONE DERIVATIVES

    Directory of Open Access Journals (Sweden)

    Kuppusamy Asokkumar

    2012-09-01

    Full Text Available Objective Soluble epoxide hydrolase (sEH belongs to the α/β -hydrolase superfamily, a subclass of α/β proteins. Chalcones are chemical compounds that show hopeful obliging efficacy in controlling numerous diseases. The main objective of the study is to evaluate the sEH inhibitory activity of some synthesized chalcone derivatives and identification of its mode of inhibition. Methods Four different chalcone derivatives (PC-1 to PC-4 were selected for synthesis by Claisen-Schmidt method. The in vitro sEH inhibitory activity was performed for the synthesized compounds by fluorimetric assay. The percentage of sEH activity and IC50 values were calculated for the synthesized compounds. Dissociation constant were determined by following the method described by Lineweaver-Burks plot.Results and Conclusions The IC50 value obtained for PC-1, PC-2, PC-3, and PC-4 were found to be 0.8213 µg/mL, 2.64 µg/mL, 0.2490 µg/mL and 0.5238 µg/mL respectively. The order of potency (IC50 of the chalcone and chalcone oxide in sEH inhibition assay was PC-3 > PC-4 > PC-1 >PC-2. All the compounds (PC-1, PC-2, PC-3 showed mixed type of inhibition except PC-4 which showed non-competitive type of inhibition. Further in vivo studies are to be carried out for these compounds to confirm their activity and explore the mechanism by which these compounds act and rationalize their use.

  15. Synthesis of heterocyclic chalcone derivatives and their radical scavenging ability toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals

    Energy Technology Data Exchange (ETDEWEB)

    Hwang, Kijun; Kim, Hoseok; Kim, Beomtae [Research Center of Bioactive Materials, Hwaseong (Korea, Republic of); Han, Incheol [Chonbuk National Univ., Jeonju (Korea, Republic of)

    2012-04-15

    A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalcones was distinctly demonstrated in our work.

  16. Enantioselective conjugate addition of diethylzinc to chalcone catalyzed by Co(acac)2 and chiral amino alcohols

    NARCIS (Netherlands)

    Vries, André H.M. de; Feringa, Bernard

    1997-01-01

    Co(acac)2 in the presence of chiral ligands has been employed as catalyst for the enantioselective conjugate addition of diethylzinc to chalcone. With chiral amino alcohols derived from (+)-camphor, enantioselectivities up to 83% were achieved.

  17. Synthesis of heterocyclic chalcone derivatives and their radical scavenging ability toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals

    International Nuclear Information System (INIS)

    A series of heterocyclic chalcone derivatives bearing heterocycles such as thiophene or furan ring as an isostere of benzene ring were carefully prepared, and the influence of heterocycles on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities was systematically investigated. Structure-activity relationships (SAR) analysis showed that the activities of thiophene ring-containing chalcones were higher than those of furan ring containing chalcones, and the presence of methyl substituent of heterocyclic ring distinctly affected the activities compared with non-substituted heterocycles in an opposite manner, with the 4'-methyl group of thiophene ring increasing activity and the 3'-methyl group of the furan ring decreasing activity. The distinct isosteric effect of heterocycles (i.e., thiophene or furan ring) on radical scavenging activities of heterocyclic chalcones was distinctly demonstrated in our work

  18. Chalcone derivatives cause accumulation of colon cancer cells in the G2/M phase and induce apoptosis

    Czech Academy of Sciences Publication Activity Database

    Kello, M.; Drutovič, Dávid; Bago Pilátová, M.; Tischlerová, V.; Perjesi, P.; Mojžíš, J.

    2016-01-01

    Roč. 150, č. 1 (2016), s. 32-38. ISSN 0024-3205 Institutional support: RVO:67985904 Keywords : chalcones * colorectal cancer * antiproliferative Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 2.702, year: 2014

  19. Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core

    OpenAIRE

    Sándor B. Ötvös; Chi-Ting Hsieh; Yang-Chang Wu; Jih-Heng Li; Fang-Rong Chang; Ferenc Fülöp

    2016-01-01

    Flow chemistry-based syntheses of deuterium-labeled analogs of important antidiabetic chalcones were achieved via highly controlled partial C≡C bond deuteration of the corresponding 1,3-diphenylalkynones. The benefits of a scalable continuous process in combination with on-demand electrolytic D2 gas generation were exploited to suppress undesired over-reactions and to maximize reaction rates simultaneously. The novel deuterium-containing chalcone derivatives may have interesting biological ef...

  20. Synthetic and Mechanistic Studies on the Solvent-Dependent Copper-Catalyzed Formation of Indolizines and Chalcones

    OpenAIRE

    Albaladejo Maricó, María José; Alonso Valdés, Francisco; González Soria, María José

    2015-01-01

    Copper nanoparticles supported on activated carbon have been found to catalyze the multicomponent synthesis of indolizines from pyridine-2-carbaldehyde derivatives, secondary amines, and terminal alkynes in dichloromethane; in the absence of solvent, however, heterocyclic chalcones are formed. We provide compelling evidence that both processes take place through aldehyde–amine–alkyne coupling intermediates. In contrast to other well-known mechanisms for chalcone formation from aldehydes and a...

  1. Elicitor rapidly induces chalcone synthase mRNA in Phaseolus vulgaris cells at the onset of the phytoalexin defense response

    OpenAIRE

    Ryder, Thomas B.; Cramer, Carole L; Bell, John N.; Robbins, Mark P.; Dixon, Richard A.; Lamb, Chris J.

    1984-01-01

    DNAs complementary to poly(A)+ RNA present in elicitor-treated cells of Phaseolus vulgaris L. were inserted into pBR325 and used to transform Escherichia coli strain JA221. A clone was identified that contained sequences complementary to mRNA encoding chalcone synthase, a regulatory enzyme of phenylpropanoid biosynthesis, which catalyzes the first reaction of a branch pathway specific to flavonoid and isoflavonoid biosynthesis. Rapid, marked but transient increases in chalcone synthase mRNA i...

  2. Antibacterial activity of three newly-synthesized chalcones & synergism with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus

    Directory of Open Access Journals (Sweden)

    Dragana D Bozic

    2014-01-01

    Interpretation & conclusions: o0 ur study demonstrated that three newly-synthesized chalcones exhibited significant anti-MRSA effect and synergism with non-β-lactam antibiotics. The most effective compound was 1,3-Bis-(2-hydroxy-phenyl-propenone. Our results provide useful information for future research of possible application of chalcones in combination with conventional anti-MRSA therapy as promising new antimicrobial agents.

  3. Inhibition of mitogen activated protein kinases increases the sensitivity of A549 lung cancer cells to the cytotoxicity induced by a kava chalcone analog

    OpenAIRE

    Janel K Warmka; Solberg, Eric L.; Zeliadt, Nicholette A.; Srinivasan, Balasubramanian; Charlson, Aaron T.; Xing, Chengguo; Wattenberg, Elizabeth V.

    2012-01-01

    We are interested in investigating the biological activity of chalcones, a major class of compounds found in the beverage kava, in order to develop potent and selective chemopreventive candidates. Consumption of kava in the South Pacific Islands is inversely correlated with cancer incidence, even among smokers. Accordingly, chalcones have anti-cancer activities in animal and cell culture models. To investigate signaling pathways that affect chalcone action we studied a potent analog, (E)-3-(3...

  4. A quantitative analysis of weak intermolecular interactions & quantum chemical calculations (DFT) of novel chalcone derivatives

    Science.gov (United States)

    Chavda, Bhavin R.; Gandhi, Sahaj A.; Dubey, Rahul P.; Patel, Urmila H.; Barot, Vijay M.

    2016-05-01

    The novel chalcone derivatives have widespread applications in material science and medicinal industries. The density functional theory (DFT) is used to optimized the molecular structure of the three chalcone derivatives (M-I, II, III). The observed discrepancies between the theoretical and experimental (X-ray data) results attributed to different environments of the molecules, the experimental values are of the molecule in solid state there by subjected to the intermolecular forces, like non-bonded hydrogen bond interactions, where as isolated state in gas phase for theoretical studies. The lattice energy of all the molecules have been calculated using PIXELC module in Coulomb -London -Pauli (CLP) package and is partitioned into corresponding coulombic, polarization, dispersion and repulsion contributions. Lattice energy data confirm and strengthen the finding of the X-ray results that the weak but significant intermolecular interactions like C-H…O, Π- Π and C-H… Π plays an important role in the stabilization of crystal packing.

  5. Oxidation of Chalcones by Morpholinium Chlorochromate with Oxalic Acid as Catalyst: Kinetic and Mechanistic Study

    Directory of Open Access Journals (Sweden)

    K. Rajalakshmi

    2013-01-01

    Full Text Available The kinetics of oxidation of chalcones by morpholinium chlorochromate (MCC has been studied in 55% acetic acid-water (v/v medium. The reaction showed unit order dependence each with respect to oxidant and catalyst and fractional order with respect to substrate and H+ ion. Increased ionic strength has no effect on the reaction rate. In the case of substituted chalcones, the order with respect to substrate varies depending upon the nature of the substituent present in the ring. In general, the electron withdrawing substituents retard the reaction rate while the electron releasing substituents enhance the rate of the reaction. From the kinetic data obtained, the activation parameters have been calculated and a suitable mechanism has been proposed.

  6. Synthesis and Antibacterial Activity of Some Heterocyclic Chalcone Analogues Alone and in Combination with Antibiotics

    Directory of Open Access Journals (Sweden)

    Tuong-Ha Do

    2012-06-01

    Full Text Available A series of simple heterocyclic chalcone analogues have been synthesized by Claisen Schmidt condensation reactions between substituted benzaldehydes and heteroaryl methyl ketones and evaluated for their antibacterial activity. The structures of the synthesized chalcones were established by IR and 1H-NMR analysis. The biological data shows that compounds p5, f6 and t5 had strong activities against both susceptible and resistant Staphylococcus aureus strains, but not activity against a vancomycin and methicillin resistant Staphylococcus aureus isolated from a human sample. The structure and activity relationships confirmed that compounds f5, f6 and t5 are potential candidates for future drug discovery and development.

  7. Heteroaryl Chalcones: Design, Synthesis, X-ray Crystal Structures and Biological Evaluation

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2013-10-01

    Full Text Available Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a–i containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities. The results indicate the tested compounds show a varied range of inhibition values against all the tested microbial strains. Compound 3c with a p-fluoro substituent on the phenyl ring exhibits elevated antimicrobial activity, whereas the compounds 3e and 3f displayed the least antimicrobial activities. The compounds 3d, 3e, 3f and 3i showed good ferric and cupric reducing abilities, and the compounds 3b and 3c showed the weakest reducing power in the series.

  8. Heteroaryl chalcones: design, synthesis, X-ray crystal structures and biological evaluation.

    Science.gov (United States)

    Kumar, C S Chidan; Loh, Wan-Sin; Ooi, Chin Wei; Quah, Ching Kheng; Fun, Hoong-Kun

    2013-01-01

    Chalcone derivatives have attracted increasing attention due to their numerous pharmacological activities. Changes in their structures have displayed high degree of diversity that has proven to result in a broad spectrum of biological activities. The present study highlights the synthesis of some halogen substituted chalcones 3(a-i) containing the 5-chlorothiophene moiety, their X-ray crystal structures and the evaluation of possible biological activities such as antibacterial, antifungal and reducing power abilities. The results indicate the tested compounds show a varied range of inhibition values against all the tested microbial strains. Compound 3c with a p-fluoro substituent on the phenyl ring exhibits elevated antimicrobial activity, whereas the compounds 3e and 3f displayed the least antimicrobial activities. The compounds 3d, 3e, 3f and 3i showed good ferric and cupric reducing abilities, and the compounds 3b and 3c showed the weakest reducing power in the series. PMID:24132195

  9. Eco-friendly synthesis and in vitro antibacterial activities of some novel chalcones.

    Science.gov (United States)

    Khan, Salman A; Asiri, Abdullah M; Alamry, Khalid A; El-Daly, Samy A; Zayed, Mohie A M

    2013-01-01

    Chalcone derivatives have been synthesized by reaction of 1-(2,5-dimethyl-furan-3-yl)-ethanone with corresponding active aldehyde in ethanolic NaOH in microwave oven. The structure of these compounds was established by elemental analysis, IR, 1H-NMR, 13C-NMR, and EI-MS spectral analysis. The anti-bacterial activity of these compounds was first tested in vitro by the disc diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC) was determined with the reference of standard drug Chloramphenicol. The results showed that pyrazol containing chalcone (compound 8) inhibited both types of bacteria (Gram-positive and Gram-negative) better than chloramphenicol. PMID:24397034

  10. Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents.

    Science.gov (United States)

    Solankee, Anjani; Kapadia, Kishor; Ana Cirić; Soković, Marina; Doytchinova, Irini; Geronikaki, Athina

    2010-02-01

    Base catalysed condensation of ketone 5 with different aldehydes give chalcones, 2.4-bis-(phenylamino)-6-[4'-{3''-(4'''-substituted phenyl/2'''-furanyl/2'''-thienyl)-2''-propenon-1''-yl}phenylamino]-s-thriazines 6a-e. These chalcones on cyclization with hydrazine hydrate in the presence of glacial acetic acid, guanidine nitrate in the presence of alkali and malononitrile in the presence of ammonium acetate give the corresponding acetylpyrazolines 7a-e, aminopyrimidines 8a-e and cyanopyridines 9a-e respectively. The products 6a-e, 7a-e, 8a-e and 9a-e were fully characterized by spectroscopic and elemental analysis and also tested for antibacterial activity. PMID:19926364

  11. Two minor chalcone acetylglycosides from the roots extract of Glycyrrhiza uralensis.

    Science.gov (United States)

    Lee, Ji Eun; Lee, Ji Young; Kim, Jinhee; Lee, Kwangho; Choi, Sang Un; Ryu, Shi Yong

    2015-07-01

    An extensive phytochemical investigation on the roots of Glycyrrhiza uralensis led to the isolation of two new minor chalcone acetylglycosides, i.e., 6″-O-acetylisoliquiritin (1) and 6″-O-acetylneoisoliquiritin (2), including 16 kinds of known constituents (3-18) of flavonoids, chalcones and triterpene saponins. The chemical structures of 1 and 2 were established by spectroscopic analyses of them, particularly by the aid of two-dimensional NMR experiments, COSY, DEPT, HSQC and HMBC. Some isolated components except 1 and 2 exhibited significant inhibitory effects on the proliferation of cultured tumor cell lines, such as A549, SK-OV-3, A-498, and HCD15, in vitro. PMID:25479707

  12. Flemingin-Type Prenylated Chalcones from the Sarawak Rainforest Plant Desmodium congestum.

    Science.gov (United States)

    Rees, Karlee A; Bermudez, Cindy; Edwards, David J; Elliott, Alysha G; Ripen, Jovita E; Seta, Cynthia; Huang, Johnny X; Cooper, Matthew A; Fraser, James A; Yeo, Tiong Chia; Butler, Mark S

    2015-08-28

    In an ongoing program to identify new anti-infective leads, an extract derived from whole plant material of Desmodium congestum collected in the Sarawak rainforest was found to have anti-MRSA activity. Bioassay-guided isolation led to the isolation of two new prenylated chalcones, 5'-O-methyl-3-hydroxyflemingin A (1) and 5'-O-methylflemingin C (2), which were closely related to the flemingins previously isolated from various Flemingia species. Chalcones 1 and 2, which were determined to be 4:6 enantiomeric mixtures by chiral HPLC, exhibited moderate activity against a panel of Gram-positive bacteria and were also cytotoxic to the HEK293 human embryonic kidney cell line. PMID:26284978

  13. Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism

    Directory of Open Access Journals (Sweden)

    Christophe Curti

    2007-04-01

    Full Text Available An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-ylethanone or 2-bromo-1-(4-nitrophenylethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a SRN1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues.

  14. An efficient synthesis of pyrazole chalcones under solvent free conditions at room temperature

    Institute of Scientific and Technical Information of China (English)

    Parvin Kumar; Sunil Kumar; Khalid Husain; Ashwani Kumar

    2011-01-01

    An easy,safe,solvent free and effective method for the synthesis of pyrazole-substituted chalcones has been achieved by grinding pyrazole aldehydes and acetophenones in the presence of activated barium hydroxide(C-200) in high yield within short span of time.All reactions were carried out just by grinding the two reactants in the presence of activated barium hydroxide(C-200).Results are also compared with sodium hydroxide and potassium hydroxide.

  15. Genome-Wide Identification, Characterization and Expression Analysis of the Chalcone Synthase Family in Maize

    OpenAIRE

    Yahui Han; Ting Ding; Bo Su; Haiyang Jiang

    2016-01-01

    Members of the chalcone synthase (CHS) family participate in the synthesis of a series of secondary metabolites in plants, fungi and bacteria. The metabolites play important roles in protecting land plants against various environmental stresses during the evolutionary process. Our research was conducted on comprehensive investigation of CHS genes in maize (Zea mays L.), including their phylogenetic relationships, gene structures, chromosomal locations and expression analysis. Fourteen CHS gen...

  16. Synthesis, Characterization and antimicrobial evaluation of New Chalcone Derivatives From3- benzyloxy-4-methoxybenzaldehyde

    Directory of Open Access Journals (Sweden)

    L. Benmekhbi

    2015-09-01

    Full Text Available A series of chalcone derivatives (2a–i were prepared via the reaction of 3-benzyloxy-4-methoxybenzaldehyde with the appropriately acetophenon derivatives. The structures of all the newchalcone derivatives (2a–i synthesized in this study were established on the basis of 1H NMR and 13C NMR spectral data, and elemental analyses The antibacterial activitie of the synthesized compounds (2a- i was carried out by well diffusion and MIC method.

  17. Cis-regulatory Evolution of Chalcone-Synthase Expression in the Genus Arabidopsis

    OpenAIRE

    de Meaux, J. (Juliette); Pop, A.(National Institute for Physics and Nuclear Engineering, Bucharest, Romania); Mitchell-Olds, T.

    2006-01-01

    The contribution of cis-regulation to adaptive evolutionary change is believed to be essential, yet little is known about the evolutionary rules that govern regulatory sequences. Here, we characterize the short-term evolutionary dynamics of a cis-regulatory region within and among two closely related species, A. lyrata and A. halleri, and compare our findings to A. thaliana. We focused on the cis-regulatory region of chalcone synthase (CHS), a key enzyme involved in the synthesis of plant sec...

  18. Synthesis, Characterization and antimicrobial evaluation of New Chalcone Derivatives From3- benzyloxy-4-methoxybenzaldehyde

    OpenAIRE

    L. Benmekhbi; Mosbah, S.; A. Khelifa Baghdouch; L. Bencharif

    2015-01-01

    A series of chalcone derivatives (2a–i) were prepared via the reaction of 3-benzyloxy-4-methoxybenzaldehyde with the appropriately acetophenon derivatives. The structures of all the newchalcone derivatives (2a–i) synthesized in this study were established on the basis of 1H NMR and 13C NMR spectral data, and elemental analyses The antibacterial activitie of the synthesized compounds (2a- i) was carried out by well diffusion and MIC method.

  19. Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

    OpenAIRE

    Zhihua Wan; Deyu Hu; Pei Li; Dandan Xie; Xiuhai Gan

    2015-01-01

    A series of novel 4-thioquinazoline derivatives containing chalcone moiety were designed, synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited moderate to good anti-TMV activity. In particular, compounds M2 and M6 possessed appreciable protection activities against TMV in vivo, with 50% effective concentration (EC50) values of 138.1 and 154.8 μg/mL, respectively, which were superior to that of Ri...

  20. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation.

    Science.gov (United States)

    Liaras, K; Geronikaki, A; Glamočlija, J; Cirić, A; Soković, M

    2011-05-15

    As part of ongoing studies in developing new antimicrobials, we report the synthesis of a new class of structurally novel derivatives, that incorporate two known bioactive structures a thiazole and chalcone, to yield a class of compounds with interesting antimicrobial properties. Evaluation of antibacterial activity showed that almost all the compounds exhibited greater activity than reference drugs and thus could be promising novel drug candidates. PMID:21524583

  1. Design and synthesis of novel indole-chalcone fibrates as lipid lowering agents.

    Science.gov (United States)

    Sashidhara, Koneni V; Dodda, Ranga Prasad; Sonkar, Ravi; Palnati, Gopala Reddy; Bhatia, Gitika

    2014-06-23

    A series of novel indole-chalcone fibrates were synthesized and their hypolipidemic activity was evaluated in triton WR-1339 induced hyperlipidemic rat model. Preliminary studies indicated that the hybrids 19, 24 and 29 exhibited potent in vitro antioxidant and significant in vivo antidyslipidemic effects. Our results suggest that these new hybrid architectures may serve as promising leads for the development of next generation lipid lowering agents. PMID:24871900

  2. Antifungal chalcones and new caffeic acid esters from Zuccagnia punctata acting against soybean infecting fungi.

    Science.gov (United States)

    Svetaz, Laura; Tapia, Alejandro; López, Silvia N; Furlán, Ricardo L E; Petenatti, Elisa; Pioli, Rosanna; Schmeda-Hirschmann, Guillermo; Zacchino, Susana A

    2004-06-01

    The crude methanolic extract of Zuccagnia punctata was active toward the fungal pathogens of soybean Phomopsis longicolla and Colletotrichum truncatum. Assay guided fractionation led to the isolation of two chalcones, one flavanone and a new caffeoyl ester derivative as the compounds responsible for the antifungal activity. Another new caffeoyl ester derivative was isolated from the antifungal chloroform extract but proved to be inactive against the soybean infecting fungi up to 50 microg/mL PMID:15161186

  3. [Chalcones and their heterocyclic analogs as potential therapeutic agents in bacterial diseases].

    Science.gov (United States)

    Opletalová, V

    2000-11-01

    Chalcones and their heterocyclic analogues possess a number of biological effects. Their antifungal effects were reported in the previous communication (Opletalová V., Sedivý D.: Ces. a Slov. Farm. 48, 252 (1999)). The present review is devoted to the antibacterial activity of these compounds. For antibacterial activity, the presence of the enone aggregate in the molecule is important. Hydrogenated analogues are less effective or ineffective, saturated brominated analogues are effective probably after a metabolic transformation into unsaturated alpha-bromochalcone. In the rings, substitution with a hydroxyl is advantageous, in some cases also substitution with a lipophilic substituent, e.g. a halogen or an alkyl, proved to be advantageous. On the other hand, substitution with amino groups often results in a decrease in effectiveness. Effectiveness of chalcones and their derivatives against gram-positive microorganisms is usually higher than against gram-negative bacteria. Some analogues, however, inhibited also the growth of gram-negative strains. With regard to increased incidence of tuberculosis in recent years, antimycobacterial effectiveness of chalcones and their derivatives is especially interesting. PMID:11367546

  4. Ferrocenyl-cymantrenyl hetero-bimetallic chalcones: Synthesis, structure and biological properties

    Science.gov (United States)

    Mishra, Sasmita; Tirkey, Vijaylakshmi; Ghosh, Avishek; Dash, Hirak R.; Das, Surajit; Shukla, Madhulata; Saha, Satyen; Mobin, Sheikh M.; Chatterjee, Saurav

    2015-04-01

    Two new ferrocenyl-cymantrenyl bimetallic chalcones, [(CO)3Mn(η5-C5H4)C(O)CHdbnd CH(η5-C5H4)Fe(η5-C5H5)] (1) and [{(CO)3Mn(η5-C5H4)C(O)CHdbnd CH(η5-C5H4)}2Fe] (2) have been synthesized. Their reactivity study with triphenylphosphine and bis-(diphenylphosphino)ferrocene led to the isolation of phosphine substituted bimetallic chalcones (3-6). Single crystal X-ray structural characterization for 1 and its phosphine analogue (3) reveals their different conformational identity with anti-conformation for 1, while syn-conformation for 3. Investigation of antimalarial and antibacterial activities was carried out for compounds 1 and 2 against two strains of Plasmodium falciparum (3D7, K1) and four bacterial strains. TD-DFT calculation was performed for compound 1 and electrochemical properties were studied for bimetallic chalcone compounds by cyclic voltammetric technique.

  5. Improved small-molecule macroarray platform for the rapid synthesis and discovery of antibacterial chalcones.

    Science.gov (United States)

    Stringer, Joseph R; Bowman, Matthew D; Weisblum, Bernard; Blackwell, Helen E

    2011-03-14

    Bacterial resistance to current antibiotics is a major global health threat. Consequently, there is an urgent need for the identification of new antibacterial agents. We are applying the small-molecule macroarray platform to rapidly synthesize and screen compounds for activity against methicillin-resistant Staphylococcus aureus (MRSA). Herein, we report the synthesis of a 1,3-diphenyl-2-propen-1-one (chalcone) macroarray using a Rink-amide linker-derivatized cellulose support. The Rink linker allowed for the incorporation of a broader array of library building blocks relative to our previous syntheses because milder reaction conditions could be utilized; significantly higher compound loadings were also achieved (~80% vs ~15%). Analysis of the 174-member chalcone macroarray in off-support antibacterial screening assays revealed three chalcones with minimum inhibitory concentration (MIC) values against MRSA comparable to currently used antibacterial drugs and low hemolytic activities. These results serve to further showcase and extend the utility of the small molecule macroarray for antibacterial discovery. PMID:21210707

  6. Synthesis and anti-cancer activity evaluation of novel prenylated and geranylated chalcone natural products and their analogs.

    Science.gov (United States)

    Wang, Hao-Meng; Zhang, Li; Liu, Jiang; Yang, Zhao-Liang; Zhao, Hong-Ye; Yang, Yao; Shen, Di; Lu, Kui; Fan, Zhen-Chuan; Yao, Qing-Wei; Zhang, Yong-Min; Teng, Yu-Ou; Peng, Yu

    2015-03-01

    Four natural chalcones bearing prenyl or geranyl groups, i.e., bavachalcone (1a), xanthoangelol (1b), isobavachalcone (1c), and isoxanthoangelol (1d) were synthesized by using a regio-selective iodination and the Suzuki coupling reaction as key steps. The first total synthesis of isoxanthoangelol (1d) was achieved in 36% overall yield. A series of diprenylated and digeranylated chalcone analogs were also synthesized by alkylation, regio-selective iodination, aldol condensation, Suzuki coupling and [1,3]-sigmatropic rearrangement. The structures of the 11 new derivatives were confirmed by (1)H NMR, (13)C NMR and HRMS. The anticancer activity of these new chalcone derivatives against human tumor cell line K562 were evaluated by MTT assay in vitro. SAR studies suggested that the 5'-prenylation/geranylation of the chalcones significantly enhance their cytotoxic activity. Among them, Bavachalcone (1a) displayed the most potent cytotoxic activity against K562 with IC50 value of 2.7 μM. The morphology changes and annexin-V/PI staining studies suggested that those chalcone derivatives inhibited the proliferation of K562 cells by inducing apoptosis. PMID:25590864

  7. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents

    Directory of Open Access Journals (Sweden)

    Maher A. El-Hashash

    2015-12-01

    Full Text Available A number of novel heterocyclic chalcone derivatives can be synthesized by thermal and microwave tools. Treatment of 4-(4-Acetylamino- and/or 4-bromo-phenyl-4-oxobut-2-enoic acids with hydrogen peroxide in alkaline medium were afforded oxirane derivatives 2. Reaction of the epoxide 2 with 2-amino-5-aryl-1,3,4-thiadiazole derivatives yielded chalcone of imidazo[2,1-b]thiadiazole derivative 4 via two thermal routes. In one pot reaction of 4-bromoacetophenone, diethyloxalate, and 2-amino-5-aryl-1,3,4-thiadiazole derivatives in MW irradiation (W 250 and T 150 °C under eco-friendly conditions afforded an unsuitable yield of the desired chalcone 4d. The chalcone derivatives 4 were used as a key starting material to synthesize some new spiroheterocyclic compounds via Michael and aza-Michael adducts. The chalcone 4f was similar to the aryl-oxo-vinylamide derivatives for the inhibition of tyrosine kinase and cancer cell growth. The electron-withdrawing substituents, such as halogens, and 2-amino-1,3,4-thiadiazole moeity decreasing the electron density, thereby decreasing the energy of HOMO, and the presence of imidazothiadiazole moiety should improve the antibacterial activity. Thus, the newly synthesized compounds were evaluated for their anti-bacterial activity against (ATCC 25923, (ATCC 10987, (ATCC 274, and (SM514. The structure of the newly synthesized compounds was confirmed by elemental analysis and spectroscopic data.

  8. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents.

    Science.gov (United States)

    El-Hashash, Maher A; Rizk, Sameh A; Atta-Allah, Saad R

    2015-01-01

    A number of novel heterocyclic chalcone derivatives can be synthesized by thermal and microwave tools. Treatment of 4-(4-Acetylamino- and/or 4-bromo-phenyl)-4-oxobut-2-enoic acids with hydrogen peroxide in alkaline medium were afforded oxirane derivatives 2. Reaction of the epoxide 2 with 2-amino-5-aryl-1,3,4-thiadiazole derivatives yielded chalcone of imidazo[2,1-b]thiadiazole derivative 4 via two thermal routes. In one pot reaction of 4-bromoacetophenone, diethyloxalate, and 2-amino-5-aryl-1,3,4-thiadiazole derivatives in MW irradiation (W 250 and T 150 °C) under eco-friendly conditions afforded an unsuitable yield of the desired chalcone 4d. The chalcone derivatives 4 were used as a key starting material to synthesize some new spiroheterocyclic compounds via Michael and aza-Michael adducts. The chalcone 4f was similar to the aryl-oxo-vinylamide derivatives for the inhibition of tyrosine kinase and cancer cell growth. The electron-withdrawing substituents, such as halogens, and 2-amino-1,3,4-thiadiazole moeity decreasing the electron density, thereby decreasing the energy of HOMO, and the presence of imidazothiadiazole moiety should improve the antibacterial activity. Thus, the newly synthesized compounds were evaluated for their anti-bacterial activity against (ATCC 25923), (ATCC 10987), (ATCC 274,) and (SM514). The structure of the newly synthesized compounds was confirmed by elemental analysis and spectroscopic data. PMID:26690393

  9. Effects of a herbal gel containing carvacrol and chalcones on alveolar bone resorption in rats on experimental periodontitis.

    Science.gov (United States)

    Botelho, Marco Antonio; Rao, Vietla Satyanarayana; Montenegro, Danusa; Bandeira, Mary Anne Menezes; Fonseca, Said Gonçalves Cruz; Nogueira, Nadia Accioly Pinto; Ribeiro, Ronaldo Albuquerque; Brito, Gerly Anne Castro

    2008-04-01

    Carvacrol and dimeric chalcones are the respective bioactive components of Lippia sidoides and Myracrodruon urundeuva, popular medicinal plants of Northeastern Brazil with proven antimicrobial and antiinflammatory properties. Periodontal disease is associated with inflammation and microbiological proliferation, thus the study aimed to investigate the effect of a topical gel based on carvacrol and chalcones in the experimental periodontal disease (EPD) in rats. Animals were treated with carvacrol and/or chalcones gel, immediately after EPD induction, three times a day for 11 days. Appropriate controls were included in the study. Animals were weighed daily. They were killed on day 11, the mandibles dissected and alveolar bone loss was measured. The periodontium were examined at histopathology and the neutrophil influx into the gingiva was assayed using myeloperoxidase activity. The bacterial flora were assessed through culture of the gingival tissue. Alveolar bone loss was significantly (p < 0.05) inhibited by combined carvacrol and chalcones gel, compared with the vehicle and non-treated groups. The treatment with the combined gel reduced tissue lesion at histopathology, decreased myeloperoxidase activity in gingival tissue and inhibited the growth of oral microorganisms as well as the weight loss. Carvacrol and chalcones combination gel has a beneficial effect upon EPD in this model. PMID:18338370

  10. Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

    Science.gov (United States)

    Subramanian, M.; Vanangamudi, G.; Thirunarayanan, G.

    2013-06-01

    A series of 2,5-dimethyl-3-furyl chalcones [2E-1-(2,5-dimethyl-3-furyl)-3-(substituted phenyl)-2-propen-1-ones] have been synthesized by Hydrotalcite catalyzed aldol condensation between 3-acetyl-2,5-dimethylfuron and substituted benzaldehydes. Yields of chalcones are more than 80%. These chalcones were characterized by their physical constants and spectral data. The group frequencies of infrared ν(cm-1) of CO s-cis and s-trans, CH in-plane and out of plane, CHdbnd CH out of plane, lbond2 Cdbnd Crbond2 out of plane modes, NMR chemical shifts δ(ppm) of Hα, Hβ, CO, Cα and Cβ of these chalcones were correlated with Hammett substituent constants, F and R parameters using single and multi-regression analyses. From the results of statistical analyses, the effects of substituents on the group frequencies are explained. Antibacterial, antifungal and insect antifeedant activities of these chalcones have been studied.

  11. Genotoxic, Cytotoxic, Antigenotoxic, and Anticytotoxic Effects of Sulfonamide Chalcone Using the Ames Test and the Mouse Bone Marrow Micronucleus Test.

    Directory of Open Access Journals (Sweden)

    Carolina Ribeiro E Silva

    Full Text Available Chalcones present several biological activities and sulfonamide chalcone derivatives have shown important biological applications, including antitumor activity. In this study, genotoxic, cytotoxic, antigenotoxic, and anticytotoxic activities of the sulfonamide chalcone N-{4-[3-(4-nitrophenylprop-2-enoyl]phenyl} benzenesulfonamide (CPN were assessed using the Salmonella typhimurium reverse mutation test (Ames test and the mouse bone marrow micronucleus test. The results showed that CPN caused a small increase in the number of histidine revertant colonies in S. typhimurium strains TA98 and TA100, but not statistically significant (p > 0.05. The antimutagenicity test showed that CPN significantly decreased the number of His+ revertants in strain TA98 at all doses tested (p 0.05. Additionally, CPN co-administered with MMC significantly increased PCE/NCE ratio at all doses tested, demonstrating its anticytotoxic effect. In summary, CPN presented genotoxic, cytotoxic, antigenotoxic, and anticytotoxic properties.

  12. Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core.

    Science.gov (United States)

    Ötvös, Sándor B; Hsieh, Chi-Ting; Wu, Yang-Chang; Li, Jih-Heng; Chang, Fang-Rong; Fülöp, Ferenc

    2016-01-01

    Flow chemistry-based syntheses of deuterium-labeled analogs of important antidiabetic chalcones were achieved via highly controlled partial C≡C bond deuteration of the corresponding 1,3-diphenylalkynones. The benefits of a scalable continuous process in combination with on-demand electrolytic D2 gas generation were exploited to suppress undesired over-reactions and to maximize reaction rates simultaneously. The novel deuterium-containing chalcone derivatives may have interesting biological effects and improved metabolic properties as compared with the parent compounds. PMID:26959006

  13. Synthesis and Anti-Bacterial Activities of a Bis-Chalcone Derived from Thiophene and Its Bis-Cyclized Products

    OpenAIRE

    Asiri, Abdullah M.; Khan, Salman A.

    2011-01-01

    A chalcone was prepared by the reaction of terephthalaldehyde with 3-acetyl-2,5-dimethylthiophene. Treatment of this chalcone with thiosemicarbazide/phenyl hydrazine/guanidine hydrochloride/thiourea afforded the corresponding pyrazoline,  pyrazole, and pyrimidine in good yields. All the new compounds have been characterized by IR, 1H-NMR, 13C-NMR, GC-MS and elemental analyses. The anti-bacterial activity of these compounds were first tested in vitro by the disk diffusion assay against two Gra...

  14. Synthesis, growth, vibrational spectral investigations and structure-property relationship of an organic NLO crystal: 3,4-Dimethoxy chalcone

    Science.gov (United States)

    Alen, S.; Sajan, D.; Joseph, Lynnette; Chaitanya, K.; Shettigar, Venkataraya; Jothy, V. Bena

    2015-09-01

    3,4-Dimethoxy chalcone, a nonlinear optical material, was synthesized and noncentro symmetric single crystals were grown in solution by slow evaporation technique. Thermal analysis such as DSC revealed a good thermal stability of 3,4-dimethoxy chalcone. The FT-IR and FT-Raman spectral studies were carried out to investigate the structural properties of the title compound. The molecular orbitals and natural bond analysis of this material were calculated by Density Functional Theory calculations. The second harmonic conversion efficiency was determined using the Kurtz powder technique, which is 8 times that of urea.

  15. Synthesis and Regioselective Reaction of Some Unsymmetrical Heterocyclic Chalcone Derivatives and Spiro Heterocyclic Compounds as Antibacterial Agents

    OpenAIRE

    El-Hashash, Maher A.; Rizk, Sameh A.; Saad R. Atta-Allah

    2015-01-01

    A number of novel heterocyclic chalcone derivatives can be synthesized by thermal and microwave tools. Treatment of 4-(4-Acetylamino- and/or 4-bromo-phenyl)-4-oxobut-2-enoic acids with hydrogen peroxide in alkaline medium were afforded oxirane derivatives 2. Reaction of the epoxide 2 with 2-amino-5-aryl-1,3,4-thiadiazole derivatives yielded chalcone of imidazo[2,1-b]thiadiazole derivative 4 via two thermal routes. In one pot reaction of 4-bromoacetophenone, diethyloxalate, and 2-amino-5-aryl-...

  16. Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core

    Directory of Open Access Journals (Sweden)

    Sándor B. Ötvös

    2016-03-01

    Full Text Available Flow chemistry-based syntheses of deuterium-labeled analogs of important antidiabetic chalcones were achieved via highly controlled partial C≡C bond deuteration of the corresponding 1,3-diphenylalkynones. The benefits of a scalable continuous process in combination with on-demand electrolytic D2 gas generation were exploited to suppress undesired over-reactions and to maximize reaction rates simultaneously. The novel deuterium-containing chalcone derivatives may have interesting biological effects and improved metabolic properties as compared with the parent compounds.

  17. Synthetic Chalcones with Potent Antioxidant Ability on H2O2-Induced Apoptosis in PC12 Cells

    OpenAIRE

    Jian-Zhang Wu; Chan-Chan Cheng; Lai-Lai Shen; Zhan-Kun Wang; Shou-Biao Wu; Wu-Lan Li; Su-Hua Chen; Rong-Ping Zhou; Pei-Hong Qiu

    2014-01-01

    Chalcone derivatives (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one and (E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one (Compounds 1 and 2) have been demonstrated to be potent anti-inflammatory agents in our previous study. In light of the relationship of intracellular mechanisms between anti-inflammatories and antioxidants, we further designed and synthesized a series of chalcone derivatives based on 1 and 2, to explore their antioxidant efficacy. The maj...

  18. Synthetic Chalcones with Potent Antioxidant Ability on H2O2-Induced Apoptosis in PC12 Cells

    OpenAIRE

    Wu, Jian-Zhang; Cheng, Chan-Chan; Shen, Lai-Lai; Wang, Zhan-Kun; Wu, Shou-Biao; Li, Wu-Lan; Chen, Su-Hua; Zhou, Rong-Ping; Qiu, Pei-Hong

    2014-01-01

    Chalcone derivatives (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one and (E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one (Compounds 1 and 2) have been demonstrated to be potent anti-inflammatory agents in our previous study. In light of the relationship of intracellular mechanisms between anti-inflammatories and antioxidants, we further designed and synthesized a series of chalcone derivatives based on 1 and 2, to explore their antioxidant efficacy. The major...

  19. In vitro and in vivo anti-glioma activity of a chalcone-quinoxaline hybrid.

    Science.gov (United States)

    Loch-Neckel, Gecioni; Bicca, Maíra Assunção; Leal, Paulo César; Mascarello, Alessandra; Siqueira, Jarbas Mota; Calixto, João B

    2015-01-27

    Chalcones are important compounds that exhibit multiple biological activities, including anti-inflammatory, antimitotic and antibacterial properties. In the present study, we have analyzed the potential anti-cancer activity of a chalcone named N9 (a hybrid chalcone-quinoxaline compound) using in vitro and in vivo experimental glioma models. Here, we report N9-induced inhibition of cell proliferation and also N9-induced cell death in a concentration-dependent manner in U87-MG glioma cells. These effects of N9 appear to be associated with its ability to inhibit the expression of cell cycle-associated proteins, and also the augmentation in the expression of the p21 (p21/Cip1) protein, a cyclin-dependent kinase inhibitor. Additionally, N9 also potentiates the production of the pro-apoptotic markers Bax and p53 via inhibition of MDM2. Moreover, our results show that N9 also significantly enhanced apoptosis of U87-MG cells with disruption of mitochondrial membrane potential, generation of ROS and caspase-9 activation. In vivo experiments carried out in a murine xenograft model of U87-MG revealed that N9 produced a significant reduction of tumors volume when compared to vehicle treated mice. Collectively, data demonstrate that N9 possess in vitro and in vivo anti-cancer activity, an effect that seems to involve the induction of p53 and p21 proteins, as well as, the activation of mitochondrial apoptosis pathway associated with the inhibition of protein MDM2. Overall, this study suggests N9 is affecting a variety of intracellular pathways related to tumor apoptosis. Perhaps N9 or derivate molecules could represent new potential drugs for cancer therapeutics. PMID:25461314

  20. Synthesis of α,β-Unsaturated Ketones as Chalcone Analogues via a SRN1 Mechanism

    OpenAIRE

    Patrice Vanelle; Armand Gellis; Christophe Curti

    2007-01-01

    An electron-transfer chain reaction between 2-nitropropane anion and α-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form α,β-unsaturated ketones via a SRN1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues....

  1. The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans.

    Science.gov (United States)

    Wang, Yuan-Hua; Dong, Huai-Huai; Zhao, Fei; Wang, Jie; Yan, Fang; Jiang, Yuan-Ying; Jin, Yong-Sheng

    2016-07-01

    To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2'-hydroxy-4'-methoxychalcone (8) exhibited the most potent in vitro (FICI=0.007) effects. The structure activity relationship of the compounds are then discussed. PMID:27210436

  2. Synthesis and Evaluation of 125I Labeled Chalcone Derivatives Containing Bithiophene Moiety as Potential Aβ Probes

    OpenAIRE

    Peng, Cheng; CUI Meng-chao; LIANG, ZHI-GANG; Liu, Ting-Ting

    2015-01-01

    In continuation of the investigation on the bithiophene structure as potential Aβ probes, two halogenated chalcone derivatives containing bithiophene moiety were designed and evaluated as imaging probes for Aβ plaques. In vitro fluorescence staining indicated that they could stain Aβ plaques in the brain sections of AD model mice specifically, in vitro binding assay further confirmed that they displayed high binding affinities to Aβ aggregates (Ki=2.33 nM and 0.88 nM). One radio-iodinated pro...

  3. Superior characteristics of organic chalcone single crystals as efficient nonlinear optical material

    Science.gov (United States)

    Kiran, A. John; Kim, H. C.; Kim, K.; Rotermund, F.; Ravindra, H. J.; Dharmaprakash, S. M.; Lim, H.

    2008-03-01

    High-quality biaxial single crystals of chalcone derivatives were grown by solution growth technique. Their molecular structures were designed to possess large second-order nonlinearities by choosing proper donor/acceptor groups while retaining a high transparency in the visible and infrared spectral regions. The second-order nonlinear optical coefficients, determined by applying the Maker fringe technique, were found to be much larger than those of LiB3O5, KTiOPO4, KH2PO4, and urea. The advantages, such as easy synthesis and crystal growth, low cutoff wavelength (7.2GW/cm2), make these organic crystals promising for efficient frequency doubling.

  4. Synthesis, characterization and dynamic NMR studies of a novel chalcone based N-substituted morpholine derivative

    Science.gov (United States)

    Baskar, R.; Baby, C.; Moni, M. S.; Subramanian, K.

    2013-05-01

    The synthesis of a novel chalcone based N-substituted morpholine derivative namely, (E)-1-(biphenyl-4-yl)-3-(4-(5-morpholinopentyloxy) phenyl) prop-2-en-1-one (BMPP), using a two step protocol is reported. The compound is characterized by FTIR, GC-MS and FTNMR spectroscopy techniques. Advanced 2D NMR techniques such as gradient enhanced COSY, HSQC, HMBC and NOESY were employed to establish through-bond and through-space correlations. Dynamic NMR measurements were carried out to obtain the energy barrier to ring inversion of the morpholine moiety.

  5. Novel Chalcone-Thiazole Hybrids as Potent Inhibitors of Drug Resistant Staphylococcus aureus.

    Science.gov (United States)

    Sashidhara, Koneni V; Rao, K Bhaskara; Kushwaha, Pragati; Modukuri, Ram K; Singh, Pratiksha; Soni, Isha; Shukla, P K; Chopra, Sidharth; Pasupuleti, Mukesh

    2015-07-01

    A series of novel hybrids possessing chalcone and thiazole moieties were synthesized and evaluated for their antibacterial activities. In general this class of hybrids exhibited potency against Staphylococcus aureus, and in particular, compound 27 exhibited potent inhibitory activity with respect to other synthesized hybrids. Furthermore, the hemolytic and toxicity data demonstrated that the compound 27 was nonhemolytic and nontoxic to mammalian cells. The in vivo studies utilizing a S. aureus septicemia model demonstrated that compound 27 was as potent as vancomycin. The results of antibacterial activities underscore the potential of this scaffold that can be utilized for developing a new class of novel antibiotics. PMID:26191371

  6. Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms.

    Science.gov (United States)

    Karaman, Isa; Gezegen, Hayreddin; Gürdere, M Burcu; Dingil, Alparslan; Ceylan, Mustafa

    2010-02-01

    In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined. PMID:20151389

  7. DFT study and microbiology of some coumarin-based compounds containing a chalcone moiety

    Directory of Open Access Journals (Sweden)

    Špirtović-Halilović Selma

    2014-01-01

    Full Text Available In the present investigation, a series of coumarin-based compounds containing a chalcone moiety were studied for their in vitro and in silico properties. DFT global chemical reactivity descriptors (chemical hardness, total energy, electronic chemical potential and electrophilicity are calculated for four synthesized compounds and used to predict their relative stability and reactivity. The antibacterial activities of all compounds have been screened against Bacillus subtilis (ATCC No. 6633 and Bacillus cereus (ATCC No. 11778. Quantum-chemical calculations indicate that antibacterial activity correlates well with chemical reactivity descriptors of molecules.

  8. Conjugate Addition of Indoles to α,β-Unsaturated Ketones (Chalcones) Catalyzed by KHSO4 under Ultrasonic Conditions

    Institute of Scientific and Technical Information of China (English)

    ZENG Xiao-Fei; JI Shun-Jun; SHEN Shu-Su

    2007-01-01

    Conjugate addition of indoles to a variety of α,β-unsaturated ketones (chalcones) mediated by a catalytic amount of KHSO4 at room temperature under ultrasonic conditions to afford the corresponding Michael adducts in good to excellent yields was reported.

  9. Synthesis, crystal structure and spectral characteristics of highly fluorescent chalcone-based coumarin in solution and in polymer matrix

    Czech Academy of Sciences Publication Activity Database

    Ghouili, A.; Dušek, Michal; Petříček, Václav; Ben Ayed, T.; Ben Hassen, R.

    2014-01-01

    Roč. 75, č. 2 (2014), s. 188-193. ISSN 0022-3697 Grant ostatní: AV ČR(CZ) Praemium Academiae Institutional support: RVO:68378271 Keywords : coumarin chalcone * fluorescence * structure determination Subject RIV: BM - Solid Matter Physics ; Magnetism Impact factor: 1.853, year: 2014

  10. Design, synthesis, molecular docking and biological evaluation of new dithiocarbamates substituted benzimidazole and chalcones as possible chemotherapeutic agents.

    Science.gov (United States)

    Bacharaju, Keerthana; Jambula, Swathi Reddy; Sivan, Sreekanth; Jyostnatangeda, Saritha; Manga, Vijjulatha

    2012-05-01

    A series of novel dithiocarbamates with benzimidazole and chalcone scaffold have been designed synthesised and evaluated for their antimitotic activity. Compounds 4c and 9d display the most promising antimitotic activity with IC(50) of 1.66 μM and 1.52 μM respectively. PMID:22460028

  11. Iodine-catalyzed addition of 2-mercaptoethanol to chalcone derivatives: Synthesis of the novel β-mercapto carbonyl compounds

    OpenAIRE

    Gürkan Yerli; Hayreddin Gezegen; Mustafa Ceylan

    2012-01-01

    In this study, a series of novel β-mercapto carbonyl derivatives (3-(2-hydroxyethylthio)-1,3-diarylpropan-1-one) (5a-i) were prepared by addition of 2-mercaptoethanol (4) to chalcones (3a-i) in the presence of catalytic amount of iodine (10 mol %) in CH 2Cl 2.

  12. Iodine-catalyzed addition of 2-mercaptoethanol to chalcone derivatives: Synthesis of the novel β-mercapto carbonyl compounds

    Directory of Open Access Journals (Sweden)

    Gürkan Yerli

    2012-01-01

    Full Text Available In this study, a series of novel β-mercapto carbonyl derivatives (3-(2-hydroxyethylthio-1,3-diarylpropan-1-one (5a-i were prepared by addition of 2-mercaptoethanol (4 to chalcones (3a-i in the presence of catalytic amount of iodine (10 mol % in CH 2Cl 2.

  13. Enantioselective conjugate addition of diethylzinc to chalcone catalyzed by Co(acac)(2) and chiral amino alcohols

    NARCIS (Netherlands)

    de Vries, A.H.M.; Feringa, B.L.

    1997-01-01

    Co(acac)(2) in the presence of chiral ligands has been employed as catalyst for the enantioselective conjugate addition of diethylzinc to chalcone. With chiral amino alcohols derived from (+)-camphor, enantioselectivities up to 83% were achieved. (C) 1997 Elsevier Science Ltd.

  14. Iodobenzene diacetate-mediated isomerization of pyrazolyl chalcones and their cytotoxicity and anti-microbial activity

    Indian Academy of Sciences (India)

    Mahavir Parshad; Vikas Verma; Devinder Kumar; Balasubramanian Narasimhan; Smit Kour; Shashank Singh; Payare Lal Sangwan

    2015-03-01

    Synthesis of cis (E)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-phenyl/aryl/heteroarylprop-2-en-1-ones from 1-phenyl-3-methyl-4-acetylpyrazol-5-one was achieved in good yield. s-cis (E)-1-(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-arylprop-2-en-1-ones were isomerized to s-trans (E)-4-(3-(phenyl/aryl/heteroaryl)acryloyl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-ones using iodobenzene diacetate in dichloromethane at room temperature in excellent yield. The structure and geometry of these , -unsaturated ketones (pyrazolyl ketones) were established with the help of NMR, 2D NMR and HRMS techniques. The cytotoxicity of pyrazolyl chalcones showed that s-cis (E) 1-(5-Hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-methylphenyl)-prop-2-en-1-one is active at very low concentrations (IC50 13.3 M) against colon cancer cell line (HCT-116). The in vitro anti-microbial studies of pyrazolyl chalcones were also tested against grampositive (B. subtilis, S. aureus) and gram-negative bacteria (E. coli) and for anti-fungal activity against C. albicans and A. niger.

  15. Ultrasound accelerated Claisen-Schmidt condensation: A green route to chalcones

    International Nuclear Information System (INIS)

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This 'green' method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy

  16. Novel pyrazine analogs of chalcones: synthesis and evaluation of their antifungal and antimycobacterial activity.

    Science.gov (United States)

    Kucerova-Chlupacova, Marta; Kunes, Jiri; Buchta, Vladimir; Vejsova, Marcela; Opletalova, Veronika

    2015-01-01

    Infectious diseases, such as tuberculosis and invasive mycoses, represent serious health problems. As a part of our long-term efforts to find new agents for the treatment of these diseases, a new series of pyrazine analogs of chalcones bearing an isopropyl group in position 5 of the pyrazine ring was prepared. The structures of the compounds were corroborated by IR and NMR spectroscopy and their purity confirmed by elemental analysis. The susceptibility of eight fungal strains to the studied compounds was tested. The results have been compared with the activity of some previously reported propyl derivatives. The only strain that was susceptible to the studied compounds was Trichophyton mentagrophytes. It was found that replacing a non-branched propyl with a branched isopropyl did not have a decisive and unequivocal influence on the in vitro antifungal activity against T. mentagrophytes. In vitro activity against Trichophyton mentagrophytes comparable with that of fluconazole was exhibited by nitro-substituted derivatives. Unfortunately, no compound exhibited efficacy comparable with that of terbinafine, which is the most widely used agent for treating mycoses caused by dermatophytes. Some of the prepared compounds were assayed for antimycobacterial activity against M. tuberculosis H37Rv. The highest potency was also displayed by nitro-substituted compounds. The results of the present study are in a good agreement with our previous findings and confirm the positive influence of electron-withdrawing groups on the B-ring of chalcones on the antifungal and antimycobacterial activity of these compounds. PMID:25587786

  17. New antimicrobial combinations: substituted chalcones- oxacillin against methicillin resistant Staphylococcus aureus

    Directory of Open Access Journals (Sweden)

    Juan Manuel Talia

    2011-06-01

    Full Text Available Staphylococcus aureus, the most virulent Staphylococcus species, is also the prevalent pathogen isolated from hospitalized patients and the second most common from patients in outpatient settings. In general, bacteria have the genetic ability to transmit and acquire resistance to drugs, which are utilized as therapeutic agents. Related studies of antimicrobial activity indicate that crude extracts containing flavonoids, triterpenes and steroids have showed significative activity against several Staphylococcus aureus strains. Combination effects between flavonoids and antibiotics also have been reported. The aim of the present work was to investigate in vitro synergism between several chalcones substituted in combination with oxacillin, an antibiotic used conventionally against S. aureus ATCC 43 300 that is resistant to meticillin, using the kinetic turbidimetric method developed earlier. The results were satisfactory for all assayed combinations and in accordance with the mechanism of bacteriostatic inhibition previously proposed, except for 2´,4´-dihydroxy-3´-methoxychalcone - oxacillin. The best combination was 2´,3´-dihydroxychalcone - oxacillin (MIC: 11.2 μg/mL. Further investigations are needed to characterize the interaction mechanism with antibiotics. Thus, chalcones - oxacillin combination could lead to the development of new antibiotics against methicillin resistant S. aureus infection.

  18. Chalcone-based Selective Inhibitors of a C4 Plant Key Enzyme as Novel Potential Herbicides

    Science.gov (United States)

    Nguyen, G. T. T.; Erlenkamp, G.; Jäck, O.; Küberl, A.; Bott, M.; Fiorani, F.; Gohlke, H.; Groth, G.

    2016-06-01

    Weeds are a challenge for global food production due to their rapidly evolving resistance against herbicides. We have identified chalcones as selective inhibitors of phosphoenolpyruvate carboxylase (PEPC), a key enzyme for carbon fixation and biomass increase in the C4 photosynthetic pathway of many of the world’s most damaging weeds. In contrast, many of the most important crop plants use C3 photosynthesis. Here, we show that 2‧,3‧,4‧,3,4-Pentahydroxychalcone (IC50 = 600 nM) and 2‧,3‧,4‧-Trihydroxychalcone (IC50 = 4.2 μM) are potent inhibitors of C4 PEPC but do not affect C3 PEPC at a same concentration range (selectivity factor: 15–45). Binding and modeling studies indicate that the active compounds bind at the same site as malate/aspartate, the natural feedback inhibitors of the C4 pathway. At the whole plant level, both substances showed pronounced growth-inhibitory effects on the C4 weed Amaranthus retroflexus, while there were no measurable effects on oilseed rape, a C3 plant. Growth of selected soil bacteria was not affected by these substances. Our chalcone compounds are the most potent and selective C4 PEPC inhibitors known to date. They offer a novel approach to combat C4 weeds based on a hitherto unexplored mode of allosteric inhibition of a C4 plant key enzyme.

  19. Enzymatic Properties and Mutational Studies of Chalcone Synthase from Physcomitrella patens

    Directory of Open Access Journals (Sweden)

    Mahiran Basri

    2012-08-01

    Full Text Available PpCHS is a member of the type III polyketide synthase family and catalyses the synthesis of the flavonoid precursor naringenin chalcone from p-coumaroyl-CoA. Recent research reports the production of pyrone derivatives using either hexanoyl-CoA or butyryl-CoA as starter molecule. The Cys-His-Asn catalytic triad found in other plant chalcone synthase predicted polypeptides is conserved in PpCHS. Site directed mutagenesis involving these amino acids residing in the active-site cavity revealed that the cavity volume of the active-site plays a significant role in the selection of starter molecules as well as product formation. Substitutions of Cys 170 with Arg and Ser amino acids decreased the ability of the PpCHS to utilize hexanoyl-CoA as a starter molecule, which directly effected the production of pyrone derivatives (products. These substitutions are believed to have a restricted number of elongations of the growing polypeptide chain due to the smaller cavity volume of the mutant’s active site.

  20. Electronic memory devices based on the chalcone with negative electrostatic potential regions

    Energy Technology Data Exchange (ETDEWEB)

    Yan, Bao-Long; Sun, Ru; Ge, Jian-Feng, E-mail: ge_jianfeng@hotmail.com; Wang, Dong; Li, Hua; Lu, Jian-Mei, E-mail: lujm@suda.edu.cn

    2013-10-01

    The molecular electrostatic potential (ESP) properties were used for the explanation of organic electric memory ability. Several chalcone compounds, owning a negative ESP region locates at the oxygen atom, were selected in this paper to validate the selection of compounds for organic memory materials. The synthesis, characterization, fabrication of the organic memory devices and the electrical properties for them were reported, and they were shown as WORM (write once read many times) type memory devices. The molecular geometries were optimized by the addition of a changeable electric field in the x direction inside the molecules using FF-DFT (Finite Field-Density Functionary Theory) method. The relationship between ESP of the molecules under different electric field and the property was discussed, and the mechanisms associated with the memory effect were also elucidated from DFT calculation results. - Highlights: • The molecular electrostatic potential (ESP) properties were used. • The chalcone compounds were used for the WORM type device. • The molecular geometries were optimized by the addition of a changeable electric field in the x direction. • The structure–property relationship was discussed.

  1. Synthesis, Antiviral Bioactivity of Novel 4-Thioquinazoline Derivatives Containing Chalcone Moiety

    Directory of Open Access Journals (Sweden)

    Zhihua Wan

    2015-06-01

    Full Text Available A series of novel 4-thioquinazoline derivatives containing chalcone moiety were designed, synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited moderate to good anti-TMV activity. In particular, compounds M2 and M6 possessed appreciable protection activities against TMV in vivo, with 50% effective concentration (EC50 values of 138.1 and 154.8 μg/mL, respectively, which were superior to that of Ribavirin (436.0 μg/mL. The results indicated that chalcone derivatives containing 4-thioquinazoline moiety could effectively control TMV. Meanwhile, the structure-activity relationship (SAR of the target compounds, studied using the three-dimensional quantitative structure-activity relationship (3D-QSAR method of comparative molecular field analysis (CoMFA based on the protection activities against TMV, demonstrated that the CoMFA model exhibited good predictive ability with the cross-validated q2 and non-cross-validated r2 values of 0.674 and 0.993, respectively. Meanwhile, the microscale thermophoresis (MST experimental showed that the compound M6 may interaction with the tobacco mosaic virus coat protein (TMV CP.

  2. Functionalized chalcones with basic functionalities have antibacterial activity against drug sensitive Staphylococcus aureus.

    Science.gov (United States)

    Liu, X L; Xu, Y J; Go, M L

    2008-08-01

    A library of chalcones with basic functionalities were evaluated for antibacterial activity against drug sensitive strains of Staphylococcus aureus and Escherichia coli. The most active compounds were 2-52 and 2-57 (MIC 6.3 microM S. aureus). These compounds had no activity against E. coli (MIC>100 microM). Both compounds were characterized by a ring A that was substituted with 2-hydroxy-4,6-dimethoxy-3-(1-methylpiperidin-4-yl) groups. The phenolic OH and 1-methylpiperidinyl groups were required for activity but the phenolic OH may play a more critical role. While the compounds were comparable to licochalcone A in terms of antibacterial activity, they caused less hemolysis of sheep erythrocytes at high concentrations (100 microM). It was noted that the structural requirements for limiting hemolytic activity were less stringent than those required for antibacterial activity. The present findings suggest that the chalcone framework is an attractive template for optimization to achieve better potency, lower toxicity and a wider spectrum of antibacterial activity. PMID:18031869

  3. A mutation in the rice chalcone isomerase gene causes the golden hull and internode 1 phenotype.

    Science.gov (United States)

    Hong, Lilan; Qian, Qian; Tang, Ding; Wang, Kejian; Li, Ming; Cheng, Zhukuan

    2012-07-01

    The biosynthesis of flavonoids, important secondary plant metabolites, has been investigated extensively, but few mutants of genes in this pathway have been identified in rice (Oryza sativa). The rice gold hull and internode (gh) mutants exhibit a reddish-brown pigmentation in the hull and internode and their phenotype has long been used as a morphological marker trait for breeding and genetic study. Here, we characterized that the gh1 mutant was a mutant of the rice chalcone isomerase gene (OsCHI). The result showed that gh1 had a Dasheng retrotransposon inserted in the 5′ UTR of the OsCHI gene, which resulted in the complete loss of OsCHI expression. gh1 exhibited golden pigmentation in hulls and internodes once the panicles were exposed to light. The total flavonoid content in gh1 hulls was increased threefold compared to wild type. Consistent with the gh1 phenotype, OsCHI transcripts were expressed in most tissues of rice and most abundantly in internodes. It was also expressed at high levels in panicles before heading, distributed mainly in lemmas and paleae, but its expression decreased substantially after the panicles emerged from the sheath. OsCHI encodes a protein functionally and structurally conserved to chalcone isomerases in other species. Our findings demonstrated that the OsCHI gene was indispensable for flux of the flavonoid pathway in rice. PMID:22286805

  4. Ultrasound accelerated Claisen-Schmidt condensation: A green route to chalcones

    Energy Technology Data Exchange (ETDEWEB)

    Calvino, V. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Picallo, M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Lopez-Peinado, A.J. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain); Martin-Aranda, R.M. [Dpto. de Quimica Inorganica y Quimica Tecnica, Facultad de Ciencias, Universidad Nacional de Educacion a Distancia (UNED), C/Senda del Rey, 9. E-28040 Madrid (Spain)]. E-mail: rmartin@ccia.uned.es; Duran-Valle, C.J. [Dpto. de Quimica Inorganica, Facultad de Ciencias, Universidad de Extremadura, Avenida de Elvas s/n., 06071 Badajoz (Spain)

    2006-06-30

    Chalcones have been synthesized under sonochemical irradiation by Claisen-Schmidt condensation between benzaldehyde and acetophenone. Two basic activated carbons (Na and Cs-Norit) have been used as catalysts. The effect of the ultrasound activation has been studied. A substantial enhancing effect in the yield was observed when the carbon catalyst was activated under ultrasonic waves. This 'green' method (combination of alkaline-doped carbon catalyst and ultrasound waves) has been applied to the synthesis of several chalcones with antibacterial properties achieving, in all cases, excellent activities and selectivities. A comparative study under non-sonic activation has showed that the yields are lower in silent conditions, indicating that the sonication exerts a positive effect on the activity of the catalyst. Cs-doped carbon is presented as the optimum catalyst, giving excellent activity for this type of condensation. Cs-Norit carbon catalyst can compete with the traditional NaOH/EtOH when the reaction is carried out under ultrasounds. The role of solvent in this reaction was studied with ethanol. High conversion was obtained in absence of solvent. The carbons were characterized by thermal analysis, nitrogen adsorption and X-ray photoelectron spectroscopy.

  5. Hydrogenation of chalcones using hydrogen permeating through a Pd and palladized Pd electrodes

    Energy Technology Data Exchange (ETDEWEB)

    Gutierrez, M., E-mail: mcgutier@unse.edu.a [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Nazareno, M.A. [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Sosa, V. [Departamento de Quimica Organica, Facultad de Ciencias Quimicas, Universidad Nacional de Cordoba, Agencia postal 4, Casilla 61, 5000, Cordoba (Argentina); Lopez de Mishima, B.A., E-mail: bmishima@unse.edu.a [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina); Mishima, H.T. [INQUINOA - CONICET, Instituto de Ciencias Quimicas, Facultad de Agronomia Agroindustrias, Universidad Nacional de Santiago del Estero, Avda, Belgrano (S) 1912, 4200, Santiago del Estero (Argentina)

    2010-08-01

    The hydrogenation of benzalacetone and benzalacetophenone was carried out using atomic hydrogen permeating through a palladium membrane. A two-compartment cell separated by a Pd sheet or a palladized Pd (Pd/Pd black) sheet electrode was employed. The reduction products were identified by (GC) gas chromatography, UV-vis absorption spectroscopy and NMR spectroscopy. The carbon-carbon double bond was hydrogenated and the benzylacetone and benzylacetophenone were obtained as products using palladium catalyst. The current efficiency for hydrogenation reaction increases when the current density for water electrolysis decreases and depends on the initial chalcone concentration. It is over 90% at the concentration of 10 mmol L{sup -1}. The hydrogen absorption and diffusion into and through a palladium membrane electrode has been studied by using an electrochemical impedance spectroscopy method. The impedance results would indicate that the hydrogen permeated through the membrane is consumed by the chalcone during the hydrogenation process keeping as the permeable boundary condition in the outer side of the Pd membrane the hydrogen activity almost zero. The hydrogen entering the metal through an adsorbed state and the rate of hydrogen absorption is diffusion-controlled.

  6. A facile synthesis of 1,2,3-triazolyl indole hybrids via SbCl3-catalysed Michael addition of indoles to 1,2,3-triazolyl chalcones

    Indian Academy of Sciences (India)

    Poovan Shanmugavelan; Murugan Sathishkumar; Sangaraiah Nagarajan; Alagusundaram Ponnuswamy

    2012-07-01

    An efficient, facile and environmentally benign synthesis of a library of 1,2,3-triazolyl chalcone hybrids (3a-u) has been accomplished by grinding the reactants at room temperature in excellent yields in very short reaction time. Subsequently, SbCl3 catalysed Michael addition of indoles to the chalcones afford 1,2,3-triazolyl indole hybrids (5a-l) in excellent yields.

  7. Molecular structures of chalcone podands: A prognosis of photoinduced transformations in the crystals

    Science.gov (United States)

    Ovchinnikova, I. G.; Fedorova, O. V.; Slepukhin, P. A.; Litvinov, I. A.; Rusinov, G. L.

    2009-01-01

    A series of chalcone podands with the propenone group in the ortho position of the bridging aryl substituent with respect to the oxyethylene fragment is synthesized. The influence of the preorganization of the chalcone podand molecules in crystals on their ability to participate in topochemical reactions is investigated. From analyzing the X-ray structural data, the highest probability of the solid-state photochemical [2 + 2]cycloaddition is predicted for podands with phenyl substituents and the oxyethylene fragment containing two or three oxygen atoms. The X-ray structural data for the chalcone podand C32H26O4 ( 3a) are as follows: a = 7.904(9) Å, b = 14.92(2) Å, c = 21.30(3) Å, β = 91.7(1)°, monoclinic system, space group P21/ c, Z = 4, V = 2510(5) Å3, ρ = 1.26 g/cm3, and R = 0.046; C34H30O5 ( 3b): a = 15.738(9) Å, b = 11.889(2) Å, c = 15.0830(15) Å, β = 105.47(14)°, monoclinic system, space group C2/ c, Z = 4, V = 2720.0(9) Å3, ρ = 1.266 g/cm3, and R = 0.0418; C32H24N2O8 ( 4a): a = 17.9416(18) Å, b = 10.9703(8) Å, c = 41.699(2) Å, β = 105.970(11)°, monoclinic system, space group P21/ c, Z = 4, V = 2781.4(5) Å3, ρ = 1.348 g/cm3, and R = 0.0426; C36H32N2O10 ( 4c): a = 7.6286(5)Å, b = 17.9398(10) Å, c = 11.5890(3)Å, β = 95.287(4)°, monoclinic system, space group P21/ n, Z = 2, V = 1579.27(14) Å3, ρ = 1.372 g/cm3, and R = 0.0377; and C28H22O6 ( 5a): a = 15.6032(10) Å, b = 8.1131(5) Å, c = 17.7334(11) Å, β = 91.381(5)°, monoclinic system, space group C2/ c, Z = 4, V = 2244.2(2) Å3, ρ = 1.345 g/cm3, and R = 0.0309.

  8. Structural correlation of some heterocyclic chalcone analogues and evaluation of their antioxidant potential.

    Science.gov (United States)

    Kumar, C S Chidan; Loh, Wan-Sin; Ooi, Chin Wei; Quah, Ching Kheng; Fun, Hoong-Kun

    2013-01-01

    A series of six novel heterocyclic chalcone analogues 4(a-f) has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC₀ values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent. PMID:24077177

  9. Structural Correlation of Some Heterocyclic Chalcone Analogues and Evaluation of Their Antioxidant Potential

    Directory of Open Access Journals (Sweden)

    Hoong-Kun Fun

    2013-09-01

    Full Text Available A series of six novel heterocyclic chalcone analogues 4(a–f has been synthesized by condensing 2-acetyl-5-chlorothiophene with benzaldehyde derivatives in methanol at room temperature using a catalytic amount of sodium hydroxide. The newly synthesized compounds are characterized by IR, mass spectra, elemental analysis and melting point. Subsequently; the structures of these compounds were determined using single crystal X-ray diffraction. All the synthesized compounds were screened for their antioxidant potential by employing various in vitro models such as DPPH free radical scavenging assay, ABTS radical scavenging assay, ferric reducing antioxidant power and cupric ion reducing antioxidant capacity. Results reflect the structural impact on the antioxidant ability of the compounds. The IC50 values illustrate the mild to good antioxidant activities of the reported compounds. Among them, 4f with a p-methoxy substituent was found to be more potent as antioxidant agent.

  10. Synthesis, characterization and antiamoebic activity of chalcones bearing N-substituted ethanamine tail.

    Science.gov (United States)

    Leeza Zaidi, Saadia; Mittal, Sonam; Rajala, Maitreyi S; Avecilla, Fernando; Husain, Mohammad; Azam, Amir

    2015-06-15

    A series of chalcones (4-21) possessing N-substituted ethanamine were synthesized by the aldol condensation reaction of 1-(4-(2-substituted ethoxy)phenyl)ethanones with different aldehydes preceded by the reaction of 2-chloro N-substituted ethanamine hydrochloride and 4-hydroxy acetophenone. The structure of all the synthesized compounds was elucidated by various spectral and X-ray diffraction studies. The compounds were screened against HM1: IMSS strain of Entamoeba histolytica and cytotoxicity was performed on A549 (non-small cell lung cancer cell line) cells by MTT assay. Out of eighteen compounds twelve showed better activity then the standard drug metronidazole. The compound 9, 14 and 19 showed good cell viability, hence were least toxic. PMID:26021707

  11. An anther-specific chalcone synthase-like gene D5 related to rice pollen development

    Institute of Scientific and Technical Information of China (English)

    2000-01-01

    It was shown in a previous analysis that D5 gene from rice (Oryza sativa L.) was an anther-specific gene encoding a chalcone synthase-related protein. In this study, D5 gene was found specifically expressed in tapetum cells as well as in the peripheral cells of the vascular bundle of rice anthers by RNA in situ hybridization. In order to study its function, D5 was transformed into rice in both sense and antisense directions driven by a rice Actin 1 promoter. It has been observed that the pollen grains from the antisense D5 transgenic rice plants are abnormal, indicating that D5 plays a critical role in rice pollen development.

  12. Solid state structural and theoretical investigations of a biologically active chalcone

    Science.gov (United States)

    Abbas, Asghar; Gökce, Halil; Bahceli, Semiha; Bolte, Michael; Naseer, Muhammad Moazzam

    2016-05-01

    The computational methods are presently emerging as an efficient and reliable tool for predicting structural properties of biologically important compounds. In the present manuscript, the solid state structural and theoretical investigations of a biologically active chalcone i-e (E)-3-(4-(hexyloxy)phenyl)-1-phenylprop-2-en-1-one (6c) have been reported. The solid state structure of 6c was measured by X-ray crystallographic technique whereas the optimized molecular geometry, vibrational frequencies, the simulated UV-vis spectra (in gas and in methanol solvent), 1H and 13C NMR chemical shift (in gas and in chloroform solvent) values, HOMO-LUMO analysis, the molecular electrostatic potential (MEP) surface and thermodynamic parameters were calculated by using DFT/B3LYP method with 6-311++G(d,p) basis set in ground state. The results of the theoretical investigations were found to be in good agreement with experimental data.

  13. Design, synthesis and antiproliferative activity studies of novel dithiocarbamate-chalcone derivates.

    Science.gov (United States)

    Fu, Dong-Jun; Zhang, Sai-Yang; Liu, Ying-Chao; Zhang, Li; Liu, Jun-Ju; Song, Jian; Zhao, Ruo-Han; Li, Feng; Sun, Hui-Hui; Liu, Hong-Min; Zhang, Yan-Bing

    2016-08-15

    A series of novel dithiocarbamate-chalcone derivates were designed, synthesized and evaluated for antiproliferative activity against three selected cancer cell lines (EC-109, SK-N-SH and MGC-803). Majority of the synthesized compounds exhibited moderate to potent activity against all the cancer cell lines assayed. Particularly, compounds II2 and II5 exhibited the excellent growth inhibition against SK-N-SH with IC50 values of 2.03μM and 2.46μM, respectively. Further mechanism studies revealed that compound II2 could obviously inhibit the proliferation of SK-N-SH cells by inducing apoptosis and arresting the cell cycle at G0/G1 phase. PMID:27423479

  14. Synthesis and anti-proliferative activity of fluoro-substituted chalcones.

    Science.gov (United States)

    Burmaoglu, Serdar; Algul, Oztekin; Anıl, Derya Aktas; Gobek, Arzu; Duran, Gulay Gulbol; Ersan, Ronak Haj; Duran, Nizami

    2016-07-01

    A series of novel fluoro-substituted chalcone derivatives have been synthesized. All synthesized compounds were characterized by (1)H nuclear magnetic resonance (NMR), (13)C NMR, and elemental analysis. Their anti-proliferative activities were evaluated against five cancer cells lines, namely, A549, A498, HeLa, A375, and HepG2 using the MTT method. Most of the compounds showed moderate to high activity with IC50 values in the range of 0.029-0.729μM. Of all the synthesized compounds, 10 and 19 exhibited the most potent anti-proliferative activities against cancer cells, and 10 was identified as the most promising compound. PMID:27217001

  15. Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives.

    Science.gov (United States)

    Hussaini, Syed Mohammed Ali; Yedla, Poornachandra; Babu, Korrapati Suresh; Shaik, Thokhir B; Chityal, Ganesh Kumar; Kamal, Ahmed

    2016-07-01

    A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same as combretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulphorhodamine B(SRB) assay indicated compound 12c to be the most active compound from the series with GI50 value of 6.7 μm against the human liver carcinoma cell line HepG2. Interestingly, the intermediate 11c exhibited more promising cytotoxicity demonstrating GI50 value of 1.3 μm against the prostate cancer cell line DU145. Compounds 11c and 12c caused accumulation of cells in G2/M phase and inhibited tubulin polymerization. Furthermore, these compounds reduce the mitochondrial membrane potential and activate caspases 3 and 9, thereby indicating their ability to trigger apoptosis. PMID:26854643

  16. Synthesis and photoisomerization reactions of norbornadienes possessing chalcone chromophore and reactions of the formed quadricyclane derivatives

    Energy Technology Data Exchange (ETDEWEB)

    Hasegawa, Eietsu; Mukai, Toshio; Toda, Takashi

    1988-08-10

    For efficient utilization of solar light energy, 2-aroyl-3-arylnorbornadienes derivatives (1)(with long wave absorption band) which possess a chalcone chromophore were synthesized, and the photoisomerization reactions were investigated. (1) possess the absorption band in visible light region corresponding to the kind of substitutional group introduced. Quadricyclane derivatives (2) were formed with the quantum yields of 0.06-0.60 in the photoisomerizations though they differ correspond to the substitutional group. (2) were shifted easily to (1) with heating, furthermore, isomerizations of (2) to (1) were carried out in good yields by contact with silver perchlorate, trifluoroacetic acid and even with silica gel. Photoisomerization reactions of (2) gave tricyclane derivatives (7) added ethanol in high yield, in leaving at room temperature after mixing with ethanol. (1 fig, 7 tabs, 24 refs)

  17. Combinatorial synthesis, lead identification, and antitumor study of a chalcone-based positional-scanning library.

    Science.gov (United States)

    Ullah, Ahsan; Ansari, Farzana Latif; Nazir, Samina; Mirza, Bushra

    2007-02-01

    A 175-member chalcone library was designed and synthesized from seven differently substituted acetophenones (A(1)-A(7)) and 25 differently substituted aryl or heteroaryl aldehydes (B(1)-B(25)). Potential lead compounds were identified by deconvolution of a two-dimensional library matrix via positional scanning, and the members of the most-active sub-libraries were synthesized and screened against crown-gall tumors with the aid of the potato-disc assay. The resulting hits gave rise to significant antitumor activities, with no antibacterial effect on the tumor-producing bacterium Agrobacterium tumefaciens. Two identified lead structures, (2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one (A(1)B(9)) and the hydroxy analogue (2E)-3-(2-chlorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (A(2)B(9)), are promising candidates to be developed into highly effective anticancer chemotherapeutics. PMID:17311221

  18. Synthesis and Selective Cytotoxic Activities on Rhabdomyosarcoma and Noncancerous Cells of Some Heterocyclic Chalcones.

    Science.gov (United States)

    Do, Tuong-Ha; Nguyen, Dai-Minh; Truong, Van-Dat; Do, Thi-Hong-Tuoi; Le, Minh-Tri; Pham, Thanh-Quan; Thai, Khac-Minh; Tran, Thanh-Dao

    2016-01-01

    Chemically diverse heterocyclic chalcones were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against rhabdomyosarcoma (RMS) and noncancerous cell line (LLC-PK1). The influence of heteroaryl patterns on rings A and B was studied. Heterocycle functionalities on both rings, such as phenothiazine, thiophene, furan and pyridine were evaluated. Notably, the introduction of three methoxy groups at positions 3, 4, 5 on ring B appears to be critical for cytotoxicity. The best compound, with potent and selective cytotoxicity (IC50 = 12.51 μM in comparison with the value 10.84 μM of paclitaxel), contains a phenothiazine moiety on ring A and a thiophene heterocycle on ring B. Most of the potential compounds only show weak cytoxicity on the noncancerous cell line LLC-PK1. PMID:27005608

  19. Synthesis and Selective Cytotoxic Activities on Rhabdomyosarcoma and Noncancerous Cells of Some Heterocyclic Chalcones

    Directory of Open Access Journals (Sweden)

    Tuong-Ha Do

    2016-03-01

    Full Text Available Chemically diverse heterocyclic chalcones were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against rhabdomyosarcoma (RMS and noncancerous cell line (LLC-PK1. The influence of heteroaryl patterns on rings A and B was studied. Heterocycle functionalities on both rings, such as phenothiazine, thiophene, furan and pyridine were evaluated. Notably, the introduction of three methoxy groups at positions 3, 4, 5 on ring B appears to be critical for cytotoxicity. The best compound, with potent and selective cytotoxicity (IC50 = 12.51 μM in comparison with the value 10.84 μM of paclitaxel, contains a phenothiazine moiety on ring A and a thiophene heterocycle on ring B. Most of the potential compounds only show weak cytoxicity on the noncancerous cell line LLC-PK1.

  20. Molecular cloning and expression profiling of a chalcone synthase gene from Lamiophlomis rotata

    Indian Academy of Sciences (India)

    Qiao Feng; Geng Gui-Gong; Zeng Yang; Xie Hui-Chun; Jin Lan; Shang Jun; Chen Zhi

    2015-06-01

    Lamiophlomis rotata is a renowned Chinese medicinal plant. Chalcone synthase (CHS) is important in flavonoid and isoflavonoid biosynthesis, catalysing the formation of naringenin chalcone in plants. A full-length cDNA encoding the CHS gene was cloned from L. rotata based on the highly conserved CHS gene sequences of Labiatae plants. A blast search showed its homology (named LrCHS) with other CHS genes of Labiate plants. The full-length genomic DNA of LrCHS was 2026 bp with one intron of 651 bp, two exons of 178 bp and 998 bp, flanked by a 73 bp $5'$-UTR and a 126 bp $3'$-UTR. The cDNA sequence of the LrCHS gene had an 1176 bp open reading frame encoding a 391 amino acid protein of 42,798 Da. The CHS protein predicted from L. rotata showed 79–86% identity with CHS of other plant species. We conducted a phylogenetic analysis of nine families containing 48 plants and L. rotata based on the full amino acid sequences of CHS proteins. Consequently, LrCHS was located in the Labiatae branch. Additionally, we examined LrCHS gene expression patterns in different tissues by quantitative real-time PCR with specific primers. The expression analysis showed preferential expression of LrCHS in flowers and leaves during the flowering stage. Total flavonoid content and CHS gene expression exhibited similar patterns during L. rotata organ development. In agreement with its function as an elicitor-responsive gene, LrCHS expression was coordinated by methyl jasmonate and UV light, and induced between 6 and 18 h. These results provide a molecular basis for additional functional studies of LrCHS in L. rotata.

  1. Chalcone-imidazolone conjugates induce apoptosis through DNA damage pathway by affecting telomeres

    Directory of Open Access Journals (Sweden)

    Kamal Ahmed

    2011-04-01

    Full Text Available Abstract Background Breast cancer is one of the most prevalent cancers in the world and more than one million women are diagnosed leading to 410,000 deaths every year. In our previous studies new chalcone-imidazolone conjugates were prepared and evaluated for their anticancer activity in a panel of 53 human tumor cell lines and the lead compounds identified were 6 and 8. This prompted us to investigate the mechanism of apoptotic event. Results Involvement of pro-apoptotic protein (Bax, active caspase-9 and cleavage of retinoblastoma protein was studied. Interestingly, the compounds caused upregulation of p21, check point proteins (Chk1, Chk2 and as well as their phosphorylated forms which are known to regulate the DNA damage pathway. Increased p53BP1 foci by immunolocalisation studies and TRF1 suggested the possible involvement of telomere and associated proteins in the apoptotic event. The telomeric protein such as TRF2 which is an important target for anticancer therapy against human breast cancer was extensively studied along with proteins involved in proper functioning of telomeres. Conclusions The apoptotic proteins such as Bax, active caspase-9 and cleaved RB are up-regulated in the compound treated cells revealing the apoptotic nature of the compounds. Down regulation of TRF2 and upregulation of the TRF1 as well as telomerase assay indicated the decrease in telomeric length revealing telomeric dysfunction and thereby controlling the rapid rate of cell proliferation. In summary, chalcone-imidazolone conjugates displayed significant DNA damage activity particularly at telomeres and caused both apoptosis and senescence-like growth arrest which suggested that these compounds have potential activity against breast carcinoma.

  2. Theoretical and Experimental Study of Inclusion Complexes of β-Cyclodextrins with Chalcone and 2',4'-Dihydroxychalcone.

    Science.gov (United States)

    Sancho, Matias I; Andujar, Sebastian; Porasso, Rodolfo D; Enriz, Ricardo D

    2016-03-31

    The inclusion complexes formed by chalcone and 2',4'-dihydroxychalcone with β-cyclodextrin have been studied combining experimental (phase solubility diagrams, Fourier transform infrared spectroscopy) and molecular modeling (molecular dynamics, quantum mechanics/molecular mechanics calculations) techniques. The formation constants of the complexes were determined at different temperatures, and the thermodynamic parameters of the process were obtained. The inclusion of chalcone in β-cyclodextrin is an exothermic process, while the inclusion of 2',4'-dihydroxychalcone is endothermic. Free energy profiles, derived from umbrella sampling using molecular dynamics simulations, were constructed to analyze the binding affinity and the complexation reaction at a molecular level. Hybrid QM/MM calculations were also employed to obtain a better description of the energetic and structural aspects of the complexes. The intermolecular interactions that stabilize both inclusion complexes were characterized by means of quantum atoms in molecules theory and reduce density gradient method. The calculated interactions were experimentally observed using FTIR. PMID:26950264

  3. Synthesis and Anti-Bacterial Activities of a Bis-Chalcone Derived from Thiophene and Its Bis-Cyclized Products

    Directory of Open Access Journals (Sweden)

    Abdullah M. Asiri

    2011-01-01

    Full Text Available A chalcone was prepared by the reaction of terephthalaldehyde with 3-acetyl-2,5-dimethylthiophene. Treatment of this chalcone with thiosemicarbazide/phenyl hydrazine/guanidine hydrochloride/thiourea afforded the corresponding pyrazoline,  pyrazole, and pyrimidine in good yields. All the new compounds have been characterized by IR, 1H-NMR, 13C-NMR, GC-MS and elemental analyses. The anti-bacterial activity of these compounds were first tested in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria, and then the minimum inhibitory concentration (MIC was determined with the reference of standard drug chloramphenicol. The results showed that the pyrazoline derivative is better at inhibiting growth of both types of bacteria (Gram-positive and Gram-negative compared to chloramphenicol.

  4. Synthesis, crystal structure and spectral characteristics of highly fluorescent chalcone-based coumarin in solution and in polymer matrix

    Science.gov (United States)

    Ghouili, Afef; Dusek, Michal; Petricek, Vaclav; Ayed, Taïcir Ben; Hassen, Rached Ben

    2014-02-01

    A new coumarin chalcone 3-((2E)-3-(2-hydroxyphenyl) prop-2-enoyl)-4-hydroxy-2(H)-chromen-2-one was synthesized using the Claisen Schmidt reaction by the condensation of 3-acetyl-4-hydroxycoumarin and 2-hydroxybenzaldehyde using a mild organic base. This novel compound was characterized by 1H NMR, FT-IR and UV-vis spectroscopy. Single crystal X-ray diffraction investigation at low temperature (T=120 K) shows that this compound exhibits an intramolecular O3-H…O hydrogen bond, the coumarin ring and the phenyl group are nearly coplanar and the crystal packing is stabilized by intermolecular O3-H…O contacts and π-π stacking interactions. This ortho-hydroxyphenyl-4-hydroxycoumarin chalcone exhibits a strong blue-green emission under visible light excitation at 470 nm. The fluorescence behaviors of this compound doped in poly(methyl methacrylate) (PMMA) were investigated.

  5. Synthesis, characterization, theoretical, anti-bacterial and molecular docking studies of quinoline based chalcones as a DNA gyrase inhibitor.

    Science.gov (United States)

    Abdullah, Muhammad Imran; Mahmood, Asif; Madni, Murtaza; Masood, Sara; Kashif, Muhammad

    2014-06-01

    A series of fourteen (A1-A14) new qunioline based chalcones were synthesized by condensing 2,7-dichloro-8-methyl-3-formyl quinoline with acetophenone and acetylthiophenes, and subsequently characterized by IR, NMR and Mass spectroscopy. All the compounds were screened for antibacterial activities and found potentially active antibacterial agents. Bioassay, theoretical and dockings studies with DNA gyrase (the enzyme required for super coiling of DNA of bacteria) results showed that the type and positions of the substituents seemed to be critical for their antibacterial activities. The bromo and chloro substituted chalcone displayed high anti-bacterial activity. The A4 and A6 showed high interaction with DNA gyrase, contributing high free binding energy (ΔG -8.18 and -8.88 kcal). PMID:24747187

  6. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells.

    Science.gov (United States)

    Miranda, C L; Aponso, G L; Stevens, J F; Deinzer, M L; Buhler, D R

    2000-02-28

    The objective of this study was to determine if prenylchalcones (open C-ring flavonoids) and prenylflavanones from hops and beer are inducers of quinone reductase (QR) in the mouse hepatoma Hepa 1c1c7 cell line. All the prenylchalcones and prenylflavanones tested were found to induce QR but not CYP1A1 in this cell line. In contrast, the synthetic chalcone, chalconaringenin, and the flavanone, naringenin, with no prenyl or geranyl groups, were ineffective in inducing QR. The hop chalcones, xanthohumol and dehydrocycloxanthohumol hydrate, also induced QR in the Ah-receptor-defective mutant cell line, Hepa 1c1c7 bp(r)c1. Thus, the prenylflavonoids represent a new class of monofunctional inducers of QR. PMID:10737704

  7. Growth Inhibitory and Apoptosis-inducing Effects of Xanthohumol, a Prenylated Chalcone Present in Hops, in Human Prostate Cancer Cells

    OpenAIRE

    DEEB, D.; Gao, X; Jiang, H.; Arbab, A.S.; Dulchavsky, S. A.; Gautam, S.C.

    2010-01-01

    Promotion of apoptosis in cancer cells could potentially lead to the regression and improved prognosis of hormone-refractory prostate cancer. Xanthohumol (XN), a prenylated chalcone-derived from hops, has shown strong antitumorigenic activity towards diverse types of cancer cells. In the present study, the growth-inhibitory and apoptosis-inducing activity of XN was tested in hormone-sensitive and hormone-refractory human prostate cancer cells lines. Cell growth/viability assay (MTS) demonstra...

  8. The Effect of Trans-Chalcone on Amylase Activity, Blood Glucose and Lipid Levels in Diabetic and Non Diabetic Rats

    OpenAIRE

    Najafian, M.; Ebrahim-Habibi, A.; P Yaghmaei; Parivar, K.; Larijani, B.

    2011-01-01

    Introduction & Objective: Alpha amylase is the most important decomposing enzyme in starch. Digestion and absorption of starch in the intestine can be prevented and also the blood sugar levels can be controlled by restrain and control of alpha amylase. The aim of this study was to evaluate the effect of trans-chalcone on amylase activity, blood glucose and lipid levels in diabetic and non diabetic rats. Materials & Methods: This experimental study was conducted in 1388 at Tehran Universit...

  9. Inhibitory activity of cyclohexenyl chalcone derivatives and flavonoids of fingerroot, Boesenbergia rotunda (L.), towards dengue-2 virus NS3 protease.

    Science.gov (United States)

    Kiat, Tan Siew; Pippen, Richard; Yusof, Rohana; Ibrahim, Halijah; Khalid, Norzulaani; Rahman, Noorsaadah Abd

    2006-06-15

    Boesenbergia rotunda (L.) cyclohexenyl chalcone derivatives, 4-hydroxypanduratin A and panduratin A, showed good competitive inhibitory activities towards dengue 2 virus NS3 protease with the Ki values of 21 and 25 microM, respectively, whilst those of pinostrobin and cardamonin were observed to be non-competitive. NMR and GCMS spectroscopic data formed the basis of assignment of structures of the six compounds isolated. PMID:16621533

  10. Chalcone isomerase cDNA cloning and mRNA induction by fungal elicitor, wounding and infection

    OpenAIRE

    Mehdy, Mona C.; Lamb, Christopher J.

    1987-01-01

    The environmentally regulated synthesis of phenylpropanoid natural products was studied by examining the expression of the gene encoding chalcone isomerase (CHI). This enzyme catalyzes a step common to the synthesis of flavonoid pigments and isoflavonoid phytoalexins. A λgt11 library was constructed using mRNA from cell cultures of bean (Phaseolus vulgaris L.) treated with fungal elicitor. Two positive clones were obtained by screening 105 recombinants with an antiserum to purified bean CHI. ...

  11. Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD.

    OpenAIRE

    Allegretta, Giuseppe; Weidel, Elisabeth; Empting, Martin; Hartmann, Rolf W.

    2015-01-01

    A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the ac...

  12. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    OpenAIRE

    Elver Otero; Sebastián Vergara; Sara M. Robledo; Wilson Cardona; Miguel Carda; Vélez, Ivan D; Carlos Rojas; Felipe Otálvaro

    2014-01-01

    Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V) panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmani...

  13. New eco-friendly animal bone meal catalysts for preparation of chalcones and aza-Michael adducts

    Directory of Open Access Journals (Sweden)

    Riadi Yassine

    2012-06-01

    Full Text Available Abstract Two efficient reactions were successfully carried out using Animal Bone Meal (ABM and potassium fluoride or sodium nitrate doped ABMs as new heterogeneous catalysts under very mild conditions. After preparation and characterization of the catalysts, we first report their use in a simple and convenient synthesis of various chalcones by Claisen–Schmidt condensation and then in an aza-Michael addition involving several synthesized chalcones with aromatic amines. All the reactions were carried out at room temperature in methanol; the chalcone synthesis was also achieved in water environment under microwave irradiation. Doping ABM enhances the rate and yield at each reaction. Catalytic activities are discussed and the ability to re-use the ABM is demonstrated. Results For Claisen–Schmidt the use of ABM alone, yields never exceeded 17%. In each entry, KF/ABM and NaNO3/ABM (79-97% gave higher yields than using ABM alone under thermic condition. Also the reaction proceeded under microwave irradiation in good yields (72-94% for KF/ABM and 81-97% for NaNO3/ABM and high purity. For aza-Michael addition the use of ABM doped with KF or NaNO3 increased the catalytic activity remarkably. The very high yields could be noted (84-95% for KF/ABM and 81-94% for NaNO3/ABM. Conclusion The present method is an efficient and selective procedure for the synthesis of chalcones an aza-Michael adducts. The ABM and doped ABMs are a new, inexpensive and attractive solid supports which can contribute to the development of catalytic processes and reduced environmental problems.

  14. A study on CYP1A inhibitory action of E-2-(4'-methoxybenzylidene)-1-benzosuberone and some related chalcones and cyclic chalcone analogues

    International Nuclear Information System (INIS)

    In vivo investigation of E-2-(4'-methoxybenzylidene)-1-benzosuberone (4a) on the 7,12-dimethylbenz[a]anthracene (DMBA)-induced onco/tumor suppressor gene expressions suggested that inhibition of metabolic activation of DMBA might play a role in the observed activity of the compound. In order to explore this possible biological action we have investigated whether 4a and some of its structurally related analogues had inhibitory effects on the CYP1A enzymes. During our study 7-ethoxyresorufin O-dealkylation activity of CYP1A isoenzymes was measured in liver microsomes prepared from 3-methylcholanthrene treated male rats. Inhibition constants (Ki values) were determined by using different concentrations of 7-ethoxyresorufin and the investigated chalcones (1), E-2-benzylidene-1-indanones (2), -tetralones (3) and -benzosuberones (4). Each compound was found to be a strong competitive inhibitor of the CYP1A enzymes. Their inhibitory activity was comparable with or even higher than that of 7,8-benzoflavone, the known strong CYP1A inhibitor used as reference substance. By proper selection of the substituents on the benzylidene moiety we investigated how the inhibitory activity (Ki value) of 1-4 varied as a function of the ring size (n=0, 5, 6, 7) carbon atoms, and the nature as well as the position of the substituents. To test applicability of the previously set structural requirements for binding of xenobiotics to the CYP1A enzymes we compared some topological, physico-chemical and quantum mechanical parameters of 1-4 with 7-ethoxyresorufin and 7,8-benzoflavone, the investigated CYP1A substrate and inhibitor, respectively

  15. Synthesis of Chalcone with Phosphotungstic Acid Catalyst%磷钨酸催化合成查尔酮

    Institute of Scientific and Technical Information of China (English)

    谭昌会; 郑荣选; 罗淑云; 林俏焰

    2012-01-01

    文章研究了以间硝基苯甲醛和苯乙酮为原料,磷钨酸为催化剂,缩合反应合成查尔酮。考察了催化剂用量、反应温度、反应时间及溶剂醋酸用量等因素对反应的影响。结果表明合成查尔酮的较佳条件是:反应温度是118℃,反应的时间5 h,磷钨酸为4 g,乙酸用量为20 mL的条件下,查尔酮的收率达到63.7%。%The paper studied chalcone was synthesized by condensation reaction of nitrobenzaldehyde and acetophenone using phosphotungstic acid as catalyst.The results showed that the better synthesis of chalcone conditions: reaction temperature 118 ℃,reaction time 5 h,phosphotungstic acid 4 g,20 mL acetic acid under the conditions of dosage,the yield of chalcone reached 63.7 %.

  16. Studies of manufacturing controlled-release graphene acid and catalyzing synthesis of chalcone with Claisen-Schmidt condensation reaction

    Science.gov (United States)

    Li, Jihui; Feng, Jia; Li, Mei; Wang, Qiaolian; Su, Yumin; Jia, Zhixin

    2013-07-01

    In the paper, graphene acid (GA) was manufactured, using flake graphite as raw material, and the acidity and the structure of GA were characterized as well as. Then, chalcone was synthesized in the presence of GA, using acetophenone and benzaldehyde as the reactant. The results showed that the acidity of GA was for pH = 1.12 in aqueous solution, and it was structured by the graphene sheets with the spaces between the graphene sheet and the graphene sheet and sulfuric acid (H2SO4) and acetic acid (CH3CO2H) inside the spaces. At the same time, the results also exhibited that the chalcone yield was able to reach 60.36% when GA dosage was 5 g, and the chalcone yields could attain apart 60.36, 52.05 and 31.16% when 5 g of GA was used thrice. This shows that GA is not only a high-performance catalyst, but also a controlled-release catalyst.

  17. Synthesis, biological evaluation, mechanism of action and quantitative structure-activity relationship studies of chalcones as antibacterial agents.

    Science.gov (United States)

    Sivakumar, Ponnurengam Malliappan; Priya, Sobana; Doble, Mukesh

    2009-04-01

    Forty-eight chalcone analogs were synthesized and their in vitro antibacterial activity against Staphylococcus aureus NCIM 5021, Bacillus subtilis NCIM 2718, Phaseolus vulgaris NCIM 2813, Escherichia coli NCIM 2931, Salmonella typhi 2501 and Enterobacter aerogenes NCIM 5139 were evaluated by microdilution broth assay. Quantitative structure-activity relationships were developed for all the cases (r(2) = 0.68-0.79; r(2)(adj) = 0.58-0.78; q(2) = 0.51-0.68; F = 13.02-61.51). Size, polarizability, electron-donating/withdrawing and hydrophilic nature of the molecule determine the activity against these Gram-positive and Gram-negative bacteria. Staphylococcus aureus was the most and S. typhi was the least hydrophobic of these organisms. These chalcones act better against more hydrophobic organisms. The more active chalcones have log P between 1.5 and 3. Compound 24, one of the most active compounds, was found to act by damaging the cell wall of S. aureus. Slimicidal activity of five of the most active compounds (24, 31, 32, 34 and 37) was found to be in the range of 48-60% against S. aureus and 40-54% against E. coli. A correlation was observed among the hydrophobicity of the compounds, hydrophobicity of the bacterial cell surface and the antibacterial activity of the compound. PMID:19291103

  18. Synthesis, characterization and biological activities of novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units

    Directory of Open Access Journals (Sweden)

    Mustafa Ceylan

    2013-09-01

    Full Text Available Novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units were synthesized starting from 1,3-cyclohexadine (4 and maleic anhydride (5. Addition of maleic anhydride (5 to 1,3-cyclehexadine (4 gave an endo-adduct, 3a,4,7,7a-tetrahydro-4,7-ethano-2-benzofuran-1,3-dione (6, in 90% yield. Heating the solution of the adduct dione (6 and 1-(4-aminophenylethanone (7 in the presence of Et 3N in toluene at 110 oC for 24 hours afforded 2-(4-acetylphenyl-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3-dione (8 in high yield. Piperidine-catalyzed addition of benzaldehyde derivatives (9a-i to the compound 8 in CH 2Cl 2 at 55 oC gave the expected chalcone derivatives (10-i in the range of 42% - 96% yields. The antibacterial activities of the chalcone derivatives (10a-i were evaluated against human pathogenic microorganism and the compounds showed low activity compared to the standard, name of the standard.

  19. Molecular structures of chalcone podands: A prognosis of photoinduced transformations in the crystals

    Energy Technology Data Exchange (ETDEWEB)

    Ovchinnikova, I. G., E-mail: iov@ios.uran.ru; Fedorova, O. V.; Slepukhin, P. A. [Russian Academy of Sciences, I. Ya. Postovsky Institute of Organic Synthesis, Ural Division (Russian Federation); Litvinov, I. A., E-mail: litvinov@iopc.knc.ru [Russian Academy of Sciences, A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center (Russian Federation); Rusinov, G. L. [Russian Academy of Sciences, I. Ya. Postovsky Institute of Organic Synthesis, Ural Division (Russian Federation)

    2009-01-15

    A series of chalcone podands with the propenone group in the ortho position of the bridging aryl substituent with respect to the oxyethylene fragment is synthesized. The influence of the preorganization of the chalcone podand molecules in crystals on their ability to participate in topochemical reactions is investigated. From analyzing the X-ray structural data, the highest probability of the solid-state photochemical [2 + 2]cycloaddition is predicted for podands with phenyl substituents and the oxyethylene fragment containing two or three oxygen atoms. The X-ray structural data for the chalcone podand C{sub 32}H{sub 26}O{sub 4} (3a) are as follows: a = 7.904(9) A, b = 14.92(2) A, c = 21.30(3) A, {beta} = 91.7(1){sup o}, monoclinic system, space group P2{sub 1}/c, Z = 4, V = 2510(5) A{sup 3}, {rho} = 1.26 g/cm{sup 3}, and R = 0.046; C{sub 34}H{sub 30}O{sub 5} (3b): a = 15.738(9) A, b = 11.889(2) A, c = 15.0830(15) A, {beta} = 105.47(14){sup o}, monoclinic system, space group C2/c, Z = 4, V = 2720.0(9) A{sup 3}, {rho} = 1.266 g/cm{sup 3}, and R = 0.0418; C{sub 32}H{sub 24}N{sub 2}O{sub 8} (4a): a = 17.9416(18) A, b = 10.9703(8) A, c = 41.699(2) A, {beta} = 105.970(11){sup o}, monoclinic system, space group P2{sub 1}/c, Z = 4, V = 2781.4(5) A{sup 3}, {rho} = 1.348 g/cm{sup 3}, and R = 0.0426; C{sub 36}H{sub 32}N{sub 2}O{sub 10} (4c): a = 7.6286(5)A, b = 17.9398(10) A, c = 11.5890(3)A, {beta} = 95.287(4){sup o}, monoclinic system, space group P2{sub 1}/n, Z = 2, V = 1579.27(14) A{sup 3}, {rho} = 1.372 g/cm{sup 3}, and R = 0.0377; and C{sub 28}H{sub 22}O{sub 6} (5a): a = 15.6032(10) A, b = 8.1131(5) A, c = 17.7334(11) A, {beta} = 91.381(5){sup o}, monoclinic system, space group C2/c, Z = 4, V = 2244.2(2) A{sup 3}, {rho} = 1.345 g/cm{sup 3}, and R = 0.0309.

  20. Identification of Chalcones as Fasciola hepatica Cathepsin L Inhibitors Using a Comprehensive Experimental and Computational Approach

    Science.gov (United States)

    Ferraro, Florencia; Merlino, Alicia; dell´Oca, Nicolás; Gil, Jorge; Tort, José F.; Gonzalez, Mercedes; Cerecetto, Hugo; Cabrera, Mauricio

    2016-01-01

    Background Increased reports of human infections have led fasciolosis, a widespread disease of cattle and sheep caused by the liver flukes Fasciola hepatica and Fasciola gigantica, to be considered an emerging zoonotic disease. Chemotherapy is the main control measure available, and triclabendazole is the preferred drug since is effective against both juvenile and mature parasites. However, resistance to triclabendazole has been reported in several countries urging the search of new chemical entities and target molecules to control fluke infections. Methodology/Principle Findings We searched a library of forty flavonoid derivatives for inhibitors of key stage specific Fasciola hepatica cysteine proteases (FhCL3 and FhCL1). Chalcones substituted with phenyl and naphtyl groups emerged as good cathepsin L inhibitors, interacting more frequently with two putative binding sites within the active site cleft of the enzymes. One of the compounds, C34, tightly bounds to juvenile specific FhCL3 with an IC50 of 5.6 μM. We demonstrated that C34 is a slow-reversible inhibitor that interacts with the Cys-His catalytic dyad and key S2 and S3 pocket residues, determinants of the substrate specificity of this family of cysteine proteases. Interestingly, C34 induces a reduction in NEJ ability to migrate through the gut wall and a loss of motility phenotype that leads to NEJ death within a week in vitro, while it is not cytotoxic to bovine cells. Conclusions/Significance Up to date there are no reports of in vitro screening for non-peptidic inhibitors of Fasciola hepatica cathepsins, while in general these are considered as the best strategy for in vivo inhibition. We have identified chalcones as novel inhibitors of the two main Cathepsins secreted by juvenile and adult liver flukes. Interestingly, one compound (C34) is highly active towards the juvenile enzyme reducing larval ability to penetrate the gut wall and decreasing NEJ´s viability in vitro. These findings open new avenues

  1. Identification of Chalcones as Fasciola hepatica Cathepsin L Inhibitors Using a Comprehensive Experimental and Computational Approach.

    Directory of Open Access Journals (Sweden)

    Florencia Ferraro

    2016-07-01

    Full Text Available Increased reports of human infections have led fasciolosis, a widespread disease of cattle and sheep caused by the liver flukes Fasciola hepatica and Fasciola gigantica, to be considered an emerging zoonotic disease. Chemotherapy is the main control measure available, and triclabendazole is the preferred drug since is effective against both juvenile and mature parasites. However, resistance to triclabendazole has been reported in several countries urging the search of new chemical entities and target molecules to control fluke infections.We searched a library of forty flavonoid derivatives for inhibitors of key stage specific Fasciola hepatica cysteine proteases (FhCL3 and FhCL1. Chalcones substituted with phenyl and naphtyl groups emerged as good cathepsin L inhibitors, interacting more frequently with two putative binding sites within the active site cleft of the enzymes. One of the compounds, C34, tightly bounds to juvenile specific FhCL3 with an IC50 of 5.6 μM. We demonstrated that C34 is a slow-reversible inhibitor that interacts with the Cys-His catalytic dyad and key S2 and S3 pocket residues, determinants of the substrate specificity of this family of cysteine proteases. Interestingly, C34 induces a reduction in NEJ ability to migrate through the gut wall and a loss of motility phenotype that leads to NEJ death within a week in vitro, while it is not cytotoxic to bovine cells.Up to date there are no reports of in vitro screening for non-peptidic inhibitors of Fasciola hepatica cathepsins, while in general these are considered as the best strategy for in vivo inhibition. We have identified chalcones as novel inhibitors of the two main Cathepsins secreted by juvenile and adult liver flukes. Interestingly, one compound (C34 is highly active towards the juvenile enzyme reducing larval ability to penetrate the gut wall and decreasing NEJ´s viability in vitro. These findings open new avenues for the development of novel agents to control

  2. Photo-alignment of low-molecular mass nematic liquid crystals on photochemically bifunctional chalcone-epoxy film by irradiation of a linearly polarized UV light

    International Nuclear Information System (INIS)

    Photocrosslinkable chalcone-epoxy compound comprising 1,3-bis-(4-hydroxy-phenyl)-propenone was synthesized for fabricating the photo-alignment layer of liquid crystals. Chalcone group was introduced into the main chain unit of the epoxy oligomer. We observed a photodimerization behavior and an optical anisotropy of this material by irradiation of a linearly polarized UV(LP-UV) light. With a trace amount of cationic photo initiator (TRS-HFA), polymerization of epoxy groups was also conducted at the similar wavelength range used for photodimerization . Linearly polarized UV irradiation on the chalcone-epoxy films with cationic photoinitiator induced optical anisotropy of the film and the resultant film can be used for alignment layers for low molecular weight nematic liquid crystals

  3. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs

    Directory of Open Access Journals (Sweden)

    Oswal Nikhil

    2009-09-01

    Full Text Available Abstract Garcinol, harvested from Garcinia indica, has traditionally been used in tropical regions and appreciated for centuries; however its biological properties are only beginning to be elucidated. There is ample data to suggest potent antioxidant properties of this compound which have been used to explain most of its observed biological activities. However, emerging evidence suggests that garcinol could be useful as an anti-cancer agent, and it is increasingly being realized that garcinol is a pleiotropic agent capable of modulating key regulatory cell signaling pathways. Here we have summarized the progress of our current research knowledge on garcinol and its observed biological activities. We have also provided an explanation of observed properties based on its chemical structure and provided an insight into the structure and properties of chalcones, the precursors of garcinol. The available data is promising but more detailed investigations into the various properties of this compound, particularly its anti-cancer activity are urgently needed, and it is our hope that this review will stimulate further research for elucidating and appreciating the value of this nature's wonder agent.

  4. Chalcone synthase genes from milk thistle (Silybum marianum): isolation and expression analysis.

    Science.gov (United States)

    Sanjari, Sepideh; Shobbar, Zahra Sadat; Ebrahimi, Mohsen; Hasanloo, Tahereh; Sadat-Noori, Seyed-Ahmad; Tirnaz, Soodeh

    2015-12-01

    Silymarin is a flavonoid compound derived from milk thistle (Silybum marianum) seeds which has several pharmacological applications. Chalcone synthase (CHS) is a key enzyme in the biosynthesis of flavonoids; thereby, the identification of CHS encoding genes in milk thistle plant can be of great importance. In the current research, fragments of CHS genes were amplified using degenerate primers based on the conserved parts of Asteraceae CHS genes, and then cloned and sequenced. Analysis of the resultant nucleotide and deduced amino acid sequences led to the identification of two different members of CHS gene family,SmCHS1 and SmCHS2. Third member, full-length cDNA (SmCHS3) was isolated by rapid amplification of cDNA ends (RACE), whose open reading frame contained 1239 bp including exon 1 (190 bp) and exon 2 (1049 bp), encoding 63 and 349 amino acids, respectively. In silico analysis of SmCHS3 sequence contains all the conserved CHS sites and shares high homology with CHS proteins from other plants.Real-time PCR analysis indicated that SmCHS1 and SmCHS3 had the highest transcript level in petals in the early flowering stage and in the stem of five upper leaves, followed by five upper leaves in the mid-flowering stage which are most probably involved in anthocyanin and silymarin biosynthesis. PMID:26690515

  5. Integrated kinetic studies and computational analysis on naphthyl chalcones as mushroom tyrosinase inhibitors.

    Science.gov (United States)

    Radhakrishnan, Sini; Shimmon, Ronald; Conn, Costa; Baker, Anthony

    2015-10-01

    Melanin helps to protect skin from the damaging ultraviolet radiation of the sun. Tyrosinase, the key enzyme in melanogenesis is responsible for coloration of skin, hair and eyes. This enzyme is considered to have a critical role in governing the quality and economics of fruits and vegetables, as tyrosinase activity can lead to spoilage through browning. Development of tyrosinase inhibitors is a promising approach to combat hyperpigmentation conditions like ephelides, lentigo, freckles and post-inflammatory hyperpigmentation. In the present study, we have used a docking algorithm to simulate binding between tyrosinase and hydroxy-substituted naphthyl chalcone oxime compounds and studied the inhibition of tyrosinase. The results of virtual screening studies indicated that the estimated free energy of binding of all the docked ligands ranged between -19.29 and -9.12 kcal/mol. Two of the oximes synthesized were identified as competitive tyrosinase inhibitors and were found to be twice as potent as the control kojic acid with their IC50 values of 12.22 μM and 19.45 μM, respectively. This strategy of integrating experimental and virtual screening methods could give better insights to explore potent depigmentation agents. PMID:26318997

  6. Evolution of mustard (Brassica juncea Coss) subspecies in China: evidence from the chalcone synthase gene.

    Science.gov (United States)

    Chen, F B; Liu, H F; Yao, Q L; Fang, P

    2016-01-01

    To explore the phylogenetic relationship, genome donor, and evolutionary history of the polyploid mustard (Brassica juncea) from China, eighty-one sequences of the chalcone synthase gene (Chs) were analyzed in 43 individuals, including 34 B. juncea, 2 B. rapa, 1 B. nigra, 2 B. oleracea, 1 B. napus, 1 B. carinata, and 2 Raphanus sativus. A maximum likelihood analysis showed that sequences from B. juncea were separated into two well-supported groups in accordance with the A and B genomes, whereas the traditional phenotypic classification of B. juncea was not wholly supported by the molecular results. The SplitsTree analysis recognized four distinct groups of Brassicaceae, and the median-joining network analysis recognized four distinct haplotypes of Chs. The estimates of Tajima's D, Fu and Li's D, and Fu and Li's F statistic for the Chs gene in the B genome were negative, while those in the A genome were significant. The results indicated that 1) the Chs sequences revealed a high level of sequence variation in Chinese mustard, 2) both tree and reticulate evolutions existed, and artificial selection played an important role in the evolution of Chinese mustard, 3) the original parental species of Chinese mustard are B. rapa var. sinapis arvensis and B. nigra (derived from China), 4) nucleotide variation in the B genome was higher than that in the A genome, and 5) cultivated mustard evolved from wild mustard, and China is one of the primary origins of B. juncea. PMID:27173323

  7. Chalcone synthase genes from milk thistle (Silybum marianum): isolation and expression analysis

    Indian Academy of Sciences (India)

    Sepideh Sanjari; Zahra Sadat Shobbar; Mohsen Ebrahimi; Tahereh Hasanloo; Seyed-Ahmad Sadat-Noor; Soodeh Tirnaz

    2015-12-01

    Silymarin is a flavonoid compound derived from milk thistle (Silybum marianum) seeds which has several pharmacological applications. Chalcone synthase (CHS) is a key enzyme in the biosynthesis of flavonoids; thereby, the identification of encoding genes in milk thistle plant can be of great importance. In the current research, fragments of genes were amplified using degenerate primers based on the conserved parts of Asteraceae genes, and then cloned and sequenced. Analysis of the resultant nucleotide and deduced amino acid sequences led to the identification of two different members of gene family, 1 and 2. Third member, full-length cDNA (3) was isolated by rapid amplification of cDNA ends (RACE), whose open reading frame contained 1239 bp including exon 1 (190 bp) and exon 2 (1049 bp), encoding 63 and 349 amino acids, respectively. In silico analysis of SmCHS3 sequence contains all the conserved CHS sites and shares high homology with CHS proteins from other plants. Real-time PCR analysis indicated that 1 and 3 had the highest transcript level in petals in the early flowering stage and in the stem of five upper leaves, followed by five upper leaves in the mid-flowering stage which are most probably involved in anthocyanin and silymarin biosynthesis.

  8. Transcriptional activation of the parsley chalcone synthase promoter in heterologous pea and yeast systems.

    Science.gov (United States)

    Kalbin; Strid; Frohnmeyer

    1999-11-01

    Introduction by electroporation of different parsley (Petroselinum crispum) CHS-promoter/beta-glucuronidase(GUS)-reporter constructs into pea (Pisum sativum L.) protoplasts leads to a high constitutive GUS-expression and to the loss of the light-inducibility seen in the homologous parsley protoplast system. These results indicate that Unit 1 of the parsley CHS-promoter is only partly responsible for the GUS-expression detected. Instead, additional cis-elements, which are located downstream within 100 bp from the transcriptional start site, mediate the de-repression in pea protoplasts. In contrast, in yeast (Saccharomyces cerevisiae) cells, the GUS expression from the heterologous CHS/GUS construct is controlled by elements between Unit 1 and -100 bp. In both pea and yeast cells, transcription factors different from those regulating UV-responsiveness in parsley, are probably mediating the constitutive expression from the heterologous construct. The results with pea protoplasts imply that protoplastation of pea leaf cells itself induces de-repression as a result of stress to the protoplasts. This notion was strengthened by the finding that mRNA levels of the endogenous chalcone synthase were drastically increased as the result of the protoplastation procedure. PMID:10580282

  9. Synthesis, growth, structure and characterization of chalcone crystal: A novel organic NLO material

    Science.gov (United States)

    Agilandeshwari, R.; Meenatchi, V.; Meenakshisundaram, S. P.

    2016-08-01

    Single crystals of a chalcone, (E)-3-(4-bromophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (BHP), were grown by the slow evaporation solution growth technique. The structure is elucidated by single-crystal X-ray diffraction analysis and the crystal belongs to the monoclinic system with noncentrosymmetric space group P21. Optical studies reveal that the absorption is minimum in the visible region and the cut-off wavelength is at ∼468 nm. The band-gap energy was estimated by the application of the Kubelka-Munk algorithm. The powder X-ray diffraction pattern reveals the good crystallinity of the as-grown specimen. The vibrational patterns in FT-IR are used to identify the functional groups and thermal studies indicate the stability of the material. The second harmonic generation efficiency (SHG), as estimated by Kurtz and Perry powder technique, reveals the superior nonlinear optical character of this material. Hirshfeld surface analysis is done to quantify the intermolecular interactions, responsible for developing a nonlinear atmosphere. As-grown crystals were further characterized by SEM, NMR, mass spectrometry and elemental analysis.

  10. Molecular and Biochemical Analysis of Chalcone Synthase from Freesia hybrid in flavonoid biosynthetic pathway.

    Directory of Open Access Journals (Sweden)

    Wei Sun

    Full Text Available Chalcone synthase (CHS catalyzes the first committed step in the flavonoid biosynthetic pathway. In this study, the cDNA (FhCHS1 encoding CHS from Freesia hybrida was successfully isolated and analyzed. Multiple sequence alignments showed that both the conserved CHS active site residues and CHS signature sequence were found in the deduced amino acid sequence of FhCHS1. Meanwhile, crystallographic analysis revealed that protein structure of FhCHS1 is highly similar to that of alfalfa CHS2, and the biochemical analysis results indicated that it has an enzymatic role in naringenin biosynthesis. Moreover, quantitative real-time PCR was performed to detect the transcript levels of FhCHS1 in flowers and different tissues, and patterns of FhCHS1 expression in flowers showed significant correlation to the accumulation patterns of anthocyanin during flower development. To further characterize the functionality of FhCHS1, its ectopic expression in Arabidopsis thaliana tt4 mutants and Petunia hybrida was performed. The results showed that overexpression of FhCHS1 in tt4 mutants fully restored the pigmentation phenotype of the seed coats, cotyledons and hypocotyls, while transgenic petunia expressing FhCHS1 showed flower color alteration from white to pink. In summary, these results suggest that FhCHS1 plays an essential role in the biosynthesis of flavonoid in Freesia hybrida and may be used to modify the components of flavonoids in other plants.

  11. Isolation and characterization of a chalcone isomerase gene promoter from potato cultivars.

    Science.gov (United States)

    Chen, M; Zhu, W J; You, X; Liu, Y D; Kaleri, G M; Yang, Q

    2015-01-01

    Chalcone isomerase (CHI) is a key enzyme involved in anthocyanin metabolism. Previous research on CHI has mainly focused on cDNA cloning and gene expression. In the current study, the 1425-bp potato CHI promoter (PCP) was isolated from four potato cultivars (Heijingang, Zhongshu 7, Désirée, and Favorita) using PCR and DNA sequencing. The PCP contained many cis-regulatory elements (CREs) related to anthocyanin metabolism, tissue specificity, light response, stress, and hormone induction. Of the PCP CREs identified, 19 were common to those found in the higher plants examined, based on plant CRE databases. Multiple sequence alignment showed six single nucleotide variation sites in PCP among the potato cultivars examined, resulting in changes in the number of CREs connected with tissue specificity, anthocyanin metabolism, and light response. The 665-bp PCP fragments from Favorita and 1425-bp PCP fragments from Heijingang were used to construct plant expression vectors, which may be a useful tool for biological engineering. A transient expression assay demonstrated that the two PCP fragments from Heijingang could direct the expression of a green fluorescent protein gene in onion epidermis and a β-glucuronidase gene in all potato tuber tissues with different colors, suggesting that the single nucleotide variation in the PCP did not affect its activity, and that silencing of the CHI gene in Favorita may be attributed to other regulatory factors. PMID:26782538

  12. Measurement, correlation and dissolution thermodynamics of biological active chalcone in organic solvents at different temperatures

    International Nuclear Information System (INIS)

    Highlights: • Solubility of chalcone in maximum in non-polar solvent chloroform. • Among different alcohols, Solubility is maximum in 1-butanol and minimum in methanol. • The positive ΔH and ΔG suggest endothermic and spontaneous dissolution process. • The negative entropy in THF and ethyl acetate suggests more ordered structure in these solutions. • The positive entropy suggests less ordered structure in solutions. - Abstract: The present study reports the synthesis, characterization and solubility of (E)-2-(4-chlorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one. The compound was synthesized by standard process. The purity was monitored by TLC and confirmation of structure was done by using mass, IR and 1H NMR spectral techniques. Further, solubility study of this synthesized compound was conducted in methanol, ethanol, 1-propanol, 1-butanol, tetrahydrofuran (THF), ethyl acetate (EA), acetone (AC) and chloroform (CF) at temperatures ranging from (293.15 to 323.15) K under atmospheric pressure. Further, the solubility data were correlated against temperature and were found to increase with temperature. The modified Apelblat and Buchowski–Ksiazczak λh equations were used to correlate the experimental solubility data. Further, some thermodynamic parameters such as dissolution enthalpy (ΔH), Gibbs free energy (ΔG) and entropy (ΔS) of mixing have also been calculated. The positive enthalpy and Gibbs free energy values suggest the dissolution process to be endothermic and spontaneous

  13. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs.

    Science.gov (United States)

    Padhye, Subhash; Ahmad, Aamir; Oswal, Nikhil; Sarkar, Fazlul H

    2009-01-01

    Garcinol, harvested from Garcinia indica, has traditionally been used in tropical regions and appreciated for centuries; however its biological properties are only beginning to be elucidated. There is ample data to suggest potent antioxidant properties of this compound which have been used to explain most of its observed biological activities. However, emerging evidence suggests that garcinol could be useful as an anti-cancer agent, and it is increasingly being realized that garcinol is a pleiotropic agent capable of modulating key regulatory cell signaling pathways. Here we have summarized the progress of our current research knowledge on garcinol and its observed biological activities. We have also provided an explanation of observed properties based on its chemical structure and provided an insight into the structure and properties of chalcones, the precursors of garcinol. The available data is promising but more detailed investigations into the various properties of this compound, particularly its anti-cancer activity are urgently needed, and it is our hope that this review will stimulate further research for elucidating and appreciating the value of this nature's wonder agent. PMID:19725977

  14. Synthesis and anti-proliferative activity of novel azazerumbone conjugates with chalcones.

    Science.gov (United States)

    Truong, Vuong Van; Nam, Tran Duy; Hung, Truong Ngoc; Nga, Nguyen Thi; Quan, Pham Minh; Chinh, Luu Van; Jung, Sang-Hun

    2015-11-15

    The conjugation of azazerumbone ((3E,7E,11E)-5,5,8,12-tetramethylazacyclododeca-3,7,11-trien-2-one (7)) and 2,4-dihydroxychalcones was carried out for the preparation of novel target compounds 9a-g with 1-ethylene-4-methylene-1,2,3-triazole linker and 10a-f with propylene linker between amide nitrogen of azazerumbone and 4-hydroxy group of chalcone. The anti-proliferative activity of these compounds against the LU-1, Hep-G2, MCF-7 and SW480 human cancer cell lines were significantly improved compared to those of azazerumbone or zerumbone. The anti-proliferative activities of (3E,7E,11E)-1-((1-(2-(3-hydroxy-4-((E)-3-(3-methoxyphenyl)acryloyl)phenoxy)ethyl)-1H-1,2,3-triazol-4-yl)methyl)-5,5,8,12-tetramethyl azacyclododeca-3,7,11-trien-2-one (9b) and (3E,7E,11E)-1-(3-(4-((E)-3-(3,4,5-trimethoxyphenyl)acryloyl)phenoxy)propyl)-5,5,8,12-tetramethylazacyclododeca-3,7,11-trien-2-one (10d) are nearly comparable to those of ellipticine. PMID:26459207

  15. Genome-Wide Identification, Characterization and Expression Analysis of the Chalcone Synthase Family in Maize.

    Science.gov (United States)

    Han, Yahui; Ding, Ting; Su, Bo; Jiang, Haiyang

    2016-01-01

    Members of the chalcone synthase (CHS) family participate in the synthesis of a series of secondary metabolites in plants, fungi and bacteria. The metabolites play important roles in protecting land plants against various environmental stresses during the evolutionary process. Our research was conducted on comprehensive investigation of CHS genes in maize (Zea mays L.), including their phylogenetic relationships, gene structures, chromosomal locations and expression analysis. Fourteen CHS genes (ZmCHS01-14) were identified in the genome of maize, representing one of the largest numbers of CHS family members identified in one organism to date. The gene family was classified into four major classes (classes I-IV) based on their phylogenetic relationships. Most of them contained two exons and one intron. The 14 genes were unevenly located on six chromosomes. Two segmental duplication events were identified, which might contribute to the expansion of the maize CHS gene family to some extent. In addition, quantitative real-time PCR and microarray data analyses suggested that ZmCHS genes exhibited various expression patterns, indicating functional diversification of the ZmCHS genes. Our results will contribute to future studies of the complexity of the CHS gene family in maize and provide valuable information for the systematic analysis of the functions of the CHS gene family. PMID:26828478

  16. Ruthenium(II) carbonyl complexes containing chalconates and triphenylphosphine/arsine

    Indian Academy of Sciences (India)

    P Viswanathamurthi; M Muthukumar

    2011-09-01

    A series of new hexa-coordinated ruthenium(II) carbonyl complexes of the type [RuCl(CO)(EPh3)(B)(L1−4)] (4-15) (E = P or As; B = PPh3, AsPh3 or Py; L = 2'-hydroxychalcone) were synthesized from the reaction of [RuHCl(CO)(EPh3)2(B)] (1-3) (E = P or As; B = PPh3, AsPh3 or Py) with equimolar chalcone in benzene under reflux. The new complexes have been characterized by analytical and spectroscopic (IR, electronic, 1H, 31P{1H}, and 13C NMR) methods. On the basis of data obtained, an octahedral structure has been assigned for all the complexes. The complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of -methylmorpholine--oxide (NMO) as co-oxidant and were also found to be efficient transfer hydrogenation catalysts. The antifungal properties of the ligands and their complexes have also been examined and compared with standard Bavistin.

  17. Antibacterial activity and QSAR of chalcones against biofilm-producing bacteria isolated from marine waters.

    Science.gov (United States)

    Sivakumar, P M; Prabhawathi, V; Doble, M

    2010-04-01

    Biofouling in the marine environment is a major problem. In this study, three marine organisms, namely Bacillus flexus (LD1), Pseudomonas fluorescens (MD3) and Vibrio natriegens (MD6), were isolated from biofilms formed on polymer and metal surfaces immersed in ocean water. Phylogenetic analysis of these three organisms indicated that they were good model systems for studying marine biofouling. The in vitro antifouling activity of 47 synthesized chalcone derivatives was investigated by estimating the minimum inhibitory concentration against these organisms using a twofold dilution technique. Compounds C-5, C-16, C-24, C-33, C-34 and C-37 were found to be the most active. In the majority of the cases it was found that these active compounds had hydroxyl substitutions. A quantitative structure-activity relationship (QSAR) was developed after dividing the total data into training and test sets. The statistical measures r(2), [image omitted] (>0.6) q(2) (>0.5) and the F-ratio were found to be satisfactory. Spatial, structural and electronic descriptors were found to be predominantly affecting the antibiofouling activity of these compounds. Among the spatial descriptors, Jurs descriptors showed their contribution in all the three antibacterial QSARs. PMID:20544550

  18. Co-suppression in transgenic Petunia hybrida expressing chalcone synthase A (chsA)

    Institute of Scientific and Technical Information of China (English)

    LI; Yan; (

    2001-01-01

    [1]Napoli, C., Lemieux, C., Jorgensen, R., Introduction of a chimeric chalone synthase gene into petunia results in reversible cosuppession of homologous genes in trans, The Plant Cell, 1990, 2: 279-289.[2]Van der Krol, A.R., Mur, L.A., Beld, M. M. et al., Flavonnoid genes in petunia: addition of a limited number of gene copies may lead to a suppression of gene expression, The Plant Cell, 1990, 2: 291-299.[3]Manika, P.B., Bhadra, U., Birchler, J., Cosuppression in Drosophila: gene silencing of Alcohol dehydrogenase by White-Adh transgene is Polycomb dependent, Cell, 1997, 90: 479-498.[4]de Carvalho Niebel, F., Frendo, P., Van Montagu, M. et al., Post-transcriptional cosuppression of ?-1,3-glucanase transgene expression in homozygous plants, EMBO J., 1992, 11: 2595-2602.[5]Van Blokland, R., Van der Geest, N., Mol, J. N. M. et al., Transgene-mediated suppression of chalcone synthase expression in Petunia hybrida results from an increase in RNA turnover, The Plant Cell, 1994, 6: 861-877.[6]Stam, M., Mol, J. N. M., Kooter, J. M., The silence of genes in transgenic plants, Annals of Bot., 1997, 79: 3-12.[7]Vaucheret, H., Beclin, C., Elmayan, T. et al., Transgene-induced gene silencing in plants, Plant J., 1998, 16(6): 651-659.[8]Shao, L., Li, Y., Yang, M. Z. et al., Transformation of Petunia hybrida with chalcone synthase A (chsA) resulting flower colour alteration and male sterility, Acta Botanica Sinica (in Chinese), 1996, 38(7): 517-524.[9]Koes, R. E., Spelt, C. E., Mol, J. N. M., The chalcone synthase multigene family of Petunia hybrida (V30): differential, light-regulated expression during flower development and UV light induction, Plant Mol. Biol., 1989, 12: 213-225.[10]Drews, G. N., Beals, T. P., Bul, A. Q. et al., Regional and cell-specific expression patterns during petal development, The Plant Cell, 1992, 4: 1383-1404.[11]Martin, C., Gerats, T., Control of pigment biosynthesis genes during petal development, The

  19. Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship

    Science.gov (United States)

    Akhtar, Muhammad Nadeem; Sakeh, Nurshafika M.; Zareen, Seema; Gul, Sana; Lo, Kong Mun; Ul-Haq, Zaheer; Shah, Syed Adnan Ali; Ahmad, Syahida

    2015-04-01

    Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1-10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20-14.38 μM values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1-3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.

  20. Synthesis and evaluation of new indole-based chalcones as potential antiinflammatory agents.

    Science.gov (United States)

    Özdemir, Ahmet; Altintop, Mehlika Dilek; Turan-Zitouni, Gülhan; Çiftçi, Gülşen Akalın; Ertorun, İpek; Alataş, Özkan; Kaplancikli, Zafer Asim

    2015-01-01

    In the present work, new indole-based chalcone derivatives were obtained via the reaction of 5-substituted-1H-indole-3-carboxaldehydes/1-methylindole-3-carboxaldehyde with appropriate acetophenones. The synthesized compounds were investigated for their in vitro COX-1 and COX-2 inhibitory activity. The most effective COX inhibitors were also evaluated for their in vivo antiinflammatory and antioxidant activities in LPS induced sepsis model. Furthermore, the CCK-8 assay was carried out to determine cytotoxic effects of all compounds against NIH/3T3 mouse embryonic fibroblast cells. 3-(5-Bromo-1H-indol-3-yl)-1-(4-cyanophenyl)prop-2-en-1-one (6) can be considered as a non-selective COX inhibitor (COX-1 IC50 = 8.1 ± 0.2 μg/mL, COX-2 IC50 = 9.5 ± 0.8 μg/mL), whereas 3-(5-methoxy-1H-indol-3-yl)-1-(4-(methylsulfonyl)phenyl)prop-2-en-1-one (1) inhibited only COX-1 (IC50 = 8.6 ± 0.1 μg/mL). According to in vivo studies, these compounds also displayed antiinflammatory and antioxidant activities. PMID:25462246

  1. Chalcone based azacarboline analogues as novel antitubulin agents: design, synthesis, biological evaluation and molecular modelling studies.

    Science.gov (United States)

    Sharma, Sahil; Kaur, Charanjit; Budhiraja, Abhishek; Nepali, Kunal; Gupta, Manish K; Saxena, A K; Bedi, P M S

    2014-10-01

    The present study involves the design of a series of 3-aryl-9-acetyl-pyridazino[3,4-b]indoles as constrained chalcone analogues. A retrosynthetic route was proposed for the synthesis of target compounds. All the synthesized compounds were evaluated for in-vitro cytotoxicity against THP-1, COLO-205, HCT-116 and A-549 human cancer cell lines. The results indicated that 2a, 3a, 5a and 6a possessed significant cytotoxic potential with an IC50 value ranging from 1.13 to 5.76 μM. Structure activity relationship revealed that the nature of both Ring A and Ring B influences the activity. Substitution of methoxy groups on the phenyl ring (Ring A) and unsubstituted phenyl ring (Ring B) were found to be the preferred structural features. The most potent compound 2a was further tested for tubulin inhibition. Compound 2a was found to significantly inhibit the tubulin polymerization (IC50 value - 2.41 μM against THP-1). Compound 2a also caused disruption of microtubule assembly as evidenced by Immunoflourescence technique. The significant cytotoxicity and tubulin inhibition by 2a was rationalized by molecular modelling studies. The most potent structure was docked at colchicine binding site (PDB ID-1SA0) and was found to be stabilized in the cavity via various hydrophobic and hydrogen bonding interactions. PMID:25128667

  2. Synthesis and biological evaluation of indole-chalcone derivatives as β-amyloid imaging probe.

    Science.gov (United States)

    Cui, Mengchao; Ono, Masahiro; Kimura, Hiroyuki; Liu, Bo Li; Saji, Hideo

    2011-02-01

    A series of chaclone derivatives containing an indole moiety were evaluated in competitive binding assays with Aβ(1-42) aggregates versus [(125)I]IMPY. The affinity of these compounds ranged from 4.46 to >1008 nM, depending on the substitution on the phenyl ring. Fluorescent staining in vitro showed that one compound with a N,N-dimethylamino group intensely stained Aβ plaques within brain sections of AD transgenic mice. The radioiodinated probe [(125)I]-(E)-3-(1H-indol-5-yl)-1-(4-iodophenyl)prop-2-en-1-one, [(125)I]4, was prepared and autoradiography in sections of brain tissue from an animal model of AD showed that it labeled Aβ plaques specifically. However, experiments with normal mice indicated that [(125)I]4 exhibited a low uptake into the brain in vivo (0.41% ID/g at 2 min). Additional chemical modifications of this indole-chalcone structure may lead to more useful imaging agents for detecting β-amyloid plaques in the brains of AD patients. PMID:21216142

  3. Study Progress on Synthesis 3′,5′-Hydrocarbon Chalcones%3′,5′-烃基查尔酮的合成进展

    Institute of Scientific and Technical Information of China (English)

    陈泓霖; 黄初升; 刘红星; 杨进华; 郑少龙

    2015-01-01

    Isopentenyl and geranyl structure units generally exist in flavonoids ,chalcone and other natural products .Chalcone in isopentenyl and geranyl structure has anti‐cancer ,antioxidant activity which is popularly favored .There are domestic and foreign reports about many synthesis methods of prenylated and geranyl chalcone .In this paper ,two research directions from acetophenone or chalcone as raw material base are summarized ,making a summary on methods for synthesis of 3′,5′position as in isopentenyl or geranyl chalcones in recent years ,and providing more new methods for developing synthesis of 3′,5′position with reference to isopentenyl or geranyl chalcone.%异戊烯基和香叶基结构单元普遍存在于黄酮类、查尔酮类等天然产物。异戊烯基和香叶基结构的查尔酮具有抗癌、抗氧化活性等生理活性而备受青睐。国内外报道了许多异戊烯基和香叶基结构的查尔酮合成方法。本文从苯乙酮或查尔酮为原料基础的两个研究方向进行总结,综述了近年来关于3′,5′位为异戊烯基或香叶基的查尔酮的合成方法,为更多3′,5′位为异戊烯基或香叶基的查尔酮的合成新方法被研发提供参考。

  4. 4'-Acetoamido-4-hydroxychalcone, a chalcone derivative, inhibits glioma growth and invasion through regulation of the tropomyosin 1 gene

    International Nuclear Information System (INIS)

    Research highlights: → 4'-Acetoamido-4-hydroxychalcone (AHC) has anti-cancer property for glioma. → 4'-Acetoamido-4-hydroxychalcone (AHC) increased tropomyosin expreesion through activattion of PKA signaling. → 4'-Acetoamido-4-hydroxychalcone (AHC) inhibits glioma cell migration and invasion. → In vivo administration of 4'-acetoamido-4-hydroxychalcone (AHC) reduced tumor growth. -- Abstract: Chalcones are precursors of flavonoids and have been shown to have anti-cancer activity. Here, we identify the synthetic chalcone derivative 4'-acetoamido-4-hydroxychalcone (AHC) as a potential therapeutic agent for the treatment of glioma. Treatment with AHC reduced glioma cell invasion, migration, and colony formation in a concentration-dependent manner. In addition, AHC inhibited vascular endothelial growth factor-induced migration, invasion, and tube formation in HUVECs. To determine the mechanism underlying the inhibitory effect of AHC on glioma cell invasion and migration, we investigated the effect of AHC on the gene expression change and found that AHC affects actin dynamics in U87MG glioma cells. In actin cytoskeleton regulating system, AHC increased tropomyosin expression and stress fiber formation, probably through activation of PKA. Suppression of tropomyosin expression by siRNA or treatment with the PKA inhibitor H89 reduced the inhibitory effects of AHC on glioma cell invasion and migration. In vivo experiments also showed that AHC inhibited tumor growth in a xenograft mouse tumor model. Together, these data suggest that the synthetic chalcone derivative AHC has potent anti-cancer activity through inhibition of glioma proliferation, invasion, and angiogenesis and is therefore a potential chemotherapeutic candidate for the treatment of glioma.

  5. Synthetic Chalcones with Potent Antioxidant Ability on H2O2-Induced Apoptosis in PC12 Cells

    Directory of Open Access Journals (Sweden)

    Jian-Zhang Wu

    2014-10-01

    Full Text Available Chalcone derivatives (E-3-(4-hydroxy-3-methoxyphenyl-1-(4-methoxyphenyl prop-2-en-1-one and (E-3-(4-hydroxyphenyl-1-(4-methoxyphenyl prop-2-en-1-one (Compounds 1 and 2 have been demonstrated to be potent anti-inflammatory agents in our previous study. In light of the relationship of intracellular mechanisms between anti-inflammatories and antioxidants, we further designed and synthesized a series of chalcone derivatives based on 1 and 2, to explore their antioxidant efficacy. The majority of the derivatives exhibited strong protective effects on PC12 (PC12 rat pheochromocytoma cells exposed to H2O2, and all compounds were nontoxic. A preliminary structure-activity relationship was proposed. Compounds 1 and 1d ((E-2-methoxy-4-(3-(4-methoxyphenyl-3-oxoprop-1-en-1-yl phenyl acrylate exerted the action in a good dose-dependent manner. Quantitative RT-PCR (qRT-PCR and western blot analysis showed that 1 and 1d significantly improve the expression of nuclear factor erythroid 2 p45-related factor 2 (Nrf2-dependent antioxidant genes g-Glutamylcysteine Ligase Catalytic Subunit (GCLC and heme oxygenase-1 (HO-1 and their corresponding proteins (γ-glutamyl cysteine synthase (γ-GCS and HO-1 in PC12 cells. Inhibition of GCLC and HO-1 by specific inhibitors, l-buthionine-S-sulfoximine (BSO and zinc protoporphyrin (ZnPP, respectively, partially reduce the protective effect of 1 and 1d. These data present a series of novel chalcone analogs, especially compounds 1 and 1d, as candidates for treating oxidative stress-related disease by activating the Nrf2-antioxidant responsive element (ARE pathway.

  6. Synthetic Chalcones with Potent Antioxidant Ability on H2O2-Induced Apoptosis in PC12 Cells

    Science.gov (United States)

    Wu, Jian-Zhang; Cheng, Chan-Chan; Shen, Lai-Lai; Wang, Zhan-Kun; Wu, Shou-Biao; Li, Wu-Lan; Chen, Su-Hua; Zhou, Rong-Ping; Qiu, Pei-Hong

    2014-01-01

    Chalcone derivatives (E)-3-(4-hydroxy-3-methoxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one and (E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one (Compounds 1 and 2) have been demonstrated to be potent anti-inflammatory agents in our previous study. In light of the relationship of intracellular mechanisms between anti-inflammatories and antioxidants, we further designed and synthesized a series of chalcone derivatives based on 1 and 2, to explore their antioxidant efficacy. The majority of the derivatives exhibited strong protective effects on PC12 (PC12 rat pheochromocytoma) cells exposed to H2O2, and all compounds were nontoxic. A preliminary structure-activity relationship was proposed. Compounds 1 and 1d ((E)-2-methoxy-4-(3-(4-methoxyphenyl)-3-oxoprop-1-en-1-yl) phenyl acrylate) exerted the action in a good dose-dependent manner. Quantitative RT-PCR (qRT-PCR) and western blot analysis showed that 1 and 1d significantly improve the expression of nuclear factor erythroid 2 p45-related factor 2 (Nrf2)-dependent antioxidant genes g-Glutamylcysteine Ligase Catalytic Subunit (GCLC) and heme oxygenase-1 (HO-1) and their corresponding proteins (γ-glutamyl cysteine synthase (γ-GCS) and HO-1) in PC12 cells. Inhibition of GCLC and HO-1 by specific inhibitors, l-buthionine-S-sulfoximine (BSO) and zinc protoporphyrin (ZnPP), respectively, partially reduce the protective effect of 1 and 1d. These data present a series of novel chalcone analogs, especially compounds 1 and 1d, as candidates for treating oxidative stress-related disease by activating the Nrf2-antioxidant responsive element (ARE) pathway. PMID:25318055

  7. Synthesis of alpha,beta-unsaturated ketones as chalcone analogues via a S(RN)1 mechanism.

    Science.gov (United States)

    Curti, Christophe; Gellis, Armand; Vanelle, Patrice

    2007-01-01

    An electron-transfer chain reaction between 2-nitropropane anion and alpha-bromoketones derived from nitrobenzene and nitrothiophene was demonstrated by mechanistic study and a specific convenient synthetic protocol. Thus, 2-bromo-1-(5-nitrothiophen-2-yl)ethanone or 2-bromo-1-(4-nitrophenyl)ethanone were reacted with several cyclic nitronate anions to form alpha,beta-unsaturated ketones via a S(RN)1 mechanism. This new method can be used to synthesize a wide variety of chalcone analogues. PMID:17851431

  8. Synthesis of Diarylpyrazoles Containing a Phenylsulphone or Carbonitrile Moiety and their Chalcones as Possible Anti-Inflammatory Agents

    OpenAIRE

    Nassar, Ekhlass; Abdel-Aziz, Hatem A.; Hany S. Ibrahim; Mansour, Ahmed M.

    2011-01-01

    A series of chalcone-based diarylpyrazoles containing a phenylsulphone or carbonitrile moiety was synthesized. Thus, 3-acetylpyrazoles 6a–c and 10a–c were used as useful substrates in facile synthesis of functional pyrazoles 7a–f and 11a–f, respectively. The anti-inflammatory activity and ulcerogenic effect were evaluated and some of the obtained products possessed a significant anti-inflammatory activity. 1-[1-(3-Methylphenyl)-5-phenyl-4-(phenylsulfonyl)-1H-pyrazol-3-yl]ethanone (6b) showed ...

  9. Synthesis, characterization and biological activities of novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units

    OpenAIRE

    Mustafa Ceylan; İsa Karaman; Meryem Keçeci Sarıkaya

    2013-01-01

    Novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units were synthesized starting from 1,3-cyclohexadine (4) and maleic anhydride (5). Addition of maleic anhydride (5) to 1,3-cyclehexadine (4) gave an endo-adduct, 3a,4,7,7a-tetrahydro-4,7-ethano-2-benzofuran-1,3-dione (6), in 90% yield. Heating the solution of the adduct dione (6) and 1-(4-aminophenyl)ethanone (7) in the presence of Et 3N in toluene at 110 oC for 24 hours afforded 2-(4-acetylphenyl)-3a,4,7,7a-tetrahydro-1H...

  10. Derivatives of Δ 2-pyrazoline-products of 1,5-diaminotetrazole interaction with chalcone: Molecular structure and spectral properties

    Science.gov (United States)

    Kolos, N. N.; Paponov, B. V.; Orlov, V. D.; Lvovskaya, M. I.; Doroshenko, A. O.; Shishkin, O. V.

    2006-03-01

    1,5-diaminotetrazole at conditions of its interaction with chalcones (1,3-diphenylpropenones) in hot DMF undergoes Dimroth rearrangement to 5-tetrazolylhydrazine, which results in formation of 1-(5-tetrazolyl)-3,5-diaryl-Δ 2-pyrazolines ( I). Structure of the obtained products was confirmed by their parallel synthesis and X-ray structural analysis. Unusual fluorescence behavior of the tetrazolopyrazolynes in polar solvents was attributed to the dissociation of their highly acidic tetrazole N-H group. The last hypothesis was confirmed at the investigation of the protolytic interactions of I with tertiary amine.

  11. Synthesis and evaluation of ethyleneoxylated and allyloxylated chalcone derivatives for imaging of amyloid β plaques by SPECT

    OpenAIRE

    Fuchigami, Takeshi; Yamashita, Yuki; Haratake, Mamoru; Ono, Masahiro; Yoshida, Sakura; Nakayama, Morio

    2014-01-01

    We report radioiodinated chalcone derivatives as new SPECT imaging probes for amyloid β (Aβ) plaques. The monoethyleneoxy derivative 2 and allyloxy derivative 8 showed a high affinity for Aβ(1-42) aggregates with Ki values of 24 and 4.5 nM, respectively. Fluorescent imaging demonstrated that 2 and 8 clearly stained thioflavin-S positive Aβ plaques in the brain sections of Tg2576 transgenic mice. In vitro autoradiography revealed that [125I]2 displayed no clear accumulation toward Aβ plaques i...

  12. Pharmacophore Modeling, Atom based 3D-QSAR and Docking Studies of Chalcone derivatives as Tubulin inhibitors

    OpenAIRE

    Naresh Kandakatla; Geetha Ramakrishnan; J. Karthikeyan; Rajasekhar Chekkara

    2014-01-01

    Tubulin is attractive target for anticancer drug design and their inhibitors are useful in treatment of various cancers. Pharmacophore and Atom based QSAR studies were carried out for series of Chalcone derivatives. Pharmacophore model was developed using 38 compounds, having pIC50 ranging 4.003 to 6.552. The best Pharmacophoric hypothesis AHHRR.10 (one H-acceptor, two hydrophobic groups, two aromatic rings) had survival score of 4.824. Atom based 3D QSAR was built for the best hypothesis w...

  13. The chalcone compound isosalipurposide (ISPP) exerts a cytoprotective effect against oxidative injury via Nrf2 activation

    International Nuclear Information System (INIS)

    The chalcone compound isosalipurposide (ISPP) has been successfully isolated from the native Korean plant species Corylopsis coreana Uyeki (Korean winter hazel). However, the therapeutic efficacy of ISPP remains poorly understood. This study investigated whether ISPP has the capacity to activate NF-E2-related factor (Nrf2)-antioxidant response element (ARE) signaling and induce its target gene expression, and to determined the protective role of ISPP against oxidative injury of hepatocytes. In HepG2 cells, nuclear translocation of Nrf2 is augmented by ISPP treatment. Consistently, ISPP increased ARE reporter gene activity and the protein levels of glutamate cysteine ligase (GCL) and hemeoxygenase (HO-1), resulting in increased intracellular glutathione levels. Cells pretreated with ISPP were rescued from tert-butylhydroperoxide-induced reactive oxygen species (ROS) production and glutathione depletion and consequently, apoptotic cell death. Moreover, ISPP ameliorated the mitochondrial dysfunction and apoptosis induced by rotenone which is an inhibitor of complex 1 of the mitochondrial respiratory chain. The specific role of Nrf2 activation by ISPP was demonstrated using an ARE-deletion mutant plasmid and Nrf2-knockout cells. Finally, we observed that extracellular signal-regulated kinase (ERK) and AMP-activated protein kinase (AMPK), but not protein kinase C (PKC)-δ or other mitogen-activated protein kinases (MAPKs), are involved in the activation of Nrf2 by ISPP. Taken together, our results demonstrate that ISPP has a cytoprotective effect against oxidative damage mediated through Nrf2 activation and induction of its target gene expression in hepatocytes. - Highlights: • We investigated the effect of ISPP on Nrf2 activation. • ISPP increased Nrf2 activity and its target gene expression. • ISPP inhibited the mitochondrial dysfunction and ROS production. • Nrf2 activation by ISPP is dependent on ERK1/2 and AMPK phosphorylation. • ISPP may be a promising

  14. The chalcone compound isosalipurposide (ISPP) exerts a cytoprotective effect against oxidative injury via Nrf2 activation

    Energy Technology Data Exchange (ETDEWEB)

    Han, Jae Yun [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of); Cho, Seung Sik [College of Pharmacy, Mokpo National University, Muan, Jeonnam 535-729 (Korea, Republic of); Yang, Ji Hye; Kim, Kyu Min; Jang, Chang Ho [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of); Park, Da Eon [College of Pharmacy, Mokpo National University, Muan, Jeonnam 535-729 (Korea, Republic of); Bang, Joon Seok [Graduate School of Clinical Pharmacy, Sookmyung Women' s University, Seoul (Korea, Republic of); Jung, Young Suk [College of Pharmacy, Pusan National University, Busan (Korea, Republic of); Ki, Sung Hwan, E-mail: shki@chosun.ac.kr [College of Pharmacy, Chosun University, Gwangju 501-759 (Korea, Republic of)

    2015-08-15

    The chalcone compound isosalipurposide (ISPP) has been successfully isolated from the native Korean plant species Corylopsis coreana Uyeki (Korean winter hazel). However, the therapeutic efficacy of ISPP remains poorly understood. This study investigated whether ISPP has the capacity to activate NF-E2-related factor (Nrf2)-antioxidant response element (ARE) signaling and induce its target gene expression, and to determined the protective role of ISPP against oxidative injury of hepatocytes. In HepG2 cells, nuclear translocation of Nrf2 is augmented by ISPP treatment. Consistently, ISPP increased ARE reporter gene activity and the protein levels of glutamate cysteine ligase (GCL) and hemeoxygenase (HO-1), resulting in increased intracellular glutathione levels. Cells pretreated with ISPP were rescued from tert-butylhydroperoxide-induced reactive oxygen species (ROS) production and glutathione depletion and consequently, apoptotic cell death. Moreover, ISPP ameliorated the mitochondrial dysfunction and apoptosis induced by rotenone which is an inhibitor of complex 1 of the mitochondrial respiratory chain. The specific role of Nrf2 activation by ISPP was demonstrated using an ARE-deletion mutant plasmid and Nrf2-knockout cells. Finally, we observed that extracellular signal-regulated kinase (ERK) and AMP-activated protein kinase (AMPK), but not protein kinase C (PKC)-δ or other mitogen-activated protein kinases (MAPKs), are involved in the activation of Nrf2 by ISPP. Taken together, our results demonstrate that ISPP has a cytoprotective effect against oxidative damage mediated through Nrf2 activation and induction of its target gene expression in hepatocytes. - Highlights: • We investigated the effect of ISPP on Nrf2 activation. • ISPP increased Nrf2 activity and its target gene expression. • ISPP inhibited the mitochondrial dysfunction and ROS production. • Nrf2 activation by ISPP is dependent on ERK1/2 and AMPK phosphorylation. • ISPP may be a promising

  15. Synthesis, X-ray crystal structures and catecholase activity investigation of new chalcone ligands

    Science.gov (United States)

    Thabti, Salima; Djedouani, Amel; Rahmouni, Samra; Touzani, Rachid; Bendaas, Abderrahmen; Mousser, Hénia; Mousser, Abdelhamid

    2015-12-01

    The reaction of dehydroacetic acid DHA carboxaldehyde and RCHO derivatives (R = quinoleine-8-; indole-3-; pyrrol-2- and 4-(dimethylamino)phenyl - afforded four new chalcone ligands (4-hydroxy-6-methyl-3-[(2E)-3-quinolin-8-ylprop-2-enoyl]-2H-pyran-2-one) L1, (4-hydroxy-3-[(2E)-3-(1H-indol-3-yl)prop-2-enoyl]-6-methyl-2H-pyran-2-one) L2, (4-hydroxy-6-methyl-3-[(2E)-3-(1H-pyrrol-2-yl)prop-2-enoyl]-2H-pyran-2-one) L3, and (3-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-4-hydroxy-6-methyl-2H-pyran-2-one) L4. L3 and L4 were characterized by X-ray crystallography. Molecules crystallize with four and two molecules in the asymmetric unit, respectively and adopt an E conformation about the Cdbnd C bond. Both structures are stabilized by an extended network O-H … O. Furthermore, N-H … O and C-H … O hydrogen bonds are observed in L3 and L4 structures, respectively. The in situ generated copper (II) complexes of the four compounds L1, L2, L3 and L4 were examined for their catalytic activities and were found to catalyze the oxidation reaction of catechol to o-quinone under atmospheric dioxygen. The rates of this oxidation depend on three parameters: ligand, ion salts and solvent nature and the combination L2[Cu (CH3COO)2] leads to the faster catalytic process.

  16. Direct Asymmetric Michael Additions of Ketones to Nitroolefins and Chalcones Catalyzed by a Chiral C2-Symmetric Pyrrolidine-based Tetraamine

    Institute of Scientific and Technical Information of China (English)

    马世俊; 吴璐璐; 刘明; 王永梅

    2012-01-01

    C2-Symmetric pyrrolidine-based tetraamine, available from commercially starting materials, showed good cata- lytic activity for asymmetric Michael additions of ketones to nitroalkenes especially to chalcones. The reactions proceeded to give the corresponding products in good yields and in a highly selective manner.

  17. Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.

    Science.gov (United States)

    Tran, Thanh-Dao; Do, Tuong-Ha; Tran, Ngoc-Chau; Ngo, Trieu-Du; Huynh, Thi-Ngoc-Phuong; Tran, Cat-Dong; Thai, Khac-Minh

    2012-07-15

    A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4'-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2',2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA. PMID:22727643

  18. Application of chalcones in heterocycles synthesis: Synthesis of 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues of 1,4-benzodiazepin-5-carboxamides linked through an oxyphenyl bridge

    Indian Academy of Sciences (India)

    N Kaur; D Kishore

    2013-05-01

    Versatility of chalcone derivative of 2-(4'-acetyl)-phenoxyl-5-carboxamido-1,4-benzodiazepin-5-(4'-methylpiperazinyl)-carboxamide (6) was explored to provide an easy one-pot access to its 2-(isoxazolo, pyrazolo and pyrimido) substituted analogues 9, 10, 11, 12, 13, 14, 15, and 16.

  19. One-pot synthesis of new series 3,4,5-trisubstituted-dihydroisoxazoline derivatives via 1,3-dipolar cycloaddition of nitrile oxides with chalcones

    Indian Academy of Sciences (India)

    Raad Kasim Yhya; K M Lokanatha Rai; Ebraheem Abdu Musad

    2013-07-01

    We have synthesized a series of novel isoxazolines via 1,3-dipolar cycloaddition reaction. Aromatic aldoximes undergo oxidative-dehydrogenation with chloramine-T to give nitrile oxides, which were reacted with chalcones to afford of 3,4,5-trisubstituted 4,5-dihydroisoxazolines in a good yield.

  20. Synthesis of benzimidazolyl chalcones derivatives%苯并咪唑类查耳酮衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    陈国锋; 贾慧明; 张立艳; 宋亚丽; 董晓云; 贾乔羽

    2012-01-01

    本文对苯并咪唑类查耳酮衍生物的合成方法进行了研究,利用2-(4-氨基苯基)-1H-苯并咪唑与取代的肉桂酰氯反应合成出一系列苯并咪唑类查耳酮衍生物,并用IR、MS和1H NMR对目标化合物进行了表征.该方法具有操作简单、反应时间短及收率高的特点.%Process for synthesis of benzimidazolyl chalcones derivatives was described. Some benzimidazolyl chalcones were synthesized by condensation of 4-(lH-benzo[d]imidazol-2-yl)benzenamine and substituted cinnamoyl chlorides in presence of pyridine and characterized by their physical constants, IR, MS and 1 H NMR. This methodology offered the competitive advantages of a simple procedure,shorter reaction times and high product yields.

  1. Synthesis and photophysical properties of novel chloroquinoline based chalcone derivates containing 1,2,3-triazole moiety

    Energy Technology Data Exchange (ETDEWEB)

    Singh, Harjinder; Sindhu, Jayant; Khurana, Jitender M., E-mail: jmkhurana@chemistry.du.ac.in

    2015-02-15

    A series of novel chloroquinoline based chalcones containing 1,2,3-triazole moiety were synthesized. All new compounds were characterized by {sup 1}H NMR, {sup 13}C NMR, mass spectra and single crystal X-ray diffraction study. The absorbance, fluorescence spectra and quantum yield of all compounds were investigated in methanol. Photophysical properties of 1-(1-(7-chloroquinolin-4-yl)-5-methyl-1H-1,2,3-triazol-4-yl) -3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3a) were investigated in detail. The effect of various solvents over emission spectra of 3a was studied using Kamlet–Taft and Catalan polarity scales. The quantum yield of 3a in various solvents was also recorded. The ground state and excited state dipole moments of compound 3a were determined using solvatochromic methods. The ground state dipole moment was estimated to be 1.081 D, while excited state dipole moment was found in the range of 11.969–3.801 D. Thermal stability of compound 3a and its precursor was also investigated using thermogravimetric analysis. - Highlights: • Novel quinoline based chalcones-1,2,3-triazole derivatives were synthesized. • The photophysical properties of all compounds were investigated in methanol. • The excited state and ground state dipole moment is estimated from various methods. • Kamlet–Taft and Catalan solvatochromism was investigated.

  2. Synthesis and properties of novel photosensitive poly(arylene ether sulfone) containing chalcone moiety in the main chain

    Energy Technology Data Exchange (ETDEWEB)

    Wen Pushan [Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission and Ministry of Education, Hubei Province, South-Central University for Nationalities, Wuhan 430074 (China); Wang Lei [Department of Materials Physics and Chemistry, School of Materials Science and Engineering, University of Science and Technology Beijing, Beijing 100083 (China); Zhang Aiqing [Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission and Ministry of Education, Hubei Province, South-Central University for Nationalities, Wuhan 430074 (China); Li Xiangdan, E-mail: xiangdanli@yahoo.com.cn [Key Laboratory of Catalysis and Materials Science of the State Ethnic Affairs Commission and Ministry of Education, Hubei Province, South-Central University for Nationalities, Wuhan 430074 (China); Lee, Myong-Hoon, E-mail: mhlee2@chonbuk.ac.kr [Department of Polymer/Nano Science and Technology, Chonbuk National University, Jeonju 561-756 (Korea, Republic of)

    2011-04-15

    Research highlights: {yields} A series of novel photosensitive poly(arylene ether sulfone)s (PAESs) containing chalcone moiety in the main chain have been successfully synthesized. {yields} The photo-crosslinking of polymer film was carried out under UV irradiation without photoinitiator. {yields} The resulting polymers showed good thermal stability and excellent chemical stability after crosslinking. - Abstract: A new series of photosensitive poly(arylene ether sulfone)s containing chalcone moiety in the main chain were synthesized from 4,4'-dihydroxychalcone (4DHC), 4,4'-difluorodiphenylsulfone (DFDPS) and bisphenol A (BPA). This series of polymers were characterized by {sup 1}H NMR, FT-IR, UV spectroscopy, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The polymers were stable up to 400 deg. C, which indicates that the polymers possess good thermal properties. The polymers were found to be soluble in polar solvents and chlorinated solvents. However, the polymers were insoluble in hydrocarbons and in hydroxyl group-containing solvents. After the irradiation of UV light, the thin polymer film was crosslinked to give an insoluble film in the absence of a photoinitiator or sensitizers. The rate of photocrosslinking was also examined and discussed.

  3. Synthesis and photophysical properties of novel chloroquinoline based chalcone derivates containing 1,2,3-triazole moiety

    International Nuclear Information System (INIS)

    A series of novel chloroquinoline based chalcones containing 1,2,3-triazole moiety were synthesized. All new compounds were characterized by 1H NMR, 13C NMR, mass spectra and single crystal X-ray diffraction study. The absorbance, fluorescence spectra and quantum yield of all compounds were investigated in methanol. Photophysical properties of 1-(1-(7-chloroquinolin-4-yl)-5-methyl-1H-1,2,3-triazol-4-yl) -3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3a) were investigated in detail. The effect of various solvents over emission spectra of 3a was studied using Kamlet–Taft and Catalan polarity scales. The quantum yield of 3a in various solvents was also recorded. The ground state and excited state dipole moments of compound 3a were determined using solvatochromic methods. The ground state dipole moment was estimated to be 1.081 D, while excited state dipole moment was found in the range of 11.969–3.801 D. Thermal stability of compound 3a and its precursor was also investigated using thermogravimetric analysis. - Highlights: • Novel quinoline based chalcones-1,2,3-triazole derivatives were synthesized. • The photophysical properties of all compounds were investigated in methanol. • The excited state and ground state dipole moment is estimated from various methods. • Kamlet–Taft and Catalan solvatochromism was investigated

  4. 新型查尔酮衍生物的合成及酪氨酸酶活性%Synthesis and Activity on Tyrosinase of Novel Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    牛超; 李根; 买迪娜; 阿吉艾克拜尔·艾萨

    2014-01-01

    合成了8个新型含苯并噻唑环的查尔酮衍生物及8个酰胺查尔酮,并对化合物的结构进行了表征.生物活性测试结果表明,化合物4d,4h,5d,7b 和7d 表现出一定的酪氨酸酶激动活性,其中化合物7d 对酪氨酸酶的活性最好,其 EC50=9.6μmol/ L,优于阳性对照药8-MOP(EC50=14.8μmol/ L).%Ver-nohia anthelmintica L was endemic plant in Xinjiang, which was often used in the treatment of Vitiligo. It was believed that the chalcone compounds of Ver-nohia anthelmintica L played an important role in this treatment. Since it may activate tyrosinase and improve the melanin production, many chalcone com-pounds and derivatives were described as potential inhibitor on tyrosinase which may act as skin lightening and whitening agents. However, chalcones which showed activator effect were seldom reported. In order to search for chalcones with high activities on tyrosinase, eight novel chalcone derivatives containing benzothiazole and eight amide-derived chalcones were synthesized in this work. All the compounds were identified by 1 H NMR, 13 C NMR, IR, HRMS and evaluated their activator effect on tyrosinase by measuring the oxidation rate of L-dopa. Compared with the reference drug 8-methoxypsoralen, compounds 4d, 4h, 5d, 7b and 7d showed some activator effect on tyrosinase. Amomg them, compound 7d demonstrated more potent activity with EC50 =9. 6 μmol/ L than 8-methoxypsoralen, which EC50 value was 14. 8 μmol/ L. Further structural modification of this novel chalcones containing benzothiazole will be required for improving the solubility of them.

  5. Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

    International Nuclear Information System (INIS)

    Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 μM), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series. (author)

  6. Synthesis and biological evaluation of benzo[d][1,3]dioxol-5-yl chalcones as antiproliferating agents.

    Science.gov (United States)

    Kamal, Ahmed; Balakrishna, Moku; Loka Reddy, Velatooru; Riyaz, Syed; Bagul, Chandrakant; Satyanarayana, Bethu Murali; Venkateswar Rao, Janapala

    2015-11-01

    A series of chalcone derivatives were designed, synthesized, and evaluated for their cytotoxic potential. These molecules have showed promising cytotoxic activity with IC50 values ranging from 5.24 to 63.12 μm. Among them, conjugates 16k, 16m and 16t showed significant antiproliferative activity with IC50 values ranging from 5.24 to 10.39 μm in MDA-MB-231 cell line. These compounds were further investigated for their effect on cell membrane blebbing, chromatin condensation, DNA fragmentation, Hoechst staining, annexin V, and cell cycle arrest (G2/M). The Western blot experiments revealed up regulation of pro-apoptotic Bax and downregulation of antiapoptotic Bcl-2. The studies also indicated reduction of mitochondrial membrane potential and increase in the levels of caspase-3 and caspase-7. PMID:26032623

  7. Spectroscopic and nonlinear optical properties of new chalcone fluorescent probes for bioimaging applications: a theoretical and experimental study.

    Science.gov (United States)

    Krawczyk, Przemysław; Pietrzak, Marek; Janek, Tomasz; Jędrzejewska, Beata; Cysewski, Piotr

    2016-06-01

    In this study, the newly synthesized non-centrosymmetric, 4-dimethylamino-3'-isothiocyanatochalcone (PKA) compound was presented. This compound belongs to the chalcone group, and its main purpose is to be used in biomedical imaging as a fluorescence dye. For this reason, the linear and nonlinear properties in solvents of different polarity were thoroughly studied. In accordance with the requirements for a fluorochrome, the PKA compound is characterized by strong absorption, large Stokes' shifts, relatively high fluorescence quantum yields and high nonlinear optical response. Moreover, the isothiocyanate reactive probe was conjugated with Concanavalin A. Conventional fluorescence microscopy imaging of Candida albicans cells incubated with the PKA-Concanavalin A, is presented. The results of this study show that the novel conjugate PKA-Concanavalin A could be a promising new probe for cellular labelling in biological and biomedical research. Graphical abstract Spectroscopic behavior of the PKA dye. PMID:27168200

  8. Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

    Energy Technology Data Exchange (ETDEWEB)

    Borchhardt, Deise M.; Oliva, Glaucius; Andricopulo, Adriano D. [Universidade de Sao Paulo, Sao Carlos (USP), SP (Brazil). Centro de Biotecnologia Molecular Estrutural. Lab. de Quimica Medicinal e Computacional; Mascarello, Alessandra; Chiaradia, Louise Domeneghini; Nunes, Ricardo J.; Yunes, Rosendo A. [Universidade Federal de Santa Catarina (UFSC), Florianopolis, SC (Brazil). Centro de Ciencias Fisicas e Matematicas. Lab. Estrutura e Atividade

    2010-07-01

    Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC{sub 50} values in the range of 20-60 {mu}M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series. (author)

  9. Studies of synthetic chalcone derivatives as potential inhibitors of secretory phospholipase A2, cyclooxygenases, lipoxygenase and pro-inflammatory cytokines

    Directory of Open Access Journals (Sweden)

    Jantan I

    2014-09-01

    Full Text Available Ibrahim Jantan,1,* Syed Nasir Abbas Bukhari,1,* Olayiwola A Adekoya,2 Ingebrigt Sylte3 1Drug and Herbal Research Centre, Faculty of Pharmacy, Universiti Kebangsaan Malaysia, Kuala Lumpur, Malaysia; 2Department of Pharmacy, Faculty of Health Science, UiT The Arctic University of Norway, Tromsø, Norway; 3Department of Medical Biology, Faculty of Health Science, UiT The Arctic University of Norway, Tromsø, Norway *These authors contributed equally to this work Abstract: Arachidonic acid metabolism leads to the generation of key lipid mediators which play a fundamental role during inflammation. The inhibition of enzymes involved in arachidonic acid metabolism has been considered as a synergistic anti-inflammatory effect with enhanced spectrum of activity. A series of 1,3-diphenyl-2-propen-1-one derivatives were investigated for anti-inflammatory related activities involving inhibition of secretory phospholipase A2, cyclooxygenases, soybean lipoxygenase, and lipopolysaccharides-induced secretion of interleukin-6 and tumor necrosis factor-alpha in mouse RAW264.7 macrophages. The results from the above mentioned assays exhibited that the synthesized compounds were effective inhibitors of pro-inflammatory enzymes and cytokines. The results also revealed that the chalcone derivatives with 4-methlyamino ethanol substitution seem to be significant for inhibition of enzymes and cytokines. Molecular docking experiments were carried out to elucidate the molecular aspects of the observed inhibitory activities of the investigated compounds. Present findings increase the possibility that these chalcone derivatives might serve as a beneficial starting point for the design and development of improved anti-inflammatory agents. Keywords: anti-inflammatory, tumor necrosis factor-alpha, lipopolysaccharides, molecular docking

  10. A green approach to the synthesis of chalcones via Claisen-Schmidt condensation reaction using cesium salts of 12-tungstophosphoric acid as a reusable nanocatalyst

    International Nuclear Information System (INIS)

    The catalytic efficacy of different cesium salts of 12-tungstophosphoric acid as nanocatalysts was checked in Claisen-Schmidt condensation of aldehydes and ketones under solvent-free conditions to produce chalcones. The reaction is fast and environmentally benign with excellent selectivity for the synthesis of chalcones. Results of potentiometric titration and catalytic reactivity of the catalysts indicated that the catalytic reactivity should be directly proportional to the strength and number of the surface acid sites, which are the ones accessible to the reactants. Reusability of the catalysts and acidic properties of reused catalysts were investigated. Coking could cause a loss in catalyst acidity, leading to a decrease in the product yield. But the amount of coke remains constant in successive runs. Furthermore, the use of this catalyst is feasible because of its easy preparation and handling, and stability. Large-scale synthesis is also beneficial in this method. Two new compounds are synthesized and fully characterized. (author)

  11. Neuroprotective effect of synthetic chalcone derivatives as competitive dual inhibitors against μ-calpain and cathepsin B through the downregulation of tau phosphorylation and insoluble Aβ peptide formation.

    Science.gov (United States)

    Jeon, Kyung-Hwa; Lee, Eunyoung; Jun, Kyu-Yeon; Eom, Ji-Eun; Kwak, Soo Yeon; Na, Younghwa; Kwon, Youngjoo

    2016-10-01

    A series of chalcone derivatives were synthesized and evaluated for their μ-calpain and cathepsin B inhibitory activities. Among the tested chalcone derivatives, two compounds, 7 and 11, showed potent inhibitory activities against μ-calpain and cathepsin B and were selected for further evaluation. Compounds 7 and 11 showed enzyme inhibitory activities at the cellular level and displayed neuroprotective effects against oxidative stress-induced apoptosis in SH-SY5Y cells, a human neuroblastoma cell line. Moreover, compounds 7 and 11 reduced p25 formation, tau phosphorylation and insoluble Aβ peptide formation. Enzyme kinetic experiments and docking studies revealed that compounds 7 and 11 competitively inhibited both μ-calpain and cathepsin B enzymes. PMID:27318120

  12. Distribution of Flavonoids and Cyclohexenyl Chalcone Derivatives in Conventional Propagated and In Vitro-Derived Field-Grown Boesenbergia rotunda (L.) Mansf.

    Science.gov (United States)

    Tan, Boon Chin; Tan, Siew Kiat; Wong, Sher Ming; Ata, Nabeel; Rahman, Noorsaadah Abd; Khalid, Norzulaani

    2015-01-01

    The distribution patterns of flavonoids and cyclohexenyl chalcone derivatives in conventional propagated (CP) and in vitro-derived (CPA) field-grown plants of an important medicinal ginger, Boesenbergia rotunda, are described. A total of eight compounds were extracted from six organs (rootlet, rhizome, shoot base, maroon stem, stalk, and leaf) of the CP and CPA plants. Five major chromatographic peaks, namely, alpinetin, pinocembrin, pinostrobin, 4-hydroxypanduratin A, and panduratin A, were consistently observed by high performance liquid chromatography. Nonaerial organs had higher levels of flavonoids than the aerial ones for all types of samples. Among the compounds detected, pinostrobin and 4-hydroxypanduratin A were the most abundant flavonoid and cyclohexenyl chalcone derivative, respectively. The distribution and abundance of the bioactive compounds suggested that the shoot base could be more potentially useful for medicinal application than other organs of the plant and may be the site of storage or occurrence of biosynthetic enzymatic activities. PMID:25883671

  13. Distribution of Flavonoids and Cyclohexenyl Chalcone Derivatives in Conventional Propagated and In Vitro-Derived Field-Grown Boesenbergia rotunda (L. Mansf.

    Directory of Open Access Journals (Sweden)

    Boon Chin Tan

    2015-01-01

    Full Text Available The distribution patterns of flavonoids and cyclohexenyl chalcone derivatives in conventional propagated (CP and in vitro-derived (CPA field-grown plants of an important medicinal ginger, Boesenbergia rotunda, are described. A total of eight compounds were extracted from six organs (rootlet, rhizome, shoot base, maroon stem, stalk, and leaf of the CP and CPA plants. Five major chromatographic peaks, namely, alpinetin, pinocembrin, pinostrobin, 4-hydroxypanduratin A, and panduratin A, were consistently observed by high performance liquid chromatography. Nonaerial organs had higher levels of flavonoids than the aerial ones for all types of samples. Among the compounds detected, pinostrobin and 4-hydroxypanduratin A were the most abundant flavonoid and cyclohexenyl chalcone derivative, respectively. The distribution and abundance of the bioactive compounds suggested that the shoot base could be more potentially useful for medicinal application than other organs of the plant and may be the site of storage or occurrence of biosynthetic enzymatic activities.

  14. Design, Synthesis and Structure-Activity Relationships of Novel Chalcone-1,2,3-triazole-azole Derivates as Antiproliferative Agents.

    Science.gov (United States)

    Zhang, Sai-Yang; Fu, Dong-Jun; Yue, Xiao-Xin; Liu, Ying-Chao; Song, Jian; Sun, Hui-Hui; Liu, Hong-Min; Zhang, Yan-Bing

    2016-01-01

    A series of novel chalcone-1,2,3-triazole-azole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, EC-109 and MGC-803). Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound I-21 showed the most excellent antiproliferative activity with an IC50 value of 1.52 μM against SK-N-SH cancer cells. Further mechanism studies revealed that compound I-21 induced morphological changes of SK-N-SH cancer cells possibly by inducing apoptosis. Novel chalcone-1,2,3-triazole-azole derivatives in this work might be a series of promising lead compounds to develop anticancer agents for treating neuroblastoma. PMID:27213317

  15. Design, Synthesis and Structure-Activity Relationships of Novel Chalcone-1,2,3-triazole-azole Derivates as Antiproliferative Agents

    Directory of Open Access Journals (Sweden)

    Sai-Yang Zhang

    2016-05-01

    Full Text Available A series of novel chalcone-1,2,3-triazole-azole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, EC-109 and MGC-803. Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound I-21 showed the most excellent antiproliferative activity with an IC50 value of 1.52 μM against SK-N-SH cancer cells. Further mechanism studies revealed that compound I-21 induced morphological changes of SK-N-SH cancer cells possibly by inducing apoptosis. Novel chalcone-1,2,3-triazole-azole derivatives in this work might be a series of promising lead compounds to develop anticancer agents for treating neuroblastoma.

  16. Structure-based drug design of a novel family of chalcones as PPARα agonists: virtual screening, synthesis, and biological activities in vitro

    Institute of Scientific and Technical Information of China (English)

    Xiang-hua LI; Han-jun ZOU; An-hui WU; Yang-liang YE; Jian-hua SHEN

    2007-01-01

    Aim: To design and synthesize a novel class of peroxisome proliferator-activated receptors (PPAR)α agonists, which is obtained by the combination of the classi- cal fibrate "head group", a linker with appropriate length and a chalcone. Methods: Thirty seven compounds were designed and identified employing the virtual screening approach. Six compounds were then selected for synthesis and bioas- say according to the virtual screening results, structural similarity, and synthetic complexity. Results: Six new compounds (4b and 4d-h) were synthesized and bioassayed. All were found to be potent PPARα agonists, compound 4 h being the most prominent with a 50% effective concentration value of 0.06 μmol/L. Conclusion: This study provides a promising novel family of chalcones with a potential hypolipidemic effect.

  17. Trans-chalcone and quercetin down-regulate fatty acid synthase gene expression and reduce ergosterol content in the human pathogenic dermatophyte Trichophyton rubrum

    OpenAIRE

    Bitencourt, Tamires Aparecida; Komoto, Tatiana Takahasi; Massaroto, Bruna Gabriele; Miranda, Carlos Eduardo Saraiva; Beleboni, Rene Oliveira; Marins, Mozart; Fachin, Ana Lúcia

    2013-01-01

    Background Fatty acid synthase (FAS) is a promising antifungal target due to its marked structural differences between fungal and mammalian cells. The aim of this study was to evaluate the antifungal activity of flavonoids described in the scientific literature as FAS inhibitors (quercetin, trans-chalcone, ellagic acid, luteolin, galangin, and genistein) against the dermatophyte Trichophyton rubrum and their effects on fatty acid and ergosterol synthesis. Methods The antifungal activity of th...

  18. CuO-promoted construction of N-2-aryl-substituted-1,2,3-triazoles via azide-chalcone oxidative cycloaddition and post-triazole arylation.

    Science.gov (United States)

    Zhang, Yuanqing; Li, Xiaolong; Li, Jihui; Chen, Jinying; Meng, Xu; Zhao, Mingming; Chen, Baohua

    2012-01-01

    An efficient one-pot three-component stepwise approach for the synthesis of N-2-aryl-substituted-1,2,3-triazoles has been developed. By using this azide-chalcone oxidative cycloaddition and post-triazole arylation, a series of N-2-aryl-substituted-1,2,3-triazoles are readily prepared under mild conditions in excellent yields and high regioselectivity. Both the catalyst and substrates are readily available. PMID:22133007

  19. Changes in Phytochemical Synthesis, Chalcone Synthase Activity and Pharmaceutical Qualities of Sabah Snake Grass (Clinacanthus nutans L.) in Relation to Plant Age

    OpenAIRE

    Ali Ghasemzadeh; Alireza Nasiri; Jaafar, Hawa Z. E.; Ali Baghdadi; Izham Ahmad

    2014-01-01

    In the current study, changes in secondary metabolite synthesis and the pharmaceutical quality of sabah snake grass leaves and buds were considered in relation to plant age (1 month, 6 months, and 1 year old). The activity of the enzyme chalcone synthase (CHS, EC 2.3.1.74) was measured, as it is a key enzyme for flavonoid production. Significant differences in total flavonoid (TF) production were observed between the three plant growth periods and the different plant parts. The highest conten...

  20. Differential induction of chalcone synthase mRNA activity at the onset of phytoalexin accumulation in compatible and incompatible plant-pathogen interactions

    OpenAIRE

    Bell, John N.; Dixon, Richard A.; Bailey, John A.; Rowell, Pat M.; Lamb, Chris J.

    1984-01-01

    Changes in the mRNA activity of chalcone synthase, the first enzyme of phenylpropanoid metabolism specific to flavonoid/isoflavonoid biosynthesis, have been investigated in relation to expression of the phytoalexin defense response in race-cultivar specific interactions between hypocotyls of Phaseolus vulgaris and the partially biotrophic fungus Colletotrichum lindemuthianum, causal agent of anthracnose. In an incompatible interaction (host resistant) there is an early but localized increase ...

  1. Distribution of Flavonoids and Cyclohexenyl Chalcone Derivatives in Conventional Propagated and In Vitro-Derived Field-Grown Boesenbergia rotunda (L.) Mansf.

    OpenAIRE

    2015-01-01

    The distribution patterns of flavonoids and cyclohexenyl chalcone derivatives in conventional propagated (CP) and in vitro-derived (CPA) field-grown plants of an important medicinal ginger, Boesenbergia rotunda, are described. A total of eight compounds were extracted from six organs (rootlet, rhizome, shoot base, maroon stem, stalk, and leaf) of the CP and CPA plants. Five major chromatographic peaks, namely, alpinetin, pinocembrin, pinostrobin, 4-hydroxypanduratin A, and panduratin A, were ...

  2. Involvement of Salicylic Acid on Antioxidant and Anticancer Properties, Anthocyanin Production and Chalcone Synthase Activity in Ginger (Zingiber officinale Roscoe) Varieties

    OpenAIRE

    Ehsan Karimi; Jaafar, Hawa Z. E.; Ali Ghasemzadeh

    2012-01-01

    The effect of foliar application of salicylic acid (SA) at different concentrations (10−3 M and 10−5 M) was investigated on the production of secondary metabolites (flavonoids), chalcone synthase (CHS) activity, antioxidant activity and anticancer activity (against breast cancer cell lines MCF-7 and MDA-MB-231) in two varieties of Malaysian ginger, namely Halia Bentong and Halia Bara. The results of high performance liquid chromatography (HPLC) analysis showed that application of SA induced t...

  3. CoMFA, CoMSIA, HQSAR and Molecular Docking Analysis of Ionone-based Chalcone Derivatives as Antiprostate Cancer Activity

    OpenAIRE

    Sharma, R.; Dhingra, N.; Patil, S

    2016-01-01

    Androgen receptor has been proved to be effective site for treatment of prostate cancer. Molecular modeling methods performed on forty-three ionone based chalcones derivatives as anti-prostate cancer activity. The designed comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship models produced statistically significant results with the cross-validated correlation coefficients (q2) of 0.527, 0.550 and 0.670, non-cr...

  4. CoMFA, CoMSIA, HQSAR and molecular docking analysis of ionone-based chalcone derivatives as antiprostate cancer activity

    OpenAIRE

    Sharma, R.; Dhingra, N.; Patil, S

    2016-01-01

    Androgen receptor has been proved to be effective site for treatment of prostate cancer. Molecular modeling methods performed on forty-three ionone based chalcones derivatives as anti-prostate cancer activity. The designed comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship models produced statistically significant results with the cross-validated correlation coefficients (q2) of 0.527, 0.550 and 0.670, non-cr...

  5. The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2).

    Science.gov (United States)

    Kraege, Stefanie; Stefan, Katja; Juvale, Kapil; Ross, Thomas; Willmes, Thomas; Wiese, Michael

    2016-07-19

    During the last decade it has been found that chalcones and quinazolines are promising inhibitors of ABCG2. The combination of these two scaffolds offers a new class of heterocyclic compounds with potentially high inhibitory activity against ABCG2. For this purpose we investigated 22 different heterodimeric derivatives. In this series only methoxy groups were used as substituents as these had been proven superior for inhibitory activity of chalcones. All compounds were tested for their inhibitory activity, specificity and cytotoxicity. The most potent ABCG2 inhibitor in this series showed an IC50 value of 0.19 μM. It possesses low cytotoxicity (GI50 = 93 μM), the ability to reverse MDR and is nearly selective toward ABCG2. Most compounds containing dimethoxy groups showed slight activity against ABCB1 too. Among these three compounds (17, 19 and 24) showed even higher activity toward ABCB1 than ABCG2. All inhibitors were further screened for their effect on basal ATPase activity. Although the basal ATPase activity was partially stimulated, the compounds were not transported by ABCG2. Thus, quinazoline-chalcones are a new class of effective ABCG2 inhibitors. PMID:27100033

  6. Binary classification of chalcone derivatives with LDA or KNN based on their antileishmanial activity and molecular descriptors selected using the Successive Projections Algorithm feature-selection technique.

    Science.gov (United States)

    Goodarzi, Mohammad; Saeys, Wouter; de Araujo, Mario Cesar Ugulino; Galvão, Roberto Kawakami Harrop; Vander Heyden, Yvan

    2014-01-23

    Chalcones are naturally occurring aromatic ketones, which consist of an α-, β-unsaturated carbonyl system joining two aryl rings. These compounds are reported to exhibit several pharmacological activities, including antiparasitic, antibacterial, antifungal, anticancer, immunomodulatory, nitric oxide inhibition and anti-inflammatory effects. In the present work, a Quantitative Structure-Activity Relationship (QSAR) study is carried out to classify chalcone derivatives with respect to their antileishmanial activity (active/inactive) on the basis of molecular descriptors. For this purpose, two techniques to select descriptors are employed, the Successive Projections Algorithm (SPA) and the Genetic Algorithm (GA). The selected descriptors are initially employed to build Linear Discriminant Analysis (LDA) models. An additional investigation is then carried out to determine whether the results can be improved by using a non-parametric classification technique (One Nearest Neighbour, 1NN). In a case study involving 100 chalcone derivatives, the 1NN models were found to provide better rates of correct classification than LDA, both in the training and test sets. The best result was achieved by a SPA-1NN model with six molecular descriptors, which provided correct classification rates of 97% and 84% for the training and test sets, respectively. PMID:24090733

  7. Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel

    Directory of Open Access Journals (Sweden)

    Joana Fonseca

    2016-07-01

    Full Text Available We previously reported that prenylated chalcone 2 (PC2, the O-prenyl derivative (2 of 2′-hydroxy-3,4,4′,5,6′-pentamethoxychalcone (1, induced cytotoxicity of tumor cells via disruption of p53-MDM2 interaction. However, the cellular changes through which PC2 exerts its cytotoxic activity and its antitumor potential, remain to be addressed. In the present work, we aimed to (i characterize the effect of PC2 on mitotic progression and the underlying mechanism; and to (ii explore this information to evaluate its ability to sensitize tumor cells to paclitaxel in a combination regimen. PC2 was able to arrest breast adenocarcinoma MCF-7 and non-small cell lung cancer NCI-H460 cells in mitosis. All mitosis-arrested cells showed collapsed mitotic spindles with randomly distributed chromosomes, and activated spindle assembly checkpoint. Live-cell imaging revealed that the compound induced a prolonged delay (up to 14 h in mitosis, culminating in massive cell death by blebbing. Importantly, PC2 in combination with paclitaxel enhanced the effect on cell growth inhibition as determined by cell viability and proliferation assays. Our findings demonstrate that the cytotoxicity induced by PC2 is mediated through antimitotic activity as a result of mitotic spindle damage. The enhancement effects of PC2 on chemosensitivity of cancer cells to paclitaxel encourage further validation of the clinical potential of this combination.

  8. Prenylated Chalcone 2 Acts as an Antimitotic Agent and Enhances the Chemosensitivity of Tumor Cells to Paclitaxel.

    Science.gov (United States)

    Fonseca, Joana; Marques, Sandra; Silva, Patrícia M A; Brandão, Pedro; Cidade, Honorina; Pinto, Madalena M; Bousbaa, Hassan

    2016-01-01

    We previously reported that prenylated chalcone 2 (PC2), the O-prenyl derivative (2) of 2'-hydroxy-3,4,4',5,6'-pentamethoxychalcone (1), induced cytotoxicity of tumor cells via disruption of p53-MDM2 interaction. However, the cellular changes through which PC2 exerts its cytotoxic activity and its antitumor potential, remain to be addressed. In the present work, we aimed to (i) characterize the effect of PC2 on mitotic progression and the underlying mechanism; and to (ii) explore this information to evaluate its ability to sensitize tumor cells to paclitaxel in a combination regimen. PC2 was able to arrest breast adenocarcinoma MCF-7 and non-small cell lung cancer NCI-H460 cells in mitosis. All mitosis-arrested cells showed collapsed mitotic spindles with randomly distributed chromosomes, and activated spindle assembly checkpoint. Live-cell imaging revealed that the compound induced a prolonged delay (up to 14 h) in mitosis, culminating in massive cell death by blebbing. Importantly, PC2 in combination with paclitaxel enhanced the effect on cell growth inhibition as determined by cell viability and proliferation assays. Our findings demonstrate that the cytotoxicity induced by PC2 is mediated through antimitotic activity as a result of mitotic spindle damage. The enhancement effects of PC2 on chemosensitivity of cancer cells to paclitaxel encourage further validation of the clinical potential of this combination. PMID:27483224

  9. Theoretical study of the asymmetric phase-transfer mediated epoxidation of chalcone catalyzed by chiral crown ethers derived from monosaccharides

    Science.gov (United States)

    Makó, Attila; Menyhárd, Dóra K.; Bakó, Péter; Keglevich, György; Tőke, László

    2008-12-01

    The synthesis of a novel, optically active crown ether derived from α- D-altropyranoside is described. A significantly different asymmetric induction was generated by the α- D-glucopyranoside-, α- D-mannopyranoside- and α- D-altropyranoside-based chiral crown catalysts in the epoxidation of trans-chalcone with tert-butyl hydroperoxide under phase-transfer catalytic conditions. It was shown that absolute configuration of the crown-ring fused carbon atoms of the monosaccharides has a great impact on the enantioselectivity. The asymmetric induction could be well explained by considering the possible mechanistic pathway. Molecular modeling (MCMM) and subsequent DFT calculations - in accordance with the experimental results - indicate that the use of glucopyranoside-based catalyst 1 and that of mannopyranoside-based crown ether 2 results in the preferred formation of the opposite antipodes (2 R,3 S and 2 S,3 R, respectively) of the corresponding epoxyketone. At the same time, practically no asymmetric induction was proved if altropyranoside-based crown 3 is applied as the catalyst. The computational results are in qualitative agreement with the experimental data.

  10. Design, synthesis and antibacterial study of new potent and selective coumarin-chalcone derivatives for the treatment of tenacibaculosis.

    Science.gov (United States)

    Vazquez-Rodriguez, Saleta; Lama López, Raquel; Matos, Maria João; Armesto-Quintas, Gabriel; Serra, Silvia; Uriarte, Eugenio; Santana, Lourdes; Borges, Fernanda; Muñoz Crego, Angeles; Santos, Ysabel

    2015-11-01

    With the aim of finding new chemical entities selective for fish pathogens to avoid drug resistance in humans, a series of coumarin-chalcone hybrid compounds with different patterns of substitution were designed and synthesized. Their antibacterial activity was evaluated against important types of human bacteria strains (Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa) and against a fourteen strains of the marine pathogen Tenacibaculum maritimum, responsible for tenacibaculosis in fish, which is an important disease that causes great economical loss in the aquaculture industry. All the amino derivatives 5-12 presented high activity against different strains of T. maritimum, no activity against any of the three human pathogenic bacteria strains and no toxicity. Compounds 6, 7 and 11 were the most promising molecules. The most sensitive strains to these compounds were LL01 8.3.8 and LL01 8.3.1, being compound 11 up to 20 times more active than enrofloxacin. Therefore these scaffolds are good candidates for aquaculture treatments, avoiding possible drug resistance problems in humans. PMID:26433630

  11. In vivo phase II-enzymes inducers, as potential chemopreventive agents, based on the chalcone and furoxan skeletons.

    Science.gov (United States)

    Cabrera, Mauricio; Mastandrea, Ignacio; Otero, Gabriel; Cerecetto, Hugo; González, Mercedes

    2016-04-15

    Cancer chemoprevention involves prevention/delay/reverse of the carcinogenic process through administration of cancer chemopreventive agents (CCA). Compounds which are able to induce detoxification-enzymes, especially monofunctional phase II enzymes, have become in excellent approaches for new CCA. Herein, we report the synthesis of new furoxanyl chalcone-like hybrid compounds as CCA. In vitro studies showed that phenylfuroxanyl derivatives 6 and 9 displayed the best activities being 9 the greatest monofunctional-inducer. Additionally, compounds were non-mutagenic against TA98 Salmonella typhimurium strain (Ames test) and could be used in the prevention of the progression of pre-malignant lesions for their cytotoxic activity against tumoral cells. In vivo proof of concept showed increment on phase II-enzymes activities in liver, colon and mammary gland having derivative 9 the best induction profiles. We probed Nrf2 nuclear translocation is operative for both compounds allowing to exert protective effects via expression of downstream phase-II enzymes. PMID:26970663

  12. Synthesis, Leishmanicidal and Cytotoxic Activity of Triclosan-Chalcone, Triclosan-Chromone and Triclosan-Coumarin Hybrids

    Directory of Open Access Journals (Sweden)

    Elver Otero

    2014-08-01

    Full Text Available Twelve hybrids derived from triclosan were obtained via Williamson etherification of O-triclosan alkyl bromide plus chalcone and O-coumarin or O-chromone alkyl bromide plus triclosan, respectively. Structures of the products were elucidated by spectroscopic analysis. The synthesized compounds were evaluated for antileishmanial activity against L. (V panamensis amastigotes. Cytotoxic activity was also evaluated against mammalian U-937 cells. Compounds 7–9 and 17, were active against Leishmania parasites (EC50 = 9.4; 10.2; 13.5 and 27.5 µg/mL, respectively and showed no toxicity toward mammalian cells (>200 µg/mL. They are potential candidates for antileishmanial drug development. Compounds 25–27, were active and cytotoxic. Further studies using other cell types are needed in order to discriminate whether the toxicity shown by these compounds is against tumor or non-tumor cells. The results indicate that compounds containing small alkyl chains show better selectivity indices. Moreover, Michael acceptor moieties may modify both the leishmanicidal activity and cytotoxicity. Further studies are required to evaluate if the in vitro activity against Leishmania panamensis demonstrated here is also observed in vivo.

  13. Development of fluorinated methoxylated chalcones as selective monoamine oxidase-B inhibitors: Synthesis, biochemistry and molecular docking studies.

    Science.gov (United States)

    Mathew, Bijo; Mathew, Githa Elizabeth; Uçar, Gülberk; Baysal, Ipek; Suresh, Jerad; Vilapurathu, Jobin Kunjumon; Prakasan, Aneesh; Suresh, Jeethu Kuruppath; Thomas, Anjana

    2015-10-01

    A series of methoxylated chalcones with fluoro and trifluoromethyl derivatives were synthesized and investigated for their ability to inhibit human monoamine oxidase A and B. The chemical structures of the compounds have been characterized by means of their (1)H NMR, (13)C NMR, Mass spectroscopic datas and elemental analysis. The results demonstrate that these compounds are reversible and selective MAO-B inhibitors with a competitive mode of inhibition. The most potent compound (2E)-1-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl] prop-2-en-1-one showed the best activity and higher selectivity towards hMAO-B with Ki and SI values of 0.22±0.01μM and 0.05 comparable to that standard drug, Selegiline Ki and SI values were found as 0.33±0.03μM and 0.04, respectively. Molecular docking studies were carried out to further explain the in vitro results of the new compounds, and to identify the hypothetical binding mode for the compounds inside the inhibitor binding cavity of hMAO-B. PMID:26189013

  14. Likelihood analysis of the chalcone synthase genes suggests the role of positive selection in morning glories (Ipomoea).

    Science.gov (United States)

    Yang, Ji; Gu, Hongya; Yang, Ziheng

    2004-01-01

    Chalcone synthase (CHS) is a key enzyme in the biosynthesis of flavonoides, which are important for the pigmentation of flowers and act as attractants to pollinators. Genes encoding CHS constitute a multigene family in which the copy number varies among plant species and functional divergence appears to have occurred repeatedly. In morning glories (Ipomoea), five functional CHS genes (A-E) have been described. Phylogenetic analysis of the Ipomoea CHS gene family revealed that CHS A, B, and C experienced accelerated rates of amino acid substitution relative to CHS D and E. To examine whether the CHS genes of the morning glories underwent adaptive evolution, maximum-likelihood models of codon substitution were used to analyze the functional sequences in the Ipomoea CHS gene family. These models used the nonsynonymous/synonymous rate ratio (omega = d(N)/ d(S)) as an indicator of selective pressure and allowed the ratio to vary among lineages or sites. Likelihood ratio test suggested significant variation in selection pressure among amino acid sites, with a small proportion of them detected to be under positive selection along the branches ancestral to CHS A, B, and C. Positive Darwinian selection appears to have promoted the divergence of subfamily ABC and subfamily DE and is at least partially responsible for a rate increase following gene duplication. PMID:14743314

  15. Pharmacophore Modeling, Atom based 3D-QSAR and Docking Studies of Chalcone derivatives as Tubulin inhibitors

    Directory of Open Access Journals (Sweden)

    Naresh Kandakatla

    2014-09-01

    Full Text Available Tubulin is attractive target for anticancer drug design and their inhibitors are useful in treatment of various cancers. Pharmacophore and Atom based QSAR studies were carried out for series of Chalcone derivatives. Pharmacophore model was developed using 38 compounds, having pIC50 ranging 4.003 to 6.552. The best Pharmacophoric hypothesis AHHRR.10 (one H-acceptor, two hydrophobic groups, two aromatic rings had survival score of 4.824. Atom based 3D QSAR was built for the best hypothesis with training set of 31 and test set of 7 compounds using PLS factor. The obtained QSAR model has excellent regression coefficient of R2 = 0.954, cross validated correlation coefficient q2 = 0.681, Pearson-R = 0.886 and Fisher ratio F = 136.9. The QSAR results explain electron withdrawing, positive, negative ionic and hydrophobic groups are crucial for tubulin inhibition. The docking studies of these inhibitors on the active site of the beta-tubulin shows crucial hydrogen bond interactions with the Gln11, Asn101, Thr145 amino acids. These findings provide designing of novel compounds with better tubulin inhibitory potential.

  16. Optimisation of onion peroxidase-catalysed formation of aureusidin using 2',4',6',3,4-pentahydroxy chalcone as substrate

    Directory of Open Access Journals (Sweden)

    SONIA MOUSSOUNI

    2014-08-01

    Full Text Available Previous investigations demonstrated that crude peroxidase (POD obtained from onion solid wastes has the ability to catalyse the formation of the aurone aureusidin (ARS, using 2´,4´,6´,3,4-pentahydroxy chalcone (PHC as substrate, although this reaction under physiological conditions is mediated by a polyphenol oxidase-like enzyme, called aureusidin synthase (AS. In this study, a crude onion POD preparation was used to study the effect of some critical factors affecting the reaction, including reaction time, pH and temperature. The optimal set of conditions was identified by deploying central composite factorial design and response surface methodology. The results obtained showed that the optimum values for pH and temperature were 5 and 20°C, respectively, while time was found to exert a statistically non-significant effect. These values were the same or very close to optimal conditions found for structurally different onion POD substrates. The outcome was discussed with regard to the applicability of the onion POD as a versatile tool of biocatalysis.

  17. Synthesis of a series of novel dihydroartemisinin monomers and dimers containing chalcone as a linker and their anticancer activity.

    Science.gov (United States)

    Gaur, Rashmi; Pathania, Anup Singh; Malik, Fayaz Ahmad; Bhakuni, Rajendra Singh; Verma, Ram Kishor

    2016-10-21

    A new series of monomer and dimer derivatives of dihydroartemisinin (DHA) containing substituted chalcones as a linker were synthesized and investigated for their cytotoxicity in human cancer cell lines HL-60 (leukemia), Mia PaCa-2 (pancreatic cancer), PC-3 (prostate cancer), LS180 (colon cancer) and HEPG2 (hepatocellular carcinoma). Some of these derivatives have greater antiproliferative and cytotoxic effects in tested cell lines than parent compound DHA. The structures of the all compounds were confirmed by IR, (1)H NMR and mass spectral data. Among the new derivatives, compounds 8, 14, 15, 20 and 24 were found to be more active than parent DHA against tested human cancer cell lines. DHA derivatives were found to be most active in human leukemia cell lines with compounds 8, 14, 15, 20 and 24 showed IC50 values less than 1 μM for 48 h whereas DHA has IC50 value of 2 μM at same time period. The most potent compounds 8 with IC50 = 0.3 μM (at par with doxorubicin (IC50 = 0.3 μM)) and 15 with IC50 = 0.4 μM, of the series, six and three times active than DHA (with IC50 = 2 μM) respectively were selected for further mechanistic work in human leukemia HL-60 cells. PMID:27371926

  18. Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of nonapoptotic cell death.

    Science.gov (United States)

    Robinson, Michael W; Overmeyer, Jean H; Young, Ashley M; Erhardt, Paul W; Maltese, William A

    2012-03-01

    Methuosis is a novel caspase-independent form of cell death in which massive accumulation of vacuoles derived from macropinosomes ultimately causes cells to detach from the substratum and rupture. We recently described a chalcone-like compound, 3-(2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e., MIPP), which can induce methuosis in glioblastoma and other types of cancer cells. Herein, we describe the synthesis and structure-activity relationships of a directed library of related compounds, providing insights into the contributions of the two aryl ring systems and highlighting a potent derivative, 3-(5-methoxy, 2-methyl-1H-indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e., MOMIPP) that can induce methuosis at low micromolar concentrations. We have also generated biologically active azide derivatives that may be useful for future studies aimed at identifying the protein targets of MOMIPP by photoaffinity labeling techniques. The potential significance of these studies is underscored by the finding that MOMIPP effectively reduces the growth and viability of Temozolomide-resistant glioblastoma and doxorubicin-resistant breast cancer cells. Thus, it may serve as a prototype for drugs that could be used to trigger death by methuosis in cancers that are resistant to conventional forms of cell death (e.g., apoptosis). PMID:22335538

  19. Role of nuclear factor-κB and heme oxygenase-1 in the mechanism of action of an anti-inflammatory chalcone derivative in RAW 264.7 cells

    OpenAIRE

    Alcaraz, María José; Vicente, Ana María; Araico, Amparo; Dominguez, José N; Terencio, María Carmen; Ferrándiz, María Luisa

    2004-01-01

    The synthetic chalcone 3′,4′,5′,3,4,5-hexamethoxy-chalcone (CH) is an anti-inflammatory compound able to reduce nitric oxide (NO) production by inhibition of inducible NO synthase protein synthesis. In this work, we have studied the mechanisms of action of this compound.CH (10–30 μM) prevents the overproduction of NO in RAW 264.7 macrophages stimulated with lipopolysaccharide (1 μg ml−1) due to the inhibition of nuclear factor κB (NF-κB) activation.We have shown that treatment of cells with C...

  20. α,β-Unsaturated Carbonyl System of Chalcone-Based Derivatives is Responsible for Broad Inhibition of Proteasomal Activity and Preferential Killing of Human Papilloma Virus (HPV)-Positive Cervical Cancer Cells

    OpenAIRE

    Bazzaro, Martina; Anchoori, Ravi K.; Mudiam, Mohana Krishna R; Issaenko, Olga; Kumar, Srinivas; Karanam, Balasubramanyam; Lin, Zhenhua; Vogel, Rachel Isaksson; Gavioli, Riccardo; Destro, Federica; Ferretti, Valeria; Roden, Richard BS; Khan, Saeed R.

    2010-01-01

    Proteasome inhibitors have potential for the treatment of cervical cancer. We describe the synthesis and biological characterization of a new series of 1,3-diphenylpropen-1-one (chalcone)-based derivatives lacking the boronic acid moieties of the previously reported chalcone-based proteasome inhibitor 3,5-bis-(4-boronic acid-benzylidene)-1-methyl-piperidin- 4-one and bearing a variety of amino acid substitutions on the amino-group of the 4-piperidone. Our lead compound 2 (RA-1) inhibits prote...

  1. 查耳酮的合成及体外抗真菌活性%Synthesis of a New Series of Chalcone Derivatives and Their Antifungal Activities

    Institute of Scientific and Technical Information of China (English)

    李正香; 李安良

    2004-01-01

    目的合成查耳酮类化合物并测定其抗真菌活性. 方法利用Claisen-Schmidt反应合成查耳酮,并针对四种真菌(白色念珠菌、新生隐球菌、烟曲霉菌、红色毛癣菌)做了体外抗真菌活性筛选. 结果显示所合成化合物大多具有体外抗真菌活性,尤其化合物8, 其针对浅表菌的抗真菌活性与氟康唑相当.本文还对部分查耳酮的合成做了一些探索.结论所合成的查耳酮均有不同程度的抗真菌活性,其化学结构差异与抗菌活性相关.%Aim To study the antifungal effect of chalcone derivatives. Methods Sixteen chalcone derivatives were synthesized and confirmed by 1H NMR and IR spectra, and tested for antifungal activity against four common pathogenic fungi. Their structure-activity relationship is discussed. Results Among 16 title compounds, there were 5 new compounds, which have not been reported before. The preliminary antifungal test showed that all title compounds exhibited antifungal activities to a certain extent. The activity of compound 8 against Trichophyton rubrum had a potency equal to that of fluconazole, with a MIC of 4 μg·mL-1. Conclusion Sixteen chalcones were prepared and their antifungal activities against four common pathogenic fungi in vitro were examined. Some of them exhibited antifungal activities to a certain extent.

  2. 4'-Acetoamido-4-hydroxychalcone, a chalcone derivative, inhibits glioma growth and invasion through regulation of the tropomyosin 1 gene

    Energy Technology Data Exchange (ETDEWEB)

    Ku, Bo Mi [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of); Ryu, Hyung Won [Division of Applied Life Science (BK21 Program), EB-NCRC, Institute of Agriculture Life Science, Graduate School of Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Lee, Yeon Kyung; Ryu, Jinhyun; Jeong, Joo Yeon; Choi, Jungil [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of); Cho, Hee Jun [Department of Microbiology, Research Institute of Life Science, College of Natureal Sciences, Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Park, Ki Hun, E-mail: khpark@gnu.ac.kr [Division of Applied Life Science (BK21 Program), EB-NCRC, Institute of Agriculture Life Science, Graduate School of Gyeongsang National University, Jinju 660-701 (Korea, Republic of); Kang, Sang Soo, E-mail: kangss@gnu.ac.kr [Department of Anatomy and Neurobiology, Institute of Health Sciences, School of Medicine, Gyeongsang National University, Jinju 660-751 (Korea, Republic of)

    2010-11-19

    Research highlights: {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) has anti-cancer property for glioma. {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) increased tropomyosin expreesion through activattion of PKA signaling. {yields} 4'-Acetoamido-4-hydroxychalcone (AHC) inhibits glioma cell migration and invasion. {yields} In vivo administration of 4'-acetoamido-4-hydroxychalcone (AHC) reduced tumor growth. -- Abstract: Chalcones are precursors of flavonoids and have been shown to have anti-cancer activity. Here, we identify the synthetic chalcone derivative 4'-acetoamido-4-hydroxychalcone (AHC) as a potential therapeutic agent for the treatment of glioma. Treatment with AHC reduced glioma cell invasion, migration, and colony formation in a concentration-dependent manner. In addition, AHC inhibited vascular endothelial growth factor-induced migration, invasion, and tube formation in HUVECs. To determine the mechanism underlying the inhibitory effect of AHC on glioma cell invasion and migration, we investigated the effect of AHC on the gene expression change and found that AHC affects actin dynamics in U87MG glioma cells. In actin cytoskeleton regulating system, AHC increased tropomyosin expression and stress fiber formation, probably through activation of PKA. Suppression of tropomyosin expression by siRNA or treatment with the PKA inhibitor H89 reduced the inhibitory effects of AHC on glioma cell invasion and migration. In vivo experiments also showed that AHC inhibited tumor growth in a xenograft mouse tumor model. Together, these data suggest that the synthetic chalcone derivative AHC has potent anti-cancer activity through inhibition of glioma proliferation, invasion, and angiogenesis and is therefore a potential chemotherapeutic candidate for the treatment of glioma.

  3. Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents

    OpenAIRE

    Hery Suwito; Jumina; Mustofa; Pratiwi Pudjiastuti; Much Zaenal Fanani; Yoko Kimata-Ariga; Ritsuko Katahira; Toru Kawakami; Toshimichi Fujiwara; Toshiharu Hase; Hasnah Mohd Sirat; Ni Nyoman Tri Puspaningsih

    2014-01-01

    Some chalcones have been designed and synthesized using Claisen-Schmidt reactions as inhibitors of the ferredoxin and ferredoxin-NADP+ reductase interaction to pursue a new selective antimalaria agent. The synthesized compounds exhibited inhibition interactions between PfFd-PfFNR in the range of 10.94%–50%. The three strongest inhibition activities were shown by (E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (50%), (E)-1-(4-aminophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (38.16%...

  4. Design, Synthesis and Structure-Activity Relationships of Novel Chalcone-1,2,3-triazole-azole Derivates as Antiproliferative Agents

    OpenAIRE

    Sai-Yang Zhang; Dong-Jun Fu; Xiao-Xin Yue; Ying-Chao Liu; Jian Song; Hui-Hui Sun; Hong-Min Liu; Yan-Bing Zhang

    2016-01-01

    A series of novel chalcone-1,2,3-triazole-azole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three selected cancer cell lines (SK-N-SH, EC-109 and MGC-803). Most of the synthesized compounds exhibited moderate to good activity against all the cancer cell lines selected. Particularly, compound I-21 showed the most excellent antiproliferative activity with an IC50 value of 1.52 μM against SK-N-SH cancer cells. Further mechanism studies revealed t...

  5. Organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin on chalcones: Synthesis, NMR and single-crystal X-ray diffraction studies of novel warfarin analogues

    Science.gov (United States)

    Talhi, Oualid; Fernandes, José A.; Pinto, Diana C. G. A.; Almeida Paz, Filipe A.; Silva, Artur M. S.

    2015-08-01

    The synthesis of a new series of warfarin analogues by convenient organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin to chalcone derivatives is described. 1H NMR spectroscopy evidenced the presence of a predominant acyclic open-form together with the cyclic hemiketal tautomers of the resulting Michael adducts. The acyclic open-form has been unequivocally proved by single-crystal X-ray diffraction analysis. The use of the B ring ortho-hydroxychalcone synthons in this reaction has led to a diastereoselective synthesis of warfarin bicyclo[3.3.1]nonane ketal derivatives.

  6. Synthesis and evaluation of indole-based chalcones as inducers of methuosis, a novel type of non-apoptotic cell death

    OpenAIRE

    Robinson, Michael W.; Overmeyer, Jean H.; Young, Ashley M.; Erhardt, Paul W.; Maltese, William A.

    2012-01-01

    Methuosis is a novel caspase-independent form of cell death in which massive accumulation of vacuoles derived from macropinosomes ultimately causes cells to detach from the substratum and rupture. We recently described a chalcone-like compound, 3-(2-methyl-1H indol-3-yl)-1-(4-pyridinyl)-2-propen-1-one (i.e. MIPP), which can induce methuosis in glioblastoma and other types of cancer cells. Herein we describe the synthesis and structure-activity relationships of a directed library of related co...

  7. Enhanced expression and differential inducibility of soybean chalcone synthase genes by supplemental UV-B in dark-grown seedlings

    International Nuclear Information System (INIS)

    By developing gene-specific RT-PCR and using filters to allow transmission down to 290 nm (UV-B+) or blocking all radiation below 320 nm (UV-B(-)), the effect of UV-B+ and UV-B- light on expression of each of the presently known seven members of soybean chalcone synthase (CHS) gene family in dark-grown seedlings was analyzed. Dark expression was detectable already in 18 h dark-germinating embryos, with progressive increases on successive days, suggesting that chs belongs to a class of genes expressed very early during germination, and that the expression at this stage is either constitutive or induced by non-light-dependent factors present in the seed or made available following imbibition. Exposure of 18 h dark-germinating embryos to UV-B- or to UV-B+ light did not lead to an increase in chs signal. However, the 24 h dark-germinating embryos showed a distinct effect of UV-B+, interestingly coinciding with the stage when the head of seedlings was in the process of being pushed up above ground by stem elongation, suggesting the possibility of a developmental switch modulating the appearance of UV-B response. The response to UV-B- was most prominent in chs1 and almost silent in chs2, while the up-regulation by UV-B+ was most prominent in chs5 and chs6 and much less so in chs2. Interestingly, chs2 was noted to be the only member of the Gmchs gene family devoid of H-box, raising the possibility that the H-box may be a good indicator of the photo-inducibility of a chs gene. (author)

  8. Topical formulation containing hesperidin methyl chalcone inhibits skin oxidative stress and inflammation induced by ultraviolet B irradiation.

    Science.gov (United States)

    Martinez, Renata M; Pinho-Ribeiro, Felipe A; Steffen, Vinicius S; Caviglione, Carla V; Pala, Danilo; Baracat, Marcela M; Georgetti, Sandra R; Verri, Waldiceu A; Casagrande, Rubia

    2016-04-01

    Skin exposure to ultraviolet B (UVB) irradiation has increased significantly in recent years due to ozone depletion, and it represents the main cause of many skin diseases. Hesperidin methyl chalcone (HMC) is a compound used to treat vascular diseases that has demonstrated anti-inflammatory activities in pre-clinical studies. Herein, we tested the antioxidant activity of HMC in cell free systems and the in vivo effects of a stable topical formulation containing HMC in a mouse model of skin oxidative stress and inflammation induced by UVB irradiation. HMC presented ferric reducing power, neutralized 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and hydroxyl free radicals, and inhibited lipid peroxidation. In hairless mice, a topical formulation containing HMC inhibited UVB irradiation-induced skin edema, depletion of antioxidant capacity (ferric and ABTS reducing abilities and catalase activity), lipid peroxidation, superoxide anion production and mRNA expression of gp91phox (nicotinamide adenine dinucleotide phosphate [NADPH] oxidase 2 sub-unity). In addition, HMC inhibited UVB irradiation-induced depletion of reduced glutathione levels by maintaining glutathione peroxidase-1 and glutathione reductase mRNA expression, prevented down-regulation of nuclear factor erythroid 2-related factor 2 (Nrf2) mRNA expression and increased heme oxygenase-1 mRNA expression. Finally, we demonstrated that topical application of the formulation containing HMC inhibited cytokine (TNF-α, IL-1β, IL-6, and IL-10) production induced by UVB irradiation. Therefore, this topical formulation containing HMC is a promising new therapeutic approach to protecting the skin from the deleterious effects of UVB irradiation. PMID:27021784

  9. In vitro anti-inflammatory, cytotoxic and antioxidant activities of boesenbergin A, a chalcone isolated from Boesenbergia rotunda (L.) (fingerroot)

    International Nuclear Information System (INIS)

    The current in vitro study was designed to investigate the anti-inflammatory, cytotoxic and antioxidant activities of boesenbergin A (BA), a chalcone derivative of known structure isolated from Boesenbergia rotunda. Human hepatocellular carcinoma (HepG2), colon adenocarcinoma (HT-29), non-small cell lung cancer (A549), prostate adenocarcinoma (PC3), and normal hepatic cells (WRL-68) were used to evaluate the cytotoxicity of BA using the MTT assay. The antioxidant activity of BA was assessed by the ORAC assay and compared to quercetin as a standard reference antioxidant. ORAC results are reported as the equivalent concentration of Trolox that produces the same level of antioxidant activity as the sample tested at 20 µg/mL. The toxic effect of BA on different cell types, reported as IC50, yielded 20.22 ± 3.15, 10.69 ± 2.64, 20.31 ± 1.34, 94.10 ± 1.19, and 9.324 ± 0.24 µg/mL for A549, PC3, HepG2, HT-29, and WRL-68, respectively. BA displayed considerable antioxidant activity, when the results of ORAC assay were reported as Trolox equivalents. BA (20 µg/mL) and quercetin (5 µg/mL) were equivalent to a Trolox concentration of 11.91 ± 0.23 and 160.32 ± 2.75 µM, respectively. Moreover, the anti-inflammatory activity of BA was significant at 12.5 to 50 µg/mL and without any significant cytotoxicity for the murine macrophage cell line RAW 264.7 at 50 µg/mL. The significant biological activities observed in this study indicated that BA may be one of the agents responsible for the reported biological activities of B. rotunda crude extract

  10. Comparative molecular field analysis and molecular docking studies on novel aryl chalcone derivatives against an important drug target cysteine protease in Plasmodium falciparum.

    Science.gov (United States)

    Thillainayagam, Mahalakshmi; Anbarasu, Anand; Ramaiah, Sudha

    2016-08-21

    The computational studies namely molecular docking simulations and Comparative Molecular Field Analysis (CoMFA) are executed on series of 52 novel aryl chalcones derivatives using Plasmodium falciparum cysteine proteases (falcipain - 2) as vital target. In the present study, the correlation between different molecular field effects namely steric and electrostatic interactions and chemical structures to the inhibitory activities of novel aryl chalcone derivatives is inferred to perceive the major structural prerequisites for the rational design and development of potent and novel lead anti-malarial compound. The apparent binding conformations of all the compounds at the active site of falcipain - 2 and the hydrogen-bond interactions which could be used to modify the inhibitory activities are identified by using Surflex-dock study. Statistically significant CoMFA model has been developed with the cross-validated correlation coefficient (q(2)) of 0.912 and the non-cross-validated correlation coefficient (r(2)) of 0.901. Standard error of estimation (SEE) of 0.210, with the optimum number of components is ten. The predictability of the derived model is examined with a test set consists of sixteen compounds and the predicted r(2) value is found to be 0.924. The docking and QSAR study results confer crucial suggestions for the optimization of novel 1,3-diphenyl-2-propen-1-one derivatives and synthesis of effective anti- malarial compounds. PMID:27185536

  11. 对甲苯磺酸催化查尔酮的合成%Synthtsis of Chalcone Catalyzed by P-toluenesulfonic Acid

    Institute of Scientific and Technical Information of China (English)

    谭昌会; 郑荣选; 罗淑云; 林俏焰

    2012-01-01

    研究了查耳酮的制备方法和缩合反应的影响因素选择最佳的反应条件,实验的结果表明,合成查尔酮的缩合反应的较佳条件是:n(苯乙酮)加(间硝基苯甲醛)=1∶1,反应温度是70℃,反应的时间3h,对甲笨磺酸为3 g,乙酸用量为20 mL,在此条件下查尔酮的收率达71.6%.%Synthesis methods of chalcone were studied, affecting factors of the condensation reaction were discussed so as to select the best reaction conditions. The experimental results show that the better reaction conditions of the synthesis are as follows: n (m-nitrobenzaldehyde) / n (preparation) = 1 : 1, the reaction temperature is 70 ℃, the reaction time is 3 h, p-toluene sulfonic acid dosage and acetic acid dosage are 3 g and 20 mL , respectively. Under above conditions, the chalcone yield can reach 71.6%.

  12. Synthesis of Novel Chalcone-piperazine Derivatives%新型查尔酮哌嗪衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    王秀丽; 王子杰; 毛泽伟

    2016-01-01

    4-Dimethylamino-4′-(1-piperazinyl)chalcone(2) was preapared by aldol condensation and substitution , using 4-dimethylaminobenzaldehyde and 4′-fluoroacetophenone as materials .Six novel chalcone-piperazine derivatives , in yields of 71% ~88%, were synthesized by reaction of 2 with haloalkanes.The structures were characterized by 1 H NMR, 13 C NMR and HR-MS.%以4-二甲氨基苯甲醛和2-溴-4′-氟苯乙酮为原料,经缩合和取代反应制得4-二甲氨基-4′-(1-哌嗪基)查尔酮(2);2与卤代烃反应合成了6个新型的查尔酮哌嗪衍生物,收率71%~88%,其结构经1 H NMR,13 C NMR和HR-MS表征。

  13. CoMFA, CoMSIA, HQSAR and molecular docking analysis of ionone-based chalcone derivatives as antiprostate cancer activity

    Directory of Open Access Journals (Sweden)

    R Sharma

    2016-01-01

    Full Text Available Androgen receptor has been proved to be effective site for treatment of prostate cancer. Molecular modeling methods performed on forty-three ionone based chalcones derivatives as anti-prostate cancer activity. The designed comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship models produced statistically significant results with the cross-validated correlation coefficients (q2 of 0.527, 0.550 and 0.670, non-cross-validated correlation coefficients (r2 0.636, 0.671 and 0.746 and predicted r2 (Pred r2 of 0.621, 0.563 and 0.732, respectively. Furthermore, bioactive conformation was explored and explained by docking of the potent compound 25 into the binding site of androgen receptor. Present study deals with comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship and molecular docking studies of the ionone-based chalcones and their derivatives, obtained from literature. The model obtained could be effectively used as a channeling tool for further structure modification and designing of some novel potent anti-prostate cancer compounds.

  14. Preparation of highly ordered mesoporous AlSBA-15-SO 3H hybrid material for the catalytic synthesis of chalcone under solvent-free condition

    Science.gov (United States)

    Li, Wei; Xu, Kejin; Xu, Leilei; Hu, Jianglei; Ma, Fengyan; Guo, Yihang

    2010-03-01

    Single-step preparation of SBA-15 materials functionalized with both propylsulfonic acid groups and aluminum species (AlSBA-15-SO 3H) was carried out by hydrothermal treatment of a mixture of aluminum isopropoxide, 3-mercaptopropyltriethoxysilane, tetraethoxysilane, and triblock copolymer surfactant. At Si/Al molar ratio of 11-96, the materials exhibited well-ordered hexagonally arranged mesopores with pore diameter of ca. 9 nm, BET surface area of 546.9-666.0 m 2 g -1, and pore volume of 0.82-1.03 cm 3 g -1. As-prepared AlSBA-15-SO 3H was successfully used in the Claisen-Schmidt condensation reaction of benzaldehyde with acetophenone to produce chalcone under solvent-free condition, and the influence of the reaction parameters including temperatures, molar ratios of BZD to APN, and aluminum loadings were considered during the chalcone synthesis procedure. It showed that AlSBA-15-SO 3H exhibited significantly high catalytic activity and selectivity, outperforming the reference catalysts such as sulfuric acid, ZSM-5, and acidic MCM-49. In addition, the catalytic stability and regeneration of AlSBA-15-SO 3H was studied.

  15. Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3-d]pyrimidine-Based Chromophore

    Directory of Open Access Journals (Sweden)

    Yuh Wen Ho

    2013-01-01

    Full Text Available Cyclization of 4-methyl-2-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carbonitrile 1 with chloroacetone in DMF in the presence of excess potassium carbonate anhydrous gave the 1-(5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidin-6-ylethanone 3, which can react with 2,5-dimethoxytetrahydrofuran in glacial acetic acid producing the 1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-ylthieno[2,3-d]pyrimidin-6-yl]ethanone 4. On the other hand, a series of novel 3-aryl-1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl-thieno[2,3-d]pyrimidin-6-yl]prop-2-en-1-one chalcone dyes 6a—n were obtained by the condensation reaction of 1-[4-methyl-2-phenyl-5(1H-pyrrol-1-ylthieno[2,3-d]-pyrimidin-6-yl]ethanone 4 with appropriate aldehydes. The structures of chalcone dyes were characterized by IR, 1H NMR, mass, elemental analysis, and UV-Vis spectroscopy. The dyes were applied to polyester fibers for creating hues ranging from greenish-yellow to orange; their spectral characteristics, substituent effect in DMF solution, fastness properties, and colorimetric assessment are also discussed.

  16. CoMFA, CoMSIA, HQSAR and Molecular Docking Analysis of Ionone-based Chalcone Derivatives as Antiprostate Cancer Activity.

    Science.gov (United States)

    Sharma, R; Dhingra, N; Patil, S

    2016-01-01

    Androgen receptor has been proved to be effective site for treatment of prostate cancer. Molecular modeling methods performed on forty-three ionone based chalcones derivatives as anti-prostate cancer activity. The designed comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship models produced statistically significant results with the cross-validated correlation coefficients (q(2)) of 0.527, 0.550 and 0.670, non-cross-validated correlation coefficients (r(2)) 0.636, 0.671 and 0.746 and predicted r(2) (Pred r(2)) of 0.621, 0.563 and 0.732, respectively. Furthermore, bioactive conformation was explored and explained by docking of the potent compound 25 into the binding site of androgen receptor. Present study deals with comparative molecular field analysis, comparative similarity indices analysis and hologram quantitative structure activity relationship and molecular docking studies of the ionone-based chalcones and their derivatives, obtained from literature. The model obtained could be effectively used as a channeling tool for further structure modification and designing of some novel potent anti-prostate cancer compounds. PMID:27168682

  17. Cloning and Sequence Analyzing of Chalcone Synthase Gene in Loropetalum chinense var.Rubrum%红花檵木CHS基因的克隆与序列分析

    Institute of Scientific and Technical Information of China (English)

    许威; 于晓英; 陈己任; 符红艳; 胡博文; 陈彦斌; 李达

    2013-01-01

    查尔酮合酶(chalcone synthase,CHS)是进入类黄酮和花色素苷次生代谢的第1个关键酶.根据植物查尔酮合成酶保守区序列设计引物,以红花檵木Loropetalurn chinense var.Rubrum)大叶红的嫩叶为材料,用RT-PCR方法,分离得到了一个查尔酮合成酶基因的eDNA(GenBank登录号为JQ609678),将该基因命名为Lc vrCHS1.该序列长927 bp,编码232个氨基酸残基.其核苷酸序列与GenBank已登录的同样来源的核桃、山茶属植物CHS序列同源性达83%,与其他科植物(绣球花、葡萄、桃、马铃薯、甘草、领春木属)CHS序列同源性也达到80%以上;其编码的氨基酸序列与山茶属、葡萄、鳄梨、洋梨、沙梨、映山红CHS基因编码的氨基酸序列同样具有高度同源性,同源性高达98%.%Chalcone synthase (chalcone synthase, CHS) is the key enzyme that catalyzes the first step in flavonoids biosynthesis and anthocyanins secondary metabolites. A full-length cDNA encoding CHS was cloned from the young leaves of Loropetalurn chinense var. rubrum by RT-PCR using specific primers based on the highly conserved sequences of plant CHS that had already known. Blast search revealed that it was a new gene, and was named as LcvrCHSl (GenBank accession: JQ609678). The sequence was 927 bp, encoding 232 amino acid residues. It had 83% sequence homology with walnut and camellia that had been logged in GenBank; with other genus plants (hydrangea, grapes, peaches, potatoes, licorice, Euptelea genus), CHS sequence homology was also more than 80%; with other plants (camellia, grapes, avocados, bartlett pear, sand pear, azalea), CHS sequence also had high homology, up to 98% homology.

  18. Antiproliferative Activity and Induction of Apoptosis in PC-3 Cells by the Chalcone Cardamonin from Campomanesia adamantium (Myrtaceae in a Bioactivity-Guided Study

    Directory of Open Access Journals (Sweden)

    Aislan Cristina Rheder Fagundes Pascoal

    2014-02-01

    Full Text Available The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employed as a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae leaves and fruits were evaluated against prostate cancer cells (PC-3. The compound (2E-1-(2,4-dihydroxy-6-methoxyphenyl-3-phenylprop-2-en-1-one, cardamonin was isolated from ethanol extracts of C. adamantium leaves in a bioactivity-guided study and quantified by UPLC-MS/MS. In vitro studies showed that the isolated chalcone cardamonin inhibited prostate cancer cell proliferation and decreased the expression of NFkB1. Moreover, analysis by flow cytometry showed that this compound induced DNA fragmentation, suggesting an effect on apoptosis induction in the PC-3 cell line.

  19. Antiproliferative activity and induction of apoptosis in PC-3 cells by the chalcone cardamonin from Campomanesia adamantium (Myrtaceae) in a bioactivity-guided study.

    Science.gov (United States)

    Pascoal, Aislan Cristina Rheder Fagundes; Ehrenfried, Carlos Augusto; Lopez, Begoña Gimenez-Cassina; de Araujo, Thiago Matos; Pascoal, Vinicius D'ávila Bitencourt; Gilioli, Rovilson; Anhê, Gabriel Forato; Ruiz, Ana Lúcia Tasca Goes; Carvalho, João Ernesto de; Stefanello, Maria Elida Alves; Salvador, Marcos José

    2014-01-01

    The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employed as a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae) leaves and fruits were evaluated against prostate cancer cells (PC-3). The compound (2E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one, cardamonin) was isolated from ethanol extracts of C. adamantium leaves in a bioactivity-guided study and quantified by UPLC-MS/MS. In vitro studies showed that the isolated chalcone cardamonin inhibited prostate cancer cell proliferation and decreased the expression of NFkB1. Moreover, analysis by flow cytometry showed that this compound induced DNA fragmentation, suggesting an effect on apoptosis induction in the PC-3 cell line. PMID:24514747

  20. 4’-苯氧基查尔酮类衍生物的合成%Synthesis of 4'-phenoxy Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    李苗苗; 徐志刚; 时志春

    2012-01-01

    Choosing diphenyl ether as the starting material,1-(4-phenoxyphenyl)ethanone was abtained through the friedel-crafts reaction.After reacted with benzaldehyde derivatives in different ways,eight unreported 4'-phenoxy chalcone derivatives were gained.The structures of all synthesized compounds were determined by 1H NMR and ESI-MS.%以联苯醚为起始原料,经傅克酰基化合成4-联苯醚乙酮,与苯甲醛衍生物以不同方式进行羟醛缩合反应,设计合成一系列4'-苯氧基查尔酮类衍生物。产物结构均经ESI-MS和1H NMR确认,合成了8种未见报道的4'-苯氧基查尔酮。

  1. A Study on Synthesis Process of 2-Hydroxyl Chalcon%2-羟基查耳酮合成工艺的研究

    Institute of Scientific and Technical Information of China (English)

    刘健

    2015-01-01

    Chalcone is a key intermediate for pharmaceutical synthesis of flavonoids widely used as medicine. The classical method of synthesis of 2- hydroxy chalcone uses trimethoxy benzene as raw material, and uses acetyl chloride reaction to produce trimethoxy acetophenone, and then it reacts with two methoxy phenyl ac-etaldehyde to produce chalcones. Experimental results show that using the aluminum chloride as catalyst in carbon disulfide solution, when trimethoxy benzene and acetyl chloride ratio is1:1.05, stirring at a constant temperature of 40 DEG C, 2, 4, 6-trimethoxy phenyl ethyl ketone yield can reach the highest percentage, 92%. 2, 4, 6-trimethoxy phenyl ethyl ketone react with 2,4-two methoxy benzaldehydeto produce 2- hydroxy chalcone, with reactant ratio of ethanol solution of 1:1. When 2, 4, 6-trimethoxy acetophenone and amount of 50% KOH ratio is 1:4, the reaction yield is 96%, the total yield of the reaction 88%,which is the optimal re-action condition for industrial production.%查尔酮是合成广泛应用的医药黄酮类化合物的关键中间体,2-羟基查耳酮的经典合成方法是以三甲氧基苯为原料,与乙酰氯反应生成三甲氧基苯乙酮,再与二甲氧基苯乙醛发生反应生成查耳酮。实验结果表明,以三氯化铝为催化剂,在二硫化碳溶液中,三甲氧基苯和乙酰氯配比为1:1.05时,在恒温40℃搅拌,得到的2,4,6-三甲氧基苯乙酮产率最高,为92%。2,4,6-三甲氧基苯乙酮再与2,4-二甲氧基苯甲醛反应得到2-羟基查耳酮,大量的乙醇溶液中反应物配比1:1,2,4,6-三甲氧基苯乙酮与50%的KOH加入量配比为1:4,反应收率为96%,最后总反应收率为88%,为工业生产最佳反应条件。

  2. Antioxidant activities of [60]fullerene derivatives from chalcone, flavone and flavanone: A ONIOM approach via H-atom and electron transfer mechanism

    Science.gov (United States)

    Thong, Nguyen Minh; Dao, Duy Quang; Ngo, Thi Chinh; Huyen, Trinh Le; Nam, Pham Cam

    2016-05-01

    Antioxidant properties of C60 flavonoid conjugates were computationally examined via their O-H bond dissociation enthalpies (BDEs) and ionization energies (IEs) using two-layer ONIOM and PM6 methods, respectively. Eight ONIOM((RO)B3LYP/6-311++G(2df,2p):PM6) models were evaluated by computing BDE(O-H)s of a series of polyphenol. Synthetic mechanism of C60 flavonoid conjugates was also explored via the potential energy surfaces of reaction between C60 and malonate flavonoid derivatives (chalcone, flavone and flavanone) at the B3LYP/6-31G(d)//PM6. Antioxidant activities of C60 flavonoid conjugates were discussed via hydrogen atom transfer, single electron transfer mechanisms and the effect of C60 on the BDE(O-H)s and IEs of these compounds.

  3. Synthesis, characterization, and crystal structure of sulfonamide chalcone: ( E)-4-methoxy- N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)-benzenesulfonamide

    Science.gov (United States)

    Kobkeatthawin, T.; Chantrapromma, S.; Chidan Kumar, C. S.; Fun, H.-K.

    2015-12-01

    The title sulfonamide chalcone derivative was synthesized by condensation reaction of N-(4-acetylphenyl)-4-methoxybenzenesulfonamide and 3,4,5-trimethoxybenzaldehyde in basic solution. The structure was determined using FT-IR, 1H-NMR and UV-Vis spectroscopy. The crystal structure was characterized by single crystal X-ray structure analysis: triclinic system, sp. gr. P overline 1, Z = 2; a = 7.9273(5), b = 9.3159(6), c = 18.0174(12) Å, α = 94.6420(18)°, β = 93.0310(17)°, γ = 114.9200(15)°. In crystal packing, the molecules are linked by N-H···O hydrogen bonds into chains along the [100] direction. The crystal is further stabilized by weak C-H···O and C-H···π interactions.

  4. Synthesis and antimicrobial evaluation of L-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone.

    Science.gov (United States)

    Jin, Xin; Zheng, Chang-Ji; Song, Ming-Xia; Wu, Yan; Sun, Liang-Peng; Li, Yin-Jing; Yu, Li-Jun; Piao, Hu-Ri

    2012-10-01

    Four novel series of compounds, including the l-phenylalanine-derived C5-substituted rhodanine (6a-q, 7a-j) and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone (9a-e, 11a-e) have been designed, synthesized, characterized, and evaluated for their antibacterial activity. Some of these compounds showed significant antibacterial activity against Gram-positive bacterias, especially against the strains of multidrug-resistant clinical isolates, among which compounds 6c-e, 6g, 6i, 6j and 6q exhibiting high levels of antimicrobial activity against Staphylococcus aureus RN4220 with minimum inhibitory concentration (MIC) values of 2 μg/mL. Compound 6q showed the most potent activity of all of the compounds against all of the test multidrug-resistant clinical isolates tested. Unfortunately, however, none of the compounds were active against Gram-negative bacteria at 64 μg/mL. PMID:22982124

  5. A novel chalcone derivative attenuates the diabetes-induced renal injury via inhibition of high glucose-mediated inflammatory response and macrophage infiltration

    Energy Technology Data Exchange (ETDEWEB)

    Fang, Qilu [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Zhao, Leping [Department of Pharmacy, the Affiliated Yueqing Hospital, Wenzhou Medical University, Wenzhou, Zhejiang (China); Wang, Yi; Zhang, Yali [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Li, Zhaoyu [Department of International High School, Shanghai Jiaotong University Nanyang Affiliated (Kunshan) School, Minhang District, Shanghai (China); Pan, Yong; Kanchana, Karvannan; Wang, Jingying; Tong, Chao [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China); Li, Dan, E-mail: yqyyld@163.com [Department of Nephrology, the Affiliated Yueqing Hospital, Wenzhou Medical University, Wenzhou, Zhejiang (China); Liang, Guang, E-mail: wzmcliangguang@163.com [Chemical Biology Research Center, School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou, Zhejiang (China)

    2015-01-15

    Inflammation plays a central role in the development and progression of diabetic nephropathy (DN). Researches on novel anti-inflammatory agents may offer new opportunities for the treatment of DN. We previously found a chalcone derivative L6H21 could inhibit LPS-induced cytokine release from macrophages. The aim of this study was to investigate whether L6H21 could ameliorate the high glucose-mediated inflammation in NRK-52E cells and attenuate the inflammation-mediated renal injury. According to the results, L6H21 showed a great inhibitory effect on the expression of pro-inflammatory cytokines, cell adhesion molecules, chemokines, and macrophage adhesion via down-regulation of NF-κB/MAPKs activity in high glucose-stimulated renal NRK-52E cells. Further, in vivo oral administration with L6H21 at a dosage of 20 mg/kg/2 days showed a decreased expression of pro-inflammatory cytokines, cell adhesion molecules, which subsequently contributed to the inhibition on renal macrophage infiltration, the reduction of serum creatinine and BUN levels, and the improvement on the fibrosis and pathological changes in the renal tissues of diabetic mice. These findings provided that chalcone derived L6H21 may be a promising anti-inflammatory agent and have the potential in the therapy of diabetic nephropathy, and importantly, MAPK/NF-κB signaling system may be a novel therapeutic target for human DN in the future. - Highlights: • Inflammation plays a central role in the development of diabetic nephropathy. • Compound L6H21 reduced the high glucose-mediated inflammation in NRK-52E cells. • Compound L6H21 attenuated the inflammation-mediated renal injury. • L6H21 exhibited anti-inflammatory effects via inactivation of NF-κB/MAPKs. • MAPKs/NF-κB may be a novel therapeutic target in diabetic nephropathy treatment.

  6. 一类新型含炔基结构查尔酮的合成及表征%Synthesis and Characterization of Novel Chalcones Containing Alkynyl Structure

    Institute of Scientific and Technical Information of China (English)

    刘运奎; 张巍; 陈小玲; 徐振元

    2014-01-01

    报道了一种新型含炔基查尔酮的合成方法,以邻溴苯甲醛和含取代基苯乙炔为原料,通过Sonogashira偶联反应,生成的炔基苯甲醛进一步与苯乙酮反应生成含炔基结构的查尔酮,此类查尔酮在过渡金属催化的串联反应研究领域有着重要的作用,该类化合物拓展了金、钯、铜等过渡金属参与催化的有机合成反应的底物范围,对进一步研究过渡金属参与的串联反应有一定的指导意义。该方法具有原料简单易得、反应过程操作容易、收率高等优点,产物经红外、核磁共振和质谱等分析手段确证结构。%We reported a controlled synthesis of novel chalcones containing alkynyl structure ,via Sonogashira coupling reaction of a kind of 2-bromobenzaldehyde and ethynylbenzene, then via a further response of 2-(Phenylethynyl)benzaldehyde and acetophenone. This kind of chalcones are important in transition metal reactions, this new compounds expand the scopes of substrates of transition metal reactions. The results of this investigation were used as a guide for the preparation of a series of substrations in high yield of tandem organic reactions.

  7. Synthetic Process Optimization of Chalcone Derivative under Microwave Irradiation%微波辅助合成查尔酮衍生物的工艺

    Institute of Scientific and Technical Information of China (English)

    张国喜; 杨金凤; 姬广军; 李炳奇

    2011-01-01

    Eight chalcone derivatives (3a~3d,4a~4d) were synthesized by benzaldehyde(2e,2f) and substituted acetonphenone (la~Id) under microwave irradiation conditions, which is to further study the preparation of new pyrazoline. The structures were confirmed by 1H-NMR,IR,MS and elementary analysis. The synthesis technology chalcone (3a) was studied. Effects of raw materials mole ratio,reaction time and microwave radiation power on the reaction yield were investigated. The optimal synthesis conditions are benzaldehyde to acetophenone mole ratio,microwave power reaction,microwave irradiation time. The synthesis reaction were easily worked up with short time,high yields and green initiative.%本文应用微波辐射技术,以苯甲醛衍生物(1a~1d)和苯乙酮衍生物(2e,2f)为原料,合成了8种查尔酮衍生物(3a~3d,4a~4d),它们是重要的有机中间体,其结构经1H NMR,IR,MS和元素分析表征;研究了查尔酮3a的合成工艺,考察了物料比微波辐射时间辐射功率对产率的影响,通过正交实验确定查尔酮的最佳合成条件为:苯甲醛与苯乙酮的物质的量之比1∶ 1,微波功率140W,微波反应时间为25 min,产率85%~92%.

  8. Design, synthesis and preliminary structure-activity relationship investigation of nitrogen-containing chalcone derivatives as acetylcholinesterase and butyrylcholinesterase inhibitors: a further study based on Flavokawain B Mannich base derivatives.

    Science.gov (United States)

    Liu, Haoran; Fan, Haoqun; Gao, Xiaohui; Huang, Xueqing; Liu, Xianjun; Liu, Linbo; Zhou, Chao; Tang, Jingjing; Wang, Qiuan; Liu, Wukun

    2016-08-01

    In order to study the structure-activity relationship of Flavokawain B Mannich-based derivatives as acetylcholinesterase (AChE) inhibitors in our recent investigation, 20 new nitrogen-containing chalcone derivatives (4 a-8d) were designed, synthesized, and evaluated for AChE inhibitory activity in vitro. The results suggested that amino alkyl side chain of chalcone dramatically influenced the inhibitory activity against AChE. Among them, compound 6c revealed the strongest AChE inhibitory activity (IC50 value: 0.85 μmol/L) and the highest selectivity against AChE over BuChE (ratio: 35.79). Enzyme kinetic study showed that the inhibition mechanism of compound 6c against AChE was a mixed-type inhibition. The molecular docking assay showed that this compound can both bind with the catalytic site and the peripheral site of AChE. PMID:26186269

  9. 4’-甲氧基-2’-羟基查尔酮及衍生物的合成与活性%Synthesis and Activity Detection of 4′- Methoxy -2′- Hydroxy Chalcone and its Derivatives

    Institute of Scientific and Technical Information of China (English)

    郑高亮; 卢俊; 余心哲; 郁建平

    2015-01-01

    以对甲氧基苯乙酮和苯甲醛衍生物为原料,在无水乙醇为溶剂的条件下,采用浓度为2.5mol/L的NaOH溶液为催化剂,经aldol缩合获得了8种查尔酮衍生物,采用1 HNMR、13 CNMR、MS 对其进行了结构表征。采用MTT法测定了2种查尔酮衍生物的乳腺癌MDA231细胞抑制活性,并使用了原料作为对照组,实验结果表明对照检查几乎没抗乳腺癌MAD231细胞活性,实验组有一定抗乳腺癌MAD231细胞活性,查尔酮及衍生物有作为抗癌药物的潜在价值。%With methoxy acetophenone and benzaldehyde derivatives as raw materials, anhydrous ethanol as solvent, and 2. 5 mol/L NaOH solution as catalyst, eight chalcone derivatives were synthesized by the aldol condensation, and their structures were characterized by 1 H-NMR, 13 C NMR and MS. Activity of two chal-cone derivatives for inhibiting breast cancer MDA231 cells were determined by MTT method. The results showed that two chalcone derivatives somewhat had practical activity of anti-breast cancer MAD231 cells, conversely, the raw materials had no anti-breast cancer effect, indicating that chalcone and its derivatives were promising for antitumor drug exploitation.

  10. Inhibition of Epithelial CC-Family Chemokine Synthesis by the Synthetic Chalcone DMPF-1 via Disruption of NF-κB Nuclear Translocation and Suppression of Experimental Asthma in Mice

    OpenAIRE

    Revathee Rajajendram; Chau Ling Tham; Mohamad Nadeem Akhtar; Mohd Roslan Sulaiman; Daud Ahmad Israf

    2015-01-01

    Asthma is associated with increased pulmonary inflammation and airway hyperresponsiveness. The interaction between airway epithelium and inflammatory mediators plays a key role in the pathogenesis of asthma. In vitro studies evaluated the inhibitory effects of 3-(2,5-dimethoxyphenyl)-1-(5-methylfuran-2-yl)prop-2-en-1-one (DMPF-1), a synthetic chalcone analogue, upon inflammation in the A549 lung epithelial cell line. DMPF-1 selectively inhibited TNF-α-stimulated CC chemokine secretion (RANTES...

  11. Involvement of Salicylic Acid on Antioxidant and Anticancer Properties, Anthocyanin Production and Chalcone Synthase Activity in Ginger (Zingiber officinale Roscoe Varieties

    Directory of Open Access Journals (Sweden)

    Ehsan Karimi

    2012-11-01

    Full Text Available The effect of foliar application of salicylic acid (SA at different concentrations (10−3 M and 10−5 M was investigated on the production of secondary metabolites (flavonoids, chalcone synthase (CHS activity, antioxidant activity and anticancer activity (against breast cancer cell lines MCF-7 and MDA-MB-231 in two varieties of Malaysian ginger, namely Halia Bentong and Halia Bara. The results of high performance liquid chromatography (HPLC analysis showed that application of SA induced the synthesis of anthocyanin and fisetin in both varieties. Anthocyanin and fisetin were not detected in the control plants. Accordingly, the concentrations of some flavonoids (rutin and apigenin decreased significantly in plants treated with different concentrations of SA. The present study showed that SA enhanced the chalcone synthase (CHS enzyme activity (involving flavonoid synthesis and recorded the highest activity value of 5.77 nkat /mg protein in Halia Bara with the 10−5 M SA treatment. As the SA concentration was decreased from 10−3 M to 10−5 M, the free radical scavenging power (FRAP increased about 23% in Halia Bentong and 10.6% in Halia Bara. At a concentration of 350 μg mL−1, the DPPH antioxidant activity recorded the highest value of 58.30%–72.90% with the 10−5 M SA treatment followed by the 10−3 M SA (52.14%–63.66% treatment. The lowest value was recorded in the untreated control plants (42.5%–46.7%. These results indicate that SA can act not only as an inducer but also as an inhibitor of secondary metabolites. Meanwhile, the highest anticancer activity against MCF-7 and MDA-MB-231 cell lines was observed for H. Bara extracts treated with 10−5 M SA with values of 61.53 and 59.88%, respectively. The results suggest that the high anticancer activity in these varieties may be related to the high concentration of potent anticancer components including fisetin and anthocyanin. The results thus indicate that the synthesis of

  12. Synthesis, characterization and biological activities of some Ru(II) complexes with substituted chalcones and their applications as chemotherapeutics against breast cancer

    Science.gov (United States)

    Singh, Ashok K.; Saxena, Gunjan; Dixit, Shivani; Hamidullah; Singh, Sachin K.; Singh, Sudheer K.; Arshad, M.; Konwar, Rituraj

    2016-05-01

    Four new Ru(II) DMSO complexes with substituted chalcone ligands viz. (E)-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (HL1), (E)-1-(2-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (HL2), (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (HL3) and (E)-1-(2-hydroxyphenyl)-3-(4-Chlorophenyl)prop-2-en-1-one (HL4) have been synthesized, and characterized by micro-analyses, IR, 1H NMR, UV-Vis and ESI-MS and screened for anti-cancer activity against breast cancer cell lines (MCF-7 and MDA MB-231). Compounds HL4 and [Ru(HL1) (O-DMSO)3(S-DMSO)]Cl (M1R) showed significant anti-breast cancer activity as evident from cytotoxicity, morphological and nuclear changes, DNA fragmentation and cell cycle arrest in breast cancer cells. UV-Vis and CD-spectra analysis showed HL4 and M1R interfered with DNA absorption spectra possibly due to DNA binding whereas these compounds were devoid of DNA topoisomerase inhibiting activity. Thus, these Ru(II) compounds have been established as new leads for future optimization by improving anti-cancer potency and safety.

  13. Synthesis and Characterization of Ionone-containing Chalcones%新型含紫罗兰酮基查尔酮的合成与表征

    Institute of Scientific and Technical Information of China (English)

    刘长辉; 文瑞明; 叶晓琴; 易先文; 方磊

    2012-01-01

    在碳酸钠和氢氧化钠催化下,β-紫罗兰酮和5,6-环氧-β-紫罗兰酮与芳香醛于室温下研磨1 ~15 min,制备了8种新型含紫罗兰酮基查尔酮,其结构经1H NMR、MS、IR和元素分析表征.结果表明,β-紫罗兰酮、苯甲醛、Na2CO3与NaOH的物质的量比为20∶20:5∶15时,收率可达87.1%~94.8%,苯甲醛环上吸电子基团可促进反应进行.%Condensation of β-onone and 5,6-epoxyl-β-ionone with aromatic aldehydes by sodium carbonate and sodium hydroxide was carried out to afford eight novel ionone-containing chalcones at room temperature for 1 ~ 15 min by grinding, and their structures were characterized by 1H NMR, MS, IR and elemental analysis. The effects of substituents, the types and amounts of catalysts on the reaction were studied. The results show that the yield is 87. 1% ~94. 8% when the molar ratio of 0-ionone, benzalaldehyde, sodium carbonate and sodium hydroxide is 20:20:5:15, and electron withdrawing group promotes the condensation.

  14. Synthesis and UV absorption characteristics of ferrocenyl chalcone%二茂铁基查尔酮的合成及其紫外吸收特征

    Institute of Scientific and Technical Information of China (English)

    陈娜娜; 王文彬; 廖全斌

    2012-01-01

    Six novel ferrocenyl chalcone derivatives were synthesized via aldol condensation reaction from formyl ferrocene and substituted acetophenones,which were then characterized by the 1H NMR.IR.MS and elemental analysis. The UV absorption studies indicated that the target compounds exhibited three strong absorption peaks within the range of 200 nm ~ 400 nm with apparent molar absorption coefficient of 104 or more,which were considerable with commercial UV absorber of BP3.%以甲酰二茂铁、取代苯乙酮为原料,经羟醛缩合反应合成了6个未见报道的含二茂铁基团的查尔酮类化合物(2a ~2f),并通过1H NMR、IR、MS和元素分析进行了结构表征.对产物的紫外吸收特征研究发现,所合成的化合物在200nm~400 nm范围内有三个较强的吸收峰,表观摩尔吸光系数在104以上,与商用紫外吸收剂BP3相当.

  15. Chemoselective biohydrogenation of chalcone (2Ε)-3-(1,3-benzodioxole-5-yl)-1-phenyl-2-propen-1-one mediated by baker yeasts immobilized in polymeric supports

    International Nuclear Information System (INIS)

    In this study, the yeast Saccharomyces cerevisiae, baker's yeast (BY) was immobilized in poly(ethylene oxide) (PEO), poly(vinyl alcohol) (PVA), sodium caseinate (SC), gelatin (G) films and in agar (A) and gelatin (G) gels, and used as a biocatalyst in the biohydrogenation reaction of (2Ε)-3-(1,3-benzodioxyl-5-yl)-1-phenyl-2-propen-1-one (1). The transformation of (1) into the corresponding dehydro chalcone (2) through biohydrogenation reactions was carried out in n-hexane at 25 or 35 deg C, for 4-48 h reaction. The product conversion, under different experimental conditions, was evaluated by hydrogen nuclear magnetic resonance, 1H NMR.The highest conversion degrees were achieved using BY immobilized in agar gel, (29-47%), depending also on the temperature. Using BY immobilized in PEO, PVA, SC and G films, the conversion into (2) was lower (0-21%). The results show the feasibility of the use of BY immobilized in polymeric materials to reduce a,b-unsaturated carbonyl compounds. (author)

  16. Synthesis of newer 1,2,3-triazole linked chalcone and flavone hybrid compounds and evaluation of their antimicrobial and cytotoxic activities.

    Science.gov (United States)

    Kant, Rama; Kumar, Dharmendra; Agarwal, Drishti; Gupta, Rinkoo Devi; Tilak, Ragini; Awasthi, Satish Kumar; Agarwal, Alka

    2016-05-01

    The present study was carried out in an attempt to synthesize a new class of antimicrobial and antiplasmodial agents by copper catalyzed click chemistry to afford 25 compounds 10-14(a-e) of 1,4-disubstituted-1,2,3-triazole derivatives of chalcones and flavones. The structures of the newly synthesized compounds were established by elemental analysis, IR, (1)H NMR, (13)C NMR and Mass spectral data. The newly synthesized compounds were evaluated for their antibacterial activity against Gram positive bacteria (Staphylococcus aureus, Enterococcus faecalis), Gram negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Shigella boydii, Klebsiella pneumoniae) and antifungal activity against (Candida albicans, Candida tropicalis, Candida parapsilosis, Cryptococcus neoformans, Dermatophyte) as well as molds (Aspergillus niger, Aspergillus fumigatus). The antiplasmodial and cytotoxic activities of these compounds were also evaluated against human malaria parasite Plasmodium falciparum strain 3D7 and human hepato-cellular carcinoma cells (Huh-7), respectively. Compounds 10a, 10c, 10d, 12c and 14e showed promising antibacterial activity while compounds 10e, 11d, 11e, 12c, 13a, 13b, 13e, 14a and 14d showed good antifungal activity as compared to the corresponding standard drugs. Compound 10b was found to be the most active against Plasmodium falciparum while the remaining compounds showed moderate to weak antiplasmodial activity. However, cytotoxic activities of all compounds were found ineffective against Huh-7 cells. PMID:26922227

  17. Synthesis, characterization and biological evaluation of novel 4'-fluoro-2'-hydroxy-chalcone derivatives as antioxidant, anti-inflammatory and analgesic agents.

    Science.gov (United States)

    Abdellatif, Khaled R A; Elshemy, Heba A H; Salama, Samir A; Omar, Hany A

    2015-06-01

    In an effort to develop safe and potent anti-inflammatory agents, a series of novel 4'-fluoro-2'-hydroxychalcones 5a-d and their dihydropyrazole derivatives 6a-d was prepared. It was synthesized via aldol condensation of 4'-fluoro-2'-hydroxyacetophenone with appropriately substituted aldehydes followed by cyclization with hydrazine hydrate. All the synthesized compounds were evaluated for their antioxidant, anti-inflammatory, cyclooxygenase inhibition selectivity and analgesic activities. The dimethoxychalcone 5a and its dihydropyrazole derivative 6a showed the highest antioxidant activity, while the monomethoxychalcone 5d and its dihydropyrazole derivative 6d showed the highest analgesic and anti-inflammatory activities. It was also found that there is a close correlation between 4'-fluoro-2'-hydroxychalcones 5a-d and their dihydropyrazole derivatives 6a-d in the screened biological activities. To explain the correlation between the synthesized chalcones and their dihydropyrazole derivatives, especially for the anti-inflammatory activity, docking studies were performed. PMID:25198887

  18. Chalcone Synthase (CHS) Gene Suppression in Flax Leads to Changes in Wall Synthesis and Sensing Genes, Cell Wall Chemistry and Stem Morphology Parameters.

    Science.gov (United States)

    Zuk, Magdalena; Działo, Magdalena; Richter, Dorota; Dymińska, Lucyna; Matuła, Jan; Kotecki, Andrzej; Hanuza, Jerzy; Szopa, Jan

    2016-01-01

    The chalcone synthase (CHS) gene controls the first step in the flavonoid biosynthesis. In flax, CHS down-regulation resulted in tannin accumulation and reduction in lignin synthesis, but plant growth was not affected. This suggests that lignin content and thus cell wall characteristics might be modulated through CHS activity. This study investigated the possibility that CHS affects cell wall sensing as well as polymer content and arrangement. CHS-suppressed and thus lignin-reduced plants showed significant changes in expression of genes involved in both synthesis of components and cell wall sensing. This was accompanied by increased levels of cellulose and hemicellulose. CHS-reduced flax also showed significant changes in morphology and arrangement of the cell wall. The stem tissue layers were enlarged averagely twofold compared to the control, and the number of fiber cells more than doubled. The stem morphology changes were accompanied by reduction of the crystallinity index of the cell wall. CHS silencing induces a signal transduction cascade that leads to modification of plant metabolism in a wide range and thus cell wall structure. PMID:27446124

  19. Synthesis, Evaluation, and Mechanism Study of Novel Indole-Chalcone Derivatives Exerting Effective Antitumor Activity Through Microtubule Destabilization in Vitro and in Vivo.

    Science.gov (United States)

    Yan, Jun; Chen, Jie; Zhang, Shun; Hu, Jinhui; Huang, Ling; Li, Xingshu

    2016-06-01

    Twenty-nine novel indole-chalcone derivatives were synthesized and evaluated for antiproliferative activity. Among them, 14k exhibited most potent activity, with IC50 values of 3-9 nM against six cancer cells, which displayed a 3.8-8.7-fold increase in activity when compare with compound 2. Further investigation revealed 14k was a novel tubulin polymerization inhibitor binding to the colchicine site. Its low cytotoxicity toward normal human cells and nearly equally potent activity against drug-resistant cells revealed the possibility for cancer therapy. Cellular mechanism studies elucidated 14k arrests cell cycle at G2/M phase and induces apoptosis along with the decrease of mitochondrial membrane potential. Furthermore, good metabolic stability of 14k was observed in mouse liver microsomes. Importantly, 14k and its phosphate salt 14k-P inhibited tumor growth in xenograft models in vivo without apparent toxicity, which was better than the reference compound CA-4P and 2. In summary, 14k deserves consideration for cancer therapy. PMID:27149641

  20. Crystal growth and characterization of new nonlinear optical chalcone derivative: 1-(4-Methoxyphenyl)-3-(3, 4-dimethoxyphenyl)-2-propen-1-one

    Science.gov (United States)

    Shettigar, Venkataraya; Patil, P. S.; Naveen, S.; Dharmaprakash, S. M.; Sridhar, M. A.; Shashidhara Prasad, J.

    2006-09-01

    Synthesis and single-crystal growth of a new organic nonlinear optical (NLO) material of chalcone derivative, 1-(4-methoxyphenyl)-3-(3, 4-dimethoxyphenyl)-2-propen-1-one (DMMC) by slow evaporation technique is reported. Good-quality single crystals of size 28 mm×7 mm×3 mm are grown for a period of 20 days and characterized by FT-IR and NMR studies. The grown crystal has been subjected to single-crystal X-ray diffraction technique and cell parameters of the crystal were determined. The title compound crystallizes in monoclinic system with a noncentrosymmetric space group P2 1, with unit cell parameters a=6.4090(4) Å, b=10.4950(10) Å, c=11.4820(12) Å, β=98.336(7)°, Z=2 and V=764.15(12) Å 3. The thermal stability of the crystal was determined from TGA/DTA curve. The grown crystals were characterized for their optical transmission and mechanical hardness. The second harmonic generation (SHG) efficiency of the crystals was obtained by classical powder technique using Nd:YAG laser and it is found to be 15 times that of urea. The laser damage threshold value has been determined using Q-switched Nd:YAG laser.

  1. Synthesis, structure-activity relationship studies, and antibacterial evaluation of 4-chromanones and chalcones, as well as olympicin A and derivatives.

    Science.gov (United States)

    Feng, Li; Maddox, Marcus M; Alam, Md Zahidul; Tsutsumi, Lissa S; Narula, Gagandeep; Bruhn, David F; Wu, Xiaoqian; Sandhaus, Shayna; Lee, Robin B; Simmons, Charles J; Tse-Dinh, Yuk-Ching; Hurdle, Julian G; Lee, Richard E; Sun, Dianqing

    2014-10-23

    On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 μg/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series. PMID:25238443

  2. Chalcone Synthase (CHS) Gene Suppression in Flax Leads to Changes in Wall Synthesis and Sensing Genes, Cell Wall Chemistry and Stem Morphology Parameters

    Science.gov (United States)

    Zuk, Magdalena; Działo, Magdalena; Richter, Dorota; Dymińska, Lucyna; Matuła, Jan; Kotecki, Andrzej; Hanuza, Jerzy; Szopa, Jan

    2016-01-01

    The chalcone synthase (CHS) gene controls the first step in the flavonoid biosynthesis. In flax, CHS down-regulation resulted in tannin accumulation and reduction in lignin synthesis, but plant growth was not affected. This suggests that lignin content and thus cell wall characteristics might be modulated through CHS activity. This study investigated the possibility that CHS affects cell wall sensing as well as polymer content and arrangement. CHS-suppressed and thus lignin-reduced plants showed significant changes in expression of genes involved in both synthesis of components and cell wall sensing. This was accompanied by increased levels of cellulose and hemicellulose. CHS-reduced flax also showed significant changes in morphology and arrangement of the cell wall. The stem tissue layers were enlarged averagely twofold compared to the control, and the number of fiber cells more than doubled. The stem morphology changes were accompanied by reduction of the crystallinity index of the cell wall. CHS silencing induces a signal transduction cascade that leads to modification of plant metabolism in a wide range and thus cell wall structure. PMID:27446124

  3. Fungal plasma membrane H⁺-ATPase inhibitory activity of o-hydroxybenzylated flavanones and chalcones from Uvaria chamae P. Beauv.

    Science.gov (United States)

    Kongstad, Kenneth T; Wubshet, Sileshi G; Kjellerup, Lasse; Winther, Anne-Marie Lund; Staerk, Dan

    2015-09-01

    In our ongoing efforts of finding natural fungicides to fight food and feed spoilage during production and storage, the antifungal potential of Ghanaian Uvaria chamae P. Beauv. was investigated, with emphasis on plant metabolites targeting the fungal plasma membrane (PM) H(+)-ATPase. Ethyl acetate extract of U. chamae was subjected to high-resolution fungal PM H(+)-ATPase inhibition screening followed by structural elucidation by high-performance liquid chromatography-high-resolution mass spectrometry-solid-phase extraction-nuclear magnetic resonance spectroscopy (HPLC-HRMS-SPE-NMR). This led to identification of a series of uncommon o-hydroxybenzylated flavanones and chalcones, i.e., chamanetin (8), isochamanetin (9), isouvaretin (10), uvaretin (11), dichamanetin (12), and diuvaretin (15). Preparative-scale isolation of the active metabolites allowed determination of IC50 values for inhibition of the PM H(+)-ATPase, and growth inhibition of Saccharomyces cerevisiae and Candida albicans. These revealed a strong correlation between o-hydroxybenzyl substituents and PM H(+)-ATPase activity, with dichamanetin being the most potent compound, but showing moderate activity in the fungal growth inhibition assays. PMID:26102180

  4. Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents.

    Science.gov (United States)

    Wang, Guangcheng; Li, Chunyan; He, Lin; Lei, Kai; Wang, Fang; Pu, Yuzi; Yang, Zhuang; Cao, Dong; Ma, Liang; Chen, Jinying; Sang, Yun; Liang, Xiaolin; Xiang, Mingli; Peng, Aihua; Wei, Yuquan; Chen, Lijuan

    2014-04-01

    A new series of pyrano chalcone derivatives containing indole moiety (3-42, 49a-49r) were synthesized and evaluated for their antiproliferative activities. Among all the compounds, compound 49b with a propionyloxy group at the 4-position of the left phenyl ring and N-methyl-5-indoly on the right ring displayed the most potent cytotoxic activity against all tested cancer cell lines including multidrug resistant phenotype, which inhibits cancer cell growth with IC50 values ranging from 0.22 to 1.80μM. Furthermore, 49b significantly induced cell cycle arrest in G2/M phase and inhibited the polymerization of tubulin. Molecular docking analysis demonstrated the interaction of 49b at the colchicine binding site of tubulin. In experiments in vivo, 49b exerted potent anticancer activity in HepG2 human liver carcinoma in BALB/c nude mice. These results indicated these compounds are promising inhibitors of tubulin polymerization for the potential treatment of cancer. PMID:24629450

  5. Design and synthesis of C3-pyrazole/chalcone-linked beta-carboline hybrids: antitopoisomerase I, DNA-interactive, and apoptosis-inducing anticancer agents.

    Science.gov (United States)

    Kamal, Ahmed; Srinivasulu, Vunnam; Nayak, V Lakshma; Sathish, Manda; Shankaraiah, Nagula; Bagul, Chandrakant; Reddy, N V Subba; Rangaraj, Nandini; Nagesh, Narayana

    2014-09-01

    A series of β-carboline hybrids bearing a substituted phenyl and a chalcone/(N-acetyl)-pyrazole moiety at the C1 and C3 positions, respectively, was designed, synthesized, and evaluated for anticancer activity. These new hybrid molecules showed significant cytotoxic activity, with IC50 values ranging from indol-3-yl)prop-2-en-1-one (7 d) and 1-(3-(furan-2-yl)-5-(1-(4-(trifluoromethyl)phenyl)-9H-pyrido[3,4-b]indol-3-yl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone (8 d) could effectively cleave pBR322 plasmid DNA upon irradiation with UV light. Active hybrid 8 d inhibited DNA topoisomerase I activity efficiently and preserved DNA in the supercoiled form. To further corroborate the biological activities, as well as to understand the nature of the interaction of these hybrids with DNA, spectroscopic studies were also performed. Unlike simple β-carboline alkaloids, the binding mode of these new hybrid molecules with DNA was not similar, and both biophysical as well as molecular docking studies speculated a combilexin-type of interaction with DNA. Further, an in silico study of these β-carboline hybrids revealed their drug-like properties. PMID:24470122

  6. 自旋标记查耳酮类化合物的合成及抗肿瘤活性%Synthesis and biological evaluation of spin-labelled derivatives of chalcones

    Institute of Scientific and Technical Information of China (English)

    金岩; 刘杰; 陈世武

    2013-01-01

    目的 发现高效自旋标记查耳酮类抗肿瘤药物.方法 通过乙酰苯与芳醛在碱性条件下缩合生成查耳酮,进一步与稳定氮氧自由基酸发生酰化反应合成了一系列自旋标记的查耳酮化合物,用MTT法对合成的化合物进行体外抗肿瘤活性研究(P3SS、A549、HT-29、MDA-MB-231、8GC-7901、BEL-7402).结果 化合物3a和3c在10 μg/mL时对所有测试瘤株的抑制率均大于60%.结论 自旋标记的查耳酮酰胺类化合物具有较高的体外抗肿瘤活性.%Objective To find new spin labelled chalcones as anti-tumor drugs with potent activities and low toxicities. Methods A series spin labelled chalcones were synthesized by condensation reaction of aromatic aldehyde and acetpophenone, following acetylation. The cytotoxic activities against six tumor cell lines (P388, A-549, HT-29, MDA-MB-231, SGC-7901, BEL-7402) in vitro of synthetic compounds were also evaluated by MTT method. Results Compounds 3a and 3c showed more than 60% proliferation inhibitions against all six tested tumor cell lines in vitro. Conclusion The amides of spin-labelled chalcones present better anti-tumor activities in vitro.

  7. Synthesis of ferrocenyl chalcone compounds and their anti-breast cancer activities%二茂铁基查耳酮类化合物的合成及其抗乳腺癌活性研究

    Institute of Scientific and Technical Information of China (English)

    陈善龙; 谭娟

    2015-01-01

    Objective To design and synthesize ferrocenyl chalcone compounds, and to study their anti-breast cancer activities. Methods A series of ferrocenyl chalcones were synthesized by Claisen-Schmidt condensation reaction, and the anti-breast cancer activity was assessed by MTT method. Results Nine ferrocenyl chalcone compounds were synthesized and characterized by 1H-NMR and 13C-NMR. The preliminary biological results showed that target compounds 1 — 9 displayed significant inhibitory activities on both MCF-7 and MDA-MB-231 cell lines. Specifically, compound 6 showed the best inhibitory activity against MDA-MB-231. Conclusion This study provides reference for development of chalcone compounds with inhibitory activity in hormone-independent breast cancer.%目的:设计并合成了二茂铁基查耳酮类化合物,并对其抗乳腺癌活性进行研究。方法通过 Claisen-Schmidt 缩合反应合成含有二茂铁基的查耳酮类化合物,并通过MTT法对目标化合物的抗乳腺癌活性进行研究。结果合成了9个含有二茂铁基查耳酮类化合物,其结构均通过1H-NMR、13C-NMR进行了表征。生物活性结果表明,目标化合物1~9对MCF-7和MDA-MB-23均具有较强的抑制活性,其中化合物6对MDA-MB-231的抑制活性最强。结论本研究为开发具有抗荷尔蒙非依赖型乳腺癌活性的查耳酮类化合物提供了参考。

  8. NaOH催化无溶剂下肉桂醛类查尔酮的不饱和酮的合成%Synthesis of cinnamaldehyde's chalcone under solvent-free catalyzed by NaOH

    Institute of Scientific and Technical Information of China (English)

    丁润梅; 田大年

    2011-01-01

    Cinnamaldehyde's Chalcones have been efficiently prepared by condensation of arone and cinnamaldehyde by using NaOH as catalyst under room temperature condition. Compared with traditional methods,this method is more convenient due to the milder condition,%使用NaOH为催化剂在无溶剂条件下,在室温条件下,制备了8种肉桂醛类查尔酮化合物。结果表明该方法操作简单,条件温和,反应速度快,产率高,对环境友好,后处理简便。

  9. Flavokawain B, a kava chalcone, exhibits robust apoptotic mechanisms on androgen receptor-negative, hormone-refractory prostate cancer cell lines and reduces tumor growth in a preclinical model

    OpenAIRE

    Tang, Yaxiong; Li, Xuesen; Liu, Zhongbo; Simoneau, Anne R; Xie, Jun; Zi, Xiaolin

    2010-01-01

    Limited success has been achieved in extending the survival of patients with metastatic and hormone-refractory prostate cancer (HRPC). There is a strong need for novel agents in the treatment and prevention of HRPC. We have shown that flavokawain B (FKB), a kava chalcone, is about 4 to 12 fold more effective in reducing the cell viabilities of androgen receptor (AR)-negative, HRPC cell lines DU145 and PC-3 than AR–positive, hormone-sensitive prostate cancer cell lines LAPC4 and LNCaP, with mi...

  10. The Synthesis and Evaluation of Novel Hydroxyl Substituted Chalcone Analogs with in Vitro Anti-Free Radicals Pharmacological Activity and in Vivo Anti-Oxidation Activity in a Free Radical-Injury Alzheimer’s Model

    OpenAIRE

    Ying Pan; Yicun Chen; Qingnan Li; Xiaoyu Yu; Jinzhi Wang; Jinhong Zheng

    2013-01-01

    Alzheimer’s disease (AD) pathogenesis involves an imbalance between free radical formation and destruction. In order to obtain a novel preclinical anti-AD drug candidate, we synthesized a series of novel hydroxyl chalcone analogs which possessed anti-free radical activity, and screened their effects on scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH) and OH free radicals in vitro. Compound C7, 4,2'-dihydroxy-3,5-dimethoxychalcone was found to have potent activity in these anti-free radica...

  11. Tissue localization of u.v.-B-screening pigments and of chalcone synthase mRNA in needles of Scots pine seedlings

    International Nuclear Information System (INIS)

    Epidermal tissue was isolated from Scots pine (Pinus sylvestris L.) needles by enzymatic digestion in order to study tissue distribution of u.v.-B-screening pigments. Up to 90% of the needle content of a group of diacylated flavonol glycosides that were structurally closely related was found in the epidermal layer. Among these metabolites, 3'',6''-di-para-coumaroyl-isoquercitrin and 3'',6''-di-para-coumaroyl-astragalin were the main u.v.-B-induced compounds in cotyledons and primary needles, respectively. However, catechin and astragalin (kaempferol 3-glucoside), two non-acylated flavonoid metabolites, were only observed in total needle extracts, and at levels independent of u.v.-B treatment. According to this metabolite distribution, the mRNA of chalcone synthase, the key enzyme to flavonoids, was found in epidermal and mesophyll as well as vascular tissues. The major alkaliextractable wall-bound phenolic metabolites, astragalin, 4-coumaric acid, and ferulic acid, a minor component of the cell wall, were also found exclusively in the epidermal layer. These compounds were not stimulated by u.v.-B irradiation within the experimental period. Staining of needle cross sections and epidermal layer preparations with Naturstoffreagenz A confirmed the specific localization of wall-bound astragalin in the outer wall of the epidermal layer. Model calculations of u.v.-B absorptions at 300 nm of soluble and cell-wall-bound metabolites of the epidermal layer revealed an almost complete shielding of the mesophyll tissue from u.v.-B radiation

  12. A chalcone-related small molecule that induces methuosis, a novel form of non-apoptotic cell death, in glioblastoma cells

    Directory of Open Access Journals (Sweden)

    Bhanot Haymanti

    2011-06-01

    Full Text Available Abstract Background Methuosis is a unique form of non-apoptotic cell death triggered by alterations in the trafficking of clathrin-independent endosomes, ultimately leading to extreme vacuolization and rupture of the cell. Results Here we describe a novel chalcone-like molecule, 3-(2-methyl-1H- indol-3-yl-1-(4-pyridinyl-2-propen-1-one (MIPP that induces cell death with the hallmarks of methuosis. MIPP causes rapid accumulation of vacuoles derived from macropinosomes, based on time-lapse microscopy and labeling with extracellular fluid phase tracers. Vacuolization can be blocked by the cholesterol-interacting compound, filipin, consistent with the origin of the vacuoles from non-clathrin endocytic compartments. Although the vacuoles rapidly acquire some characteristics of late endosomes (Rab7, LAMP1, they remain distinct from lysosomal and autophagosomal compartments, suggestive of a block at the late endosome/lysosome boundary. MIPP appears to target steps in the endosomal trafficking pathway involving Rab5 and Rab7, as evidenced by changes in the activation states of these GTPases. These effects are specific, as other GTPases (Rac1, Arf6 are unaffected by the compound. Cells treated with MIPP lose viability within 2-3 days, but their nuclei show no evidence of apoptotic changes. Inhibition of caspase activity does not protect the cells, consistent with a non-apoptotic death mechanism. U251 glioblastoma cells selected for temozolomide resistance showed sensitivity to MIPP-induced methuosis that was comparable to the parental cell line. Conclusions MIPP might serve as a prototype for new drugs that could be used to induce non-apoptotic death in cancers that have become refractory to agents that work through DNA damage and apoptotic mechanisms.

  13. Changes in phytochemical synthesis, chalcone synthase activity and pharmaceutical qualities of sabah snake grass (Clinacanthus nutans L.) in relation to plant age.

    Science.gov (United States)

    Ghasemzadeh, Ali; Nasiri, Alireza; Jaafar, Hawa Z E; Baghdadi, Ali; Ahmad, Izham

    2014-01-01

    In the current study, changes in secondary metabolite synthesis and the pharmaceutical quality of sabah snake grass leaves and buds were considered in relation to plant age (1 month, 6 months, and 1 year old). The activity of the enzyme chalcone synthase (CHS, EC 2.3.1.74) was measured, as it is a key enzyme for flavonoid production. Significant differences in total flavonoid (TF) production were observed between the three plant growth periods and the different plant parts. The highest contents of TF (6.32 mg/g dry weight [DW]) and total phenolic (TP) (18.21 mg/g DW) were recorded in 6-month-old buds. Among the flavonoids isolated in this study the most important ones based on concentration were from high to low as follows: catechin > quercetin > kaempferol > luteolin. Production of phenolic acids increased from 1 to 6 months, but after 6 months up to 1 year of age, they decreased significantly. The highest contents of caffeic acid (0.307 mg/g DW) and gallic acid (5.96 mg/g DW) were recorded in 1-year and 6-month-old buds, respectively. The lowest and highest activity of CHS was recorded in 1-month and 6-month-old buds with values of 3.6 and 9.5 nkat/mg protein, respectively. These results indicate that the increment in flavonoids and phenolic acids in 6-month-old buds can be attributed to an increase in CHS activity. The highest 1,1-diphenyl-2-picrylhydrazyl (DPPH) activity was observed in the extract of 1-year-old buds followed by 6-month-old buds, with 50% of free radical scavenging (IC50) values of 64.6 and 73.5 µg/mL, respectively. Interestingly, a ferric reducing antioxidant power (FRAP) assay showed a higher activity in 6-month-old buds (488 μM of Fe(II)/g) than in 1-year-old buds (453 μM of Fe(II)/g), in contrast to the DPPH result. Significant correlations (p < 0.05) were observed between CHS enzyme activity and FRAP activity, TF, catechin, and kaempferol content. Extracts of 6-month-old bud exhibited a significant in vitro anticancer activity against

  14. Changes in Phytochemical Synthesis, Chalcone Synthase Activity and Pharmaceutical Qualities of Sabah Snake Grass (Clinacanthus nutans L. in Relation to Plant Age

    Directory of Open Access Journals (Sweden)

    Ali Ghasemzadeh

    2014-10-01

    Full Text Available In the current study, changes in secondary metabolite synthesis and the pharmaceutical quality of sabah snake grass leaves and buds were considered in relation to plant age (1 month, 6 months, and 1 year old. The activity of the enzyme chalcone synthase (CHS, EC 2.3.1.74 was measured, as it is a key enzyme for flavonoid production. Significant differences in total flavonoid (TF production were observed between the three plant growth periods and the different plant parts. The highest contents of TF (6.32 mg/g dry weight [DW] and total phenolic (TP (18.21 mg/g DW were recorded in 6-month-old buds. Among the flavonoids isolated in this study the most important ones based on concentration were from high to low as follows: catechin > quercetin > kaempferol > luteolin. Production of phenolic acids increased from 1 to 6 months, but after 6 months up to 1 year of age, they decreased significantly. The highest contents of caffeic acid (0.307 mg/g DW and gallic acid (5.96 mg/g DW were recorded in 1-year and 6-month-old buds, respectively. The lowest and highest activity of CHS was recorded in 1-month and 6-month-old buds with values of 3.6 and 9.5 nkat/mg protein, respectively. These results indicate that the increment in flavonoids and phenolic acids in 6-month-old buds can be attributed to an increase in CHS activity. The highest 1,1-diphenyl-2-picrylhydrazyl (DPPH activity was observed in the extract of 1-year-old buds followed by 6-month-old buds, with 50% of free radical scavenging (IC50 values of 64.6 and 73.5 µg/mL, respectively. Interestingly, a ferric reducing antioxidant power (FRAP assay showed a higher activity in 6-month-old buds (488 μM of Fe(II/g than in 1-year-old buds (453 μM of Fe(II/g, in contrast to the DPPH result. Significant correlations (p < 0.05 were observed between CHS enzyme activity and FRAP activity, TF, catechin, and kaempferol content. Extracts of 6-month-old bud exhibited a significant in vitro anticancer activity

  15. Synthesis, Crystal Strutures and Antitumor Activity of Novel Nitrogen Mustard-Linked Chalcones%含氮芥基查尔酮类衍生物的合成、晶体结构及抗肿瘤活性

    Institute of Scientific and Technical Information of China (English)

    方线文; 周丽珍; 成昭; 杨美盼; 杨秉勤

    2013-01-01

    A series of novel nitrogen mustard-linked chalcones 3a~3r were synthesized by linking the N,N-bis(2- chloro-ethyl)amine pharmacophore of nitrogen mustards to the chalcone's framework. Their structures were characterized by 1H NMR, IR, ESI-HRMS and X-ray techniques. The antitumor activities of the nitrogen mustard-linked chalcones were evaluated against K562 and HepG2 cell lines by an MTT assay. The results reveal that some of the title compounds exhibit potent anti-proliferative activities against selected tumor cells. Among which, compounds 3j against K562 and HepG2 with IC50 values of 20.01 and 43.46 μmol/L, and 31 against K562 and HepG2 with IC50 values of 18.6 and 21.39 μmol/L, respectively. Suitable crystals of 3e and 31 were obtained, and the X-ray diffraction analysis indicates that compounds 3b and 3e are both belong to triclinic, space group P-1.%根据拼药原理,将氮芥类抗肿瘤药物的药效基团N,N-二(2-氯乙基)氨基拼接到查尔酮结构中,合成出了一系列新型含氮芥基的查尔酮衍生物3a~3r,并用1H NMR,IR,HRMS-ESI及X射线对其结构进行了确证.采用MTT法对所合成的化合物进行了体外抗肿瘤活性测试,结果表明部分化合物对所选肿瘤细胞的增殖有较强的抑制作用,其中,化合物3j和31对K562的IC50值分别为20.01和18.6 μmol/L;对HepG2的IC50值分别为43.46和21.39 μmol/L.实验培养并得到了目标产物3e和31的晶体结构,X射线分析表明化合物3e和31都属三斜晶系,P-1空间群.

  16. Synthesis of solvent-free Michael addition reaction of 2-thio-4-thiazolidinone with chalcon%2-硫代-4-噻唑酮与查尔酮的无溶剂Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    冯驸; 黎云攀; 周红艳; 胡卫兵

    2012-01-01

    A series of novel Michael addition products of 2-thio-4-thiazolidinone to chalcone were obtained in the presence of sodium hydroxide under solvent-free condition. The advantages of this procedure were mild reaction conditions, simple protocol,and high yields. The structures of the products were confirmed by IR.1HNMR,MS and elemental analysis.%以查尔酮和2-硫代-4-噻唑酮为原料,在NaOH存在下无溶剂室温研磨反应,非常方便合成了系列未见文献报道的Michael加成产物.该方法具有反应条件温和、操作简单和产率较高等优点,并通过IR、HNMR、MS和元素分析确证产物的结构.

  17. 无溶剂条件下碱性离子液体催化查尔酮的绿色化合成%A Green Synthesis of Chalcones Catalyzed by An Alkaline Ionic Liquid under Solvent-Free Condition

    Institute of Scientific and Technical Information of China (English)

    胡晓允; 韦丽艳; 钟诗施; 谢金生

    2015-01-01

    在无溶剂条件下,将碱性离子液体—乙醇胺乙酸盐用于催化苯乙酮与醛的Claisen-Schmidt 缩合反应制备了查尔酮。结果表明:该碱性离子液体表现出良好的催化活性和循环催化性能。%An alkaline ionic liquid—2-hydroxyethyl ammonium acetate was used as catalyst for Claisen-Schmidt condensation between acetophenone and aromatic aldehydes to prepare chalcones under solvent-free condition. The results indicated that this alkaline ionic liquid showed good catalytic activity and recyclability.

  18. The Synthesis and Evaluation of Novel Hydroxyl Substituted Chalcone Analogs with in Vitro Anti-Free Radicals Pharmacological Activity and in Vivo Anti-Oxidation Activity in a Free Radical-Injury Alzheimer’s Model

    Directory of Open Access Journals (Sweden)

    Ying Pan

    2013-01-01

    Full Text Available Alzheimer’s disease (AD pathogenesis involves an imbalance between free radical formation and destruction. In order to obtain a novel preclinical anti-AD drug candidate, we synthesized a series of novel hydroxyl chalcone analogs which possessed anti-free radical activity, and screened their effects on scavenging 2,2-diphenyl-1-picrylhydrazyl (DPPH and OH free radicals in vitro. Compound C7, 4,2'-dihydroxy-3,5-dimethoxychalcone was found to have potent activity in these anti-free radical activity tests. Further research revealed that C7 could elevate glutathione peroxidase (GSH-PX and super oxide dismutase (SOD levels and lower malonaldehyde (MDA level in vivo in the Alzheimer’s model. The indication of C7’s effect on AD needs further study.

  19. 查尔酮类似化合物的合成及其抑菌活性研究%Study on Synthesis and Antifungal Activity of Chalcone Analogues

    Institute of Scientific and Technical Information of China (English)

    田珈源; 罗青春; 梁华忠; 谌晓洪

    2011-01-01

    [目的]合成查尔酮类似化合物,并研究其抑菌活性,以寻找高效、安全的抑菌活性化合物.[方法]以苯甲酰氯类化合物和胺类化合物为原料,通过酰氯的胺解反应设计并合成了16种查尔酮类似化合物,对其分子结构经红外光谱(IR)和氢核磁共振波谱(1H NMR)进行确认.[结果]该类化合物具有一定的抑菌活性,当浓度为100 mg/L时,化合物A2(2-氯-N-苯基苯甲酰胺)对水稻纹枯病(Rhizoctonia solani)和油菜菌核病菌(Sclerotiua sclerotiorum的抑制率分别达90.27%和92.56%.[结论]产物A2为查尔酮的类似化合物,且属于天然产物,在自然界中能够自然降解,不会引起环境污染;而且其化学结构简单,人工合成也比较容易,可以以此为先导化合物对其结构进行优化和改造;研究其结构和活性之间的关系,开发出高效、低毒、对非靶标生物安全的新型抑菌剂.%[Objective] To synthesize chalcone analogues and study their antifungal activity so as to find high-efficient and safe compounds with antifungal activity. [Method] With benzoyl chloride compounds and amines as the materials, 16 chalcone analogues were designed and synthe sized through the aminolysis reaction of acyl chloride, and their molecular structures were determined by IR and ' H NMR. [ Result ] The chal cone analogues had certain antifungal activity. The antifungal rate of 100 mg/L compound A2 (2-chloro-N-phenyl benzamide) against Rhizoctonia solani and Sclerotiua sclerotiorum reached 90. 27% and 92.56% , respectively. [Conclusion] Product A2 was an analogue of the natural product chalcone that could naturally degrade without causing environmental pollution. What's more, its chemical structure was simple and easy to pre pare. Using A2 as a lead compound, new high-efficient and low-toxic antifungal agents which were safe to the non-target organisms could be de veloped through optimizing its chemical structure and studying the relationship

  20. 微波辅助固相合成法制备查尔酮类的工艺研究%Study on the Preparation Technology of Microwave Assisted Solid Phase Synthesis of Chalcones

    Institute of Scientific and Technical Information of China (English)

    赵岩; 马尔霍夫・木合布力; 伊克山・亚力坤; 木合布力・阿布力孜; 哈丽玛・斯拉木江; 麦热哈巴・依明

    2016-01-01

    Methoxy-chalcone compounds were prepared by tree different methods, so as to improve the preparation technology.Acid catalyzed high temperature method, hydroxyl radical protecting method and microwave assisted solid phase method were used for aldolization reaction, respectively, the reaction type and the optimal reaction conditions were screened using the reaction yield as standard.Results showed that the reaction yield of the target compound obtained by tree different methods were 8.9%, 9.27% and 57.60%, respectively, the optimal microwave irradiation conditions were as follows: power of 150 W, reaction time of 100 s, temperature of 80 ℃.The microwave assisted solid phase synthesis could be one of the effective method for the preparation of methoxy-chalcone compounds with the advantages of pollution-free, easy operation, low cost, high yields and short reaction time.%三种不同方法合成甲氧查尔酮类化合物,筛选和优化合成工艺。采用酸催化高温法、羟基保护法和微波辅助碱催化法进行羟醛缩合反应,制备目标化合物,并以反应产率为指标筛选合成方法,优化反应条件。结果表明:用三种方法所得到的目标化合物产率分别为8.9%、9.27%和57.60%。微波辅助碱催化反应的最佳条件:设定微波功率150 W、反应时间100 s,温度80℃。微波辅助碱催化方法具有产率高、反应时间短、节能和环保等特点、是绿色合成甲氧查尔酮类化合物的有效方法之一。

  1. 微波-相转移催化合成含杂环查尔酮衍生物的研究%Synthesis Process Optimization of Heterocyclic Chalcone Derivative by Phase Transfer Catalysis

    Institute of Scientific and Technical Information of China (English)

    姬广军; 杨金凤; 刘红; 廉宜君

    2014-01-01

    查尔酮衍生化及其合成方法是合成工作者关注的一个热点。本文在微波辐射下,引入TBAB(四丁基溴化铵)作为相转移催化剂,以苯乙酮衍生物(1a~1d)、苯肼、苯乙酮衍生物(1e~1f)等为原料,合成了8种新的查尔酮衍生物(4a~4d,5a~5d);通过实验考察了物料比、微波辐射功率、微波辐射时间及催化剂用量等工艺条件对产物产率的影响;采用正交实验确定出查尔酮的最佳合成条件为:1,3-2苯基-4-甲酰基吡唑与苯乙酮物质的量比1∶1,微波输出功率为140 W,微波辐射间歇加热反应时间为30 min,四丁基溴化铵的量为0.4 g时,产率为87%~91%。%4-formylpyrazole (3a~3d) were obtained by substituted acetophenones (1a~1d) and phenylhydrazine under microwave irradiation conditions.Eight chalcone derivative (4a~4d,5a~5d) were synthesized by 3a~3d and substituted acetophenones in aqueous alkaline solution and TBAB (tertranutylammonium bromide)was phase transfer catalyst.The synthesis technology chalcone (4a) was studied.Effects of raw materials mole ratio,microwave radiation power,reaction time and dosage of phase transfer catalyst on the product yield were investigated.The optimum sythesis conditions are 1,3-2-phenyl-4-formylpyrazole to acetophenone mole ratio,microwave power reaction,microwave irradiation time,dosage of phase transfer catalyst are 1∶1,140 W,30 min and 0.4 g,respectively.The synthesis reaction were easily worked up with short time,high yields and green initiative.

  2. 超声波技术合成 N,N-二甲基-4′-羟基査尔酮%Synthesis of N, N-Dimethyl-4′-hydroxy Chalcone Using Ultrasound

    Institute of Scientific and Technical Information of China (English)

    李立忠; 周建魁; 谭冶; 何瑞; 李香丹

    2015-01-01

    采用超声波技术,以对羟基苯乙酮和4-N,N-二甲基苯甲醛为原料,HCl气体为催化剂,乙醇为溶剂,合成了具有光敏性的N,N-二甲基-4′-羟基査尔酮,产物结构经1 H-NMR、FT-IR和UV-Vis等进行了确认.结果表明:超声输出功率400 W,30℃下进行反应30 min产率最高,可达80.1%.故该方法有反应时间短、反应条件温和、产率高等优点.%Photosensitive N, N-dimethyl-4′-hydroxy chalcone was synthesized from p-hydroxyacetophenone and 4-N, N-dimethyl benzaldehyde using ethanol as solvent and dry HCl ( gas) as catalyst.The structure of the product was confirmed by 1 H-NMR, IR and UV-vis spectra.The results indicated that the yield reached the highest value of 80.1% at 30℃, under ultrasonic output power of 400 W for 30 min.The prominent feature of the present method included short reaction time, mild reaction condition, and high yield.

  3. 番茄查尔酮合成酶基因的鉴定及生物信息学分析%Identification and Bioinformatics Analysis of Chalcone Synthase Genes in Tomato

    Institute of Scientific and Technical Information of China (English)

    阮美颖; 杨悦俭; 万红建; 叶青静; 王荣青; 姚祝平; 周国治; 俞锞; 袁伟; 刘云飞

    2013-01-01

      类黄酮(Flavonoids)是植物体内一类重要的次生代谢产物,它以结合态(黄酮苷)或自由态(黄酮苷元)形式存在于水果、蔬菜、豆类和茶叶等许多植物中,对植物的生长发育有着重要的调节作用。查尔酮合成酶(Chalcone synthase, CHS, EC2.3.1.74)是植物类黄酮合成途径的第一个关键酶,在调控类黄酮的生物合成以及类黄酮的成分起着决定作用。本研究基于番茄全基因组测序数据,利用生物信息学方法,鉴定了查尔酮合成酶基因家族成员,分析其内含子-外显子的结构特征、系统发育关系,序列结构的保守性以及染色体上的分布。研究表明:查尔酮合成酶(SlCHS)是含有8个成员的多家族基因,蛋白质序列编码位于160(SlCHS05)~438(SlCHS08)个氨基酸之间;相似性在33.7%(SlCHS02和SlCHS06)~92.0%(SlCHS04和SlCHS07)之间,表明这些序列之间具有较高的遗传多样性;此外,结构分析发现这些基因均含有较少的内含子(0~2个);序列比对表明这些基因具有较高的保守性;它们不均匀分布在番茄的1、5、6、9和12号染色体上。该研究不仅有助于未来了解该基因家族的进化起源提供参考,而且可为我们进一步分析该基因家族成员的功能奠定基础。%Flavonoids are a kind of important secondary metabolites in plants. Usually, it was found in fruits, vegetables, beans, tea and many other plants as combination (flavonoid glycosides) or free states (flavonoid glyco-sides) form. It has important role in regulating plant growth and development. Chalcone synthase, the first key synthase during the process of flavonoids synthesis, plays an important role in plant growth and development. Based on the whole tomato genome sequence, we investigated gene members of the chalcone synthase family with genome database and bioinformatics analysis. We identified 8 chalcone synthase genes with protein sequence length varying

  4. 经由Domino脱HCl/Pd(OAc)2催化的Heck反应合成查尔酮%Synthesis of chalcones via domino dehydrochlorination/Pd(OAc)2-catalyzed Heck reaction

    Institute of Scientific and Technical Information of China (English)

    郭腾龙; 姜权彬; 余立坤; 余正坤

    2015-01-01

    A new method has been developed for the cross‐coupling of aryl halides with β‐chloroalkyl aryl ketones and their ester and amide analogs through a domino dehydrochlorination/Pd(OAc)2‐cata‐lyzed Heck reaction sequence. The enone intermediates generated in situ reduced the occurrence of side reactions and therefore enhanced the efficiency of the reaction. This reaction exhibited good tolerance to various functional groups on both substrates and provides rapid access to a wide range of chalcone derivatives.%通过Domino脱HCl/Pd(OAc)2催化的Heck反应实现了β-氯代烷基芳基酮、酯和酰胺与卤代芳烃的交叉偶联反应,高效合成了查尔酮类化合物。利用原位生成烯酮为中间体进行反应的策略,减少副反应的发生,从而提高反应的效率。该方法对各种官能团的容忍性好,为从氯代烷烃出发直接合成查尔酮类化合物提供了一条新途径。

  5. Inhibition of Epithelial CC-Family Chemokine Synthesis by the Synthetic Chalcone DMPF-1 via Disruption of NF-κB Nuclear Translocation and Suppression of Experimental Asthma in Mice

    Directory of Open Access Journals (Sweden)

    Revathee Rajajendram

    2015-01-01

    Full Text Available Asthma is associated with increased pulmonary inflammation and airway hyperresponsiveness. The interaction between airway epithelium and inflammatory mediators plays a key role in the pathogenesis of asthma. In vitro studies evaluated the inhibitory effects of 3-(2,5-dimethoxyphenyl-1-(5-methylfuran-2-ylprop-2-en-1-one (DMPF-1, a synthetic chalcone analogue, upon inflammation in the A549 lung epithelial cell line. DMPF-1 selectively inhibited TNF-α-stimulated CC chemokine secretion (RANTES, eotaxin-1, and MCP-1 without any effect upon CXC chemokine (GRO-α and IL-8 secretion. Western blot analysis further demonstrated that the inhibitory activity resulted from disruption of p65NF-κB nuclear translocation without any effects on the mitogen-activated protein kinase (MAPK pathway. Treatment of ovalbumin-sensitized and ovalbumin-challenged BALB/c mice with DMPF-1 (0.2–100 mg/kg demonstrated significant reduction in the secretion and gene expression of CC chemokines (RANTES, eotaxin-1, and MCP-1 and Th2 cytokines (IL-4, IL-5, and IL-13. Furthermore, DMPF-1 treatment inhibited eosinophilia, goblet cell hyperplasia, peripheral blood total IgE, and airway hyperresponsiveness in ovalbumin-sensitized and ovalbumin-challenged mice. In conclusion, these findings demonstrate the potential of DMPF-1, a nonsteroidal compound, as an antiasthmatic agent for further pharmacological evaluation.

  6. 查尔酮及其螺杂环衍生物的合成、晶体结构、抗氧化活性研究%Synthesis, Crystal Structure, Antioxidant Activity of Chalcones and Its Spiro-heterocyclic Analogues

    Institute of Scientific and Technical Information of China (English)

    吴建章; 李物兰; 陈玲姿; 楚生辉; 赵承光; 卫涛; 杨树林; 李校堃

    2012-01-01

    To synthesize new structure type chalcone analogues, and obtain chalcone analogues with good antioxidant activity. Two types of chalcone analogs, chalcones A and spiro-heterocyclic B were designed and synthesized, and the structures of 21 compounds were characterized by 1H NMR, ESI-MS and ESI-HRMS. Single-crystal of spiro-heterocyclic B was cultured, and its single-crystal structure was determined by X-ray diffraction study. The crystal structure of Bl was monoclinic system, space group C2/c, with cell dimensions of a=21.350(3) A, 6=8.6256(10) A, e=26.161(3) A. Spiro-heterocyclic B is the new structure type, and obtained by one-pot synthesis which is 1,3-dipolar cycloaddition reaction and no catalyst. The synthesis of spiro-heterocyclic B is not only high regioselectivity and stereoselectivity, but also environmentally friendly. The antioxidant activities in vitro were evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Many compounds, which can have strong activity of scavenging DPPH free radicals, were screened. In the 2 types' of chalcones analogs, the compounds with 3,4-(OH)2 in "a" ring have excellent antioxidant activities. The chalcone analogs with o-dihydroxy in benzene ring maybe have good antioxidant activities.%为了合成新结构类型查尔酮衍生物,发现具有抗氧化活性的查尔酮类化合物,设计合成了查尔酮A和螺杂环B两种类型,共21个查尔酮类似物,结构经ESI-MS,ESI-HRMS和1H NMR确认.培养出螺杂环B1的单晶,通过X衍射确证了其为单斜晶系.其中螺杂环B为新结构类型化合物,通过1,3-偶极环加成反应,用不需加催化剂的“一锅煮”方法合成,该反应具有很好的立体选择性和区域选择性、且环境友好.用DPPH法测试了所有化合物的抗氧化活性,筛选出了多个对1,1-二苯基-2-三硝基苯肼(DPPH)自由基具有良好清除率的化合物,a环3,4-OH取代的两类化合物都具有良好的抗氧化活性,苯环邻位二羟基取代的查尔

  7. Atividade alelopática de chalcona sintética, de seus precursores e de cetonas e aldeídos relacionados Allelopathic activity of synthetic chalcone, its precursors and of related cetones and aldehydes

    Directory of Open Access Journals (Sweden)

    H.R. Bitencourt

    2007-12-01

    objective of this work was to evaluate the allelopathic activity of synthetic chalcone, 2,4'-dimethoxychalcone, its precursors, 4-methoxyacetophenone (A and ortho-anisaldehyde (B, and some of their chemical alterations. The bioassays were developed under 25 ºC and photoperiod of 12 hours. The allelopathic effects of the compounds were tested on seed germination of Mimosa pudica and Senna obtusifolia weeds, under a concentration of 100, 200 and 300 mg L-1 of the compounds. The results indicated that precursor A (4-methoxyacetophenone plays an important role in allelopathic activity of the chalcones. These results show that synthesis is a possible pathway, helping to overcome problems such as characterization and isolation of natural products with herbicidal activity against weed species.

  8. Cloning and Expression Analysis of Chalcone Isomerase Gene LhCHI in Oriental Hybrid Lily (Lilium spp.)%东方百合查尔酮异构酶基因 LhCHI的克隆及表达1)

    Institute of Scientific and Technical Information of China (English)

    窦晓莹; 郎利新; 包放; 孔滢; 尚宏忠; 白锦荣; 王乃彦

    2015-01-01

    The gene LhCHI encoding chalcone isomerase (CHI) involved into flavonoids synthesis was cloned from inner tepals of Oriental hybrid lily ‘Sorbonne ’ ( LhCHI, GenBank accession No .KJ784468 ) .The cDNA of LhCHI was obtained by RT-PCR and Rapid Amplification of cDNA Ends techniques .The open reading frame of LhCHI was 702 bp in length, enco-ding a protein polypeptide of 233 amino acids with a predicted molecular weight of 25 kD and a theoretical pI of 4.7.The deduced amino acid sequence of LhCHI shared 83.3%identity with CHI from Tulipa fosteriana, and contained typical con-served catalytic chalcone elements .Quantitative real-time PCR analyzed the expression profiles of LhCHI in different tis-sues.LhCHI was constitutively expressed in root , stem, leaf, bulb, tepal, anther, style and stigma with particularly high expression in flowers .The expression level of LhCHI in later stage flowers is generally higher than that in the early stage flowers.%利用RT-PCR结合RACE的方法从东方百合‘索邦’花被片中克隆了查尔酮异构酶(CHI)基因,命名为LhCHI(GenBank登录号为KJ784468)。该基因开放阅读框702 bp,编码233个氨基酸,预测该蛋白相对分子质量25 KD,等电点( pI)为4.7。同源比对和系统进化分析表明,LhCHI基因编码的氨基酸序列具有查尔酮异构酶典型的催化活性保守位点,与百合科郁金香( Tulipa fosteriana)查尔酮异构酶序列一致性为83.3%。半定量PCR和荧光实时定量PCR分析结果表明,LhCHI基因在百合的根、茎、叶片、鳞茎、开放花被片、花药以及柱头中均有表达,花器官中相对表达量较高,花发育后期的柱头、花柱、花被片等组织中LhCHI基因表达水平普遍高于花发育早期。

  9. 查耳酮-2-羟基苯甲酰腙的超声波合成与热稳定性%Ultrasonic synthesis and thermal stability of chalcone-2-hydroxy benzoyl hydrazone

    Institute of Scientific and Technical Information of China (English)

    王燕燕; 郑长征; 王亮

    2015-01-01

    A compound of chalcone‐2‐hydroxybenzoyl hydrazone was ultrasonic synthesized through the condensation of chalcone and 2‐hydroxybenzoyl hydrazine ,and the effects of the reaction time ,the amount of solvent ,the temperature and the material ratio on the yield were discussed .Results show that under the condition of ultrasonic , the reaction time of 4. 5h , 10mL of the volume of solvent ,temperature of 75℃ and material ratio of 1∶1.2 is more ap‐propriate .The compound was characterized by elemental analysis ,infrared spectroscopy and 1 H NMR .The thermogravimetric analysis shows that the compound is stable below 190.98℃ .%以查耳酮和2‐羟基苯甲酰肼为原料,采用超声波合成查耳酮‐2‐羟基苯甲酰腙,研究反应时间、溶剂量、温度和摩尔比对收率的影响.结果表明,在超声波条件下,反应时间4.5h ,溶剂量10mL ,温度75℃和摩尔比1∶1.2较为适宜.通过元素分析、红外光谱和核磁共振氢谱对其结构进行了表征.热重分析表明标题化合物处于190.98℃以下时较为稳定.

  10. 含氮查尔酮类细胞周期蛋白依赖性激酶抑制剂的合成及抗癌活性研究Ⅳ%Synthesis and anticancer activity study of nitrogen-containing chalcones as CDK inhibitors IV

    Institute of Scientific and Technical Information of China (English)

    李艳玲; 方浩; 徐文方

    2011-01-01

    The key role of CDKs in tumorigenesis have raised great interest for the development of CDK inhibitors as potential anticancer agents. Flavopiridol,a synthetic flavone,is the fist CDK inhibitors that entered clinical trial. And chalcones,as a branch of flavone,having important effects on cancer cell growth and proliferation. Herein, based on the structure of flavopiridol, eight novel chalcones analogs were synthesized by aldol condensation of a substituted acetophenone with various benzaldehyde, acetophenone was obtained by Hoesch reaction and methylation,chalcones was then converted target compounds by Mannich reaction with morpholine. The structures of target compounds were confirmed by IR,'H-NMR and ESI-MS,and their CDK1 inhibition as well as cytotoxicity activity against HCT116 were determined with flavopiridol as a positive control. The results showed that compounds 5a,5b,5c,5d,5f,5g and 5h exhibited higher CDK1 inhibition than flavopiridol,with the IC50 values of 63. 83,46.45,59. 70,48. 97,51. 40,52. 84,45. 70 nrnol·L-1 respectively, while flavopiridol was 64. 05 nmol·L-1 ,and compounds 5g and 5h showed higher cytotoxicity against HCT116 with the Icj,, values 2. 17,2. 80 μmol·L-1 respectively. The results showed that piperidine ring of flavopiridol can be replaced by Mannich base with morpholine ring.%目的 寻找活性更好的类黄酮细胞周期蛋白依赖激酶(CDKs)抑制剂.方法 利用Mannich反应制得8个查尔酮类黄酮.结果与结论 目标化合物的结构经1R、1 H-NMR、质谱确证,并测定了化合物对CDK1的抑制活性以及对HCT116肿瘤细胞的体外抗肿瘤活性,其中有7个化合物对CDK1抑制活性高于阳性对照flavopiridol,所有化合物对HCT116肿瘤细胞均显示出较强的抑制活性.

  11. 新型含2-取代-1,3-噻唑烷的查尔酮类化合物的合成及其生物活性%Synthesis and Biological Activity of Novel Chalcone Derivatives Containing 2-Substituted-1,3-thiazolidine Ring

    Institute of Scientific and Technical Information of China (English)

    戴红; 苗文科; 刘建兵; 吴珊珊; 秦雪; 方建新

    2012-01-01

    In order to find new chalcone derivatives with good biological activity, fourteen novel chalcone compounds containing 2-substituted-l,3-thiazolidine ring were synthesized by the reaction of 2-(2-cyanoimino-l,3-thiazolidine-3-yl)-l-phenylethanone or 3-(2-cyanoimino-l,3-thiazolidine-3-yl)-l-phenylprop-l-one with different substituted benzaldehydes. All the title compounds have been confirmed by 1H NMR spectra and elemental analysis. The preliminary bioassay showed that some target compounds displayed fungicidal activities to a certain extent.%为了寻找生物活性良好的查尔酮类化合物,利用2-(2-氰基亚胺基-1,3-噻唑烷-3-基)-1-苯基乙酮或3-((2-氰基亚胺基-1,3-噻唑烷-3-基)-1-苯基-1-丙酮与取代苯甲醛发生缩合,合成了14个新型含2-取代-1,3-噻唑烷的查尔酮类化合物.其结构均经1H NMR和元素分析表征.初步的生物活性测试结果表明,在试验浓度下,部分目标化合物表现出一定的杀菌活性.

  12. Enrichment of Pinstrobin Chalcone from Leaves of Carya Cathayensis Sarg.by Macroporous Resins%大孔吸附树脂法富集山核桃叶球松素查尔酮工艺的研究

    Institute of Scientific and Technical Information of China (English)

    朱学鑫; 蒋瑞彬; 黄晶晶; 蒋福升; 金波; 钱朝东; 丁志山

    2016-01-01

    目的:考察10种大孔吸附树脂对山核桃叶球松素查尔酮(pinostrobin chalcone)富集的影响,筛选出富集球松素查尔酮的最佳大孔吸附树脂,并确定富集球松素查尔酮的工艺条件及参数.方法:以球松素查尔酮作为检测指标,进行反相HPLC法进行测定,利用静态吸附方法筛选出最佳大孔吸附树脂为SD200,并利用动态实验优化SD200型大孔吸附树脂富集球松素查尔酮的各种工艺参数.结果:由于SD200型大孔吸附树脂对球松素查尔酮具有较好的吸附力和解吸附力,因此SD200型大孔吸附树脂被选于后续的实验研究.SD200型大孔吸附树脂富集球松素查尔酮的最佳工艺如下:吸附时间为150 min,吸附温度为25℃,样品溶液中球松素查尔酮的浓.度为3.58 mg/mL,上样体积为6.5 BV,上样速度为2.0 BV/h,选择70%乙醇溶液进行洗脱,洗脱体积为10.0 BV,洗脱速度为4.0 BV/h.在此条件下,产物中球松素查尔酮的含量从样品溶液中的7.02%提高到26.06%,将近提高了4倍,其回收率为82.81%.结论:SD200型大孔吸附树脂在所确定的工艺条件下,富集球松素查尔酮效果良好,此工艺简单、高效,为球松素查尔酮的大规模制备奠定一定的基础.

  13. Antifungal and antibacterial chalcones from Myrica serrata.

    Science.gov (United States)

    Gafner, S; Wolfender, J L; Mavi, S; Hostettmann, K

    1996-02-01

    The dichloromethane extract of the leaves of Myrica serrata inhibits growth of Cladosporium cucumerinum, Bacillus subtilis, and Escherichia coli on TLC plates. Activity-guided fractionation led the isolation of 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (1), 2',4'-dihydroxy-6'-methoxy-5'-methylchalcone (aurentiacin A) (2), 2',6'-dihydroxy-4'-methoxy-3',5'-dimethyldihydrochalcone (3), 2'-hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone (4), and 2', 6'-dihydroxy-4'-methoxy-3'-methyldihydrochalcone (5). In addition, the flavanones demethoxymatteucinol (6) and cryptostrobin (7) were also identified. PMID:8720393

  14. 超声辅助或无溶剂Claisen-Schmidt反应合成含胡椒环的吲哚查尔酮%A facile synthesis of 1,3-benzodioxole-bearing indole-based chalcone via ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction

    Institute of Scientific and Technical Information of China (English)

    李阳

    2014-01-01

    A structurally novel 1,3-benzodioxole-bearing indole-based chalcone,namely(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(2-chloro-1-(4-chlorobenzyl)-1H-indol-3-yl) prop-2-en-1-one(3) was synthesized,involving the ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction of 3-acetyl-2-chloro-1-(4-chlorobenzyl) indole and piperonaldehyde. The ultrasound-assisted Claisen-Schmidt condensation reaction was carried out using 1,4-dioxane as solvent and KOH as catalyst at room temperature to give the product 3 in 78%yield. Alternatively,the reaction could also be conducted under solvent-free condition by physical grinding in a mortar and pestle to obtain 3 in comparable yield of 75%. The two procedures offered easy access to 1,3-benzodioxole-bearing indole-based chalcone in short reaction time and good yield under mild conditions.%3-乙酰基-2-氯-1-(4-氯苄基)吲哚与胡椒醛通过超声辅助或无溶剂的Claisen-Schmidt缩合反应首次合成含胡椒环的吲哚查尔酮,即(E)-3-(5-胡椒基)-1-(2-氯-1-(4-氯苄基)-1H-3-吲哚查尔酮(3)。超声辅助的合成方法使用5%KOH作为催化剂,1,4-二氧六环作为溶剂,以78%的收率得到产品3。另外,这一 Claisen-Schmidt反应也可以在无溶剂研磨条件下进行,同样也以类似的收率获得产品3(75%)。这两种方法具有操作简便、反应条件温和、收率高等优点。

  15. 新型查耳酮衍生物的合成及其初步抗蛋白酪氨酸激酶(PTKs)活性研究%Synthesis of new chalcone derivatives and the in vitro PTKs inhibitory activity

    Institute of Scientific and Technical Information of China (English)

    樊睿; 班树荣; 方莲花; 李青山

    2011-01-01

    目的 设计合成一系列全新的查耳酮类衍生物,并初步测试其蛋白酪氨酸激酶(PTKs)抑制活性.方法 以间二甲苯为原料,经硝化、还原、水解、甲氧甲基保护等反应得到中间体取代苯乙酮,该中间体再与取代苯甲醛发生羟醛缩合反应后脱保护基得到目标化合物.采用酶联免疫吸附法(ELISA),以金雀异黄素为阳性对照,对目标化合物进行体外PTKs抑制活性检测.结果 与结论合成了10个查耳酮衍生物,其中9个是未见报道的新化合物,10个化合物的结构经核磁共振氢谱和质谱确证.化合物6a及新化合物6b、6c和6d对PTKs具有良好的抑制活性.%As one kind of flavone family compounds, chalcone is a kind of high-value compounds bearing common skeleton of diphenyl acrylketone with a variety of pharmacological activities.In our previous work,flavanone derivatives were found have good inhibitory activity against protein tyrosine kinases (PTKs).Now the structural modification of flavanone derivatives was made mainly on the B ring as a new way to prepare chalcone derivatives.Ten target compounds, among them nine are new derivatives, were synthesized by aldol condensation of benzaldehyde derivatives with substituted acetophenone which were obtained by successive nitration, reduction and hydrolysis of m-xylene, followed by methoxymethyl-group protection and then deprotection.Their structures were confirmed by 1H-NMR and ESI-MS.And their protein tyrosine kinases (PTKs)inhibitory activity was investigated by ELISA with genistein as a positive control compound.The results showed that compounds 6a,6b ,6c and 6d exhibited moderate inhibitory activities against protein tyrosine kinases, with inhibition rates varied from 28.44% to 53.12%, while genistein was 50.54%.The results showed that compounds with an ortho electron-withdrawing substituent on the B ring have good activity.

  16. Synthesis of tropolone-based chalcone derivatives (E)-5-bromo-3-(3-arylacryloyl) tropolones%卓酚酮基础的查尔酮衍生物(E)-5-溴-3-(3-芳基丙烯酰基)卓酚酮的合成

    Institute of Scientific and Technical Information of China (English)

    张红; 李阳

    2012-01-01

    A facile and general synthesis of a series of new tropolone-based chalcone compounds by Claisen-Schmidt condensation reaction from 3-acetyl-5-bromotropolone and substituted benzaldehydes was described.The method using 5% aq.KOH as catalyst and 50% aq.methanol as solvent was attractive since it specifically generates(E)-isomers with high yields under mild reaction conditions.The structures of the title compounds were characterized by IR,1H NMR,and MS techniques.%3-乙酰基-5-溴-卓酚酮与不同取代的苯甲醛类化合物通过Claisen-Schmidt缩合反应合成一系列结构新颖的卓酚酮取代的查尔酮类衍生物.该方法使用5% KOH溶液作为催化剂,50%甲醇水溶液作为溶剂,具有操作简便、反应条件温和、收率高等优点.所合成标题化合物的结构经IR、1H NMR、MS和元素分析得以证实.

  17. Discussion on Synthesis and Reaction Mechanism of Chalcone Catalyzed by Acidic Ionic Liquids[BPy]HSO4 and[BMMIm]HSO4%酸性离子液体[BPy]HSO4和[BMMIm]HSO4催化合成查尔酮反应机理探讨

    Institute of Scientific and Technical Information of China (English)

    杜玉英; 韩利民; 李永栋; 竺宁; 张桂峰

    2012-01-01

    离子液体作为绿色的溶剂和催化剂具有很多独特的性质,特别是离子液体的可设计性,使其具有酸性可调的特点.分别以酸性离子液体[BPy] HSO4和[BMMIm] HSO4为催化剂,在无溶剂条件下考察了两种离子液体对Claisen-Schmidt缩合的不同催化效果,探讨了两种离子液体在查尔酮合成中可能的催化机理.%Ionic liquids (ILs) as green solvents and catalysts have unique properties such as a broad liquid range,good solvating ability,high thermal stability,and negligible vapor pressure,especially designability of ILs, which makes the acidity of ILs can be adjustable. [BPy]HSO4 and[BM-MIm]HSO4 acidic ILs catalyzing Claisen-Schmidt (CS) condensation of acetophenone with benzal-dehyde were investigated under solvent-free conditions. The plausible mechanism was elucidated for the synthesis of chalcone using the two ILs as Br0nsted acid catalysts.

  18. Cloning,Expression Analysis and Promoter Isolation of Chalcone-synthase Gene from Fruits of Nane,Prunus salicina Lindl.var.cordata%油果实中查尔酮合成酶基因 PsCHS 的克隆表达分析及其启动子的分离

    Institute of Scientific and Technical Information of China (English)

    姜翠翠; 王玉珍; 叶新福

    2016-01-01

    Chalcone-synthase (CHS,EC 2.3.1.74)is an important enzyme involved inflavonoids synthesis pathway in plants.This study aimed to investigate the gene structure and expression profile of CHS gene in the fruits of nane (Prunus salicina Lindl.var.cordata).A full-length cDNA sequence harboring a CHS gene,named PsCHS ,was successfully separated from a normalized full-length cDNA library of matured nane fruits.The up-stream promoter sequence of PsCHS was separated by genome walking strategy using primer pair designed byPsCHS sequence.The length of PsCHS was 1 442 bp with ORF of 1 176 bp and deduced amino acid of 392 aa.From the prediction by an online software,the promoter sequence of PsCHS have typical structure element TATA-box and CAAT-box, photon-response element, anaerote-induced element, endosperm-related element, MYB-bingding element and hormone-response element,etc.RT-PCR indicated that PsCHS had higher expression level at the earlier stage of development of the fruit,especially 40 d after blossom,then decreased to a lower level at the maturing stage. PsCHS seperated in this study was a member of the CHS gene family.Since CHS is a key enzyme involved in flavonoid biosynthesis pathway,PsCHS might act with a regulatory role in biosynthesis of flavonoids.%从成熟果实均一化全长 cDNA 文库中分离了编码 CHS 基因的全长 cDNA 序列,命名为 PsCHS ,根据其序列设计引物,采用 Genome Walking 方法从基因组 DNA 中分离获得 PsCHS 基因上游的调控序列,命名为 PsCHSp ,PsCHS 基因全长1442 bp,其中 ORF 1176 bp,编码392个氨基酸;采用 APA-Walking 技术,获得该基因的5′端调控区,经在线软件预测,启动子序列含有典型的结构特征元件 TATA-box 和 CAAT-box,还包含光响应元件、厌氧诱导元件、胚乳表达相关元件、MYB 结合位点以及激素响应元件;RT-PCR 结果显示,PsCHS 基因在果实发育的前期表达量较高,花后40 d 表达量最高,随

  19. A versatile route to benzodiazocine and spiropyran derivatives through chalcones

    Indian Academy of Sciences (India)

    Johnson George; Saurabh Singh; Rahul Joshi; Ramchand T Pardasani

    2013-05-01

    Syntheses of 3-(phenyl)-benzo[b]thiophene [2, 3-d][1,2] benzodiazocine derivatives have been accomplished by the reaction of 3-phenacylidine-2-benzo[b]thiophene-2-ones with o-phenylene diamine. The photolytic reaction with trans-stilbene resulted in the exclusive formation of spiro{2',5',6'-triphenyl-2H-pyran-4',3}-benzo[b]thiophene-2-one derivatives. Theoretical calculations have been performed to study the mechanism and stereoselectivity of products. Good yield and broad scope of usable substrates of industrial relevance are other prominent features of the present methodologies.

  20. Some ferrocenyl chalcones as useful candidates for cancer treatment.

    Science.gov (United States)

    Janka, Vašková; Žatko, Daniel; Ladislav, Vaško; Pál, Perjési; Janka, Poráčová; Gabriela, Mojžišová

    2015-10-01

    Although knowledge of cancer management is extensive, mortality is not currently declining in this area. It is therefore important to implement a long-term strategy that would aim to prevent these serious diseases. Ferrocene-related organometallic compounds are promising candidates for design of new drugs since they can exhibit much greater biological activity than their phenyl analogs. In our work, we focused on investigating the cytotoxic and antiproliferative effects of five ferrocenyl derivatives toward selected tumor cell lines. We found that some of these substances significantly reduced Jurkat cell survival and, to a lesser extent, that of the HeLa, MCF7, A549, and MDA cells. Long-term treatment of HeLa cell cultures with these agents resulted in a significant blockade of formation of tumor cell colonies. We found that one of the mechanisms of action of the compounds is likely to display an effect on the redox state of the mitochondria at a final concentration of 10(-4) and 10(-5) mol l(-1). Of the compounds tested, the indanonyl ferrocene derivative (C) was the most effective, especially via glutathione depletion. Based on the obtained results, it can be concluded that synthetic substances containing iron have potential antitumor activity. PMID:26019120

  1. Synthesis and nonlinear optical absorption of novel chalcone derivative compounds

    Science.gov (United States)

    Rahulan, K. Mani; Balamurugan, S.; Meena, K. S.; Yeap, G.-Y.; Kanakam, Charles C.

    2014-03-01

    3-(4-(dimethylamino)phenyl)-1-(4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)phenyl)prop-2-en-1-one was synthesized and its third order nonlinear optical properties have been investigated using a z-scan technique with nanosecond laser pulses at 532 nm. The nonlinear absorption behavior of the compound in chloroform presents a distinct difference at different laser intensity. Interestingly, the compound showed a switchover from saturable absorption (SA) to reverse saturable absorption (RSA) with the increase of excitation intensity. Our studies suggest that compound could be used as a potential candidate for optical device applications such as optical limiters.

  2. Stereoselective reductions of chalcones using biocatalyst – Daucus carota

    Directory of Open Access Journals (Sweden)

    Wender A. Silva

    2012-06-01

    Full Text Available Biocatalysis is an important area in terms the organic synthesis, where many of its features can be used to induce stereoselective synthesis of important pharmaceutical intermediates and several commercially available products. However, catalysts to induce asymmetry are not available to all, due to its high cost and reactions restrictions. Recent studies indicate that the use of vegetables available in our everyday can be an alternative to investigate its effectiveness in some stereoselective reduction with economic important and ecological implications. From the previously synthesized compound 1 was carried out methodological study aimed stereoselective reduction to its respective alcohol saturated with the intention of using it as a building block in the synthesis of compounds with activity from an methodology efficient and convergent.

  3. Kinetic Analysis of Some Chalcones and Synthetic Chalcone Analogues on the Fenton-Reaction Initiated Deoxyribose Degradation Assay1

    OpenAIRE

    Perjési, Pál; Rozmer, Zsuzsanna

    2011-01-01

    Investigation of in vitro hydroxyl radical scavenging (antioxidant) effect 4-methoxychalcone (1a) and its cyclic analogues (2a-4a), as well as their hydroxyl substituted counterparts (1b-4b) was performed by means of the Fenton-reaction initiated deoxyribose degradation assay in short term (10 minute) and long term (240 minute) experiments. The kinetic deoxyribose method provides possibility to investigate not only the short term antioxidant (hydroxyl radical scavenger) effect but the possibl...

  4. Ruthenium(II) chalconate complexes: Synthesis, characterization, catalytic, and biological studies

    Science.gov (United States)

    Muthukumar, M.; Viswanathamurthi, P.

    2009-10-01

    A series of new hexa-coordinated ruthenium(II) carbonyl complexes of the type [RuCl(CO)(EPh 3)(B)(L)] (E = P or As; B = PPh 3, AsPh 3 or Py; L = 2'-hydroxychalcones) have been prepared by reacting [RuHCl(CO)(EPh 3) 2(B)] (E = P or As; B = PPh 3, AsPh 3 or Py) with 2'-hydroxychalcones in benzene under reflux. The new complexes have been characterized by analytical and spectral (IR, electronic, 1H, 31P and 13C NMR) data. Based on the above data, an octahedral structure has been assigned for all the complexes. The new complexes exhibit catalytic activity for the oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of N-methylmorpholine- N-oxide (NMO) as co-oxidant and also found efficient catalyst in the transfer hydrogenation of ketones. The antifungal properties of the complexes have also been examined and compared with standard Bavistin.

  5. Selective Reduction of Aryl Substituted Chalcones with Zn/Ammonium/Ethanol/Water

    Institute of Scientific and Technical Information of China (English)

    WANG Yu-Lu; ZHOU Yong-Bo

    2003-01-01

    @@ The selective reduction of carbon-carbon double bonds of α, β-unsaturated carbonyl compounds has attracted great interest in organic synthesis. Of many reductive systems described in the literature, transitional metal such as Pd, Rh, Pt, Ni, Cu, Ir and their complexes are usually utilized as catalysts, hydrides of Sn, Se, Te, B and sodium dithionite have been developed to catalyze selective reduction of α, β-unsaturated carbonyl compounds.

  6. Synthesis of Chalcone under Grinding Condition%研磨法合成查尔酮

    Institute of Scientific and Technical Information of China (English)

    杨德红; 杨本勇

    2013-01-01

    采用研磨法在无溶剂和室温条件下以苯甲醛和苯乙酮为原料合成了查尔酮,讨论了碱性催化剂的筛选,催化剂用量,反应物配比等反应条件.优化后的条件是:室温下研磨20 min,以NaOH/Na2CO3作为催化剂,苯甲醛、苯乙酮和催化剂的最佳摩尔比为6∶4∶2,选用75%乙醇溶液为重结晶溶剂,查尔酮的产率可以达到80.6%.

  7. Metabolite profiling of Arabidopsis thaliana (L.) plants transformed with an antisense chalcone synthase gene

    DEFF Research Database (Denmark)

    Le Gall, G.; Metzdorff, Stine Broeng; Pedersen, Jan W.;

    2005-01-01

    silencing. The metabolite profiles of the transgenic lines were examined for unintended effects of the modification. An apparently major effect on the glucosinolate composition was shown to result from an unusual genetic variation in the ecotype and not from the modification. The modification did produce a...

  8. SYNTHESIS OF 8-HYDROXYQUINOLINE CHALCONES: TRANS CONFIGURATION, INTRAMOLECULAR HYDROGEN BONDS, BROMINATION, AND ANTIFUNGAL ACTIVITY

    OpenAIRE

    ALONSO J MARRUGO-GONZÁLEZ; VALERIE D ORLOV; ROBERTO FERNANDEZ-MAESTRE

    2012-01-01

    Nine (8-Hydroxyquinolin-5-yl)-arylpropenones were synthesized and their structures demonstrated by IR and NMRspectroscopy. These molecules showed transconfiguration and strong intramolecular hydrogen bonding; in the IR spectra of 5-formyl-8-hydroxyquinoline, 5-acetyl-8-hydroxyquinoline, 1-(8-hydroxyquinolin-5-yl)-3-phenylprop-2-en-1-one and 3-(8-hydroxyquinolin-5-yl)-1-phenylprop-2-en-1-one in CHCl3, besides the known intermolecular hydrogen band (~3180 cm-1), we identified the intramolecular...

  9. Mosquito activity of a series of chalcones and 2-pyrazoline derivatives against Aedes aegypti

    Science.gov (United States)

    Aedes aegypti (L.) (Diptera: Culicidae) transmit pathogens to humans, leading to diseases such as yellow fever and dengue fever. Repellents and insecticides are two common interventions to reduce mosquito biting and thereby disease risk. However, overreliance on a chemical or class of chemicals c...

  10. Emerging role of Garcinol, the antioxidant chalcone from Garcinia indica Choisy and its synthetic analogs

    OpenAIRE

    Oswal Nikhil; Ahmad Aamir; Padhye Subhash; Sarkar Fazlul H

    2009-01-01

    Abstract Garcinol, harvested from Garcinia indica, has traditionally been used in tropical regions and appreciated for centuries; however its biological properties are only beginning to be elucidated. There is ample data to suggest potent antioxidant properties of this compound which have been used to explain most of its observed biological activities. However, emerging evidence suggests that garcinol could be useful as an anti-cancer agent, and it is increasingly being realized that garcinol...

  11. Synthesis, growth and characterization of π conjugated organic nonlinear optical chalcone derivative

    Energy Technology Data Exchange (ETDEWEB)

    Prabhu, A.N., E-mail: ashwatha.prabhu@manipal.edu [Department of Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India); Upadhyaya, V. [Department of Physics, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India); Jayarama, A., E-mail: jayaram@mite.ac.in [Department of Physics, Mangalore Institute of Technology and Engineering (MITE), Moodabidri 574225 (India); Subrahmanya Bhat, K. [Department of Chemistry, Manipal Institute of Technology, Manipal University, Manipal 576 104 (India)

    2013-02-15

    A new potentially useful nonlinear optical organic material, 1-(5-chlorothiophen-2-yl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one, has been synthesized and grown as a high-quality single crystal by the slow evaporation technique. The grown crystals were characterized by FT-IR, NMR, thermal analysis, and UV–visible spectroscopy. The material is thermally stabile up to 111 °C. The mechanical property of the grown crystals was studied using Vickers microhardness tester and the load dependence hardness was observed. The third order nonlinear optical properties of the material such as real and imaginary part of χ{sup (3)}, nonlinear absorption coefficient and nonlinear refractive index were determined using nanosecond laser pulses at 532 nm wavelength by employing Z-scan technique. The nonlinear refractive index is found to be of the order of 10{sup −11} cm{sup 2} W{sup −1}. The magnitude of third order susceptibility is of the order of 10{sup −13} esu. The observed increase in the third order nonlinearity in these molecules clearly indicates the electronic origin. The compounds exhibit good optical limiting at 532 nm. The best optical limiting behavior of this molecule is due to the substituted strong electron donor. - Highlights: ► A novel thiophene substituted NLO crystal has been grown using methanol as solvent. ► The crystals were characterized by using FTIR, TGA/DTA and UV–visible spectroscopy. ► The n{sub 2} and χ{sup (3)} values is of the order of 10{sup −11} cm{sup 2} W{sup −1} and 10{sup −13} esu respectively. ► The crystals show better optical limiting behavior.

  12. Synthesis and in vitro antimalarial activity of novel chalcone derivatives / Frans Johannes Smit

    OpenAIRE

    Smit, Frans Johannes

    2014-01-01

    Malaria is endemic in 106 countries worldwide. This disease is caused by a parasite from the genus Plasmodium. Of the five species that infect humans, Plasmodium falciparum is the most virulent, with over three billion people at risk and around 660 000 deaths reported in 2011. Of these deaths, 91% were in the African region, while 86% were children under the age of five. In light of the widespread development of resistance by malaria parasites against the classic antimalarial drugs, such as c...

  13. SYNTHESIS OF SOME NOVEL OXADIAZOLE BASED CHALCONE DERIVATIVES AS ANTI-BACTERIAL AGENTS

    Directory of Open Access Journals (Sweden)

    P.K. Arora*, A. Mittal, G. Kaur, and A. Chauhan

    2013-01-01

    Full Text Available A series of 1, 3, 4-oxadiazole derivatives were designed and out of which six compounds have been synthesized via four step synthetic scheme and evaluated for antibacterial activity using cup plate method. The compounds were previously characterized by IR, 1H-NMR spectral analysis. The compounds with hydroxyl and methoxy substituted phenyl rings showed higher activity than the chloro substituted derivatives and standard i.e vancomycin. The antibacterial study revealed that the most promising compounds are 3-(4-hydroxyphenyl-1-(5-(2-hydroxyphenyl-2-phenyl-1,3,4-oxadiazol-3(2H-yl prop-2-en-1-one 6.4(a, 3-(4-methoxyphenyl-1-(2,5-di phenyl-1,3,4-oxadiazol-3(2H-ylprop-2-en-1-one 6.4(b, 3-(4-hydroxy phenyl-1-(2,5-diphenyl-1,3,4-oxadiazol-3(2H-ylprop-2-en-1- one 6.4(c, 3-(4-hydroxy phenyl-1-(2-(4-hydroxyphenyl-5-phenyl-1,3,4-oxadiazol-3(2H-ylprop-2-en-1-one 6.4(e, 1-(2-(4-hydroxyphenyl-5-phenyl-1,3,4-oxadiazol-3(2H-yl-3-(4-methoxy phen ylprop-2-en-1-one 6.4(f against the tested bacteria (S. aureus, B. subtilis, P. aerugenosa, E. coli. This preliminary study revealed that these compounds may be used as potential leads for further studies.

  14. SYNTHESIS AND BIOLOGICAL ACTIVITIES OF CERTAIN MESOIONIC SYDNONE COMPOUNDS CONTAINING CHALCONE MOIETY

    OpenAIRE

    Deshpande, Shreenivas R.; Pai, K. Vasantakumar

    2010-01-01

    In order to have antibacterial, analgesic and anti-inflammatory activity in the same molecule, 4-[1-oxo-3- (substituted aryl)-2-propenyl]-3-(4-chlorophenyl) sydnones were synthesized by condensing 4-acetyl-3-(4-chlorophenyl)sydnone with various substituted aryl aldehydes and characterized by spectral studies; 4-acetyl-3-(4-chlorophenyl)sydnone itself, was prepared by acetylation of 3-(4-chlorophenyl) sydnone. The newly synthesized compounds were evaluated for antibacterial and anti-inflammato...

  15. Eco-friendly Synthesis of Ceria Foam via Carboxymethylcellulose Gelation: Application for the Epoxidation of Chalcone

    Science.gov (United States)

    A simple and innovative process is described for the eco-friendly preparation of ceria foams via the carboxymethylcellulose gelation by Ce4+ cations; heat treatment of the ensuing xerogels produces ceria foams. The influence of the concentration of cerium and of the calcination t...

  16. SYNTHESIS AND CHARACTERIZATION OF A DERIVATIVE CYCLOHEXANONE CHALCONE-TYPE, AS AN INTEGRAL LABORATORY EXPERIENCE

    Directory of Open Access Journals (Sweden)

    Perla E. Hernández-González

    2015-03-01

    Full Text Available At present, chemistry teachers are searching new models that allow integrative laboratory experiences, converging interdisciplinary knowledge of the Chemistry field. With this framework of ideas, this work describes the synthesis and characterization of the (2E,6E-2,6-bis(4-methoxybenzylidenecyclohexanone compound as axis of knowledge in order to encourage the students to develop their cognitive skills, such as critical thinking and problem solving, and also interpretation and analysis of results. The compound was synthesized by a Claisen-Schmidt condensation reaction, involving an aromatic aldehyde and cyclohexanone. The compound was characterized spectroscopically by NMR, IR and UV-Vis. Melting point and solubility tests were also performed. The chemical structure was confirmed by single crystal X-Ray diffraction. In conclusion, this laboratory experience allows students to get involved with the techniques and procedures commonly used in the organic chemistry laboratory to the synthesis and characterization of organic compounds.

  17. Chalcone Synthase Gene Lineage Diversification confirms allopolyploid evolutionary relationships of European Rostrate Violets

    NARCIS (Netherlands)

    Hof, van den K.; Berg, van den R.G.; Gravendeel, B.

    2008-01-01

    Phylogenetic relationships among and within the subsections of the genus Viola are still far from resolved. We present the first organismal phylogeny of predominantly western European species of subsection Rostratae based on the plastid trnS¿trnG intron and intergenic spacer and the nuclear low-copy

  18. Synthesis and biological activities of certain mesoionic sydnone compounds containing chalcone moiety.

    Science.gov (United States)

    Deshpande, Shreenivas R; Pai, K Vasantakumar

    2010-06-01

    In order to have antibacterial, analgesic and anti-inflammatory activity in the same molecule, 4-[1-oxo-3- (substituted aryl)-2-propenyl]-3-(4-chlorophenyl) sydnones were synthesized by condensing 4-acetyl-3-(4-chlorophenyl)sydnone with various substituted aryl aldehydes and characterized by spectral studies; 4-acetyl-3-(4-chlorophenyl)sydnone itself, was prepared by acetylation of 3-(4-chlorophenyl) sydnone. The newly synthesized compounds were evaluated for antibacterial and anti-inflammatory activities by cup plate and carrageenan induced rat paw edema methods respectively. Some of the compounds showed promising antibacterial and anti-inflammatory activities. PMID:24825982

  19. Growth and structure of a new photonic crystal: Chlorine substituted chalcone

    Energy Technology Data Exchange (ETDEWEB)

    Sarveshwara, H. P., E-mail: sarvesh.heggadde@gmail.com; Menezes, Anthoni Praveen [Department of Physics, Mangalore Institute Of Technology And Engineering (MITE), Moodabidri-574225 (India); Raghavendra, S.; Dharmaprakash, S. M. [Department of Studies in Physics, Mangalore University, Mangalore -575199 (India); A, Jayarama [Department of Physics, Sadguru Swami Nithyananda Institute of Technology (SSNIT), Kanhangad 671315 (India)

    2015-06-24

    A new organic photonic material 3-(2, 4-dichlorophenyl)-1-(2,5-dimethylthiophen-3-yl)propan-1-one(DMTP) has been synthesized and crystallised in acetone solution. The functional groups present in the new material were identified by FTIR spectroscopy. The material is optically transparent in the wavelength range of 400–1100 nm. The crystal structure of DMTP was determined by single crystal X-ray diffraction. The title compound crystallizes in monoclinic system with a centrosymmetric space group P2{sub 1}/c. The Z-scan study revealed that the optical limiting property exhibited by the DMTP molecule is based on the reverse saturable absorption phenomena.

  20. Synthesis, growth and characterization of π conjugated organic nonlinear optical chalcone derivative

    International Nuclear Information System (INIS)

    A new potentially useful nonlinear optical organic material, 1-(5-chlorothiophen-2-yl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one, has been synthesized and grown as a high-quality single crystal by the slow evaporation technique. The grown crystals were characterized by FT-IR, NMR, thermal analysis, and UV–visible spectroscopy. The material is thermally stabile up to 111 °C. The mechanical property of the grown crystals was studied using Vickers microhardness tester and the load dependence hardness was observed. The third order nonlinear optical properties of the material such as real and imaginary part of χ(3), nonlinear absorption coefficient and nonlinear refractive index were determined using nanosecond laser pulses at 532 nm wavelength by employing Z-scan technique. The nonlinear refractive index is found to be of the order of 10−11 cm2 W−1. The magnitude of third order susceptibility is of the order of 10−13 esu. The observed increase in the third order nonlinearity in these molecules clearly indicates the electronic origin. The compounds exhibit good optical limiting at 532 nm. The best optical limiting behavior of this molecule is due to the substituted strong electron donor. - Highlights: ► A novel thiophene substituted NLO crystal has been grown using methanol as solvent. ► The crystals were characterized by using FTIR, TGA/DTA and UV–visible spectroscopy. ► The n2 and χ(3) values is of the order of 10−11 cm2 W−1 and 10−13 esu respectively. ► The crystals show better optical limiting behavior

  1. Growth and structure of a new photonic crystal: Chlorine substituted chalcone

    International Nuclear Information System (INIS)

    A new organic photonic material 3-(2, 4-dichlorophenyl)-1-(2,5-dimethylthiophen-3-yl)propan-1-one(DMTP) has been synthesized and crystallised in acetone solution. The functional groups present in the new material were identified by FTIR spectroscopy. The material is optically transparent in the wavelength range of 400–1100 nm. The crystal structure of DMTP was determined by single crystal X-ray diffraction. The title compound crystallizes in monoclinic system with a centrosymmetric space group P21/c. The Z-scan study revealed that the optical limiting property exhibited by the DMTP molecule is based on the reverse saturable absorption phenomena

  2. Synthesis and spectral characterization of 2'-hydroxy chalconate complexes of ruthenium(II) and their catalytic and biological applications

    Science.gov (United States)

    Muthukumar, M.; Viswanathamurthi, P.; Natarajan, K.

    2008-10-01

    The reactions of [RuHCl(CO)(B)(EPh 3) 2] (B = EPh 3 or pyridine; E = P or As) and 2'-hydroxychalcones in 1:2 ratio led to the formation of [Ru(CO)(B)(L) 2] (B = PPh 3, AsPh 3 or Py; L = 2'-hydroxychalcones). The new complexes have been characterized by analytical and spectral (IR, electronic and 1H NMR) data. They have been assigned an octahedral structure. The new complexes were found to catalyze the oxidation of alcohols to aldehydes using N-methylmorpholine- N-oxide as co-oxidant. All the new complexes were found to be active against bacteria such as E. coli, Salmonella typhi and fungi Aspergillus niger. The activity was compared with standard Streptomycin or Bavistin.

  3. Nucleotide sequence of a soybean chalcone synthase gene with a possible role in ultraviolet-B sensitivity, Gmchs6

    International Nuclear Information System (INIS)

    Recent trends in stratospheric ozone depletion and projected increases in solar UV-B radiation (280-320 nm) have intensified studies of the ecological and physiological effects of increased levels of UV-B on higher plants (Caldwell, 1981; Worrest and Caldwell, 1986). Soybean (Glycine max L. Merr) is among the most extensively studied plants because it is a key crop of worldwide importance and because its potential susceptibility to increased levels of solar UV-B has been amply documented (Teramura et al., 1990, and refs. therein). From such studies, a pair of cultivars of contrasting sensitivity to UV-B has been identified. Williams is tolerant to supplemental UV-B fluences simulating a 25% ozone depletion, whereas Essex is sensitive to the same fluences, resulting in reduction of seed yield by 20 to 25%. The possibility that this may be due to differences in UV-B-absorbing compounds has also been noted

  4. The chalcone butein from Rhus verniciflua Stokes inhibits clonogenic growth of human breast cancer cells co-cultured with fibroblasts

    Directory of Open Access Journals (Sweden)

    Tan Jenny

    2005-03-01

    Full Text Available Abstract Background Butein (3,4,2',4'-tetrahydroxychalone, a plant polyphenol, is a major biologically active component of the stems of Rhus verniciflua Stokes. It has long been used as a food additive in Korea and as an herbal medicine throughout Asia. Recently, butein has been shown to suppress the functions of fibroblasts. Because fibroblasts are believed to play an important role in promoting the growth of breast cancer cells, we investigated the ability of butein to inhibit the clonogenic growth of small numbers of breast cancer cells co-cultured with fibroblasts in vitro. Methods We first measured the clonogenic growth of small numbers of the UACC-812 human breast cancer cell line co-cultured on monolayers of serum-activated, human fibroblasts in the presence of butein (2 μg/mL or various other modulators of fibroblast function (troglitazone-1 μg/mL; GW9662-1 μM; meloxican-1 μM; and 3,4 dehydroproline-10 μg/mL. In a subsequent experiment, we measured the dose-response effect on the clonogenic growth of UACC-812 breast cancer cells by pre-incubating the fibroblasts with varying concentrations of butein (10 μg/ml-1.25 μg/mL. Finally, we measured the clonogenic growth of primary breast cancer cells obtained from 5 clinical specimens with normal fibroblasts and with fibroblasts that had been pre-treated with a fixed dose of butein (2.5 μg/mL. Results Of the five modulators of fibroblast function that we tested, butein was by far the most potent inhibitor of clonogenic growth of UACC-812 breast cancer cells co-cultured with fibroblasts. Pre-treatment of fibroblasts with concentrations of butein as low as 2.5 μg/mL nearly abolished subsequent clonogenic growth of UACC-812 breast cancer cells co-cultured with the fibroblasts. A similar dose of butein had no effect on the clonogenic growth of breast cancer cells cultured in the absence of fibroblasts. Significantly, clonogenic growth of the primary breast cancer cells was also significantly reduced or abolished when the tumor cells were co-cultured with fibroblasts that had been pre-treated with a fixed dose of butein. Conclusion We conclude that fibroblasts pre-treated with non-toxic doses of butein (a natural herbal compound no longer support the clonogenic growth of small numbers of primary breast cancer cells seeded into co-cultures. These results suggest that interference with the interaction between fibroblasts and breast cancer cells by the natural herbal compound, butein, should be further investigated as a novel experimental approach for possibly suppressing the growth of micrometastases of breast cancer.

  5. Highly Catalytic Enantioselective Addition of Diethyl Zinc to Aldehydes and Chalcone in the Presence of Chiral Ligands

    Institute of Scientific and Technical Information of China (English)

    WANG; Rui

    2001-01-01

    Catalytic asymmetric carbon-carbon bond formation is one of the most important reactions and have attracted much attention to develop more efficient enantioselective C-C formation methods in organic synthesis. In this field, asymmetric addition of diethylzinc to aldehydes[1] and conjugate addition to enones[2] have drawn special interests and have been greatly developed. Regardless of it, much spaces in these areas still exist, so it needs more extensive and intensive researches for the purpose of as follows: (1) attaching ligands to a polymer for the easy separation of the catalysts so as to be able to allow very efficient recovery and reuse of the catalysts, and the possibility of carrying out the desired transfomation in continuous mode in a flow reactor, etc., (2) searching for novel chiral catalysts with such features as more suitable for more extensive substrates varieties, and more convenient and economical as well as possessing applicable prospect, and so on. Here we report some works in these areas done in our laboratory.  ……

  6. Synthesis of Hydroxylated Chalcones and Related Derivatives%羟基查尔酮类衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    关丽萍; 尹秀梅; 全红梅; 全哲山

    2004-01-01

    4-羟基苯乙酮或2,4-二羟基苯乙酮与取代苯甲醛在乙二醇溶液中,以硼酸为催化剂,于110~120℃反应6 h,再经柱分离精制得羟基查尔酮衍生物.产物经红外光谱、核磁共振谱、质谱确认结构.此法合成虽然收率不太高,但利用此法可更简便地一步合成出羟基查尔酮类衍生物.

  7. Highly Catalytic Enantioselective Addition of Diethyl Zinc to Aldehydes and Chalcone in the Presence of Chiral Ligands

    Institute of Scientific and Technical Information of China (English)

    2001-01-01

    @@ Catalytic asymmetric carbon-carbon bond formation is one of the most important reactions and have attracted much attention to develop more efficient enantioselective C-C formation methods in organic synthesis. In this field, asymmetric addition of diethylzinc to aldehydes[1] and conjugate addition to enones[2] have drawn special interests and have been greatly developed. Regardless of it, much spaces in these areas still exist, so it needs more extensive and intensive researches for the purpose of as follows: (1) attaching ligands to a polymer for the easy separation of the catalysts so as to be able to allow very efficient recovery and reuse of the catalysts, and the possibility of carrying out the desired transfomation in continuous mode in a flow reactor, etc., (2) searching for novel chiral catalysts with such features as more suitable for more extensive substrates varieties, and more convenient and economical as well as possessing applicable prospect, and so on. Here we report some works in these areas done in our laboratory.

  8. Conversion of 2'-substituted chalcones in the presence of BSA as evidenced by (1)H NMR studies.

    Science.gov (United States)

    Raghav, Neera; Garg, Shweta; Ravish, Indu

    2016-04-01

    The emergence of albumin as a biocatalyst has created continuous interest of researchers for its application not only in the field of asymmetric oxidations and reductions but also in chemical reactions such as additions, condensations and eliminations. In the present work we report the cyclization reactions in presence of an albumin protein, Bovine Serum Albumin (BSA). The work is focused on cyclization of 2'-hydroxychalcone and 2'-aminochalcone to flavanones and azaflavanone, respectively. The results are supported by (1)H NMR studies. PMID:26723247

  9. Solvent‐free synthesis, spectral correlations and antimicrobial activities of some 3,4‐ dimethoxy chalcones

    OpenAIRE

    V. Mala; K. Sathiyamoorthi; SP Sakthinathan; D. Kamalakkannan; Suresh, R.; Vanangamudi, G.; G. Thirunarayanan

    2012-01-01

    Background: The aim of this study was to synthesise some substituted styryl 3,4-dimethoxy phenyl ketones using solvent-free SiO2-H2SO4 catalyzed aldol condensation between 3,4- dimethoxy acetophenone and substituted benzaldehydes under microwave irradiation. Then to characterize them by their analytical, physical and spectroscopic data, and also to study their the spectral correlation and antimicrobial activities.

  10. Optical, vibrational, NBO, first-order molecular hyperpolarizability and Hirshfeld surface analysis of a nonlinear optical chalcone.

    Science.gov (United States)

    Aditya Prasad, A; Muthu, K; Meenatchi, V; Rajasekar, M; Agilandeshwari, R; Meena, K; Vijila Manonmoni, J; Meenakshisundaram, S P

    2015-04-01

    The synthesis of (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (DTDO) was done and its single crystals were grown by slow evaporation solution technique from 4-methylbenzaldehyde, acetone solution at room temperature. Crystal structure is determined by single crystal X-ray diffraction analysis and reveals that it belongs to the monoclinic system with four molecules in the unit cell (space group C2). The emission of green light from the sample confirms the second harmonic generation (SHG) of the specimen responsible for nonlinear optical property. The various vibration patterns of the specimen have been investigated by Fourier transform infrared and Fourier transform Raman spectroscopy. Optimized molecular geometry, vibrational patterns of DTDO are derived from density functional theory (DFT) calculations and the results are compared with experimental one. The molecular stability and bond strengths were investigated by applying the natural bond orbital analysis. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecule has been obtained by mapping electron density with molecular electrostatic potential (MEP). Highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gaps were calculated. The other molecular properties like charge transfer are explained using Mulliken population analysis and the first-order molecular hyperpolarizability (β) of the specimen is also estimated and SHG efficiency of DTDO was found to be 3.9 times that of KDP. Fingerprint plots and Hirshfeld surfaces were used to locate and analyze the molecular surface and bonding interactions in various methodologies utilized in the establishment of the relative energies. PMID:25615677

  11. Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

    Directory of Open Access Journals (Sweden)

    Olugbenga K. Popoola

    2015-04-01

    Full Text Available Ten flavonoid-related structures viz. heliteretifolin (1, isoxanthohumol (2, 2',4',6'-trihydroxy-3'-prenylchalcone (3, isoglabranin (4, glabranin (5, 7-methoxy-isoglabranin (6, quercetin (7, 4'-methoxyquercetin (8, 4'-methoxykaempferol (9 and mosloflavone (10 were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1 is reported for the first time from a natural source, while compounds 6, 8–10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72 µM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe2+-induced lipid peroxidation (IC50 = 2.931; 6.449 µg/mL; tyrosinase (8.092; 27.573 and elastase (43.342; 86.548. Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54 µM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40 × 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07 × 103 µM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.

  12. Synthesis of 3,5-dihydroxy chalcone%3,5-二羟基查尔酮的合成

    Institute of Scientific and Technical Information of China (English)

    石秀梅; 邓士英; 邹桂华; 岳司佳

    2008-01-01

    探索黄酮类化合物的合成方法.采用一种新方法,通过酰基化、Fries重排、醇醛缩合反应,合成了3,5-二羟基查尔酮,获得了满意的收率(80%).该方法具有反应时间短、操作简便、收率高等优点.

  13. Green Synthesis of Chalcone Derivatives%查耳酮衍生物的绿色合成

    Institute of Scientific and Technical Information of China (English)

    段宏昌; 姜恒; 宫红

    2006-01-01

    目的 绿色经济地合成查耳酮衍生物.方法 以苯甲醛衍生物和苯乙酮为原料,弱碱碳酸钾为催化剂,水为溶剂,用相转移催化法合成查耳酮衍生物.结果以水作溶剂于回流条件下反应6 h,产率高达90%,产物经IR确证.结论 成功、高效、环保地合成了目标产物,并弄清了芳香醛上取代基对产率的影响.

  14. Optical, vibrational, NBO, first-order molecular hyperpolarizability and Hirshfeld surface analysis of a nonlinear optical chalcone

    Science.gov (United States)

    Aditya Prasad, A.; Muthu, K.; Meenatchi, V.; Rajasekar, M.; Agilandeshwari, R.; Meena, K.; Vijila Manonmoni, J.; Meenakshisundaram, S. P.

    2015-04-01

    The synthesis of (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (DTDO) was done and its single crystals were grown by slow evaporation solution technique from 4-methylbenzaldehyde, acetone solution at room temperature. Crystal structure is determined by single crystal X-ray diffraction analysis and reveals that it belongs to the monoclinic system with four molecules in the unit cell (space group C2). The emission of green light from the sample confirms the second harmonic generation (SHG) of the specimen responsible for nonlinear optical property. The various vibration patterns of the specimen have been investigated by Fourier transform infrared and Fourier transform Raman spectroscopy. Optimized molecular geometry, vibrational patterns of DTDO are derived from density functional theory (DFT) calculations and the results are compared with experimental one. The molecular stability and bond strengths were investigated by applying the natural bond orbital analysis. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecule has been obtained by mapping electron density with molecular electrostatic potential (MEP). Highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy gaps were calculated. The other molecular properties like charge transfer are explained using Mulliken population analysis and the first-order molecular hyperpolarizability (β) of the specimen is also estimated and SHG efficiency of DTDO was found to be 3.9 times that of KDP. Fingerprint plots and Hirshfeld surfaces were used to locate and analyze the molecular surface and bonding interactions in various methodologies utilized in the establishment of the relative energies.

  15. Synthesis, Biochemistry, and Computational Studies of Brominated Thienyl Chalcones: A New Class of Reversible MAO-B Inhibitors.

    Science.gov (United States)

    Mathew, Bijo; Haridas, Abitha; Uçar, Gülberk; Baysal, Ipek; Joy, Monu; Mathew, Githa E; Lakshmanan, Baskar; Jayaprakash, Venkatesan

    2016-06-01

    A series of (2E)-1-(5-bromothiophen-2-yl)-3-(para-substituted phenyl)prop-2-en-1-ones (TB1-TB11) was synthesized and tested for inhibitory activity toward human monoamine oxidase (hMAO). All compounds were found to be competitive, selective, and reversible toward hMAO-B except (2E)-1-(5-bromothiophen-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one (TB7) and (2E)-1-(5-bromothiophen-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one (TB8), which were selective inhibitors of hMAO-A. The most potent compound, (2E)-1-(5-bromothiophen-2-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one (TB5), showed the best inhibitory activity and higher selectivity toward hMAO-B, with Ki and SI values of 0.11±0.01 μm and 13.18, respectively. PAMPA assays for all compounds were carried out in order to evaluate the capacity of the compounds to cross the blood-brain barrier. Moreover, the most potent MAO-B inhibitor, TB5, was found to be nontoxic at 5 and 25 μm, with 95.75 and 84.59 % viability among cells, respectively. Molecular docking simulations were carried out to understand the crucial interactions responsible for selectivity and potency. PMID:27159243

  16. Imbalance in expression of hop (Humulus lupulus) chalcone synthase H1 and its regulators during hop stunt viroid pathogenesis

    Czech Academy of Sciences Publication Activity Database

    Füssy, Zoltán; Patzak, J.; Stehlík, Jan; Matoušek, Jaroslav

    2013-01-01

    Roč. 170, č. 7 (2013), s. 688-695. ISSN 0176-1617 R&D Projects: GA ČR GCP501/10/J018; GA MZe QH81052 Institutional support: RVO:60077344 Keywords : Humulus lupulus * Phenylpropanoid * Viroid Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 2.770, year: 2013

  17. Solvent‐free synthesis, spectral correlations and antimicrobial activities of some 3,4‐ dimethoxy chalcones

    Directory of Open Access Journals (Sweden)

    V. Mala

    2012-03-01

    Full Text Available Background: The aim of this study was to synthesise some substituted styryl 3,4-dimethoxy phenyl ketones using solvent-free SiO2-H2SO4 catalyzed aldol condensation between 3,4- dimethoxy acetophenone and substituted benzaldehydes under microwave irradiation. Then to characterize them by their analytical, physical and spectroscopic data, and also to study their the spectral correlation and antimicrobial activities.

  18. Strains for the production of flavonoids from glucose

    Energy Technology Data Exchange (ETDEWEB)

    Stephanopoulos, Gregory; Santos, Christine; Koffas, Mattheos

    2015-11-13

    The invention relates to the production of flavonoids and flavonoid precursors in cells through recombinant expression of tyrosine ammonia lyase (TAL), 4-coumarate:CoA ligase (4CL), chalcone synthase (CHS), and chalcone isomerase (CHI).

  19. A synthetic chalcone, 2'-hydroxy-2,3,5'-trimethoxychalcone triggers unfolded protein response-mediated apoptosis in breast cancer cells.

    Science.gov (United States)

    Lee, Da Hyun; Jung Jung, You; Koh, Dongsoo; Lim, Yoongho; Lee, Young Han; Shin, Soon Young

    2016-03-01

    The primary aim of this study was to find novel chemopreventive agents effective against breast cancer. Endoplasmic reticulum (ER) stress can induce apoptosis through the unfolded protein response (UPR). 2'-Hydroxy-2,3,5'-trimethoxychalcone (DK143) is a synthetic flavonoid derivative. The present study provides evidence supporting the role of the UPR in mediating the apoptotic effect of DK143. Treatment with DK143 triggered apoptosis through the activation of the caspase pathway in MDA-MB-231 breast cancer cells without affecting viability of MCF10A non-transformed breast epithelial cells. Further analysis revealed that DK143 produced reactive oxygen species (ROS) in MDA-MB-231 cells, but not in MCF10A cells, and upregulated the expression of ER stress sensors, including GRP78/BiP, IRE1α, CHOP, and Bim in MDA-MB-231 cells. In addition, UPR-related transcription factors, XBP-1 and CHOP, were activated by DK143. Moreover, silencing of IRE1α or CHOP by corresponding siRNA molecules attenuated DK143-induced apoptosis. Furthermore, DK143 suppressed mouse tumor growth in vivo. These results demonstrate that promoting ER stress in breast cancer cells via UPR induction might be a promising strategy for developing new chemotherapeutic or chemopreventive agents for breast cancer. PMID:26742460

  20. Antiproliferative Activity and Induction of Apoptosis in PC-3 Cells by the Chalcone Cardamonin from Campomanesia adamantium (Myrtaceae) in a Bioactivity-Guided Study

    OpenAIRE

    Pascoal, Aislan; Ehrenfried, Carlos; Lopez, Begoña; Araujo,Thiago; Pascoal, Vinicius; Gilioli, Rovilson; Anhê, Gabriel; Ruiz, Ana; Carvalho, João; Stefanello, Maria; Salvador, Marcos

    2014-01-01

    The Myrtaceae family is a common source of medicines used in the treatment of numerous diseases in South America. In Brazil, fruits of the Campomanesia species are widely used to make liqueurs, juices and sweets, whereas leaves are traditionally employed as a medicine for dysentery, stomach problems, diarrhea, cystitis and urethritis. Ethanol extracts of Campomanesia adamantium (Myrtaceae) leaves and fruits were evaluated against prostate cancer cells (PC-3). The compound (2E)-1-(2,4-dihydrox...

  1. NKC-9 acidic resin catalyzed the synthesis of chalcones%NKC-9酸性树脂非均相催化合成查耳酮

    Institute of Scientific and Technical Information of China (English)

    姜文清; 邹建平; 安礼涛

    2008-01-01

    NKC-9酸性树脂催化芳醛与苯乙酮的Claisen-Schmidt缩合合成了五种查耳酮,收率81%~92%.考察了催化剂的用量和溶剂对收率的影响.该方法产率高、操作简便.产物结构经IR、NMR数据确认.

  2. Study on synthesis of 2-hydroxyl chalcon%2-羟基查耳酮的合成工艺研究

    Institute of Scientific and Technical Information of China (English)

    苗彩霞; 洪镛裕; 邓优华

    2008-01-01

    查耳酮类化合物是合成黄酮类化合物重要的中间体,具有重要的药理作用.研究了在稀碱催化下邻羟基苯乙酮和苯甲醛在乙醇溶液中的羟醛缩合反应,溶剂可以循环使用,适合工业化生产.

  3. 超声技术在查尔酮合成中的应用研究%Application of Ultrasound Irradiation in Synthesis of Chalcones

    Institute of Scientific and Technical Information of China (English)

    黄丹; 江国庆

    2002-01-01

    查尔酮是重要的有机合成中间体.报道了在KF-Al2O3的催化下,应用超声波技术合成查尔酮类化合物的方法,并研究了超声辐射功率、辐射时间对产物产率的影响,得出了最佳的合成反应条件.控制超声功率为250 W,反应30min,查尔酮(除化合物3b)的产率达95%以上.结果表明该方法操作简单、条件温和、反应速度快、产率高.

  4. 聚乙二醇相转移催化法合成查耳酮%Synthesis of Chalcone with Phase Transfer Catalyst Polyethylene Glycol

    Institute of Scientific and Technical Information of China (English)

    蒋新宇; 赵爱丽

    2006-01-01

    以聚乙二醇(polyethylene glycol,PEG)为相转移催化剂进行了苯甲醛与苯乙酮的克莱森-施密特(Claisen-Schmidt)缩合反应,并就聚乙二醇用量、聚乙二醇相对分子质量和溶剂种类等影响因素进行了条件实验,在较优化的合成条件下,查耳酮产率可达80%.

  5. 对位取代查尔酮衍生物的合成%Synthesis of p-Substituted Chalcone Derivatives

    Institute of Scientific and Technical Information of China (English)

    董秋静; 罗春华

    2007-01-01

    以苯甲醛和苯乙酮衍生物为原料,在氢氧化钠乙醇水溶液中,室温制备了一系列的查尔酮衍生物,收率在60%~90%之间.并通过熔点、凝胶渗透色谱、紫外光谱、红外光谱和核磁共振氢谱对其结构进行了表征.

  6. Synthesis of propyl-bridged biferrocenyl chalcone%丙基桥联双二茂铁基查尔酮衍生物的合成

    Institute of Scientific and Technical Information of China (English)

    冯珊; 卫兵; 高勇

    2009-01-01

    查尔酮及其衍生物是芳香醛酮发生交叉羟醛缩合的产物,是一类重要的药物活性化合物.本文以氢氧化钠为催化剂,合成了6个丙基桥联双二茂铁基查尔嗣衍生物.产物结构经1HNMR,IR及质谱进行了表征.此方法反应时间短,产率高且易于操作.

  7. Research progress in flavones synthesis from chalcone%查尔酮合成黄酮化合物的研究进展

    Institute of Scientific and Technical Information of China (English)

    熊长海; 郑旭煦; 殷钟意; 李小红; 侯苛山

    2008-01-01

    综述了近年来各种经查尔酮环化合成黄酮化合物的反应体系、合成方法,介绍了各种反应体系的适用范围,指出了各自的优缺点及其合成黄酮化合物的产率范围,认为黄酮化合物的合成将以新技术、新方法和无污染的绿色合成为发展方向.

  8. Elevated Gene Expression in Chalcone Synthase Enzyme Suggests an Increased Production of Flavonoids in Skin and Synchronized Red Cell Cultures of North American Native Grape Berries

    OpenAIRE

    Davis, Gina; Ananga, Anthony; Krastanova, Stoyanka; Sutton, Safira; Ochieng, Joel W.; Leong, Stephen; Tsolova, Violetka

    2012-01-01

    Anthocyanins are antioxidants and are among the natural products synthesized via the flavonoid biosynthesis pathway. Anthocyanins have been recommended for dietary intake in the prevention of cardiovascular diseases, cancer, and age-related conditions such as Alzheimer's disease or dementia. With an increasingly aging population in many parts of the world, strategies for the commercial production of in vitro synchronized red cell cultures as natural antioxidants will be a significant contribu...

  9. Solvent-Free Michael Addition Reaction of Cyclohexanone with Chalcone%环己酮与查尔酮的无溶剂Michael加成反应

    Institute of Scientific and Technical Information of China (English)

    荣良策; 李小跃; 王海营; 史达清; 屠树江

    2007-01-01

    以环己酮和查尔酮为原料,在NaOH存在下无溶剂室温研磨反应,非常方便地得到Michael加成产物.该方法具有反应条件温和、操作简单和产率较高等优点,并通过IR,1H NMR和元素分析确证产物的结构.

  10. Thioxopyrimidine in Heterocyclic Synthesis III: Synthesis and Properties of Some Novel Heterocyclic Chalcone Derivatives Containing a Thieno[2,3-d]pyrimidine-Based Chromophore

    OpenAIRE

    Yuh Wen Ho; Wei Hua Yao

    2013-01-01

    Cyclization of 4-methyl-2-phenyl-6-thioxo-1,6-dihydropyrimidine-5-carbonitrile 1 with chloroacetone in DMF in the presence of excess potassium carbonate anhydrous gave the 1-(5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidin-6-yl)ethanone 3, which can react with 2,5-dimethoxytetrahydrofuran in glacial acetic acid producing the 1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)thieno[2,3-d]pyrimidin-6-yl]ethanone 4. On the other hand, a series of novel 3-aryl-1-[4-methyl-2-phenyl-5-(1H-pyrrol-1-yl)-thieno[...

  11. Design, synthesis and molecular modeling studies of few chalcone analogues of benzimidazole for epidermal growth factor receptor inhibitor in search of useful anticancer agent.

    Science.gov (United States)

    Chhajed, Santosh S; Sonawane, Sandeep S; Upasani, Chandrashekhar D; Kshirsagar, Sanjay J; Gupta, Pramodkumar P

    2016-04-01

    In the present investigation, few 3-(substitutedphenyl)-1-[2-(1-hydroxy-ethyl)]-1H-benzimidazol-1-yl)prop-2-en-1-ones are EGFR antagonist are designed, by molecular docking analysis. The synthesized compounds were tested for their in vitro anticancer activity by propidium iodide fluorescent assay and Trypan blue viability assay against colorectal cancer cell lines (HCT116) and non-small cell lung cancer cell lines (H460). Human Epithelial Kidney cell lines (HEK) are used as normal cell lines for studying effect of drug on non-cancerous cells within human body. Evaluation of cytotoxic studies of synthesized compounds CHL(1-8) reveal that compound CHL1 [IC50=7.31 and 10.16 μM against HCT116 and H460 cell lines respectively, by PI assay] and CHL8 [IC50=12.52 and 6.83 against HCT116 and H460μM cell lines respectively] possess promising cytotoxic activity. PMID:26878127

  12. Attenuation of Mycobacterium tuberculosis by Disruption of a mas-Like Gene or a Chalcone Synthase-Like Gene, Which Causes Deficiency in Dimycocerosyl Phthiocerol Synthesis

    OpenAIRE

    Sirakova, Tatiana D.; Dubey, Vinod S.; Cynamon, Michael H.; Kolattukudy, Pappachan E.

    2003-01-01

    Tuberculosis is one of the leading preventable causes of death. Emergence of drug-resistant tuberculosis makes the discovery of new targets for antimycobacterial drugs critical. The unique mycobacterial cell wall lipids are known to play an important role in pathogenesis, and therefore the genes responsible for their biosynthesis offer potential new targets. To assess the possible role of some of the genes potentially involved in cell wall lipid synthesis, we disrupted a mas-like gene, msl7, ...

  13. Studies on Synthesis of Some Novel Heterocyclic Chalcone, Pyrazoline, Pyrimidine - 2 - One, Pyrimidine - 2 - Thione, para-Acetanilide Sulphonyl and Benzoyl Derivatives and their Antimicrobial Activity

    OpenAIRE

    Mistry, Rakesh N.; K. R. Desai

    2005-01-01

    1, 2 - Dichloro benzene on chlorosulphonation by chlorosulphonic acid gives 1, 2 - [dichloro] - benzene sulphonyl chloride which on condensation with p –amino acetophenone gives 1-[acetyl] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative. This derivative undergo condensation with 2,4- dichloro benzaldehyde gives 1- [3” - (sub. phenyl) - 2” - propene - 1” - one] - 1’ , 2’ - [dichloro] - dibenz sulphonamide derivative which on reaction with 99% hydrazine hydrate and glacial acetic acid g...

  14. Syntheses of chalcones and 2-aminopyrimidines and their evaluation as monoamine oxidase inhibitors and as adenosine receptor antagonists / Sarel Johannes Robinson

    OpenAIRE

    Robinson, Sarel Johannes

    2013-01-01

    Background and rationale - Parkinson’s disease is a neurodegenerative disorder characterised by reduced levels of dopamine in the brain. The cause of Parkinson's disease is still unknown; however several theories pertaining to the etiology exist. Current treatment mainly aims at dopamine replacement, with agents such as levodopa and dopamine agonists that provide patients with symptomatic relief. This relief is unfortunately only temporary as the progression of the disease ...

  15. Fungal plasma membrane H+-ATPase inhibitory activity of o-hydroxybenzylated flavanones and chalcones from Uvaria chamae P. Beauv

    DEFF Research Database (Denmark)

    Kongstad, Kenneth Thermann; Wubshet, Sileshi Gizachew; Kjellerup, Lasse;

    2015-01-01

    In our ongoing efforts of finding natural fungicides to fight food and feed spoilage during production and storage, the antifungal potential of Ghanaian Uvaria chamae P. Beauv. was investigated, with emphasis on plant metabolites targeting the fungal plasma membrane (PM) H+-ATPase. Ethyl acetate...... extract of U. chamae was subjected to high-resolution fungal PM H+-ATPase inhibition screening followed by structural elucidation by high-performance liquid chromatography–high-resolution mass spectrometry–solid-phase extraction–nuclear magnetic resonance spectroscopy (HPLC–HRMS–SPE–NMR). This led to...

  16. Synthesis and antimicrobial studies on novel chloro-fluorine containing hydroxy pyrazolines.

    Science.gov (United States)

    Karthikeyan, Mari Sithambaram; Holla, Bantwal Shivarama; Kumari, Nalilu Suchetha

    2007-01-01

    A series of chloro-fluorine containing chalcones (3) were prepared by Claisen-Schmidt condensation. Chalcone dibromides (4) were obtained by the bromination of chalcones at room temperature. Treatment of chalcone dibromides (4) with aryloxy acid hydrazides (5) in the presence of triethylamine gave chloro-fluorine containing hydroxy pyrazolines (7) rather than the expected 1-aryloxy-3-aryl-5-aryl pyrazoles (6). The structures of the newly synthesized compounds were confirmed by IR, NMR, mass and elemental analysis. All the compounds were tested for their antibacterial and antifungal activities. Some compounds showed very good antibacterial activity and antifungal activity. PMID:17007964

  17. A novel chalcone derivative which acts as a microtubule depolymerising agent and an inhibitor of P-gp and BCRP in in-vitro and in-vivo glioblastoma models

    International Nuclear Information System (INIS)

    Over the past decades, in spite of intensive search, no significant increase in the survival of patients with glioblastoma has been obtained. The role of the blood-brain barrier (BBB) and especially the activity of efflux pumps belonging to the ATP Binding Cassette (ABC) family may, in part, explain this defect. The in-vitro activities of JAI-51 on cell proliferation were assessed by various experimental approaches in four human and a murine glioblastoma cell lines. Using drug exclusion assays and flow-cytometry, potential inhibitory effects of JAI-51 on P-gp and BCRP were evaluated in sensitive or resistant cell lines. JAI-51 activity on in-vitro microtubule polymerization was assessed by tubulin polymerization assay and direct binding measurements by analytical ultracentrifugation. Finally, a model of C57BL/6 mice bearing subcutaneous GL26 glioblastoma xenografts was used to assess the activity of the title compound in vivo. An HPLC method was designed to detect JAI-51 in the brain and other target organs of the treated animals, as well as in the tumours. In the four human and the murine glioblastoma cell lines tested, 10 μM JAI-51 inhibited proliferation and blocked cells in the M phase of the cell cycle, via its activity as a microtubule depolymerising agent. This ligand binds to tubulin with an association constant of 2 × 105 M-1, overlapping the colchicine binding site. JAI-51 also inhibited the activity of P-gp and BCRP, without being a substrate of these efflux pumps. These in vitro studies were reinforced by our in vivo investigations of C57BL/6 mice bearing GL26 glioblastoma xenografts, in which JAI-51 induced a delay in tumour onset and a tumour growth inhibition, following intraperitoneal administration of 96 mg/kg once a week. In accordance with these results, JAI-51 was detected by HPLC in the tumours of the treated animals. Moreover, JAI-51 was detected in the brain, showing that the molecule is also able to cross the BBB. These in vitro and in vivo data suggest that JAI-51 could be a good candidate for a new treatment of tumours of the CNS. Further investigations are in progress to associate the title compound chemotherapy to radiotherapy in a rat model

  18. 微波/磷钨钼酸催化下的无溶剂合成查尔酮%Synthesis of Chalcones Catalyzed with H3PW6Mo6O4O without Solvent under Microwave Irradiation

    Institute of Scientific and Technical Information of China (English)

    武文斌; 朱荣鑫; 赵菲; 王小燕; 金永生

    2011-01-01

    首次报道了一种采用微波及二氧化钛负载的磷钨钼酸在无溶剂条件下催化合成查尔酮的方法,反应收率达到文献报道水平.该反应条件温和,反应时间短,易与产品分离、对环境污染小.

  19. The novel oxygenated chalcone, 2,4-dimethoxy-4'-butoxychalcone, exhibits potent activity against human malaria parasite Plasmodium falciparum in vitro and rodent parasites Plasmodium berghei and Plasmodium yoelii in vivo

    DEFF Research Database (Denmark)

    Chen, M; Brøgger Christensen, S; Zhai, L;

    1997-01-01

    growth of both a chloroquine-susceptible (3D7) and a chloroquine-resistant (Dd2) strain of Plasmodium falciparum in a [3H]hypoxanthine uptake assay. The in vivo activity of 2,4mbc was tested in mice infected with Plasmodium berghei or Plasmodium yoelii and in rats infected with P. berghei. 2,4mbc...... activity and might be developed into a new antimalarial drug....

  20. Synthèse, caractérisation et criblage biologique de nouveaux dérivés ferrocéniques des flavonoïdes : chalcones, aurones, flavones et flavonols

    OpenAIRE

    Monserrat, Jean-Philippe

    2011-01-01

    Flavonoids are antioxidants from the plants, and their protecting effects on the organism are now well known, since they are called " nutraceuticals ". Ferrocene is a stable and lipophilic organometallic complex, possessing a stable FeII/FeIII stable redox couple. Ferrocene-containing bioactive molecules possess new biological activities. For example, ferrocene can increase the existing activity as well as the therapeutical spectrum of a drug, but can also induce additional biological propert...

  1. SYNTHESIS OF CHALCONES BY A CLAISEN – SCHMIDT REACTION USING MAGNESIUM HYDROGEN SULPHATE AS A CATALYST UNDER SOLVENT – FREE CONDITION SYNTHESIS von Chalkonen durch eine Claisen - SCHMIDT Reaktion mit MAGNESIUM Hydrogensulfat als Katalysator unter SOLVENT - FREE CONDITION

    Directory of Open Access Journals (Sweden)

    Jayapal .Maleraju, and N.Y. Sreedhar

    2013-01-01

    Full Text Available Cross aldol condensations of ketones with aromatic aldehydes are carried out efficiently in the presence of magnesium hydrogen sulfate under solvent – free conditions in good to excellent yield without the occurrence of any self – condensation.

  2. SYNTHESIS OF CHALCONES BY A CLAISEN – SCHMIDT REACTION USING MAGNESIUM HYDROGEN SULPHATE AS A CATALYST UNDER SOLVENT – FREE CONDITION SYNTHESIS von Chalkonen durch eine Claisen - SCHMIDT Reaktion mit MAGNESIUM Hydrogensulfat als Katalysator unter SOLVENT - FREE CONDITION

    OpenAIRE

    Jayapal .Maleraju, and N.Y. Sreedhar

    2013-01-01

    Cross aldol condensations of ketones with aromatic aldehydes are carried out efficiently in the presence of magnesium hydrogen sulfate under solvent – free conditions in good to excellent yield without the occurrence of any self – condensation.

  3. Cloning and Sequence Analysis of Chalcone Isomerase Gene (CHI) from Brunfelsia acuminata Flowers%鸳鸯茉莉查尔酮异构酶基因(CHI)cDNA的克隆与生物信息学分析

    Institute of Scientific and Technical Information of China (English)

    曹玉婷; 邱栋梁

    2012-01-01

    采用RT-PCR与RACE技术克隆了鸳鸯茉莉(Brunfelsia acuminata)花瓣中查尔酮异构酶基因(CHI)的全长cDNA,GenBank登录号为JN887637.该基因全长1051 bp,含有1个792 bp的开放阅读框,编码263个氨基酸,为不稳定蛋白.对保守区功能区的分析,推导CHI蛋白具有查尔酮超级家族的保守结构域,二级结构预测显示其主要以α螺旋和β折叠为主.氨基酸同源性分析表明,鸳鸯茉莉CHI蛋白与矮牵牛(Petunia hybrida)、金花茶(Camellia nitidissima)、甜樱桃(Prunus avium)、芍药(Paeonia lactiflora)、牡丹(P.suffruticosa)、菊花(Chry santhemum morifolium)等植物的同源性分别达到90%、89%、84%、85%、84%、80%.因此,CHI基因可能与鸳鸯茉莉的花色形成有关.

  4. CHS基因起源初探及其在被子植物中的进化分析%A Preliminary Study on the Origin and Evolution of Chalcone Synthase (CHS) Gene in Angiosperms

    Institute of Scientific and Technical Information of China (English)

    黄金霞; 瞿礼嘉; 杨继; 银好; 顾红雅

    2004-01-01

    利用PCR与TAlL-PCR方法,从半月苔(Lunularia cructata(L.)Dum.ex Lindb)中获得了一段长约l 000 bp的基因片段,它与已知的CHS基因在核苷酸水平上的相似性大于56%,在氨基酸水平上的相似性大于60%,所推断的氨基酸序列中酶反应的4个催化位点与已知晶体结构的紫花苜蓿MCHS2A上的催化位点相同,首次证明了苔类植物中可能存在类CHS基因,将CHS基因的起源时间推到苔藓类植物出现之前.以该序列和两种蕨类植物(Psilotumnudum(L.)Griseb.和Equisetum arvense L.)的CHS序列作为外类群,应用邻接法、最大简约法和最大似然法分别构建了被子植物的CHS的分子系统树.结果表明,大部分科中的CHS分布在不同的分支上,而十字花科、可科和禾本科各自聚成一个单系类群.以邻接树为依据,对茄科、旋花科和菊科的CHS基因进行了相对碱基替换速率的检测,发现这三个科内或科间序列的替换速率不一致.被子植物的CHS基因在基因拷贝数目、碱基替换速率以及重复/丢失事件的发生上都存在较大的差异,这种差异可能与被子植物的生活史、生活环境、花的特性以及对外界的防御系统等的多样性相关.%By using Thermal Asymmetric Interlaced PCR (TAIL-PCR) method, a DNA fragment of about 1 000 bp was amplified and cloned from a liverwort species (Lunularia cruciata (L.) Dum. ex Lindb). The nucleotide sequence of this fragment and its deduced amino acid sequence shared about 56% and 60% identity with those of exon 2 of CHS genes from vascular plants respectively. The four characteristic catalyzing sites of CHS were found conserved in the deduced amino acid sequences of the fragment when compared with other CHS sequences. This is the first report of cloning a CHS-like gene from liverworts,suggesting that the origin of CHS genes may predate liverworts. Using the CHS-like sequence from L.cruciata and CHS sequences from two fern-alien species, Psilotum nudum (L.) Griseb. and Equisetum arvense L., as outgroups, the phylogenetic trees of about 250 CHSs from 29 families of angiosperm plants were constructed by using the neighbour-joining (NJ), maximum parsimony (MP) and quartet puzzle (QP)methods. The results showed that the CHSs from most plant families were separated into two or more clades while sequences from the families Brassicaceae, Fabaceae and Poaceae were each grouped into an independent monophyletic clade. The relative base substitution rates were estimated for CHS genes in three plant families, Solanaceae, Convolvulaceae, and Asteraceae, where the heterogeneity rate was detected both within and among the families. Results indicated that CHS genes in angiosperm plants were greatly diverse in terms of copy number, base substitution rate, and duplication/deletion events, which might be correlated with the diversity of life history, habitat, floral characters, and defense system of angiosperm plants.

  5. Synthesis of Hydroxylated Chalcones Under Microwave Using TBAB in Water%四丁基溴化铵存在下水介质中微波促进2-羟基查尔酮的合成

    Institute of Scientific and Technical Information of China (English)

    徐洲; 宛瑜; 沈阳; 吴翚

    2006-01-01

    2-羟基苯乙酮与取代苯甲醛在20%NaOH水溶液中,TBAB(四丁基溴化铵)存在下,微波辐射3~7 min,合成了13种羟基查尔酮及其衍生物.产物经红外光谱,核磁共振氢谱确认结构.

  6. A new chalcone structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one: Synthesis, structural characterizations, quantum chemical investigations and biological evaluations

    Science.gov (United States)

    Thanigaimani, Kaliyaperumal; Arshad, Suhana; Khalib, Nuridayanti Che; Razak, Ibrahim Abdul; Arunagiri, C.; Subashini, A.; Sulaiman, Shaida Fariza; Hashim, Nurul Shafiqah; Ooi, Kheng Leong

    2015-10-01

    The structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one (C19H13BrO) crystallized in the triclinic system of P-1 space group. The unit cell dimensions are: a = 5.8944 (9) Å, b = 7.8190 (12) Å, c = 16.320 (2) Å, α = 102.4364 (19)°, β = 95.943 (2)°, γ = 96.274 (2)° and Z = 2. The physical properties of this compound was determined by the spectroscopic methods (FTIR and 1H and 13C NMR). Quantum chemical investigations have been employed to investigate the structural and spectral properties. The molecular structure, vibrational assignments, 1H and 13C NMR chemical shift values, non-linear optical (NLO) effect, HOMO-LUMO analysis and natural bonding orbital (NBO) analysis were calculated using HF and DFT/B3LYP methods with 6-311++G(d,p) basis set in the ground state. The results show that the theoretical calculation of the geometrical parameters, vibrational frequencies and chemical shifts are comparable with the experimental data. The crystal structure is influenced and stabilized by weak C-H⋯π interactions connecting the molecules into infinite supramolecular one dimensional ladder-like arrangement. Additionally, this compound is evaluated for their antibacterial activities against gram positive and gram negative strains using a micro dilution procedure and shows activities against a panel of microorganisms.

  7. 离子液体-水体系中Pd(OAc)2催化合成查耳酮%Synthesis of Chalcones in IL-H2O System

    Institute of Scientific and Technical Information of China (English)

    辛炳炜

    2009-01-01

    研究了一种合成查耳酮的绿色催化体系. 以Pd(OAc)2为催化剂,在[bmim][PF6]-H2O体系中,通过苯甲酰氯和苯乙烯基硼酸的偶联反应,高产率地合成了3种查耳酮化合物. [bmim][PF6]-H2O体系可以循环使用6次,催化活性无明显降低. 该体系不需要膦配体,反应条件温和,反应时间短,产率高,是制备查耳酮理想的绿色体系.

  8. A novel chalcone derivative which acts as a microtubule depolymerising agent and an inhibitor of P-gp and BCRP in in-vitro and in-vivo glioblastoma models

    Directory of Open Access Journals (Sweden)

    Souard Florence

    2009-07-01

    Full Text Available Abstract Background Over the past decades, in spite of intensive search, no significant increase in the survival of patients with glioblastoma has been obtained. The role of the blood-brain barrier (BBB and especially the activity of efflux pumps belonging to the ATP Binding Cassette (ABC family may, in part, explain this defect. Methods The in-vitro activities of JAI-51 on cell proliferation were assessed by various experimental approaches in four human and a murine glioblastoma cell lines. Using drug exclusion assays and flow-cytometry, potential inhibitory effects of JAI-51 on P-gp and BCRP were evaluated in sensitive or resistant cell lines. JAI-51 activity on in-vitro microtubule polymerization was assessed by tubulin polymerization assay and direct binding measurements by analytical ultracentrifugation. Finally, a model of C57BL/6 mice bearing subcutaneous GL26 glioblastoma xenografts was used to assess the activity of the title compound in vivo. An HPLC method was designed to detect JAI-51 in the brain and other target organs of the treated animals, as well as in the tumours. Results In the four human and the murine glioblastoma cell lines tested, 10 μM JAI-51 inhibited proliferation and blocked cells in the M phase of the cell cycle, via its activity as a microtubule depolymerising agent. This ligand binds to tubulin with an association constant of 2 × 105 M-1, overlapping the colchicine binding site. JAI-51 also inhibited the activity of P-gp and BCRP, without being a substrate of these efflux pumps. These in vitro studies were reinforced by our in vivo investigations of C57BL/6 mice bearing GL26 glioblastoma xenografts, in which JAI-51 induced a delay in tumour onset and a tumour growth inhibition, following intraperitoneal administration of 96 mg/kg once a week. In accordance with these results, JAI-51 was detected by HPLC in the tumours of the treated animals. Moreover, JAI-51 was detected in the brain, showing that the molecule is also able to cross the BBB. Conclusion These in vitro and in vivo data suggest that JAI-51 could be a good candidate for a new treatment of tumours of the CNS. Further investigations are in progress to associate the title compound chemotherapy to radiotherapy in a rat model.

  9. Regioselective [3+2] cycloaddition of chalcones with a sugar azide: easy access to 1-(5-deoxy-D-xylofuranos-5-yl)-4,5-disubstituted-1H-1,2,3-triazoles.

    Science.gov (United States)

    Singh, Nimisha; Pandey, S K; Tripathi, Rama P

    2010-08-16

    [3+2] Cycloaddition of 5-azido-5-deoxy-1,2-O-isopropylidene-alpha-d-xylofuranose with 1,3-diphenyl-prop-3-enones, followed by oxidation of the intermediate triazolines in a tandem manner, led to the regioselective formation of 4-benzoyl-1-(5-deoxy-1,2-O-isopropylidene-alpha-d-xylofuranos-5-yl)-5-phenyl-1H-1,2,3-triazoles in moderate to good yields. PMID:20579636

  10. Flavylium based dual photochromism: addressing cis-trans isomerization and ring opening-closure by different light inputs.

    Science.gov (United States)

    Gago, Sandra; Basílio, Nuno; Moro, Artur J; Pina, Fernando

    2015-04-30

    The multistate system of 4',7-dihydroxy-3-methoxyflavylium is constituted by a multiequilibrium involving trans-chalcone, cis-chalcone, hemiketal, flavylium cation and quinoidal base. This system possesses two independently addressable inter-connected photochromic systems based on the cis-trans isomerization and ring opening-closure of the hemiketal. PMID:25820365

  11. Microwave accelerated solvent-free synthesis of flavanones

    Energy Technology Data Exchange (ETDEWEB)

    Sagrera, Gabriel J. [Universidad de la Republica, Montevideo (Uruguay). Facultad de Ciencias. Dept. de Quimica Organica]. E-mail: gseoane@fq.edu.uy; Seoane, Gustavo A. [Universidad de la Republica, Montevideo (Uruguay). Facultad de Quimica

    2005-07-15

    Microwave irradiation of chalcones under solvent-free conditions resulted in a 'green-chemistry' procedure for the preparation of flavanones in very good yields. Using an unmodified household microwave oven, different mineral supports and catalysts were tested. By irradiation of chalcones with 30% TFA over silica gel, eleven known flavanones and five new compounds were prepared in high yields. (author)

  12. A Biomimetic Strategy to Access the Silybins: Total Synthesis of (−)-Isosilybin A

    OpenAIRE

    McDonald, Benjamin R.; Nibbs, Antoinette E.; Scheidt, Karl A.

    2014-01-01

    We report the first asymmetric, total synthesis of (−)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible approach to this chalcone provides an entry to the preparation of the entire isomeric family of silybin natural products.

  13. Synthesis and antimicrobial activity of some new indazolone derivatives from 1-(3,5-Dibromo-2-hydroxy-4 methyl phenyl) ethanone

    OpenAIRE

    Pawar MP; Vyas K; Shah NM; Nimavat KS

    2012-01-01

    Indazolone nucleus is present in various therapeutically important drug candidates. Chalcones are possessing versatile pharmacological activities like anti-inflammatory, antifungal, antibacterial, antioxidant, cytotoxic, anticancer, antimalarial. While the bromoacetophenone nucleus bears very good antimicrobial activity. With consideration of all these facts we synthesized new derivatives of bromo acetophenone nucleus, which reacts with aromatic aldehydes to obtained chalcone. This was furthe...

  14. Synthetic and Antibacterial Studies of Quinolinylchalcones

    Science.gov (United States)

    Azad, Muhammad; Munawar, Munawar Ali; Athar, Makshoof

    A series of quinolinyl chalcones have been prepared by the condensation of N-substituted-3-acetyl-4-hydroxyquinolin-2(1H)-ones with different aromatic aldehydes using conventional heating and ultrasound-assisted methods. The percentage yields are considerably increased in ultrasound-assisted method. The prepared chalcone derivatives were assayed for antibacterial and cytotoxicity and were found to be active.

  15. AcEST: DK958562 [AcEST

    Lifescience Database Archive (English)

    Full Text Available ... 292 4e-92 sp|Q9ZRS4|CHSY_CATRO Chalcone synthase OS=Catharanthus roseus GN... 294 8e-92 sp|Q9FUB7|CHSY_HYPAN Chalcone syntha...se 1 OS=Cicer arietinum GN=C... 283 1e-88 sp|P23569|CHSY_PUELO Chalcone synthase OS=Pueraria lobat...lcone synthase OS=Catharanthus roseus GN=CHS PE=2 SV=1 Length = 389 Score = 294 bits (7...se OS=Senna ... 293 6e-91 tr|Q2WFX2|Q2WFX2_IRIGE Chalcone synthase OS=Iris germani...se OS=Hypericum... 289 3e-89 tr|B7SQE0|B7SQE0_ABEMA Chalcone synthase OS=Abelmoschus manihot ... 289 3e-

  16. Environ: E00053 [KEGG MEDICUS

    Lifescience Database Archive (English)

    Full Text Available 90], (+)-Epicatechin [CPD:C09728], Quercetin [CPD:C00389], Chalcone-flavan dimer, Gambiriin C [CPD:C10228], Gambirtannin...birfluorescein, Resin, Mucus, Dihydrogambirtannine, Oxogambirtannine, Gambirene U

  17. Polymer-support Selenium-induced Electrophilic Cyclization: Solid-phase Synthesis of Flavonoids

    Institute of Scientific and Technical Information of China (English)

    Jian CAO; E TANG; Xuan HUANG; Lu Ling WU; Xian HUANG

    2006-01-01

    The Lewis acid mediated polystyrene supported selenium induced intramolecular cyclization of chalcones and oxidative cleavage of selenium resins gave the corresponding flavonoids in good yields and purities have been reported.

  18. Synthesis of Biologically Active Natural Component 4-Hydroxyderricin Through Water-Accelerated [3,3]-Sigmatropic Rearrangement

    Energy Technology Data Exchange (ETDEWEB)

    Kim, Sijun; Lee, Jaejun; Yoon, Hyunho; Jun, Jonggab [Hallym Univ., Chuncheon (Korea, Republic of)

    2013-09-15

    We report herein the practical and effective total synthesis of biologically active 4-hydroxyderricin, a poly-phenolic chalcone compound containing m-prenyl group at ring A. The key steps of the synthesis are Claisen-Schmidt condensation of the the two phenolic units 17 and 18 to chalcone 19 and the water-accelerated [3,3]-sigma-tropic rearrangement of 1,1-dimethyl-2-propenyl aryl ether 20 to introduce the m-prenyl unit in 4-hydroxyderricin. Two types of polyphenolic chalcones, 4-hydroxyderricin (1) and xanthoangelol (2), are especially rich in the plant, and the 4-hydroxyderricin exhibited the major responsibility for the various biological activities. Sugamoto reported the synthesis of 4-hydroxy-derricin via [1,3]-sigmatropic rearrangement of chalcone ether using montmorillonite K10 which showed relatively low rearrangement yield (Scheme 1), and this is the only reported total synthesis of 1 as far as we know.

  19. Synthesis and characterization of a series of 1,3,5-trisubstituted-2-pyrazolines derivatives using methanoic acid under thermal condition

    Directory of Open Access Journals (Sweden)

    HAFEZEH SALEHABADI

    2009-12-01

    Full Text Available An efficient and practical synthesis of 1,3,5-trisubstituted 2-pyrazoline structures was achieved through cyclization of phenylhydrazine with ,-unsaturated ketones (chalcones using methanoic acid (formic acid as catalyst under thermal condition.

  20. Differential Expression of Anthocyanin Biosynthetic Genes in Relation to Anthocyanin Accumulation in the Pericarp of Litchi Chinensis Sonn

    OpenAIRE

    Yong-Zan Wei; Fu-Chu Hu; Gui-Bing Hu; Xiao-Jing Li; Xu-Ming Huang; Hui-Cong Wang

    2011-01-01

    Litchi has diverse fruit color phenotypes, yet no research reflects the biochemical background of this diversity. In this study, we evaluated 12 litchi cultivars for chromatic parameters and pigments, and investigated the effects of abscisic acid, forchlorofenron (CPPU), bagging and debagging treatments on fruit coloration in cv. Feizixiao, an unevenly red cultivar. Six genes encoding chalcone synthase (CHS), chalcone isomerase (CHI), flavanone 3-hydroxylase (F3H), dihydroflavonol 4-reductase...

  1. Potassium tert-Butoxide Catalyzed Synthesis and Characterization of Novel 3-Aryl-3-(phenylthio)-1-(thiophen-3-yl)- propan-l-one Derivatives%Potassium tert-Butoxide Catalyzed Synthesis and Characterization of Novel 3-Aryl-3-(phenylthio)-1-(thiophen-3-yl)- propan-l-one Derivatives

    Institute of Scientific and Technical Information of China (English)

    Budak, Yakup

    2012-01-01

    A series of thiophenyl-containing 3-thiophene derivatives (4a--4i) were prepared via the reaction of chalcone-analogua compounds (3a--3i) and thiophenol in the presence of catalytic amount of KOBu-t in CH2C12 with moderate to high yields. The mechanistic pathway of the reaction was explained by the Michael-type addition of thiophenol to chalcone derivatives (3a--3i).

  2. Aurone synthase is a catechol oxidase with hydroxylase activity and provides insights into the mechanism of plant polyphenol oxidases

    OpenAIRE

    Molitor, Christian; Mauracher, Stephan Gerhard; Rompel, Annette

    2016-01-01

    Catechol oxidases and tyrosinases belong to the family of polyphenol oxidases (PPOs). In contrast to tyrosinases, catechol oxidases were so far defined to lack hydroxylase activity toward monophenols. Aurone synthase (AUS1) is a plant catechol oxidase that specializes in the conversion of chalcones to aurones (flower pigments). We evidence for the first time, to our knowledge, hydroxylase activity for a catechol oxidase (AUS1) toward its natural monophenolic substrate (chalcone). The presente...

  3. Tetramethylguanidium Lactate Ionic Liquid:Catalyst-free Medium for Michael Addition Reaction

    Institute of Scientific and Technical Information of China (English)

    2008-01-01

    A catalyst-free, facile and efficient Michael addition reaction of active methylene compounds as well as nitromethane with chalcones catalyzed by guanidinium lactate ionic liquid was done. A series of chalcones,nitromethane, and active methylene compounds were converted smoothly to the corresponding products in high yields.The simple procedure, very mild conditions, high yields, and reuse of the IL without any loss of catalytic activity make this protocol considerably attractive for academic researches and practical applications.

  4. Synthesis, Characterization, Antimicrobial Screening and Free-Radical Scavenging Activity of Some Novel Substituted Pyrazoles

    OpenAIRE

    Nagwa Mohamed Mahrous Hamada; Nadia Yousef Megally Abdo

    2015-01-01

    The present work deals with the synthesis of acetoxysulfonamide pyrazole derivatives, substituted 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives starting from substituted vanillin chalcones. Acetoxysulfonamide pyrazole derivatives were prepared from the reaction of chalcones with p-sulfamylphenylhydrazine followed by treatment with acetic anhydride. At the same time 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivati...

  5. Synthesis, Characterization, Antimicrobial Screening and Free-Radical Scavenging Activity of Some Novel Substituted Pyrazoles

    OpenAIRE

    Hamada, Nagwa; Abdo, Nadia

    2015-01-01

    The present work deals with the synthesis of acetoxysulfonamide pyrazole derivatives, substituted 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivatives starting from substituted vanillin chalcones. Acetoxysulfonamide pyrazole derivatives were prepared from the reaction of chalcones with p-sulfamylphenylhydrazine followed by treatment with acetic anhydride. At the same time 4,5-dihydropyrazole-1-carbothioamide and 4,5-dihydropyrazole-1-isonicotinoyl derivativ...

  6. Differential accumulation of plant defense gene transcripts in a compatible and an incompatible plant-pathogen interaction.

    OpenAIRE

    Bell, J N; Ryder, T B; Wingate, V P; Bailey, J.A.; Lamb, C. J.

    1986-01-01

    Phenylalanine ammonia-lyase and chalcone synthase catalyze the first reaction of phenylpropanoid biosynthesis and the first reaction of a branch pathway specific for flavonoid-isoflavonoid biosynthesis, respectively. These enzymes are key control elements in the synthesis of kievitone, phaseollin, and related isoflavonoid-derived phytoalexins. RNA blot hybridization with 32P-labeled cDNA sequences was used to demonstrate marked accumulation of phenylalanine ammonia-lyase and chalcone synthase...

  7. Co-ordinated synthesis of phytoalexin biosynthetic enzymes in biologically-stressed cells of bean (Phaseolus vulgaris L.)

    OpenAIRE

    Cramer, Carole L; Bell, John N.; Ryder, Thomas B.; Bailey, John A.; Schuch, Wolfgang; Bolwell, G. Paul; Robbins, Mark P.; Dixon, Richard A.; Lamb, Chris J.

    1985-01-01

    Changes in the rates of synthesis of three enzymes of phenyl-propanoid biosynthesis in Phaseolus vulgaris L. (dwarf French bean) have been investigated by immunoprecipitation of [35S]methionine-labeled enzyme subunits with mono-specific antisera. Elicitor causes marked, rapid but transient co-ordinated increases in the rate of synthesis of phenyl-alanine ammonia-lyase, chalcone synthase and chalcone isomerase concomitant with the phase of rapid increase in enzyme activity at the onset of accu...

  8. Modular Optimization of Heterologous Pathways for De Novo Synthesis of (2S)-Naringenin in Escherichia coli

    OpenAIRE

    Junjun Wu; Tiantian Zhou; Guocheng Du; Jingwen Zhou; Jian Chen

    2014-01-01

    Due to increasing concerns about food safety and environmental issues, bio-based production of flavonoids from safe, inexpensive, and renewable substrates is increasingly attracting attention. Here, the complete biosynthetic pathway, consisting of 3-deoxy-D-arabinoheptulosonate 7-phosphate synthase (DAHPS), chorismate mutase/prephenate dehydrogenase (CM/PDH), tyrosine ammonia lyase (TAL), 4-coumarate:CoA ligase (4CL), chalcone synthase (CHS), chalcone isomerase (CHI), malonate synthetase, and...

  9. SYNTHESIS OF 2-METHYL-5-NITRO-N-(4-(3-((3-PHENYLQUINOXALIN-2-YL METHYL PHENOXY PHENYL BENZENESULFONAMIDE AND THEIR ANTIMICROBIAL ACTIVITY Synthese von 2-Methyl-5-NITRO-N-(4 - (3 - ((3-PHENYLQUINOXALIN-2-YL Methyl phenoxy phenyl BENZENESULFONAMIDE UND IHRE antimikrobielle Aktivität.

    Directory of Open Access Journals (Sweden)

    RAJARSHI N. PATEL1*, K.B. VYAS2, PIYSH V PATEL3and DINESH S PATEL

    2013-07-01

    Full Text Available Chalcones, precursors of open chain flavonoids and isoflavonoids present in edible plants, and their derivatives have attracted increasing attention due to numerous potential pharmacological applications. They have displayed a broad spectrum of pharmacological activities. Changes in their structure have offered a high degree of diversity that has proven useful for the development of new medicinal agents having improved potency and lesser toxicity. The present review highlights the recently synthesized chalcones and their derivatives possessing important pharmacological activities.

  10. Uses of 2-Ethoxy-4(3H) quinazolinone in Synthesis of Quinazoline and Quinazolinone Derivatives of Antimicrobial Activity: The Solvent Effect

    OpenAIRE

    El-Hashash, Maher A.; Rizk, Sameh A.; El-Bassiouny, Fakhry A.; Darwish, Khalid M

    2012-01-01

    2- Ethoxy-4(3H) quinazolinone 1 was synthesized and allowed to react with various halides, namely: alkyl, benzyl, allyl, acyl, haloacetyl, crotonyl, benzoyl, 2-furoyl and 1-naphthalenesulphonyl halides affording quinazoline and quinazolinone derivatives. The reactions of compound 1 with phosphorus oxychloride, phosphorus pentasulfide, ethyl chloroformate, ethyl chloroacetate, α-bromoglucose tetraacetate, p-acylaminobenzenesulfonyl chloride, acrylonitrile, chalcone and chalcone oxide were also...

  11. New potential sodium-glucose co-transporters sugar-based inhibitors for the treatment of diabetes

    OpenAIRE

    Jesus, Ana Rita Xavier de

    2015-01-01

    Tese de doutoramento, Química (Química Orgânica), Universidade de Lisboa, Faculdade de Ciências, 2015 A small library of C-glucosyl dihydrochalcones and their aglycones, chalcones and dihydrochalcones, were synthesized aiming at preparing new C-glucosyl analogues of phlorizin, a well-known non-selective sodium-glucose co-transporter inhibitor, bearing different substituents on the dihydrochalcone moiety. Chalcones were prepared by conventional aldol condensation methods and also by microwa...

  12. Synthesis and antimycobacterial activity of novel heterocycles

    Directory of Open Access Journals (Sweden)

    M. ASHRAF ALI

    2007-01-01

    Full Text Available In the present investigation 4-hydroxy-3-methylacetophenone on condensation with various aromatic aldehydes in methanolic KOH solution yielded the corresponding chalcones (CI–CXI. These chalcones were further reacted with hydrazine hydrate in ethanol which led to the formation of pyrazoline derivatives (HI–HXI. The newly synthesized heterocyles were characterized on the basis of their chemical properties and spectroscopic data. All newly synthesized compounds were evaluated for their antimycobacterial activities against Mycobacterium tuberculosis H37Rv.

  13. Facile Synthesis of Chalcone Derivatives E-2-(Methylamino)-7-(3-(pyridinyl)acryloly)tropones%查尔酮衍生物E-2-(甲氨基)-7-(3-(吡啶基)丙烯酰基)卓酮的合成

    Institute of Scientific and Technical Information of China (English)

    常明琴; 张红; 李阳; 高文涛

    2010-01-01

    以2-乙酰基-7-(甲氨基)卓酮(1)为原料,经由与各种吡啶醛的Claisen-Schmidt缩合反应得到查尔酮衍生物E-2-(甲氨基)-7-(3-(吡啶基)丙烯酰基)卓酮 (2~5). 全部合成产物均为新化合物,未见文献报道;其结构均由红外光谱分析、1H核磁共振、质谱及元素分析得以证实.

  14. The novel oxygenated chalcone, 2,4-dimethoxy-4'-butoxychalcone, exhibits potent activity against human malaria parasite Plasmodium falciparum in vitro and rodent parasites Plasmodium berghei and Plasmodium yoelii in vivo

    DEFF Research Database (Denmark)

    Chen, M; Brøgger Christensen, S; Zhai, L;

    1997-01-01

    growth of both a chloroquine-susceptible (3D7) and a chloroquine-resistant (Dd2) strain of Plasmodium falciparum in a [3H]hypoxanthine uptake assay. The in vivo activity of 2,4mbc was tested in mice infected with Plasmodium berghei or Plasmodium yoelii and in rats infected with P. berghei. 2,4mbc...... activity and might be developed into a new antimalarial drug....

  15. Antioxidant Activity of Total Flavonoid Aglycones and the Main Compound Pinostrobin Chalcone Separated from Leaves of Carya cathayensis%山核桃叶总黄酮苷元及其主要单体成分球松素查尔酮的抗氧化活性

    Institute of Scientific and Technical Information of China (English)

    徐敏; 沈勇; 张坤; 刘楠楠; 蒋福升; 丁志山

    2013-01-01

    目的:测定山核桃叶总黄酮苷元(TFA)及其主要单体成分——球松素查尔酮(PSC)的抗氧化活性.方法:采用柱层析法分离、富集山核桃叶中的总黄酮苷元及单体化合物球松素查尔酮;测定总黄酮苷元中总酚含量,通过1,1-二苯基-2-三硝基苯肼(DPPH)自由基实验、铁离子还原/抗氧化能力(FRAP)测定法、抗脂质过氧化(LPO)实验、抗蛋白氧化羰基(PCO)生成实验,对TFA和PSC进行体外抗氧化活性研究.结果:富集的山核桃叶总黄酮苷元中总酚含量用没食子酸当量(GAE)表示为(283.75±10.82) mg·g-1;TFA和PSC对DPPH自由基清除的抑制浓度(IC50)分别为(20.05±1.74),(11.66±0.61) mg·L-1,抑制脂质过氧化的IC50分别为(74.62 ±5.39),(24.38 ±1.24) mg·L-1,抑制蛋白过氧化的IC50分别为(174.29±11.26),(86.74 ±7.89) mg·L-1;TFA和PSC均具有较强的抗氧化能力;除了对铁离子还原力外,其他各项指标化合物PSC均显著强于TFA.结论:山核桃叶中含有较高含量的黄酮苷元,其富集的总黄酮苷元具有较强的抗氧化活性,已知成分大于50%,而球松素查尔酮是其主要药效物质,值得进一步开发应用.

  16. 3'-Hydroxy-4-methoxychalcone as a potential antibacterial coating on polymeric biomaterials

    International Nuclear Information System (INIS)

    Antimicrobial property of chalcone coated high density polyethylene (HDPE), low density polyethylene (LDPE), polypropylene (PP) and polyurethane (PU) against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa is reported here. The presence of chalcone on the surface was confirmed from fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS). Bacterial adhesion decreased considerably on all the coated surfaces. Bacterial adhesion was highest on PU surface (most hydrophobic) and lowest on HDPE (most hydrophilic) surface. Chalcone seems to damage the membrane of the bacteria as well as exhibit slimicidal activity. Reasonably good correlation was observed between the CFU (Colony Forming Units) ratio (it is defined as the ratio of CFU on coated surface to the chalcone uncoated surface) at the 24th hour against both hydrophobicity of the microorganism and roughness of the coated polymeric surfaces. Increasing roughness of the polymer and hydrophobicity of the microorganisms were positively and negatively correlated respectively with CFU ratio. Hence, the chalcone coated polymers can be used in the development of newer biomaterials.

  17. 3'-Hydroxy-4-methoxychalcone as a potential antibacterial coating on polymeric biomaterials

    Energy Technology Data Exchange (ETDEWEB)

    Sivakumar, P.M., E-mail: sivamedchem@gmail.com [Department of Biotechnology, Indian Institute of Technology Madras, Adyar, Chennai 600036 (India); Iyer, Geetha, E-mail: geethu.v.iyer@gmail.com [Department of Biotechnology, Indian Institute of Technology Madras, Adyar, Chennai 600036 (India); Natesan, Lavanya [Department of Biotechnology, Indian Institute of Technology Madras, Adyar, Chennai 600036 (India); Doble, Mukesh, E-mail: mukeshd@iitm.ac.in [Department of Biotechnology, Indian Institute of Technology Madras, Adyar, Chennai 600036 (India)

    2010-08-01

    Antimicrobial property of chalcone coated high density polyethylene (HDPE), low density polyethylene (LDPE), polypropylene (PP) and polyurethane (PU) against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa is reported here. The presence of chalcone on the surface was confirmed from fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS). Bacterial adhesion decreased considerably on all the coated surfaces. Bacterial adhesion was highest on PU surface (most hydrophobic) and lowest on HDPE (most hydrophilic) surface. Chalcone seems to damage the membrane of the bacteria as well as exhibit slimicidal activity. Reasonably good correlation was observed between the CFU (Colony Forming Units) ratio (it is defined as the ratio of CFU on coated surface to the chalcone uncoated surface) at the 24th hour against both hydrophobicity of the microorganism and roughness of the coated polymeric surfaces. Increasing roughness of the polymer and hydrophobicity of the microorganisms were positively and negatively correlated respectively with CFU ratio. Hence, the chalcone coated polymers can be used in the development of newer biomaterials.

  18. 3‧-Hydroxy-4-methoxychalcone as a potential antibacterial coating on polymeric biomaterials

    Science.gov (United States)

    Sivakumar, P. M.; Iyer, Geetha; Natesan, Lavanya; Doble, Mukesh

    2010-08-01

    Antimicrobial property of chalcone coated high density polyethylene (HDPE), low density polyethylene (LDPE), polypropylene (PP) and polyurethane (PU) against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa is reported here. The presence of chalcone on the surface was confirmed from fourier transform infrared spectroscopy (FT-IR) and scanning electron microscopy (SEM) and energy dispersive spectroscopy (EDS). Bacterial adhesion decreased considerably on all the coated surfaces. Bacterial adhesion was highest on PU surface (most hydrophobic) and lowest on HDPE (most hydrophilic) surface. Chalcone seems to damage the membrane of the bacteria as well as exhibit slimicidal activity. Reasonably good correlation was observed between the CFU (Colony Forming Units) ratio (it is defined as the ratio of CFU on coated surface to the chalcone uncoated surface) at the 24th hour against both hydrophobicity of the microorganism and roughness of the coated polymeric surfaces. Increasing roughness of the polymer and hydrophobicity of the microorganisms were positively and negatively correlated respectively with CFU ratio. Hence, the chalcone coated polymers can be used in the development of newer biomaterials.

  19. Fluorinated 2'-hydroxychalcones as garcinol analogs with enhanced antioxidant and anticancer activities.

    Science.gov (United States)

    Padhye, Subhash; Ahmad, Aamir; Oswal, Nikhil; Dandawate, Prasad; Rub, Rukhsana A; Deshpande, Jyoti; Swamy, K Venkateswara; Sarkar, Fazlul H

    2010-10-01

    Chalcones are involved in the synthesis of flavonoids and are themselves known to exhibit multiple pharmacological properties. However, compared to other structurally similar phytochemicals like garcinol and curcumin, the therapeutic use of chalcones is limited because of their lower bioavailability and rapid metabolic clearance from biological system. In the present work, we have attempted to overcome these limitations in case of 2'-hydroxychalcones through bioisosteric substitution of fluoro groups in place of phenolic hydroxyls. The fluorinated chalcones were found to be more potent antioxidant and anti-proliferative compounds than their hydroxyl counterparts indicating the influence of metabolically stable C-F bonds towards bioavailability. The difluoro derivatives were found to be most effective against human pancreatic BxPC-3 cancer cells which possess up-regulated COX-2 expression and also showed activity against human breast cancer BT-20 cells with triple negative phenotype, suggesting that these compounds will have broader application in the future. PMID:20729081

  20. Synthesis and antibacterial and antifungal studies of novel nitrogen containing heterocycles from 5-Ethylpyridin-2-ethanol

    Directory of Open Access Journals (Sweden)

    Patel N

    2010-01-01

    Full Text Available A novel series of chalcones, pyrimidines and imidazolinone is described; chalcones (4a-o were prepared from the lead molecule 4-[2-(5-ethylpyridin-2-ylethoxy]benzaldehyde. Pyrimidine (5a-o derivatives were prepared from the reaction of chalcones and guanidine nitrate in alkali media. Imidazolinones (6a-o were synthesized from reaction of pyrimidine and oxazolone derivatives (prepared by Erlenmeyer azlactone synthesis. The structures of the synthesized compounds were assigned on the basis of elemental analysis, IR, 1 H and 13 C NMR spectral data. All the products were screened against different strains of bacteria and fungi. Most of these compounds showed better inhibitory activity in comparison to the standard drugs.