biologically active heterocyclic: Topics by WorldWideScience.org

Sample records for biologically active heterocyclic

An insight into the biological activities of heterocyclic-fatty acid hybrid molecules.

Science.gov (United States)

Venepally, Vijayendar; Reddy Jala, Ram Chandra

2017-12-01

Heterocyclic compounds are the interesting core structures for the development of new bioactive compounds. Fatty acids are derived from renewable raw materials and exhibit various biological activities. Several researchers are amalgamating these two bioactive components to yield bioactive hybrid molecules with some desirable features. Heterocyclic-fatty acid hybrid derivatives are a new class of heterocyclic compounds with a broad range of biological activities and significance in the field of medicinal chemistry. Over the last few years, many research articles emphasized the significance of heterocyclic-fatty acid hybrid derivatives. The present review article focuses the developments in designing and biological evaluation of heterocyclic-fatty acid hybrid molecules. Copyright © 2017. Published by Elsevier Masson SAS.
synthesis and characterization of some poly functionalized heterocyclic derivatives of expected biological activity

International Nuclear Information System (INIS)

El-sayed, M.S.

2001-01-01

The present work was aimed and designed to fulfil The following objectives : 1- Continuation of the effort done by our research group in the field of chemistry of pyridinethione derivatives and their biological activities. 2- Synthesis of several new heterocyclic derivatives containing N and/or S using the laboratory available reagents. 3- Establishment of the structures of the newly synthesized heterocyclic compounds by the data of IR, 1 H-NMR, mass spectra in addition to the elemental analysis. 4- Synthesis of some of these heterocyclic derivatives via alternative routs and this used as a tool to confirm the structures of the newly synthesized heterocyclic derivatives. 5- study of the most probable mechanisms leading to the formation of the new heterocyclic derivatives. 6- The antimicrobial activity of some of the newly synthesized heterocyclic derivatives was tested against several types of organisms
Solid-supported synthesis: From pharmacologically relevant heterocycles to biologically active surfaces

DEFF Research Database (Denmark)

Komnatnyy, Vitaly V.

for solid-phase synthesis, methods for on - and off-bead screening of combinatorial libraries and their applic ation to various biological targets. The first part of the thesis is dedicated to the development of methodology for the synthesis of structurally diverse heterocyclic scaffolds via N...... methods for the controlled organo-functionalization of titanium, one of the most prominent materials in medicinal device industry, have been suggested . Initial acidic and oxidative treatment s of the metal surface genera te reactive hydroxyl moieties , which are subsequently modified with synthetically...... versatile amine -containing reagents. Subsequent applications in antimicrobial peptide synthesis, metal -catalysis, release from the surface, and polymer grafti ng, are also presented....
Physicochemical Mechanisms of Synergistic Biological Action of Combinations of Aromatic Heterocyclic Compounds

OpenAIRE

Evstigneev, Maxim P.

2013-01-01

The mechanisms of synergistic biological effects observed in the simultaneous use of aromatic heterocyclic compounds in combination are reviewed, and the specific biological role of heteroassociation of aromatic molecules is discussed.
Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C-H Bond Activation

Energy Technology Data Exchange (ETDEWEB)

Lewis, Jared; Bergman, Robert; Ellman, Jonathan

2008-02-04

Nitrogen heterocycles are present in many compounds of enormous practical importance, ranging from pharmaceutical agents and biological probes to electroactive materials. Direct funtionalization of nitrogen heterocycles through C-H bond activation constitutes a powerful means of regioselectively introducing a variety of substituents with diverse functional groups onto the heterocycle scaffold. Working together, our two groups have developed a family of Rh-catalyzed heterocycle alkylation and arylation reactions that are notable for their high level of functional-group compatibility. This Account describes their work in this area, emphasizing the relevant mechanistic insights that enabled synthetic advances and distinguished the resulting transformations from other methods. They initially discovered an intramolecular Rh-catalyzed C-2-alkylation of azoles by alkenyl groups. That reaction provided access to a number of di-, tri-, and tetracyclic azole derivatives. They then developed conditions that exploited microwave heating to expedite these reactions. While investigating the mechanism of this transformation, they discovered that a novel substrate-derived Rh-N-heterocyclic carbene (NHC) complex was involved as an intermediate. They then synthesized analogous Rh-NHC complexes directly by treating precursors to the intermediate [RhCl(PCy{sub 3}){sub 2}] with N-methylbenzimidazole, 3-methyl-3,4-dihydroquinazolein, and 1-methyl-1,4-benzodiazepine-2-one. Extensive kinetic analysis and DFT calculations supported a mechanism for carbene formation in which the catalytically active RhCl(PCy{sub 3}){sub 2} fragment coordinates to the heterocycle before intramolecular activation of the C-H bond occurs. The resulting Rh-H intermediate ultimately tautomerizes to the observed carbene complex. With this mechanistic information and the discovery that acid co-catalysts accelerate the alkylation, they developed conditions that efficiently and intermolecularly alkylate a variety of
Synthesis and Biological Evaluation of Novel Benzimidazole Derivatives Bearing a Heterocyclic Ring at 4/5 Position

International Nuclear Information System (INIS)

Wubulikasimu, Reyila; Yang, Yanbing; Xue, Fei; Luo, Xianjin; Shao, Dongping; Li, Yuhuan; Gao, Rongmei; Ye, Weidong

2013-01-01

A series of novel benzimidazole derivatives bearing a heterocyclic ring as oxadiazole (21-32), thiadiazole (33-34), triazole (35-36) were synthesized and evaluated for their activities against Coxsackie virus B3 and B6 in Vero cells. Compounds 21-26, 31-36 with moieties of 2'-pyridyl, 3'-pyridyl and 4'-pyridyl at the 2-position and oxadiazoles, thiadiazole, or triazole substituent at the 4- or 5-position generally displayed activities against CVB3 and CVB6. Especially compound 24 (IC 50 = 1.08 μg/mL, SI = 61.7 against CVB3) was the promising candidate as lead compound for anti-enteroviral drug. It was observed in the incorporation of heterocyclic rings in benzimidazole at the 5-position could enhance their biological activities
Synthesis and Biological Activity Evaluation of Novel Heterocyclic Pleuromutilin Derivatives

Directory of Open Access Journals (Sweden)

Yunpeng Yi

2017-06-01

Full Text Available A series of pleuromutilin derivatives were synthesized by two synthetic procedures under mild reaction conditions and characterized by Nuclear Magnetic Resonance (NMR, Infrared Spectroscopy (IR, and High Resolution Mass Spectrometer (HRMS. Most of the derivatives with heterocyclic groups at the C-14 side of pleuromutilin exhibited excellent in vitro antibacterial activities against Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA, methicillin-resistant Staphylococcus epidermidis (MRSE, and vancomycin-resistant Enterococcus (VRE in vitro antibacterial activity. The synthesized derivatives which contained pyrimidine rings, 3a, 3b, and 3f, displayed modest antibacterial activities. Compound 3a, the most active antibacterial agent, displayed rapid bactericidal activity and affected bacterial growth in the same manner as that of tiamulin fumarate. Moreover, molecular docking studies of 3a and lefamulin provided similar information about the interactions between the compounds and 50S ribosomal subunit. The results of the study show that pyrimidine rings should be considered in the drug design of pleuromutilin derivatives.
Imidazole: Having Versatile Biological Activities

Directory of Open Access Journals (Sweden)

Amita Verma

2013-01-01

Full Text Available Imidazoles have occupied a unique position in heterocyclic chemistry, and its derivatives have attracted considerable interests in recent years for their versatile properties in chemistry and pharmacology. Imidazole is nitrogen-containing heterocyclic ring which possesses biological and pharmaceutical importance. Thus, imidazole compounds have been an interesting source for researchers for more than a century. The imidazole ring is a constituent of several important natural products, including purine, histamine, histidine, and nucleic acid. Being a polar and ionisable aromatic compound, it improves pharmacokinetic characteristics of lead molecules and thus is used as a remedy to optimize solubility and bioavailability parameters of proposed poorly soluble lead molecules. There are several methods used for the synthesis of imidazole-containing compounds, and also their various structure reactions offer enormous scope in the field of medicinal chemistry. The imidazole derivatives possess extensive spectrum of biological activities such as antibacterial, anticancer, antitubercular, antifungal, analgesic, and anti-HIV activities. This paper aims to review the biological activities of imidazole during the past years.
Relationship between Antifungal Activity against Candida albicans and Electron Parameters of Selected N-Heterocyclic Thioamides

Science.gov (United States)

Stachowicz, Jadwiga; Krajewska-Kułak, Elżbieta; Łukaszuk, Cecylia; Niewiadomy, A.

2014-01-01

Due to the increasing demand for new pharmaceuticals showing biological activity against pathogenic microorganisms, there is increasing search for new compounds with predicted biological activity. Variously substituted thioamide derivatives with 1.3 and 1.2 ring of thiazole and 1,3,4-thiadiazole, as well as pyrazole were assessed for their activity against Candida albicans. Activity of majority of tested thioamides was larger as compared with that of the reference drugs. The electron parameters of obtained N-heterocyclic thioamides were determined and dependencies on their biological activity against Candida albicans were studied. The best electron compliance of produced bindings with the activity against Candida albicans was observed for the derivatives containing 1,3,4-thiadiazole ring. PMID:25284926
Microwave-assisted synthesis of bio-active heterocycles in aqueous media

KAUST Repository

Polshettiwar, Vivek; Varma, Rajender S.

2010-01-01

Synthesis of bio-active heterocycles and fine chemicals in aqueous media are one of the best solutions for the development of green and sustainable protocols. To illustrate the advantages of aqueous MW chemistry in heterocycle synthesis
Transformation of saturated nitrogen-containing heterocyclic compounds by microorganisms.

Science.gov (United States)

Parshikov, Igor A; Silva, Eliane O; Furtado, Niege A J C

2014-02-01

The saturated nitrogen-containing heterocyclic compounds include many drugs and compounds that may be used as synthons for the synthesis of other pharmacologically active substances. The need for new derivatives of saturated nitrogen-containing heterocycles for organic synthesis, biotechnology and the pharmaceutical industry, including optically active derivatives, has increased interest in microbial synthesis. This review provides an overview of microbial technologies that can be valuable to produce new derivatives of saturated nitrogen-containing heterocycles, including hydroxylated derivatives. The chemo-, regio- and enantioselectivity of microbial processes can be indispensable for the synthesis of new compounds. Microbial processes carried out with fungi, including Beauveria bassiana, Cunninghamella verticillata, Penicillium simplicissimum, Aspergillus niger and Saccharomyces cerevisiae, and bacteria, including Pseudomonas sp., Sphingomonas sp. and Rhodococcus erythropolis, biotransform many substrates efficiently. Among the biological activities of saturated nitrogen-containing heterocyclic compounds are antimicrobial, antitumor, antihypertensive and anti-HIV activities; some derivatives are effective for the treatment and prevention of malaria and trypanosomiasis, and others are potent glycosidase inhibitors.
Design, synthesis and antibreast cancer MCF-7 cells biological evaluation of heterocyclic analogs of resveratrol.

Science.gov (United States)

Du, Cheng; Dong, Ming-Hui; Ren, Yu-Jie; Jin, Lu; Xu, Cheng

2017-09-01

A new series of resveratrol heterocyclic analogs (4a-m) were designed and synthesized, and their inhibitiory effects on MCF-7 cells were evaluated to investigate structure-activity relationship. The effects of these analogs on human breast cancer MCF-7 cells were also determined. Results showed that MCF-7 cells could be inhibited more potently by these analogs than by resveratrol (IC 50 = 80.0 μM). Among the analogs, compounds 4c, 4e, and 4k showed a significantly higher activity (IC 50 = 42.7, 48.1, and 43.4 μM) than resveratrol. Furthermore, the derivatives without additional heterocyclic structure in the 4'-OH position exhibited a more potent activity than that with addition heterocyclic structure. In addition, docking simulation was performed to adequately position compound 4c in a human F 1 -ATPase active site to determine a probable binding model. These heterocyclic analogs could be effective candidates for the chemoprevention of human breast cancer.
Synthesis, biological evaluation and SAR analysis of novel poly-heterocyclic compounds containing pyridylpyrazole group.

Science.gov (United States)

Wang, Bao-Lei; Zhu, Hong-Wei; Li, Zheng-Ming; Wang, Li-Zhong; Zhang, Xiao; Xiong, Li-Xia; Song, Hai-Bin

2018-03-01

In recent years, pyridylpyrazole derivatives, such as pyridylpyrazole-containing anthranilic diamide have attracted much attention by virtue of their useful insecticidal properties and unique action mode. Moreover, some pyridylpyrazole-containing compounds have also been found to possess significant fungicidal activities. With the aim of discovering new bioactive agrochemicals for crop protection, a series of poly-heterocyclic compounds containing pyridylpyrazole and aziridine, or β-lactam, or thiazolinone moieties were synthesized. A series of pyridylpyrazole-containing poly-heterocyclic compounds were obtained, and confirmed through IR, 1 H NMR, 13 C NMR, HRMS and elemental analysis. The crystalline structure of 4-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-chloro-1-mesitylazetidin-2-one (compound 13f) was determined to further illustrate a trans- configuration of the β-lactam motif. In addition, bioassays showed that most of these new compounds exhibited modest insecticidal activity towards Mythimna separate Walker at 200 µg mL -1 . Some of the compounds displayed excellent fungicidal activity towards some plant fungi, including Cercospora arachidicola (13j: EC 50 = 14.5 µg mL -1 ), Physalospora piricola (12d and 13d: EC 50 = 10.5 and 9.70 µg mL -1 ), Alternaria solani Sorauer (13j: EC 50 = 7.29 µg mL -1 ), Puccinia sorghi Schw. (13d: control efficacy 99.0 ± 2.1% at 200 µg mL -1 ) and Erysiphe graminis (14d: control efficacy 95.0 ± 1.4% at 200 µg mL -1 ). Compounds 12b-12e, 13a, 13d, 13f, 13j, 13 k and 14d could be considered potential fungicidal lead compounds to do further structural optimization. The structure-activity relationship analysis in this study brings some new understanding to the biological activities of N-pyridylpyrazole-containing compounds, and provides important information for the research and development of novel agricultural fungicides with poly-heterocyclic structures. © 2017 Society of Chemical Industry. © 2017 Society
Microwave-assisted synthesis of bio-active heterocycles in aqueous media

KAUST Repository

Polshettiwar, Vivek

2010-01-01

Synthesis of bio-active heterocycles and fine chemicals in aqueous media are one of the best solutions for the development of green and sustainable protocols. To illustrate the advantages of aqueous MW chemistry in heterocycle synthesis, in this chapter, various synthetic pathways developed in recent years in aqueous reaction media using microwave irradiation are described.
A review on bis-hydrazonoyl halides: Recent advances in their synthesis and their diverse synthetic applications leading to bis-heterocycles of biological interest

Directory of Open Access Journals (Sweden)

Ahmad Sami Shawali

2016-11-01

Full Text Available This review covers a summary of the literature data published on the chemistry of bis-hydrazonoyl halides over the last four decades. The biological activities of some of the bis-heterocyclic compounds obtained from these bis-hydrazonoyl halides are also reviewed and discussed.
Synthesis, biological evaluation and molecular modeling of a novel series of 7-azaindole based tri-heterocyclic compounds as potent CDK2/Cyclin E inhibitors.

Science.gov (United States)

Baltus, Christine B; Jorda, Radek; Marot, Christophe; Berka, Karel; Bazgier, Václav; Kryštof, Vladimír; Prié, Gildas; Viaud-Massuard, Marie-Claude

2016-01-27

From four molecules, inspired by the structural features of fascaplysin, with an interesting potential to inhibit cyclin-dependent kinases (CDKs), we designed a new series of tri-heterocyclic derivatives based on 1H-pyrrolo[2,3-b]pyridine (7-azaindole) and triazole heterocycles. Using a Huisgen type [3 + 2] cycloaddition as the convergent key step, 24 derivatives were synthesized and their biological activities were evaluated. Comparative molecular field analysis (CoMFA), based on three-dimensional quantitative structure-activity relationship (3D-QSAR) studies, was conducted on a series of 30 compounds from the literature with high to low known inhibitory activity towards CDK2/cyclin E and was validated by a test set of 5 compounds giving satisfactory predictive r(2) value of 0.92. Remarkably, it also gave a good prediction of pIC50 for our tri-heterocyclic series which reinforce the validation of this model for the pIC50 prediction of external set compounds. The most promising compound, 43, showed a micro-molar range inhibitory activity against CDK2/cyclin E and also an antiproliferative and proapoptotic activity against a panel of cancer cell lines. Copyright © 2015 Elsevier Masson SAS. All rights reserved.
Biological Screening of Newly Synthesized BIAN N-Heterocyclic Gold Carbene Complexes in Zebrafish Embryos

Science.gov (United States)

Farooq, Muhammad; Abu Taha, Nael; Butorac, Rachel R.; Evans, Daniel Anthony; Elzatahry, Ahmed A.; Elsayed, Elsayed Ahmed; Wadaan, Mohammad A. M.; Al-Deyab, Salem S.; Cowley, Alan H.

2015-01-01

N-Heterocyclic carbene (NHC) metal complexes possess diverse biological activities but have yet to be extensively explored as potential chemotherapeutic agents. We have previously reported the synthesis of a new class of NHC metal complexes N-heterocyclic with acetate [IPr(BIAN)AuOAc] and chloride [IPr(BIAN)AuCl] ligands. In the experiments reported herein, the zebrafish embryos were exposed to serial dilutions of each of these complexes for 10–12 h. One hundred percent mortality was observed at concentrations ≥50 µM. At sub-lethal concentrations (10–30 µM), both compounds influenced zebrafish embryonic development. However, quite diverse categories of abnormalities were found in exposed embryos with each compound. Severe brain deformation and notochord degeneration were evident in the case of [IPr(BIAN)AuOAc]. The zebrafish embryos treated with [IPr(BIAN)AuCl] exhibited stunted growth and consequently had smaller body sizes. A depletion of 30%–40% glutathione was detected in the treated embryos, which could account for one of the possible mechanism of neurotoxicity. The fact that these compounds are capable of both affecting the growth and also compromising antioxidant systems by elevating intracellular ROS production implies that they could play an important role as a new breed of therapeutic molecules. PMID:26501273
In vitro disposition profiling of heterocyclic compounds.

Science.gov (United States)

Keemink, Janneke; Wuyts, Benjamin; Nicolaï, Johan; Jonghe, Steven De; Stella, Alessandro; Herdewijn, Piet; Augustijns, Patrick; Annaert, Pieter

2015-08-01

Compound libraries that are screened for biological activity commonly contain heterocycles. Besides potency, drug-like properties need to be evaluated to ensure in vivo efficacy of test compounds. In this context, we determined hepatic and intestinal disposition profiles for 17 heterocyclic compounds. All studied compounds showed rapid uptake in suspended rat hepatocytes, whereas metabolism was poor and the rate-limiting step in hepatic elimination. In vitro assays demonstrated a relatively low solubility and high intestinal permeability. Based on these in vitro data, heterocycles were categorized in the biopharmaceutics classification system (BCS) and the biopharmaceutics drug disposition classification system (BDDCS) to predict disposition characteristics before clinical data are available. Our findings emphasized the importance to use hepatocytes in addition to microsomes to study metabolism, since the latter lack non-microsomal enzymes and cellular context. Moreover, intracellular exposure should be considered to gain insight in the relevant fraction of the compound available at the enzymatic site. Finally, the study reveals discrepancies associated with the classification of heterocycles in BCS versus BDDCS. These probably originate from the binary character of both systems. Copyright © 2015 Elsevier B.V. All rights reserved.
Alkoxy(alkyl)silylalkyl derivatives of nitrogen-containing heterocycles

International Nuclear Information System (INIS)

Trofimova, Ol'ga M; Voronkov, Mikhail G; Chernov, Nikolai F

1999-01-01

The published data on the synthesis, properties and transformations of alkoxy(alkyl)silylalkyl derivatives of nitrogen-containing heterocycles of the general formula Het(CH 2 ) n SiX 3 are surveyed and systematised. Data on the biological activities and applications of these compounds are presented. The bibliography includes 255 references.
Synthesis, reactions and biological activity of some new bis-heterocyclic ring compounds containing sulphur atom

Science.gov (United States)

2013-01-01

Background The derivatives of thieno[2,3-b]thiophene belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial application. Results A new building block with two electrophilic center of thieno[2,3-b]thiophene derivatives 2 has been reported by one-pot reaction of diketone derivative 1 with Br2/AcOH in excellent yield. A variety of heteroaromatics having bis(1H-imidazo[1,2a] benzimidazole), bis(1H-imidazo[1,2-b][1,2,4]triazole)-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives, dioxazolo-, dithiazolo-, and 1H-imidazolo-3-methyl-4-phenylthieno[2,3-b]thiophene derivatives as well pyrrolo, thiazolo -3-methyl-4-phenylthieno[2,3-b]thiophene derivatives have been designed, synthesized, characterized, and evaluated for their biological activity. Compounds 3–9 showed good bioassay result. These new derivatives were evaluated for anti-cancer activity against PC-3 cell lines, in vitro antioxidant potential and β-glucuronidase and α-glucosidase inhibitory activities. Compound 3 (IC50 = 56.26 ± 3.18 μM) showed a potent DPPH radical scavenging antioxidant activity and found to be more active than standard N-acetylcystein (IC50 = 105.9 ± 1.1 μM). Compounds 8a (IC50 = 13.2 ± 0.34 μM) and 8b (IC50 = 14.1 ± 0.28 μM) found as potent inhibitor of α-glucusidase several fold more active than the standard acarbose (IC50 = 841 ± 1.73 μM). Most promising results were obtained in β-glucuronidase enzyme inhibition assay. Compounds 5 (IC50 = 0.13 ± 0.019 μM), 6 (IC50 = 19.9 ± 0.285 μM), 8a (IC50 = 1.2 ± 0.0785 μM) and 9 (IC50 = 0.003 ± 0.09 μM) showed a potent inhibition of β-glucuronidase. Compound 9 was found to be several hundred fold more active than standard D-Saccharic acid 1,4-lactone (IC50 = 45.75 ± 2.16 μM). Conclusions Synthesis, characterization, and in vitro biological activity of a series of

Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine's Tool Box.

Science.gov (United States)

Martins, Pedro; Jesus, João; Santos, Sofia; Raposo, Luis R; Roma-Rodrigues, Catarina; Baptista, Pedro Viana; Fernandes, Alexandra R

2015-09-16

The majority of heterocycle compounds and typically common heterocycle fragments present in most pharmaceuticals currently marketed, alongside with their intrinsic versatility and unique physicochemical properties, have poised them as true cornerstones of medicinal chemistry. Apart from the already marketed drugs, there are many other being investigated for their promising activity against several malignancies. In particular, anticancer research has been capitalizing on the intrinsic versatility and dynamic core scaffold of these compounds. Nevertheless, as for any other promising anticancer drugs, heterocyclic compounds do not come without shortcomings. In this review, we provide for a concise overview of heterocyclic active compounds and families and their main applications in medicine. We shall focus on those suitable for cancer therapy while simultaneously addressing main biochemical modes of action, biological targets, structure-activity relationships as well as intrinsic limitation issues in the use of these compounds. Finally, considering the advent of nanotechnology for effective selective targeting of drugs, we shall discuss fundamental aspects and considerations on nanovectorization of such compounds that may improve pharmacokinetic/pharmacodynamic properties of heterocycles.
Synthesis of acetylene alcohols of heterocyclic type and the acyl derivatives

Directory of Open Access Journals (Sweden)

Moldir Dyusebaeva

2015-03-01

Full Text Available A synthesis of potentially biologically active heterocyclic amino alcohols of acetylene (Piperidine and Morpholine under the conditions of Mannich reaction accomplished and received their acyl derivatives. Pharmacological activity (antibacterial and antispasmotic of synthesized compounds, also acute toxicological characteristics studied. The study showed that the combination of DMAE-4 has antispasmodic activity with low toxicity.
N-heterocyclic carbene complexes of silver and gold as novel tools against breast cancer progression.

Science.gov (United States)

Saturnino, Carmela; Barone, Ines; Iacopetta, Domenico; Mariconda, Annaluisa; Sinicropi, Maria Stefania; Rosano, Camillo; Campana, Antonella; Catalano, Stefania; Longo, Pasquale; Andò, Sebastiano

2016-12-01

Metal carbenic complexes have received considerable attention in both the catalysis and biological fields for their potential applications in cancer and antimicrobial therapies. A small series of new silver and gold N-heterocyclic carbene complexes has been designed and synthesized. Among the tested complexes, one compound was particularly active in inhibiting anchorage-dependent and -independent breast cancer proliferation, and inducing cell apoptosis via a mitochondria-related process. The antitumor activity was associated to the transcriptional activation of the tumor suppressor gene p53 in an Sp1-dependent manner, as evidenced by biological and docking studies. Our results highlight the importance and the versatility of N-heterocyclic carbene complexes of gold and silver as useful tools against breast cancer progression.
Surface active properties and biological activity of novel nonionic surfactants containing pyrimidines and related nitrogen heterocyclic ring systems

Directory of Open Access Journals (Sweden)

El-Sayed, R.

2008-06-01

Full Text Available A series of annelated pyrimidine derivatives has been synthesized via different heterocyclization reactions of suitably functionalized 6-(4-octadecyloxyphenyl-4-oxo-2- thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile (4 with different electrophiles and nucleophiles. These heterocycles bear an active hydrogen atom (NH, OH or COOH which could be propoxylated using propylene oxide with different moles, 5, 10 and 15, to produce nonionic surfactant having a long alkyl chain with molecular weight suitable for becoming an amphiphilic molecule with correct hydrophilic-lypophilic balance which enhances solubility, biodegradability and hence lowers the toxicity to human beings and becomes environmentally friendly. In addition, the antimicrobial activities of these compounds were screened and it was found that some of these compounds have similar or higher activity compared with commercial antibiotic drugs (sulphadiazine, which make them suitable for diverse applications like the manufacturing of drugs, pesticides, emulsifiers, cosmetics, etc.Una serie de derivados pirimidínicos y relacionados han sido preparados vía diferentes reacciones de formación de heterociclos entre 6-(4-octadeciloxifenil-4-oxo-2-tioxo- 1,2,3,4-tetrahidropirimidina-5-carbonitrilo (4 y diferentes electrófilos y nucleófilos. Estos heterociclos tienen un átomo de hidrógeno activo (NH, OH, o COOH que fue propoxilado con diferentes moles de óxido de propileno (5, 10, o 15 para producir surfactantes no iónicos con una cadena alquílica larga y peso molecular apropiado para convertirse en una molécula anfifílica con un balance hidrofílico-lipofílico correcto que aumenta la solubilidad y la biodedradabilidad, decrece la toxicidad a los seres humanos, y se convierte en respetuoso con el medio ambiente. Además, las actividades antimicrobianas de estos compuestos fueron determinadas y se encontró que algunos de estos compuestos tuvieron una actividad similar o más alta que
Synthesis and in vitro biological evaluation of new pyrazole chalcones and heterocyclic diamides as potential anticancer agents

Directory of Open Access Journals (Sweden)

Sankappa Rai U.

2015-05-01

Full Text Available Synthesis and characterization of new heterocyclic pyrazole chalcones (4a–e and diamide (6a–e derivatives are described. Pyrazole chalcones were synthesized by the reaction of pyrazole aldehydes and suitable aromatic ketones. Diamides were synthesized by the reaction of phthalic acid and amines. Newly synthesized compounds were characterized by spectral studies and their biological activity was assessed in vitro using MCF-7 (human breast adenocarcinoma and HeLa (human cervical tumor cells cell lines. Few of the synthesized molecules inhibited the growth of the human breast cancer cell lines and human cervical tumor cell lines at low micromolar to nanomolar concentrations.
RESEARCH REGARDING THE POTENTIAL ACTIVITY OF SOME HETEROCYCLIC COMPOUNDS ON PLANTS GROWTH AND DEVELOPMENT

Directory of Open Access Journals (Sweden)

OANA-IRINA PATRICIU

2017-06-01

Full Text Available It is well known that growth and morphogenesis of plant tissue cultures can be improved by small amounts of some organic compounds. Heterocyclic compounds such as chromanones and thiazoles derivatives, valuable because of their potential biological activities, have also been reported as pesticides, herbicides and plant-growth regulators. In the present study, different concentrations of chromanones and thiazoles derivatives were employed to evaluate their effects on plantlets growth of Ocimum basilicum L. and Echinacea purpurea L. The studied compounds were proved to be growth inhibitors at high concentrations. A growth stimulation effect was registered at low concentration.
Heterocyclic N-oxides - A Promising Class of Agents Against Tuberculosis, Malaria and Neglected Tropical Diseases.

Science.gov (United States)

Dos Santos Fernandes, Guilherme Felipe; Pavan, Aline Renata; Dos Santos, Jean Leandro

2018-04-17

Heterocyclic N-oxides have emerged as promising agents against a number of diseases and disorders, especially infectious diseases. This review analyzes the emergence and development of this scaffold in the medicinal chemistry, focusing mainly on the discovery of new heterocyclic N-oxide compounds with potent activity against tuberculosis, malaria and neglected tropical diseases (i.e. leishmaniasis and Chagas disease). A number of heterocyclic N-oxide are described herein, nevertheless, the following chemical classes deserve to be highlighted due to the large number of reports in the literature about their promising pharmacological effects: furoxan, benzofuroxan, quinoxaline 1,4-di-N-oxide, indolone N-oxide and benzimidazole N-oxide. In order to describe those most promising compounds, we included in this review only those most biologically active heterocyclic N-oxide published since 2000. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.
Auspicious role of the steroidal heterocyclic derivatives as a platform for anti-cancer drugs.

Science.gov (United States)

Tantawy, Mohamed A; Nafie, Mohamed S; Elmegeed, Gamal A; Ali, Ibrahim A I

2017-08-01

Steroids are polycyclic compounds that have a wide range of biological activities. They are bio-synthesized from cholesterol through a series of enzyme-mediated transformations, so they are highly lipophilic and readily enter most cells to interact with intracellular receptors, making them ideal vehicles for targeting a broad array of pathologies. New curative agents for cancers have been developed from several steroidal derivatives. Some biologically important properties of modified steroids are dependent on structural features of the steroid moiety and their side chains. Therefore, chemical derivatization of steroids provides a way to modify their function, and many structure-activity relationships have been confirmed by such synthetic modifications. Several studies demonstrate that steroidal heterocyclic derivatives can be effective in the prevention and treatment of many types of hormone-dependent cancers. The present review is a concise report on steroidal heterocyclic derivatives, with special emphasis on steroid heterocyclic derivatives with 5 membered rings or six-membered rings having interesting therapeutic potential as enzyme inhibitors and cytotoxic drugs to be used as candidates for anti-cancer drug development. Copyright © 2017 Elsevier Inc. All rights reserved.
Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine’s Tool Box

Directory of Open Access Journals (Sweden)

Pedro Martins

2015-09-01

Full Text Available The majority of heterocycle compounds and typically common heterocycle fragments present in most pharmaceuticals currently marketed, alongside with their intrinsic versatility and unique physicochemical properties, have poised them as true cornerstones of medicinal chemistry. Apart from the already marketed drugs, there are many other being investigated for their promising activity against several malignancies. In particular, anticancer research has been capitalizing on the intrinsic versatility and dynamic core scaffold of these compounds. Nevertheless, as for any other promising anticancer drugs, heterocyclic compounds do not come without shortcomings. In this review, we provide for a concise overview of heterocyclic active compounds and families and their main applications in medicine. We shall focus on those suitable for cancer therapy while simultaneously addressing main biochemical modes of action, biological targets, structure-activity relationships as well as intrinsic limitation issues in the use of these compounds. Finally, considering the advent of nanotechnology for effective selective targeting of drugs, we shall discuss fundamental aspects and considerations on nanovectorization of such compounds that may improve pharmacokinetic/pharmacodynamic properties of heterocycles.
Acrolein contributes strongly to antimicrobial and heterocyclic amine transformation activities of reuterin.

Science.gov (United States)

Engels, Christina; Schwab, Clarissa; Zhang, Jianbo; Stevens, Marc J A; Bieri, Corinne; Ebert, Marc-Olivier; McNeill, Kristopher; Sturla, Shana J; Lacroix, Christophe

2016-11-07

Glycerol/diol dehydratases catalyze the conversion of glycerol to 3-hydroxypropionaldehyde (3-HPA), the basis of a multi-component system called reuterin. Reuterin has antimicrobial properties and undergoes chemical conjugation with dietary heterocyclic amines (HCAs). In aqueous solution reuterin is in dynamic equilibrium with the toxicant acrolein. It was the aim of this study to investigate the extent of acrolein formation at various physiological conditions and to determine its role in biological and chemical activities. The application of a combined novel analytical approach including IC-PAD, LC-MS and NMR together with specific acrolein scavengers suggested for the first time that acrolein, and not 3-HPA, is the active compound responsible for HCA conjugation and antimicrobial activity attributed to reuterin. As formation of the HCA conjugate was observed in vivo, our results imply that acrolein is formed in the human gut with implications on detoxification of HCAs. We propose to re-define the term reuterin to include acrolein.
A chemical-biological evaluation of rhodium(I) N-heterocyclic carbene complexes as prospective anticancer drugs.

Science.gov (United States)

Oehninger, Luciano; Küster, Laura Nadine; Schmidt, Claudia; Muñoz-Castro, Alvaro; Prokop, Aram; Ott, Ingo

2013-12-23

Rhodium(I) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these organometallics. A series of Rh(I)-NHC derivatives with 1,5-cyclooctadiene and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with moderate inhibitory activity of thioredoxin reductase (TrxR) and efficient binding to biomolecules (DNA, albumin). Biodistribution studies showed that the presence of albumin lowered the cellular uptake and confirmed the transport of rhodium into the nuclei. Changes in the mitochondrial membrane potential (MMP) were observed as well as DNA fragmentation in wild-type and daunorubicin- or vincristine-resistant Nalm-6 leukemia cells. Overall, these studies indicated that Rh(I)-NHC fragments could be used as partial structures of new antitumor agents, in particular in those drugs designed to address resistant malignant tissues. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Structure-activity relationship (SAR) study and design strategies of nitrogen-containing heterocyclic moieties for their anticancer activities.

Science.gov (United States)

Akhtar, Jawaid; Khan, Ahsan Ahmed; Ali, Zulphikar; Haider, Rafi; Shahar Yar, M

2017-01-05

The present review article offers a detailed account of the design strategies employed for the synthesis of nitrogen-containing anticancer agents. The results of different studies describe the N-heterocyclic ring system is a core structure in many synthetic compounds exhibiting a broad range of biological activities. Benzimidazole, benzothiazole, indole, acridine, oxadiazole, imidazole, isoxazole, pyrazole, triazoles, quinolines and quinazolines including others drugs containing pyridazine, pyridine and pyrimidines are covered. The following studies of these compounds suggested that these compounds showed their antitumor activities through multiple mechanisms including inhibiting protein kinase (CDK, MK-2, PLK1, kinesin-like protein Eg5 and IKK), topoisomerase I and II, microtubule inhibition, and many others. Our concise representation exploits the design and anticancer potency of these compounds. The direct comparison of anticancer activities with the standard enables a systematic analysis of the structure-activity relationship among the series. Copyright Â© 2016 Elsevier Masson SAS. All rights reserved.
Synthesis and antibacterial activity of some heterocyclic derivatives of sulfanilamide

Directory of Open Access Journals (Sweden)

B.B. Subudhi

2012-12-01

Full Text Available Considering the promising antimicrobial potential of carbonic anhydrase inhibitors and heterocyclic compounds some heterocyclic derivatives of sulfanilamide (2a-e were synthesized. The diazotisation of sulfanilamide followed by substitution with ethylacetoacetate and further condensation yielded compounds 2a-c. Schiff base of sulfanilamide with salicylaldehyde on reaction with thioglycollic acid and chloroacetyl chloride resulted in compound 2d-e. The susceptibility of Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa to the title compounds (300 μg/disc was investigated and compared to that of nitrofurantoin (300 μg/disc and ciprofloxacin (25 μg/disc. The title compounds showed good antimicrobial activity.DOI: http://dx.doi.org/10.4314/bcse.v26i3.15
Lactoperoxidase, an Antimicrobial Milk Protein, as a Potential Activator of Carcinogenic Heterocyclic Amines in Breast Cancer.

Science.gov (United States)

Sheikh, Ishfaq Ahmad; Jiffri, Essam Hussain; Kamal, Mohammad Amjad; Ashraf, Ghulam Md; Beg, Mohd Amin

2017-11-01

Lactoperoxidase (LPO) is an antimicrobial protein secreted from mammary, salivary and other mucosal glands. It is an important member of heme peroxidase enzymes and the primary peroxidase enzyme present in breast tissues. In addition to the antimicrobial properties, LPO has been shown to be associated with breast cancer etiology. Heterocyclic amines, an important class of environmental and dietary carcinogens, have been increasingly associated with breast cancer etiology. Heterocyclic amines undergo activation in breast tissue as a result of oxidation by LPO. The current study includes three important heterocyclic amines, 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-1-methy-6-phenylimidazo[4,5-b]-pyridine (PhIP), that have carcinogenic activity. The structural binding characterization of IQ, MeIQx and PhIP with LPO was done using in silico approaches. Their binding pattern and interactions with LPO amino acid residues were analyzed. The three compounds bound in the distal heme cavity of LPO without replacing the important water molecule required for oxidation of substrate compounds. PhIP displayed lesser binding affinity for LPO in comparison to IQ and MeIQx. The binding mode of heterocyclic amines in distal heme cavity of LPO resembled to that of substrate binding pattern. The three heterocyclic amines are suggested to act as LPO substrate. The undisturbed water molecule present in distal heme cavity of the LPO is expected to facilitate the oxidation and activation of the three heterocyclic amines. These activated compounds may potentially bind with DNA in breast tissues forming DNA adducts and may subsequently lead to breast cancer initiation. Copyright© 2017, International Institute of Anticancer Research (Dr. George J. Delinasios), All rights reserved.
Allobetulin and Its Derivatives: Synthesis and Biological Activity

Directory of Open Access Journals (Sweden)

Talgat S. Seitembetov

2011-03-01

Full Text Available This review covers the chemistry of allobetulin analogs, including their formation by rearrangement from betulin derivatives, their further derivatisation, their fusion with heterocyclic rings, and any further rearrangements of allobetulin compounds including ring opening, ring contraction and ring expansion reactions. In the last part, the most important biological activities of allobetulin derivatives are listed. One hundred and fifteen references are cited and the relevant literature is covered, starting in 1922 up to the end of 2010.
Degradation of phenolics, nitrogen-heterocyclics and polynuclear aromatic hydrocarbons in a rotating biological contactor.

Science.gov (United States)

Jeswani, Hansa; Mukherji, Suparna

2012-05-01

The degradation of phenolics, heterocyclics and polynuclear aromatic hydrocarbons (PAHs) in a synthetic biomass gasifier wastewater with average COD of 1388 mg/L was studied in a three stage rotating biological contactor (RBC) using the pyrene degrader, Exiguobacterium aurantiacum and activated sludge consortia (1:3 v/v). As the organic loading rate (OLR) was varied from 3.3 to 14 g/m(2)/d, the COD removal ranged from 63.3% to 92.6%. Complete removal of all the constituents was observed at the lowest OLR of 3.3g/m(2)/d. At 24h hydraulic retention time (HRT) and OLR of 6.6g/m(2)/d complete removal of pyridine, quinoline and benzene and 85-96% removal of phenol, naphthalene, phenanthrene, fluoranthene and pyrene was observed. E. aurantiacum was found to be the dominant bacteria in the biofilm. Clark's model provided good fits to data for all the three stages of the RBC. Copyright Â© 2012 Elsevier Ltd. All rights reserved.
Biological properties of novel ruthenium- and osmium-nitrosyl complexes with azole heterocycles

KAUST Repository

Novak, Maria S.; Bü chel, Gabriel E.; Keppler, Bernhard K.; Jakupec, Michael A.

2016-01-01

Since the discovery that nitric oxide (NO) is a physiologically relevant molecule, there has been great interest in the use of metal nitrosyl compounds as antitumor pharmaceuticals. Particularly interesting are those complexes which can deliver NO to biological targets. Ruthenium- and osmium-based compounds offer lower toxicity compared to other metals and show different mechanisms of action as well as different spectra of activity compared to platinum-based drugs. Novel ruthenium- and osmium-nitrosyl complexes with azole heterocycles were studied to elucidate their cytotoxicity and possible interactions with DNA. Apoptosis induction, changes of mitochondrial transmembrane potential and possible formation of reactive oxygen species were investigated as indicators of NO-mediated damage by flow cytometry. Results suggest that ruthenium- and osmium-nitrosyl complexes with the general formula (indazolium)[cis/trans-MCl4(NO)(1H-indazole)] have pronounced cytotoxic potency in cancer cell lines. Especially the more potent ruthenium complexes strongly induce apoptosis associated with depolarization of mitochondrial membranes, and elevated reactive oxygen species levels. Furthermore, a slight yet not unequivocal trend to accumulation of intracellular cyclic guanosine monophosphate attributable to NO-mediated effects was observed.
Biological properties of novel ruthenium- and osmium-nitrosyl complexes with azole heterocycles

KAUST Repository

Novak, Maria S.

2016-03-09

Since the discovery that nitric oxide (NO) is a physiologically relevant molecule, there has been great interest in the use of metal nitrosyl compounds as antitumor pharmaceuticals. Particularly interesting are those complexes which can deliver NO to biological targets. Ruthenium- and osmium-based compounds offer lower toxicity compared to other metals and show different mechanisms of action as well as different spectra of activity compared to platinum-based drugs. Novel ruthenium- and osmium-nitrosyl complexes with azole heterocycles were studied to elucidate their cytotoxicity and possible interactions with DNA. Apoptosis induction, changes of mitochondrial transmembrane potential and possible formation of reactive oxygen species were investigated as indicators of NO-mediated damage by flow cytometry. Results suggest that ruthenium- and osmium-nitrosyl complexes with the general formula (indazolium)[cis/trans-MCl4(NO)(1H-indazole)] have pronounced cytotoxic potency in cancer cell lines. Especially the more potent ruthenium complexes strongly induce apoptosis associated with depolarization of mitochondrial membranes, and elevated reactive oxygen species levels. Furthermore, a slight yet not unequivocal trend to accumulation of intracellular cyclic guanosine monophosphate attributable to NO-mediated effects was observed.
Privileged scaffolds or promiscuous binders: a glance of pyrrolo[2,1-f][1,2,4]triazines and related bridgehead nitrogen heterocycles in medicinal chemistry.

Science.gov (United States)

Song, Yu'ning; Zhan, Peng; Zhang, Qingzhu; Liu, Xinyong

2013-01-01

Pyrrolo[2,1-f][1,2,4]triazine template, a unique bridgehead nitrogen heterocycle, certainly deserves the title of "privileged scaffold" in the drug discovery field because of the versatility and potential to yield derivatives with a wide range of biological activities, such as anti-anaplastic lymphoma kinase (ALK), Janus kinase 2 (JAK2), VEGFR-2, EGFR and/or HER2, Met kinase, p38α mitogen-activated protein (MAP) kinase and insulin-like growth factor receptor (IGF-1R) kinase activities, etc. These different biological properties of pyrrolo[2,1-f][1,2,4]triazine derivatives have motivated new studies in searching for novel derivatives with improved activity and also other applications in pharmaceutical field. However, no systematic review is available in the literature on the pyrrolo[2,1- f][1,2,4]triazine derivatives concerning the design of potent drug-like compounds. Owing to the importance of this heterocyclic system, the present paper is an attempt to the pharmacological activities, structural modifications and the structure-activity relationship (SAR) reported for bridgehead nitrogen heterocycles in the current literature, making an effort to highlight the importance and therapeutic potentials of the pyrrolo[2,1-f][1,2,4]triazine scaffold and its bridgehead nitrogen bioisosters as heterocyclic privileged medicinal scaffolds.
Role of certain plant natural products or gamma radiation in the control of mutagenic activity of some heterocyclic amines

International Nuclear Information System (INIS)

Abu Ghadeer, A.R.M.; El-Sedeek, A.B.A.; Salem, A.M.; Abu Zaid, M.M.

1999-01-01

The present study was designed to use ames test to evaluate the antimutagenic effect of some natural products on the lever microsomes extracted from rats and incubated with some chemical mutagens (heterocyclic compounds). Male swiss albino rats (120-140 g) were used as the source of liver microsomes. Three natural products (Nigella extract, garlic powder and sesame oil) were used to evaluate their antimutagenic activities on six heterocyclic amines. All the tested natural products exhibited their antimutagenic activities when added to the investigated heterocyclic compounds and the most effective product was nigella sativa. another group of rats was exposed to gamma-radiation (6.5 Gy) for testing the validity of ames test in quantitating mutagenicity using liver microsomes of irradiated rats. Liver microsomes from irradiated rats showed to lose ability for metabolic activation needed for heterocyclic amines to exert their mutagenic effect on salmonella typhimurium

Biological activity of 2,3-Di (quinolyl-2)-6-methyl quinoxaline

International Nuclear Information System (INIS)

Ansar, N.; Kaban, S.; Ahmed, R.

2003-01-01

The biological activities of the nitrogen containing conjugated heterocyclic compounds are considerably used pharmaceutically as antiulcer, antimalarial, tubercluocidal and sedatives besides their uses as dyes in the textile industries, pesticides, stabilizers and inhibitors etc. 2.3-Di(quinolyl-2)-6-methyl quinoxaline was synthesized by condensation followed by ring closure reaction when 1,2-di(quinolyl-2)-1,2 ethanedione was treated with methyl and substituted o-phenylenediamine. (author)
Biological activity of 2,3-Di (quinolyl-2)-6-methyl quinoxaline

Energy Technology Data Exchange (ETDEWEB)

Ansar, N [Adamjee Government Science College, Karachi (Pakistan). Dept. of Chemistry; Kaban, S [Yildiz Technical Univ., Istanbul (Turkey). Dept. of Chemistry; Ahmed, R [University of Karachi, Karachi (Pakistan). Dept. of Chemistry

2003-06-01

The biological activities of the nitrogen containing conjugated heterocyclic compounds are considerably used pharmaceutically as antiulcer, antimalarial, tubercluocidal and sedatives besides their uses as dyes in the textile industries, pesticides, stabilizers and inhibitors etc. 2.3-Di(quinolyl-2)-6-methyl quinoxaline was synthesized by condensation followed by ring closure reaction when 1,2-di(quinolyl-2)-1,2 ethanedione was treated with methyl and substituted o-phenylenediamine. (author)
Identification of sulfur heterocycles in coal liquids and shale oils. Technical progress report, August 1, 1980-May 1, 1981

Energy Technology Data Exchange (ETDEWEB)

Lee, M. L.; Castle, R. N.

1981-01-01

The sulfur heterocycle separation scheme which was described in the last progress report was evaluated for quantitative recovery of individual components. The results indicate that recoveries can range from 10% to approx. 30% depending on the structure of the compound. During this period, 23 unsubstituted sulfur-containing heterocyclic ring systems were synthesized in oder to confirm GC/MS identifications and for biological testing. The four possible 3-ring heterocycles and the thirteen possible 4-ring heterocycles were tested for mutagenic activity in the histidine reversion (Ames assay) system. One of the 3-ring isomers, naphtho(1,2-b)-thiophene, and six of the 4-ring isomers induced mutations in Salmonella test strains. One of these compounds, phenanthro(3,4-b)thiophene, displayed approximately the same mutagenic activity as benzo(a)pyrene. A two-step adsorption chromatographic procedure was developed in order to fractionate synthetic fuels into various chemical-type classes for studying the relative concentrations and mutagenic activities of the various types. An SRC-II Heavy Distillate was fractionated into aliphatic hydrocarbons, polycyclic aromatic hydrocarbons, sulfur heterocycles, indoles and carbazoles, azaarenes, and amino polycyclic aromatic hydrocarbons. It was found that the amino-PAH fraction contained most of the mutagenic activity. A survey was made for compounds containing both nitrogen and sulfur heteroatoms in their structures. A number of these compounds were detected by GC using nitrogen- and sulfur-selective detection.
Enantioselective construction of quaternary N-heterocycles by palladium-catalysed decarboxylative allylic alkylation of lactams

KAUST Repository

Behenna, Douglas C.

2011-12-18

The enantioselective synthesis of nitrogen-containing heterocycles (N-heterocycles) represents a substantial chemical research effort and resonates across numerous disciplines, including the total synthesis of natural products and medicinal chemistry. In this Article, we describe the highly enantioselective palladium-catalysed decarboxylative allylic alkylation of readily available lactams to form 3,3-disubstituted pyrrolidinones, piperidinones, caprolactams and structurally related lactams. Given the prevalence of quaternary N-heterocycles in biologically active alkaloids and pharmaceutical agents, we envisage that our method will provide a synthetic entry into the de novo asymmetric synthesis of such structures. As an entry for these investigations we demonstrate how the described catalysis affords enantiopure quaternary lactams that intercept synthetic intermediates previously used in the synthesis of the Aspidosperma alkaloids quebrachamine and rhazinilam, but that were previously only available by chiral auxiliary approaches or as racemic mixtures. © 2012 Macmillan Publishers Limited. All rights reserved.
Handbook of heterocyclic chemistry

National Research Council Canada - National Science Library

Katritzky, Alan R

2010-01-01

... Heterocyclic Chemistry I (1984) Comprehensive Heterocyclic Chemistry II (1996) Comprehensive Heterocyclic Chemistry III (2008) Comprehensive Organic Functional Group Transformations I (1995) Compreh...
Synthesis and Radiolabeling of Modified Peptides Attached to Heterocyclic Rings and Their Possible Medical Applications

International Nuclear Information System (INIS)

Shams El-Din, H.A.A.

2012-01-01

Keeping in mind the pharmacological potential of heterocyclic rings as well as the advantage of biodegradability and biocompatibility of amino acids/peptides, in this thesis we were prompted for the following: 1. Synthesis of novel dipeptide derivatives coupled with different heterocyclic rings (pyridine, 1,2,4-triazol-pyridine, 1,3,4-oxadiazolpyridine and tetrazol-pyridine rings). 2. Characterization of the synthesized compounds on the basis of their spectral data (IR, Mass and 1 H-NMR spectra). 3. Study their antimicrobial activity as one of their expected biological activities. 4. Study the radioiodination of some synthesized dipeptide derivatives. 5. Study the biodistribution of the radiolabeled compounds in normal mice as preliminary studies for the possibility of using them as agents for imaging and treatment.
Microwave-Assisted Synthesis of Bio-Active Heterocycles and Fine Chemicals in Aqueous Media

Science.gov (United States)

Human health, especially in the aging population, mostly depends on various medicines, and researchers are combating against emerging diseases by new drug discovery. Heterocyclic compounds hold a special place among pharmaceutically active natural products as well as synthetic co...
1,2,4-Triazole-based N-heterocyclic carbene complexes of gold(I): synthesis, characterization and biological activity

Czech Academy of Sciences Publication Activity Database

Turek, J.; Růžičková, Z.; Tloušťová, Eva; Mertlíková-Kaiserová, Helena; Günterová, Jana; Rulíšek, Lubomír; Růžička, A.

2016-01-01

Roč. 30, č. 5 (2016), s. 318-322 ISSN 0268-2605 R&D Projects: GA ČR(CZ) GA14-31419S; GA MŠk LO1302 Institutional support: RVO:61388963 Keywords : gold(I) complexes * N-heterocyclic carbenes * cytotoxicity * apoptosis Subject RIV: CC - Organic Chemistry Impact factor: 2.319, year: 2016
Synthesis and antiacetylcholinesterase activity of new D-glyceraldehyde heterocyclic derivatives

Energy Technology Data Exchange (ETDEWEB)

Scorzo, Cecilia M.; Fascio, Mirta L.; D' Accorso, Norma B. [Universidad de Buenos Aires, Buenos Aires (Argentina). Facultad de Ciencias Exactas y Naturales. Dept. de Quimica Organica; Cabrera, Margarita Gutierrez; Saavedra, Luis Astudillo [Universidad de Talca (Chile). Inst. de Quimica de Productos Naturales. Lab. de Sintesis Organica

2010-07-01

We report herein the convenient procedures for the syntheses of different heterocyclic compounds from 2,3-O-isopropylidene-D-glyceraldehyde using intramolecular cyclization, 1,3-dipolar cycloaddition or bimolecular coupling reactions. The products were characterized by {sup 1}H and {sup 13}C NMR spectroscopy and elemental analysis. The new heterocycles and their derivatives were evaluated as inhibitors of acetylcholinesterase enzyme. (author)
Synthesis and antiacetylcholinesterase activity of new D-glyceraldehyde heterocyclic derivatives

International Nuclear Information System (INIS)

Scorzo, Cecilia M.; Fascio, Mirta L.; D'Accorso, Norma B.; Cabrera, Margarita Gutierrez; Saavedra, Luis Astudillo

2010-01-01

We report herein the convenient procedures for the syntheses of different heterocyclic compounds from 2,3-O-isopropylidene-D-glyceraldehyde using intramolecular cyclization, 1,3-dipolar cycloaddition or bimolecular coupling reactions. The products were characterized by 1 H and 13 C NMR spectroscopy and elemental analysis. The new heterocycles and their derivatives were evaluated as inhibitors of acetylcholinesterase enzyme. (author)
Discovery of the aryl heterocyclic amine insecticides: synthesis, insecticidal activity, field results, mode of action and bioavailability of a leading field candidate.

Science.gov (United States)

Dent, William H; Pobanz, Mark A; Geng, Chaoxian; Sparks, Thomas C; Watson, Gerald B; Letherer, Theodore J; Beavers, Kenneth W; Young, Cathy D; Adelfinskaya, Yelena A; Ross, Ronald R; Whiteker, Greg; Renga, James

2017-04-01

γ-Amino butyric acid (GABA) antagonists are proven targets for control of lepidopteran and other pests. New heterocyclic compounds with high insecticidal activity were discovered using a competitive-intelligence-inspired scaffold-hopping approach to generate analogs of fipronil, a known GABA antagonist. These novel aryl heterocyclic amines (AHAs) displayed broad-spectrum activity on a number of chewing insect pests. Through >370 modifications of the core AHA structure, a 7-pyrazolopyridine lead molecule was found to exhibit much improved activity on a number of insect pests. In field trial studies, its performance was 2-4 times lower than commercial standards and also appeared to be species dependent, with good activity seen for larvae of Spodoptera exigua, but inactivity on larvae of Trichoplusia ni. An extensive investigational biology effort demonstrated that these AHA analogs appear to have multiple modes of action, including GABA receptor antagonism and mitopotential or uncoupler activity. The limited capability in larvae of T. ni to convert the lead molecule to its associated open form correlates with the low toxicity of the lead molecule in this species. This work has provided information that could aid investigations of novel GABA antagonists. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.
Combining molecular docking and QSAR studies for modeling the anti-tyrosinase activity of aromatic heterocycle thiosemicarbazone analogues

Science.gov (United States)

Dong, Huanhuan; Liu, Jing; Liu, Xiaoru; Yu, Yanying; Cao, Shuwen

2018-01-01

A collection of thirty-six aromatic heterocycle thiosemicarbazone analogues presented a broad span of anti-tyrosinase activities were designed and obtained. A robust and reliable two-dimensional quantitative structure-activity relationship model, as evidenced by the high q2 and r2 values (0.848 and 0.893, respectively), was gained based on the analogues to predict the quantitative chemical-biological relationship and the new modifier direction. Inhibitory activities of the compounds were found to greatly depend on molecular shape and orbital energy. Substituents brought out large ovality and high highest-occupied molecular orbital energy values helped to improve the activity of these analogues. The molecular docking results provided visual evidence for QSAR analysis and inhibition mechanism. Based on these, two novel tyrosinase inhibitors O04 and O05 with predicted IC50 of 0.5384 and 0.8752 nM were designed and suggested for further research.
Biological Aspects of Emerging Benzothiazoles: A Short Review

Directory of Open Access Journals (Sweden)

Ruhi Ali

2013-01-01

Full Text Available In recent years heterocyclic compounds analogues and derivatives have attracted wide attention due to their useful biological and pharmacological properties. Benzothiazole is among the usually occurring heterocyclic nuclei in many marine as well as natural plant products. Benzothiazole is a privileged bicyclic ring system with multiple applications. It is known to exhibit a wide range of biological properties including anticancer, antimicrobial, and antidiabetic, anticonvulsant, anti-inflammatory, antiviral, antitubercular activities. A large number of therapeutic agents are synthesized with the help of benzothiazole nucleus. During recent years there have been some interesting developments in the biological activities of benzothiazole derivatives. These compounds have special significance in the field of medicinal chemistry due to their remarkable pharmacological potentialities. This review is mainly an attempt to present the research work reported in the recent scientific literature on different biological activities of benzothiazole compounds.
Antioxidant Activity of Novel Fused Heterocyclic Compounds Derived from Tetrahydropyrimidine Derivative.

Science.gov (United States)

Salem, Marwa Sayed; Farhat, Mahmoud; Errayes, Asma Omar; Madkour, Hassan Mohamed Fawzy

2015-01-01

6-(Benzo[d][1,3]dioxol-5-yl)-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile has been utilized for synthesis of the fused heterocyclic compounds namely thiazolopyrimidines, tetrazolopyrimidine, pyrimidoquinazoline, pyrimidothiazolopyrimidine, pyrimidothiazolotriazine and pyrrolothiazolopyrimidine derivatives. The newly synthesized compounds were characterized by IR, (1)H-NMR, (13)C-NMR, and mass spectral data. Antioxidant activities of all synthesized compounds were investigated.
Synthesis of heterocyclic compounds through palladium-catalyzed C-H cyclization processes.

Science.gov (United States)

Inamoto, Kiyofumi

2013-01-01

Herein, we describe our development of synthetic methods for heterocyclic compounds based on the palladium-catalyzed carbon-hydrogen bond (C-H) functionalization/intramolecular carbon-heteroatom (nitrogen or sulfur) bond formation process. By this C-H cyclization method, we efficiently prepared various N-heterocycles, including indazoles, indoles, and 2-quinolinones, as well as S-heterocycles such as benzothiazoles and benzo[b]thiophenes. Yields are typically good to high and good functional-group tolerance is observed for each process, thereby indicating that the method provides a novel, highly applicable synthetic route to the abovementioned biologically important heterocyclic frameworks. As an application of this approach, an auto-tandem-type, one-pot process involving the oxidative Heck reaction and subsequent C-H cyclization using cinnamamides and arylboronic acids as starting materials in the presence of a palladium catalyst was also developed for the rapid construction of the 2-quinolinone nucleus.
Biochemical interpretation of quantitative structure-activity relationships (QSAR) for biodegradation of N-heterocycles: a complementary approach to predict biodegradability.

Science.gov (United States)

Philipp, Bodo; Hoff, Malte; Germa, Florence; Schink, Bernhard; Beimborn, Dieter; Mersch-Sundermann, Volker

2007-02-15

Prediction of the biodegradability of organic compounds is an ecologically desirable and economically feasible tool for estimating the environmental fate of chemicals. We combined quantitative structure-activity relationships (QSAR) with the systematic collection of biochemical knowledge to establish rules for the prediction of aerobic biodegradation of N-heterocycles. Validated biodegradation data of 194 N-heterocyclic compounds were analyzed using the MULTICASE-method which delivered two QSAR models based on 17 activating (OSAR 1) and on 16 inactivating molecular fragments (GSAR 2), which were statistically significantly linked to efficient or poor biodegradability, respectively. The percentages of correct classifications were over 99% for both models, and cross-validation resulted in 67.9% (GSAR 1) and 70.4% (OSAR 2) correct predictions. Biochemical interpretation of the activating and inactivating characteristics of the molecular fragments delivered plausible mechanistic interpretations and enabled us to establish the following biodegradation rules: (1) Target sites for amidohydrolases and for cytochrome P450 monooxygenases enhance biodegradation of nonaromatic N-heterocycles. (2) Target sites for molybdenum hydroxylases enhance biodegradation of aromatic N-heterocycles. (3) Target sites for hydratation by an urocanase-like mechanism enhance biodegradation of imidazoles. Our complementary approach represents a feasible strategy for generating concrete rules for the prediction of biodegradability of organic compounds.
Facile synthesis and antimicrobial evaluation of some new heterocyclic compounds incorporating a biologically active sulfamoyl moiety.

Science.gov (United States)

Darwish, Elham S

2014-01-01

A facile and convenient synthesis of new heterocyclic compounds containing a sulfamoyl moiety suitable for use as antimicrobial agents was reported. The precursor 3-oxo-3-phenyl-N-(4-sulfamoylphenyl)propionamide was coupled smoothly with arenediazonium salt producing hydrazones which reacted with malononitrile or triethylorthoformate affording pyridazine and triazine derivatives, respectively. Also, the reactivity of the same precursor with DMF-DMA was followed by aminotriazole; aromatic aldehydes was followed by hydrazine hydrate, triethylorthoformate, or thiourea affording triazolo[1,5-a]pyrimidine, pyrazole, acrylamide, and dihydropyrimidine derivatives, respectively. On the other hand, treatment of the precursor propionamide with phenyl isothiocyanate and KOH in DMF afforded the intermediate salt which was treated with dilute HCl followed by 2-bromo-1-phenylethanone affording carboxamide derivative. While the same intermediate salt reacted in situ with chloroacetone, ethyl 2-chloroacetate, 3-(2-bromoacetyl)-2H-chromen-2-one, methyl iodide, or 2-oxo-N-phenylpropane hydrazonoyl chloride afforded the thiophene, ketene N,S-acetal, and thiadiazole derivatives, respectively. The structure of the new products was established based on elemental and spectral analysis. Antimicrobial evaluation of some selected examples from the synthesized products was carried out whereby four compounds were found to have moderate activities and one compound showed the highest activity.
Synthesis and Antimicrobial Studies of New Series of Pyrazoline Bearing Bis-Heterocycles via 1,3-Dipolar Cycloaddition Reactions

Directory of Open Access Journals (Sweden)

B. Jayashankara

2008-01-01

Full Text Available Biologically interesting bis-heterocycles bearing pyrazoline and imidazole moieties have been synthesized. 1H NMR, 13C NMR, IR and elemental analyses characterized the newly synthesized compounds. All the synthesized compounds were evaluated for their antimicrobial activity and were compared with the standard drugs. All the compounds demonstrated potent to weak antimicrobial activity.
Steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone: A convenient synthesis, antiproliferation activity, structure-activity relationships, and role of heterocyclic moiety

Science.gov (United States)

Ke, Shaoyong; Shi, Liqiao; Zhang, Zhigang; Yang, Ziwen

2017-01-01

A series of steroidal[17,16-d]pyrimidines derived from dehydroepiandrosterone were designed and prepared by a convenient heterocyclization reaction. The in vitro anticancer activities for these obtained compounds were evaluated against human cancer cell lines (HepG2, Huh-7, and SGC-7901), which demonstrated that some of these heterocyclic pyrimidine derivatives exhibited significantly good cytotoxic activities against all tested cell lines compared with 5-fluorouracil (5-FU), especially, compound 3b exhibited high potential growth inhibitory activities against all tested cell lines with the IC50 values of 5.41 ± 1.34, 5.65 ± 1.02 and 10.64 ± 1.49 μM, respectively, which might be used as promising lead scaffold for discovery of novel anticancer agents. PMID:28290501
Synthesis and biological evaluation of novel heterocyclic derivatives of combretastatin A-4.

Science.gov (United States)

Nguyen, Thi Thanh Binh; Lomberget, Thierry; Tran, Ngoc Chau; Colomb, Evelyne; Nachtergaele, Lore; Thoret, Sylviane; Dubois, Joëlle; Guillaume, Joren; Abdayem, Rawad; Haftek, Marek; Barret, Roland

2012-12-01

A novel series of combretastatin A-4 heterocyclic analogues was prepared by replacement of the B ring with indole, benzofurane or benzothiophene, attached at the C2 position. These compounds were evaluated for their abilities to inhibit tubulin assembly: derivative cis3b, having a benzothiophene, showed an activity similar to those of colchicine or deoxypodophyllotoxine. The antiproliferative and antimitotic properties of cis3b against keratinocyte cancer cell lines were also evaluated and the intracellular organization of microtubules in the cells after treatment with both stereoisomers of 3b was also determined, using confocal microscopy. Copyright © 2012 Elsevier Ltd. All rights reserved.

Heterocyclic Naphthalimides as New Skeleton Structure of Compounds with Increasingly Expanding Relational Medicinal Applications.

Science.gov (United States)

Gong, Huo-Hui; Addla, Dinesh; Lv, Jing-Song; Zhou, Cheng-He

2016-01-01

Naphthalimide compounds are an important type of nitrogen-containing aromatic heterocycles with cyclic double imides and the naphthalene framework. This π-deficient large conjugated planar structure enables naphthalimide derivatives to readily interact with various biological cations, anions, small molecules and macromolecules such as DNAs, enzymes and recetors in living organism via noncovalent bonds, therefore exhibiting extensive potentiality in relatively medicinal applications. Currently, some naphthalimides as anticancer agents have entered into clinical trials and other naphthalimide-based medicinal developments as potential drugs for treatment of various diseases are actively and unprecedentedly expanding. Naphthalimide-derived artificial ion receptors, fluorescent probes and cell imaging agents are being overwhelmingly investigated and have a diversity of potential applications in real-time detecting ions and biomolecules, understanding biological processes and determining pharmacological and pharmacokinetic properties. All the above mentions have strongly implied that naphthalimide-based derivatives as new skeleton structure of compounds possess increasingly expanding relational medicinal applications, and the related research is becoming a quite attractive active topic and newly rising highlight. Combining with our research and referring other works from literature, this work systematically reviews the current research and development of heterocyclic naphthalimides as anticancer, antibacterial, antifungal, antiviral, anti-inflammatory, antidepressant agents as well as artificial cation and anion receptors, diagnostic agents and pathologic probes, and cell imaging agents for biologically important species. Some rational design strategies, structure-activity relationships and action mechanisms are discussed. The perspectives of the future development of naphthalimide-based medicinal chemistry are also presented.
Synthesis of heterocyclic chalcone derivatives and their radical scavenging ability toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radicals

International Nuclear Information System (INIS)

Hwang, Kijun; Kim, Hoseok; Kim, Beomtae; Han, Incheol

2012-01-01

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
Stereochemical Basis for a Unified Structure Activity Theory of Aromatic and Heterocyclic Rings in Selected Opioids and Opioid Peptides

Directory of Open Access Journals (Sweden)

Joel S. Goldberg

2010-02-01

Full Text Available This paper presents a novel unified theory of the structure activity relationship of opioids and opioid peptides. It is hypothesized that a virtual or known heterocyclic ring exists in all opioids which have activity in humans, and this ring occupies relative to the aromatic ring of the drug, approximately the same plane in space as the piperidine ring of morphine. Since the rings of morphine are rigid, and the aromatic and piperidine rings are critical structural components for morphine’s analgesic properties, the rigid morphine molecule allows for approximations of the aromatic and heterocyclic relationships in subsequent drug models where bond rotations are common. This hypothesis and five propositions are supported by stereochemistry and experimental observations. Proposition #1 The structure of morphine provides a template. Proposition #2 Steric hindrance of some centric portion of the piperidine ring explains antagonist properties of naloxone, naltrexone and alvimopam. Proposition #3 Methadone has an active conformation which contains a virtual heterocyclic ring which explains its analgesic activity and racemic properties. Proposition #4 The piperidine ring of fentanyl can assume the morphine position under conditions of nitrogen inversion. Proposition #5 The first 3 amino acid sequences of beta endorphin (l-try-gly-gly and the active opioid dipeptide, l-tyr-pro, (as a result of a peptide turn and zwitterion bonding form a virtual piperazine-like ring which is similar in size, shape and location to the heterocyclic rings of morphine, meperidine, and methadone. Potential flaws in this theory are discussed. This theory could be important for future analgesic drug design.
Fusing porphyrins with polycyclic aromatic hydrocarbons and heterocycles for optoelectronic applications

Science.gov (United States)

Thompson, Mark E.; Diev, Viacheslav; Hanson, Kenneth; Forrest, Stephen R.

2015-08-18

A compound that can be used as a donor material in organic photovoltaic devices comprising a non-activated porphyrin fused with one or more non-activated polycyclic aromatic rings or one or more non-activated heterocyclic rings can be obtained by a thermal fusion process. The compounds can include structures of Formula I: ##STR00001## By heating the reaction mixture of non-activated porphyrins with non-activated polycyclic aromatic rings or heterocyclic rings to a fusion temperature and holding for a predetermined time, fusion of one or more polycyclic rings or heterocyclic rings to the non-activated porphyrin core in meso,.beta. fashion is achieved resulting in hybrid structures containing a distorted porphyrin ring with annulated aromatic rings. The porphyrin core can be olygoporphyrins.
Synthesis and Biological Activity of Some 3,5-Diaryl-1-Benzothiazolopyrazoline Derivatives: Reaction of Chalcones with 2-Hyrazinobenzothiazoles

Directory of Open Access Journals (Sweden)

Vandana Sharma

2009-01-01

Full Text Available A series of 3,5-diaryl-1-benzothiazolopyrazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and 2-hydrazinobenzothiazole in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms.
Trypanocidal 1,3-arylene diketone bis(guanylhydrazone)s. Structure-activity relationships among substituted and heterocyclic analogues.

Science.gov (United States)

Ulrich, P; Cerami, A

1984-01-01

Based on the antitrypanosomal activity of 1,3-diacetylbenzene bis(guanylhydrazone) (4) and 2,6-diacetylpyridine bis(guanylhydrazone) (17), a number of substituted and heterocyclic 1,3-arylene diketone bis(guanylhydrazone)s were prepared and tested against Trypanosoma brucei infections in mice. A wide range of ED50 values was observed among 5-substituted derivatives of 4. The 5-amino analogue 5 and 5-acetamido analogue 6 were about twice as active as 4. 1,3,5-Triacetylbenzene tris(guanylhydrazone) (12) was about 9 times as active as 4 and was approximately one-half as active as the currently used trypanocide diminazene aceturate in this test system. Other 5-derivatives had activity equivalent to or less than that of the parent compound 4. Three new heterocyclic analogues were all less active than 2,6-diacetylpyridine derivative 17 and benzene derivative 4. Ring substitution ortho to the guanylhydrazone side chains was invariably detrimental to activity. Side-chain homologues 1,3-dipentanoylbenzene bis(guanylhydrazone) and 1,3-diacetylbenzene bis(2-imidazolin-2-ylhydrazone) were essentially inactive.
Synthesis and Biological Activity of Some 3, 5-Diarylisoxazoline Derivatives: Reaction of Substituted Chalcones with Hydroxylamine Hydrochloride

Directory of Open Access Journals (Sweden)

Vandana Sharma

2010-01-01

Full Text Available A series of 3-aryl-5-styrylisoxazoline/ 3,5-diarylisoxazoline derivatives were synthesized by the reaction of appropriately substituted chalcones and hydroxylamine hydrochloride in presence of alkali in ethanol. The synthesized heterocycles have been characterized on the basis of their chemical properties and spectroscopic data. These compounds were tested for biological activity against a variety of test organisms
Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

KAUST Repository

Peshkov, Vsevolod A.

2018-03-16

This focused review aims to summarize recent developments in the processes involving additions of secondary propargylamines to various heteroallenes and subsequent transition metal-catalyzed or electrophile-mediated cyclizations. The utility of this convenient and tunable strategy spans from the carbon dioxide fixation and target-oriented synthesis of complex natural and biologically active products to the generation of extended synthetic libraries of diverse oxygen-, nitrogen- and sulfur-containing heterocycles. For comparative purposes, the analogous transformations of propargylic alcohols are also highlighted in this account.
Reactions of secondary propargylamines with heteroallenes for the synthesis of diverse heterocycles

KAUST Repository

Peshkov, Vsevolod A.; Pereshivko, Olga P.; Nechaev, Anton A.; Peshkov, Anatoly A.; Van der Eycken, Erik V.

2018-01-01

This focused review aims to summarize recent developments in the processes involving additions of secondary propargylamines to various heteroallenes and subsequent transition metal-catalyzed or electrophile-mediated cyclizations. The utility of this convenient and tunable strategy spans from the carbon dioxide fixation and target-oriented synthesis of complex natural and biologically active products to the generation of extended synthetic libraries of diverse oxygen-, nitrogen- and sulfur-containing heterocycles. For comparative purposes, the analogous transformations of propargylic alcohols are also highlighted in this account.
Anoxic degradation of nitrogenous heterocyclic compounds by activated sludge and their active sites.

Science.gov (United States)

Xu, Peng; Han, Hongjun; Zhuang, Haifeng; Hou, Baolin; Jia, Shengyong; Wang, Dexin; Li, Kun; Zhao, Qian

2015-05-01

The potential for degradation of five nitrogenous heterocyclic compounds (NHCs), i.e., imidazole, pyridine, indole, quinoline, and carbazole, was investigated under anoxic conditions with acclimated activated sludge. Results showed that NHCs with initial concentration of 50 mg/L could be completely degraded within 60 hr. The degradation of five NHCs was dependent upon the chemical structures with the following sequence: imidazole>pyridine>indole>quinoline>carbazole in terms of their degradation rates. Quantitative structure-biodegradability relationship studies of the five NHCs showed that the anoxic degradation rates were correlated well with highest occupied molecular orbital. Additionally, the active sites of NHCs identified by calculation were confirmed by analysis of intermediates using gas chromatography and mass spectrometry. Copyright © 2015. Published by Elsevier B.V.
Selected heterocyclic compounds as antioxidants. Synthesis and biological evaluation.

Science.gov (United States)

Tsolaki, E; Nobelos, P; Geronikaki, A; Rekka, E A

2014-01-01

Reactive oxygen species, oxidative stress, and oxidative damage are increasingly assigned important roles as harmful factors in pathological conditions and ageing. ROS are potentially reactive molecules derived from the reduction of molecular oxygen in the course of aerobic metabolism. ROS can also be produced through a variety of enzymes. Under normal circumstances, ROS concentrations are tightly controlled by physiological antioxidants. When excessively produced, or when antioxidants are depleted, ROS can impose oxidative damage to lipids, proteins, sugars and DNA. This reduction-oxidation imbalance, called oxidative stress, can subsequently contribute to the development and progression of tissue damage and play a role in the pathology of various diseases. An antioxidant is defined as "any substance that, when present at low concentrations compared with those of a substrate, significantly delays, prevents or removes oxidative damage to this target molecule". Despite evidence that oxidative damage contributes to a wide range of clinically important conditions, few antioxidants act as effective drugs in vivo. Inter alia, the difficulty of measuring antioxidant efficacy in vivo makes the interpretation of results from clinical trials difficult. A large number of synthetic compounds have been reported to possess antioxidant activity. Several of them derive from natural antioxidants, others have various structures. In this review, some of the most often reported classes of heterocyclic antioxidant compounds, as well as methods for evaluation of their antioxidant activity are discussed.
Methods for the synthesis of aza(deaza)xanthines as a basis of biologically active compounds

International Nuclear Information System (INIS)

Babkov, D A; Geisman, A N; Novikov, M S; Khandazhinskaya, A L

2016-01-01

The review covers methods for the synthesis of aza(deaza)xanthines, i.e., fused pyrrolo-, pyrazolo- and triazolopyrimidine heterocyclic systems, which are common core structures of various biologically active compounds. The extensive range of modern synthetic approaches is organized according to target structures and starting building blocks. The presented material is intended to benefit broad audience of specialists in the fields of organic, medicinal and pharmaceutical chemistry. The bibliography includes 195 references
Gold-catalyzed heterocyclizations in alkynyl- and allenyl-β-lactams

Directory of Open Access Journals (Sweden)

Pedro Almendros

2011-05-01

Full Text Available New gold-catalyzed methods using the β-lactam scaffold have been recently developed for the synthesis of different sized heterocycles. This overview focuses on heterocyclization reactions of allenic and alkynic β-lactams which rely on the activation of the allene and alkyne component. The mechanism as well as the regio- and stereoselectivity of the cyclizations are also discussed.
Aspartate and glutamate mimetic structures in biologically active compounds.

Science.gov (United States)

Stefanic, Peter; Dolenc, Marija Sollner

2004-04-01

Glutamate and aspartate are frequently recognized as key structural elements for the biological activity of natural peptides and synthetic compounds. The acidic side-chain functionality of both the amino acids provides the basis for the ionic interaction and subsequent molecular recognition by specific receptor sites that results in the regulation of physiological or pathophysiological processes in the organism. In the development of new biologically active compounds that possess the ability to modulate these processes, compounds offering the same type of interactions are being designed. Thus, using a peptidomimetic design approach, glutamate and aspartate mimetics are incorporated into the structure of final biologically active compounds. This review covers different bioisosteric replacements of carboxylic acid alone, as well as mimetics of the whole amino acid structure. Amino acid analogs presented include those with different distances between anionic moieties, and analogs with additional functional groups that result in conformational restriction or alternative interaction sites. The article also provides an overview of different cyclic structures, including various cycloalkane, bicyclic and heterocyclic analogs, that lead to conformational restriction. Higher di- and tripeptide mimetics in which carboxylic acid functionality is incorporated into larger molecules are also reviewed. In addition to the mimetic structures presented, emphasis in this article is placed on their steric and electronic properties. These mimetics constitute a useful pool of fragments in the design of new biologically active compounds, particularly in the field of RGD mimetics and excitatory amino acid agonists and antagonists.
Regioselective C-H imidation of five-membered heterocyclic compounds through a metal catalytic or organocatalytic approach.

Science.gov (United States)

Wang, Xin; Sun, Kai; Lv, Yunhe; Ma, Fengji; Li, Gang; Li, Donghui; Zhu, Zhonghong; Jiang, Yongqing; Zhao, Feng

2014-12-01

An efficient method for the synthesis of 2-amino and β-amino five-membered heterocyclic derivatives that are closely related to a variety of biologically active natural products is described. Regioselectivity was achieved through a metal catalytic or organocatalytic approach. Preliminary studies on the reaction mechanism suggest a radical imidation pathway; however, further studies are needed to verify the mechanism. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Metal and hydrogen catalysis in isotopic hydrogen exchange in some biologically important heterocyclic compounds

International Nuclear Information System (INIS)

Buncel, E.; Joly, H.A.; Jones, J.R.; Onyido, I.

1989-01-01

This study reports on the catalytic roles of metal and hydrogen ions in tritium exchange in some heterocyclic substrates which occur as residues in many biologically important molecules. We have found that detritiation of 1-methyl[2- 3 H]imidazole is inhibited by a number of metal ions. As well, inhibition of exchange rates was noted with Ag(I) and Cu(II) for [2- 3 H]thiazole and 1-methyl[8- 3 H]inosine, with Ag(I) for [2- 3 H]benzothiazole, and with Cu(II) for 1-methyl[8- 3 H]guanosine. A complete mechanistic description, which includes the various metal ion-coordinated species generated under the experimental conditions, is presented. The results demonstrate the reactivity order: protonated >> metal-coordinated >> neutral substrates. The differential catalytic effects of metal and hydrogen ions in these processes are discussed in terms of the extent of charge developed on the ligating heteroatom in the reaction intermediate. (author). 13 refs.; 1 fig
Solid-Phase Synthesis for the Construction of Biologically Interesting Molecules and the Total Synthesis of Trioxacarcin DC-45-A2

DEFF Research Database (Denmark)

Mikkelsen, Remi Jacob Thomsen

. Furthermore a route to another key building block was developed featuring a Stille cross-coupling.Synthesis of Poly-fused Heterocycles. In the search for new biologically active compounds a methodology for the synthesis of polyfused heterocycles was investigated. This led to the development and optimization...
The tert-Amino Effect in Heterocyclic Chemistry. Synthesis of Spiro Heterocycles

Directory of Open Access Journals (Sweden)

Y. Morzherin

2005-09-01

Full Text Available The tert-amino reaction effect was examined. A new method to synthesize spiro heterocycles is presented. It was shown that the Ã¢Â€Âœtert-amino effectÃ¢Â€Â could be applied to the formation of spiro-fused heterocycles. The formation of spiro compounds proceeds in most cases in good yields in a one-pot reaction.
Heterocyclic Scaffolds: Centrality in Anticancer Drug Development.

Science.gov (United States)

Ali, Imran; Lone, Mohammad Nadeem; Al-Othman, Zeid A; Al-Warthan, Abdulrahman; Sanagi, Mohd Marsin

2015-01-01

Cancer has been cursed for human beings for long time. Millions people lost their lives due to cancer. Despite of the several anticancer drugs available, cancer cannot be cured; especially at the late stages without showing any side effect. Heterocyclic compounds exhibit exciting medicinal properties including anticancer. Some market selling heterocyclic anticancer drugs include 5-flourouracil, methortrexate, doxorubicin, daunorubicin, etc. Besides, some natural products such as vinblastine and vincristine are also used as anticancer drugs. Overall, heterocyclic moeities have always been core parts in the expansion of anticancer drugs. This article describes the importance of heterocyclic nuclei in the development of anticancer drugs. Besides, the attempts have been made to discuss both naturally occurring and synthetic heterocyclic compounds as anticancer agents. In addition, some market selling anticancer heterocyclic compounds have been described. Moreover, the efforts have been made to discuss the mechanisms of actions and recent advances in heterocyclic compounds as anticancer agents. The current challenges and future prospectives of heterocyclic compounds have also been discussed. Finally, the suggestions for syntheses of effective, selective, fast and human friendly anticancer agents are discussed into the different sections.
Phosphorylated Derivatives of Alkaloids and Nitrogen-containing Heterocycles — Cholinesterase Inhibitors

Science.gov (United States)

Sadykov, Abid S.; Dalimov, D. N.; Godovikov, Nikolai N.

1983-10-01

The review deals with the synthesis and anticholinesterase activities of phosphorylated derivatives of certain alkaloids and nitrogen-containing heterocycles. It is shown that the conformational properties of the alkaloid and nitrogen-containing heterocycle residues in the composition of the organophosphorus inhibitor (OPI) molecule play an important role in the inhibition of the catalytic activity of cholinesterases. The type of inhibition of cholinesterases also varies as a function of chemical structure. The bibliography includes 45 references.

Electronic bond tuning with heterocyclic carbenes

KAUST Repository

Falivene, Laura

2013-01-01

We discuss the impact of the nature of the heterocyclic carbene ring, when used as a complex forming ligand, on the relative stability of key intermediates in three typical Ru, Pd and Au promoted reactions. Results show that P-heterocyclic carbenes have a propensity to increase the bonding of the labile ligand and of the substrate in Ru-promoted olefin metathesis, whereas negligible impact is expected on the stability of the ruthenacycle intermediate. In the case of Pd cross-coupling reactions, dissociation of a P-heterocyclic carbene is easier than dissociation of the N-heterocyclic analogue. In the case of the Au-OH synthon, the Au-OH bond is weakened with the P-heterocyclic carbene ligands. A detailed energy decomposition analysis is performed to rationalize these results. © 2013 The Royal Society of Chemistry.
Heterocyclic N-Oxides – An Emerging Class of Therapeutic Agents

Science.gov (United States)

Mfuh, Adelphe M.; Larionov, Oleg V.

2016-01-01

Heterocyclic N-oxides have emerged as potent compounds with anticancer, antibacterial, antihypertensive, antiparasitic, anti-HIV, anti-inflammatory, herbicidal, neuroprotective, and procognitive activities. The N-oxide motif has been successfully employed in a number of recent drug development projects. This review surveys the emergence of this scaffold in the mainstream medicinal chemistry with a focus on the discovery of the heterocyclic N-oxide drugs, N-oxide-specific mechanisms of action, drug-receptor interactions and synthetic avenues to these compounds. As the first review on this subject that covers the developments since 1950s to date, it is expected that it will inspire wider implementation of the heterocyclic N-oxide motif in the rational design of new medicinal agents. PMID:26087764
Heterocyclic Compounds: Effective α-Amylase and α-Glucosidase Inhibitors.

Science.gov (United States)

Saeedi, Mina; Hadjiakhondi, Abbas; Nabavi, Seyed Mohammad; Manayi, Azadeh

2017-01-01

Diabetes Mellitus (DM) is a metabolic disease characterized by high blood sugar levels. Recently, it has emerged as an important and global health problem with long-term complications and high economic burden. α-Amylase (α-Amy) and α-glucosidase (α-Gls) are two enzymes which are involved in the hydrolysis of starch into sugars and disaccharides leading to the increase of blood glucose level. Hence, inhibition of α-amylase and α-glucosidase plays key role in the treatment of type 2 diabetes. Heterocyclic compounds -both synthetic and naturally occurring derivatives- possess efficient biological properties. At this juncture, they have demonstrated potent inhibitory activity against α-Amy and α-Gls and were found to be versatile tools for the development of novel anti-diabetic agents.
Structure-based hybridization, synthesis and biological evaluation of novel tetracyclic heterocyclic azathioxanthone analogues as potential antitumor agents.

Science.gov (United States)

Chen, Tsung-Chih; Wu, Chia-Lun; Lee, Chia-Chung; Chen, Chun-Liang; Yu, Dah-Shyong; Huang, Hsu-Shan

2015-10-20

A series of tetracyclic heterocyclic azathioxanthones were synthesized and evaluated for cell proliferations, topoisomerase inhibitions, and NCI-60 cell panel assay, respectively. Compounds 5, 7, 8, 16, and 19 were selected for topoisomerase assay after MTT assay. 7 not only showed cytotoxic effect (IC50 = 2.84 ± 0.64 μM) in PC-3 cells but also revealed topoisomerases inhibition with IC50 (10-25 μM) and increased apoptotic cleavage of PARP and caspase 3 activity. The overall of novel azathioxanthones with different cytostatic and cytotoxic activities should be further developed as new potential candidates for anticancer drugs. Copyright © 2015 Elsevier Masson SAS. All rights reserved.
Amino substituted nitrogen heterocycle ureas as kinase insert domain containing receptor (KDR inhibitors: Performance of structure–activity relationship approaches

Directory of Open Access Journals (Sweden)

Hayriye Yilmaz

2015-06-01

Full Text Available A quantitative structure–activity relationship (QSAR study was performed on a set of amino-substituted nitrogen heterocyclic urea derivatives. Two novel approaches were applied: (1 the simplified molecular input-line entry systems (SMILES based optimal descriptors approach; and (2 the fragment-based simplex representation of molecular structure (SiRMS approach. Comparison with the classic scheme of building up the model and balance of correlation (BC for optimal descriptors approach shows that the BC scheme provides more robust predictions than the classic scheme for the considered pIC50 of the heterocyclic urea derivatives. Comparison of the SMILES-based optimal descriptors and SiRMS approaches has confirmed good performance of both techniques in prediction of kinase insert domain containing receptor (KDR inhibitory activity, expressed as a logarithm of inhibitory concentration (pIC50 of studied compounds.
Simple Method of Preparation and Characterization of New Antifungal Active Biginelli Type Heterocyclic Compounds

Science.gov (United States)

Velan, A. Senthilkumara; Joseph, J.; Raman, N.

2008-01-01

A simple, efficient and cost effective method is described for the synthesis of Biginelli type heterocyclic compounds of dihydropyrimidinones analogous. They were prepared from a reaction mixture consisting of substituted benzaldehydes, thiourea and ethylacetoacetate using ammonium dihydrogenphosphate as catalyst. The procedure for the preparation of the compounds is environmentally benign and safe which is advantageous in terms of experimentation, catalyst reusability, yields of the products, shorter reaction times and preclusion of toxic solvents. The four new synthesised compounds were tested for their antifungal activity. They have good antifungal activity comparing to the standard (Fluconazole). PMID:23997611
Radical C-H functionalization to construct heterocyclic compounds.

Science.gov (United States)

Yu, Jin-Tao; Pan, Changduo

2016-02-07

Heterocyclic compounds are widely present in natural products, pharmaceuticals and bioactive molecules. Thus, organic and pharmaceutical chemists have been making extensive efforts to construct those heterocyclic frameworks through developing versatile and efficient synthetic strategies. The direct C-H functionalization via the radical pathway has emerged as a promising and dramatic approach towards heterocycles with high atom- and step-economy. Heterocyclic compounds such as coumarins, furans, benzofurans, xanthones, benzothiazoles, indoles, indolines, oxindoles, quinolines, isoquinolines, quinoxaline, and phenanthridines have been successfully synthesized by C-H functionalization through the radical pathway. In this review, recent advances on radical C-H functionalization to construct heterocyclic compounds are highlighted with discussions.
Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands.

Science.gov (United States)

Taylor, Nicholas J; Emer, Enrico; Preshlock, Sean; Schedler, Michael; Tredwell, Matthew; Verhoog, Stefan; Mercier, Joel; Genicot, Christophe; Gouverneur, Véronique

2017-06-21

Molecules labeled with fluorine-18 ( 18 F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18 F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18 F-fluorination of aryl boron reagents with 18 F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18 F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.
The structure of active centers and the kinetic isotopic effect in the ionic polymerization of heterocyclic compounds

International Nuclear Information System (INIS)

Ponomarienko, W.A.; Berman, E.L.

1979-01-01

The method of kinetic isotopic effect has been applied to the elucidation of the structure of the active growth centres in the polymerization of some selected heterocyclic compounds. The cationic polymerization of ehtylene oxide, tetrahydrofuran and 1.3-dioxolane as well as the anionic and coordination polymerization of ethylene oxide have been discussed. (author)
Generation of N-Heterocycles via Tandem Reactions of N '-(2-Alkynylbenzylidene)hydrazides.

Science.gov (United States)

Qiu, Guanyinsheng; Wu, Jie

2016-02-01

As a powerful synthon, N '-(2-alkynylbenzylidene)hydrazides have been utilized efficiently for the construction of N-heterocycles. Since N '-(2-alkynylbenzylidene)hydrazides can easily undergo intramolecular 6-endo cyclization promoted by silver triflate or electrophiles, the resulting isoquinolinium-2-yl amides can proceed through subsequent transformations including [3 + 2] cycloaddition, nucleophilic addition, and [3 + 3] cycloaddition. Several unexpected rearrangements via radical processes were observed in some cases, which afforded nitrogen-containing heterocycles with molecular complexity. Reactive partners including internal alkynes, arynes, ketenimines, ketenes, allenoates, and activated alkenes reacted through [3 + 2] cycloaddition and subsequent aromatization, leading to diverse H-pyrazolo[5,1-a]isoquinolines with high efficiency. Nucleophilic addition to the in situ generated isoquinolinium-2-yl amide followed by aromatization also produced H-pyrazolo[5,1-a]isoquinoline derivatives when terminal alkynes, carbonyls, enamines, and activated methylene compounds were used as nucleophiles. Isoquinoline derivatives were obtained when indoles or phosphites were employed as nucleophiles in the reactions of N '-(2-alkynylbenzylidene)hydrazides. A tandem 6-endo cyclization and [3 + 3] cycloaddition of cyclopropane-1,1-dicarboxylates with N '-(2-alkynylbenzylidene)hydrazides was observed as well. Small libraries of these compounds were constructed. Biological evaluation suggested that some compounds showed promising activities for inhibition of CDC25B, TC-PTP, HCT-116, and PTP1B. © 2015 The Chemical Society of Japan & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Improve the biodegradability of post-hydrothermal liquefaction wastewater with ozone: conversion of phenols and N-heterocyclic compounds.

Science.gov (United States)

Yang, Libin; Si, Buchun; Martins, Marcio Arêdes; Watson, Jamison; Chu, Huaqiang; Zhang, Yuanhui; Tan, Xiaobo; Zhou, Xuefei; Zhang, Yalei

2017-04-01

Hydrothermal liquefaction is a promising technology to convert wet biomass into bio-oil. However, post-hydrothermal liquefaction wastewater (PHWW) is also produced during the process. This wastewater contains a high concentration of organic compounds, including phenols and N-heterocyclic compounds which are two main inhibitors for biological treatment. Thus, proper treatment is required. In this work, ozone was used to convert phenols and N-heterocyclic compounds with a dosage range of 0-4.64 mg O 3 /mL PHWW. After ozone treatment, the phenols were fully converted, and acids were produced. However, N-heterocyclic compounds were found to have a low conversion rate (21.7%). The kinetic analysis for the degradation of phenols and N-heterocyclic compounds showed that the substitute played an important role in determining the priority of ozone reactions. The OH moiety in the ring compounds (phenols and pyridinol) may form hydroxyl radical, which lead to an efficient reaction. A substantial improved biodegradability of PHWW was observed after ozone treatment. The ratio of BOD 5 /COD was increased by about 32.36%, and reached a maximum of 0.41. The improved biodegradability of PHWW was justified by the conversion of phenols and N-heterocyclic compounds.
Antiradiation compounds XV: condensations of carbon disulfide with amino, chloro, cyanomethyl, and sulfonamido heterocycles

International Nuclear Information System (INIS)

Foye, W.O.; Kauffman, J.M.; Lanzillo, J.J.; LaSala, E.F.

1975-01-01

Condensations of carbon disulfide were carried out with amino, chloro, and diamino heterocycles to give condensed ring thiazoline-2-thiones and imidazoline-2-thiones, with cyanomethyl heterocycles to give dithio acid derivatives, and with heterocyclic sulfonamides to give sulfonyldithiocarbamates. Of several examples tested, pyrido[3,2-d]thiazoline-2-thione, disodium 2-(5-chloro-2-thienyl)-3,3-dimercaptoacrylonitrile, triethylammonium 4-sulfamoylphenyldithiocarbamate, ammonium β-phenethyldithiocarbamate, and methyl N-(thiophene-2-sulfonyl)dithiocarbamate, only the last-named compound showed any radiation protection for mice. Several compounds gave negative tests for antimalarial activity
Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity

KAUST Repository

Goh, Li Min Serena; Hogerl, Manuel Peter; Jokic̈, Nadežda B.; Tanase, Alexandrina D.; Bechlars, Bettina; Baratta, Walter; Mí nk, Já nos; Kü hn, Fritz

2014-01-01

A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3-methyl-1-(2′- phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH] PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki-Miyaura cross-coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h-1 have been reached with catalyst concentrations as low as 0.01 mol-%. A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki-Miyaura cross-coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h-1, were achieved with 0.01 mol-% of the complex. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity

KAUST Repository

Goh, Li Min Serena

2014-01-29

A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3-methyl-1-(2′- phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH] PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki-Miyaura cross-coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h-1 have been reached with catalyst concentrations as low as 0.01 mol-%. A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki-Miyaura cross-coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h-1, were achieved with 0.01 mol-% of the complex. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Novel approach for heterocyclization: a clean and efficient synthesis and biological evaluation of 4-oxothiazolidines under microwave technique

International Nuclear Information System (INIS)

Desai, Krunal G.; Desai, K.R.

2006-01-01

A new selective method has been developed for rapid synthesis of 2-(aryl)-3-[2-benzoimidazolythio)-acetamidyl]-4-oxothiazolidines 4a-j by the heterocyclization of 2-{(1H-benzemidazol)-ylthio}-N-benzylidene aceto hydrazide 3a-j with HSCH2COOH under microwave irradiation (MWI) is described. The reaction rate and yield is enhanced tremendously under MWI as compared to conventional methods. All the compounds have been screened for their antifungal activity against Candida albicans and Aspergillus niger, antibacterial activity against Escherchia coli and Staphylococcus aureus. In the primary screening, some of the compounds exhibited appreciable activity. The structures of the synthesized compounds 4a-j have been characterized on the basis of their elemental analysis, IR, HNMR and Mass spectral data. (author)
N- AND O-HETEROCYCLES PRODUCED FROM THE IRRADIATION OF BENZENE AND NAPHTHALENE IN H2O/NH3-CONTAINING ICES

International Nuclear Information System (INIS)

Materese, Christopher K.; Nuevo, Michel; Sandford, Scott A.

2015-01-01

Aromatic heterocyclic molecules are an important class of molecules of astrophysical and biological significance that include pyridine, pyrimidine, and their derivatives. Such compounds are believed to exist in interstellar and circumstellar environments, though they have never been observed in the gas phase. Regardless of their presence in the gas phase in space, numerous heterocycles have been reported in carbonaceous meteorites, which indicates that they are formed under astrophysical conditions. The experimental work described here shows that N- and O-heterocyclic molecules can form from the ultraviolet (UV) irradiation of the homocyclic aromatic molecules benzene (C 6 H 6 ) or naphthalene (C 10 H 8 ) mixed in ices containing H 2 O and NH 3 . This represents an alternative way to generate aromatic heterocycles to those considered before and may have important implications for astrochemistry and astrobiology
Anti-trypanosomal activity of cationic N-heterocyclic carbene gold(I) complexes.

Science.gov (United States)

Winter, Isabel; Lockhauserbäumer, Julia; Lallinger-Kube, Gertrud; Schobert, Rainer; Ersfeld, Klaus; Biersack, Bernhard

2017-06-01

Two gold(I) N-heterocyclic carbene complexes 1a and 1b were tested for their anti-trypanosomal activity against Trypanosoma brucei parasites. Both gold compounds exhibited excellent anti-trypanosomal activity (IC 50 =0.9-3.0nM). The effects of the gold complexes 1a and 1b on the T. b. brucei cytoskeleton were evaluated. Rapid detachment of the flagellum from the cell body occurred after treatment with the gold complexes. In addition, a quick and complete degeneration of the parasitic cytoskeleton was induced by the gold complexes, only the microtubules of the detached flagellum remained intact. Both gold compounds 1a and 1b feature selective anti-trypanosomal agents and were distinctly more active against T. b. brucei cells than against human HeLa cells. Thus, the gold complexes 1a and 1b feature promising drug candidates for the treatment of trypanosome infections such as sleeping sickness (human African Trypanosomiasis caused by Trypanosoma brucei parasites). Copyright © 2017 Elsevier B.V. All rights reserved.
Mode of action of nifurtimox and N-oxide-containing heterocycles against Trypanosoma cruzi: is oxidative stress involved?

Science.gov (United States)

Boiani, Mariana; Piacenza, Lucia; Hernández, Paola; Boiani, Lucia; Cerecetto, Hugo; González, Mercedes; Denicola, Ana

2010-06-15

Chagas disease is caused by the trypanosomatid parasite Trypanosoma cruzi and threatens millions of lives in South America. As other neglected diseases there is almost no research and development effort by the pharmaceutical industry and the treatment relies on two drugs, Nifurtimox and Benznidazole, discovered empirically more than three decades ago. Nifurtimox, a nitrofurane derivative, is believed to exert its biological activity through the bioreduction of the nitro-group to a nitro-anion radical which undergoes redox-cycling with molecular oxygen. This hypothesis is generally accepted, although arguments against it have been presented. In the present work we studied the ability of Nifurtimox and five N-oxide-containing heterocycles to induce oxidative stress in T. cruzi. N-Oxide-containing heterocycles represent a promising group of new trypanosomicidal agents and their mode of action is not completely elucidated. The results here obtained argue against the oxidative stress hypothesis almost for all the studied compounds, including Nifurtimox. A significant reduction in the level of parasitic low-molecular-weight thiols was observed after Nifurtimox treatment; however, it was not linked to the production of reactive oxidant species. Besides, redox-cycling is only observed at high Nifurtimox concentrations (>400microM), two orders of magnitude higher than the concentration required for anti-proliferative activity (5microM). Our results indicate that an increase in oxidative stress is not the main mechanism of action of Nifurtimox. Among the studied N-oxide-containing heterocycles, benzofuroxan derivatives strongly inhibited parasite dehydrogenase activity and affected mitochondrial membrane potential. The indazole derivative raised intracellular oxidants production, but it was the least effective as anti-T. cruzi. Copyright 2010 Elsevier Inc. All rights reserved.
Vapor pressures and sublimation enthalpies of novel bicyclic heterocycle derivatives

International Nuclear Information System (INIS)

Blokhina, Svetlana V.; Ol’khovich, Marina V.; Sharapova, Angelica V.; Perlovich, German L.; Proshin, Alexey N.

2014-01-01

Highlights: • The vapor pressures of novel bicyclo-derivatives of amine were measured. • Thermodynamic functions of sublimation were calculated. • The influence of substituent structure and chemical nature on the vapor pressure was studied. -- Abstract: The vapor pressures of five novel bicyclic heterocycle derivatives were measured over the temperature 341.15 to 396.15 K using the transpiration method by means of an inert gas carrier. From these results the standard enthalpies and Gibbs free energies of sublimation at the temperature 298.15 K were calculated. The effects of alkyl- and chloro-substitutions on changes in the thermodynamic functions have been investigated. Quantitative structure–property relationship on the basis HYBOT physico-chemical descriptors for biologically active compounds have been developed to predict the sublimation enthalpies and Gibbs free energies of the compounds studied
Combinatorial Libraries of Bis-Heterocyclic Compounds with Skeletal Diversity

OpenAIRE

Soural, Miroslav; Bouillon, Isabelle; Krchňák, Viktor

2008-01-01

Combinatorial solid-phase synthesis of bis-heterocyclic compounds, characterized by the presence of two heterocyclic cores connected by a spacer of variable length/structure, provided structurally heterogeneous libraries with skeletal diversity. Both heterocyclic rings were assembled on resin in a combinatorial fashion.

Combinatorial Libraries of Bis-Heterocyclic Compounds with Skeletal Diversity

Science.gov (United States)

Soural, Miroslav; Bouillon, Isabelle; Krchňák, Viktor

2009-01-01

Combinatorial solid-phase synthesis of bis-heterocyclic compounds, characterized by the presence of two heterocyclic cores connected by a spacer of variable length/structure, provided structurally heterogeneous libraries with skeletal diversity. Both heterocyclic rings were assembled on resin in a combinatorial fashion. PMID:18811208
Aspects and prospects of the chemistry of organic heterocycles (review)

International Nuclear Information System (INIS)

Schroth, W.

1986-01-01

The systematics of heterocycles, their place in organic chemistry, and their significance for theory and practice are discussed. Problems of the chemistry of heterocycles are discussed on the examples of systems with various types of conjugation and ring sizes. The focus is on the principles of synthesis of heterocycles, in particular, those based on acetylene, various C 3 fragments, carbon disulfide, and maleic anhydride. Individual sections of the survey are devoted to the role of heterocycles in biosynthesis, as well as certain problems common to the chemistry of heterocycles, biochemistry, and macromolecular chemistry
Antioxidant evaluation of heterocyclic compounds by cytokinesis-block micronucleus assay.

Science.gov (United States)

Godevac, Dejan; Tesević, Vele; Vajs, Vlatka; Milosavljević, Slobodan; Stanković, Miroslava

2013-03-01

This article summarizes the results of using cytokinesis-block micronucleus (CBMN) assay to evaluate the antioxidant potential of heterocyclic compounds. Most studies were carried out with naturally occurring heterocyclic compounds such as plant polyphenols: flavonoids, xanthones, coumarins, and ellagitannins, or plant derived products (juices, extracts, supplements) rich in bioactive heterocyclic compounds. There are also some studies dealing with synthetic heterocyclic antioxidants. CBMN assay is an in vitro study that has been used to evaluate antioxidant and protective effects of heterocyclic compounds on induced chromosome aberration in human lymphocytes.
Synthesis and antimicrobial activity of some novel fused heterocyclic 1,2,4-triazolo [3,4-b][1,3,4] thiadiazine derivatives

Science.gov (United States)

Sahu, Jagdish K.; Ganguly, Swastika; Kaushik, Atul

2014-01-01

In the present investigation, the synthesis and antimicrobial evaluation of 1,2,4-triazolo [3,4-b][1,3,4] thiadiazine including different pharmacophores are aimed at. In this study, a series of 6-aryl-3- (3,4 -dialkoxyphenyl)-7H -[1,2,4]triazolo [3,4-b][1,3,4] thiadiazine (7a-7k) was synthesized by condensing 4-amino-5-(3,4-dialkoxyphenyl)-4H-[1,2,4]- triazole-3-thiol (6) with various aromatic carboxylic acids in the presence of phenacyl bromides through one-pot reaction. Eleven fused heterocyclic derivatives were successfully synthesized. The structures of these newly synthesized compounds were characterized by IR, 1H NMR and mass spectroscopic studies. All the synthesized compounds were screened for their antimicrobial evaluation. Some of the compounds exhibited promising antimicrobial activity. From the present study it may be concluded that synthesized compounds are fruitful in terms of their structural novelty and marked biological activities. These compounds could be further modified to develop potential and safer antifungal agents. PMID:24959418
Design, synthesis, antiviral activity and mode of action of phenanthrene-containing N-heterocyclic compounds inspired by the phenanthroindolizidine alkaloid antofine.

Science.gov (United States)

Yu, Xiuling; Wei, Peng; Wang, Ziwen; Liu, Yuxiu; Wang, Lizhong; Wang, Qingmin

2016-02-01

The phenanthroindolizidine alkaloid antofine and its analogues have excellent antiviral activity against tobacco mosaic virus (TMV). To simplify the structure and the synthesis of the phenanthroindolizidine alkaloid, a series of phenanthrene-containing N-heterocyclic compounds (compounds 1 to 33) were designed and synthesised, based on the intermolecular interaction of antofine and TMV RNA, and systematically evaluated for their anti-TMV activity. Most of these compounds exhibited good to reasonable anti-TMV activity. The optimum compounds 5, 12 and 21 displayed higher activity than the lead compound antofine and commercial ribavirin. Compound 12 was chosen for field trials of antiviral efficacy against TMV, and was found to exhibit better activity than control plant virus inhibitors. Compounds 5 and 12 were chosen for mode of action studies. The changes in fluorescence intensity of compounds 5 and 12 on separated TMV RNA showed that these small molecules can also bind to TMV RNA, but the mode is very different from that of antofine. The compounds combining phenanthrene and an N-heterocyclic ring could maintain the anti-TMV activity of phenanthroindolizidines, but their modes of action are different from that of antofine. The present study lays a good foundation for us to find more efficient anti-plant virus reagents. © 2015 Society of Chemical Industry.
40 CFR 721.10003 - Manganese heterocyclic tetraamine complex (generic).

Science.gov (United States)

2010-07-01

... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Manganese heterocyclic tetraamine complex (generic). 721.10003 Section 721.10003 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY... section. (2) The significant new uses are: (i) Industrial, commercial, and consumer activities...
N- AND O-HETEROCYCLES PRODUCED FROM THE IRRADIATION OF BENZENE AND NAPHTHALENE IN H{sub 2}O/NH{sub 3}-CONTAINING ICES

Energy Technology Data Exchange (ETDEWEB)

Materese, Christopher K.; Nuevo, Michel; Sandford, Scott A., E-mail: christopher.k.materese@nasa.gov [NASA Ames Research Center, Moffett Field, CA 94035 (United States)

2015-02-20

Aromatic heterocyclic molecules are an important class of molecules of astrophysical and biological significance that include pyridine, pyrimidine, and their derivatives. Such compounds are believed to exist in interstellar and circumstellar environments, though they have never been observed in the gas phase. Regardless of their presence in the gas phase in space, numerous heterocycles have been reported in carbonaceous meteorites, which indicates that they are formed under astrophysical conditions. The experimental work described here shows that N- and O-heterocyclic molecules can form from the ultraviolet (UV) irradiation of the homocyclic aromatic molecules benzene (C{sub 6}H{sub 6}) or naphthalene (C{sub 10}H{sub 8}) mixed in ices containing H{sub 2}O and NH{sub 3}. This represents an alternative way to generate aromatic heterocycles to those considered before and may have important implications for astrochemistry and astrobiology.
Synthesis, characterization and anti-proliferative activity of heterocyclic hypervalent organoantimony compounds.

Science.gov (United States)

Chen, Yi; Yu, Kun; Tan, Nian-Yuan; Qiu, Ren-Hua; Liu, Wei; Luo, Ning-Lin; Tong, Le; Au, Chak-Tong; Luo, Zi-Qiang; Yin, Shuang-Feng

2014-05-22

Three heterocyclic hypervalent organoantimony chlorides RN(CH2C6H4)2SbCl (2a R = t-Bu, 2b R = Cy, 2c R = Ph) and their chalcogenide derivatives [RN(CH2C6H4)2Sb]2O (3a R = t-Bu, 3b R = Cy, 3c R = Ph) were synthesized and characterized by techniques such as (1)H NMR, (13)C NMR, X-ray diffraction, and elemental analysis. It is found that the anti-proliferative activity detected over these compounds can be attributed to the coordination bond between the antimony and nitrogen atoms of these compounds. Moreover, a preliminary study on mechanistic action suggests that the inhibition effect is ascribable to cell cycle arrest and cell apoptosis. Copyright © 2014 Elsevier Masson SAS. All rights reserved.
Synthesis and biological activity of some heterocyclic compounds ...

Indian Academy of Sciences (India)

Administrator

lactam) moiety. 23 such as penicillin, cephalosporin and carbapenem (figure 2). It is also associated with a variety of therapeutic activities. 24–28. In continuation of our work to develop potential antimicrobial molecules,. 29,30 we report here the ...
Recent advances in the electrochemical construction of heterocycles

Directory of Open Access Journals (Sweden)

Robert Francke

2014-12-01

Full Text Available Due to the fact that the major portion of pharmaceuticals and agrochemicals contains heterocyclic units and since the overall number of commercially used heterocyclic compounds is steadily growing, heterocyclic chemistry remains in the focus of the synthetic community. Enormous efforts have been made in the last decades in order to render the production of such compounds more selective and efficient. However, most of the conventional methods for the construction of heterocyclic cores still involve the use of strong acids or bases, the operation at elevated temperatures and/or the use of expensive catalysts and reagents. In this regard, electrosynthesis can provide a milder and more environmentally benign alternative. In fact, numerous examples for the electrochemical construction of heterocycles have been reported in recent years. These cases demonstrate that ring formation can be achieved efficiently under ambient conditions without the use of additional reagents. In order to account for the recent developments in this field, a selection of representative reactions is presented and discussed in this review.
Design, Synthesis, and Biological Activity of 1,2,3-Triazolobenzodiazepine BET Bromodomain Inhibitors.

Science.gov (United States)

Sharp, Phillip P; Garnier, Jean-Marc; Hatfaludi, Tamas; Xu, Zhen; Segal, David; Jarman, Kate E; Jousset, Hélène; Garnham, Alexandra; Feutrill, John T; Cuzzupe, Anthony; Hall, Peter; Taylor, Scott; Walkley, Carl R; Tyler, Dean; Dawson, Mark A; Czabotar, Peter; Wilks, Andrew F; Glaser, Stefan; Huang, David C S; Burns, Christopher J

2017-12-14

A number of diazepines are known to inhibit bromo- and extra-terminal domain (BET) proteins. Their BET inhibitory activity derives from the fusion of an acetyl-lysine mimetic heterocycle onto the diazepine framework. Herein we describe a straightforward, modular synthesis of novel 1,2,3-triazolobenzodiazepines and show that the 1,2,3-triazole acts as an effective acetyl-lysine mimetic heterocycle. Structure-based optimization of this series of compounds led to the development of potent BET bromodomain inhibitors with excellent activity against leukemic cells, concomitant with a reduction in c- MYC expression. These novel benzodiazepines therefore represent a promising class of therapeutic BET inhibitors.
Synthesis and research of benzylamides of some isocyclic and heterocyclic acids as potential anticonvulsants.

Science.gov (United States)

Strupińska, Marzanna; Rostafińska-Suchar, Grazyna; Pirianowicz-Chaber, Elzbieta; Stables, James P; Jiang, Jeff; Paruszewski, Ryszard

2013-01-01

A series of benzylamides of isocyclic and heterocyclic acids was synthesized and tested in Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Near all synthesized derivatives of heterocyclic acids showed activity. All obtained derivatives of mono- and bicyclic isocyclic acids were inactive. The power of action of heterocyclic acids derivatives seems does not depend upon kind of heteroatom (N, O or S). One of the compounds (2-furoic acid benzylamide (4)) appeared most promising. It showed in minimal clonic seizure (6Hz) test (ASP) in rats after i. p. administration: MES ED50 = 36.5 mg/kg, TOX TD50 = 269.75 mg/kg, and PI = 7.39.
Greener and Expeditious Synthesis of Bioactive Heterocycles using Microwave Irradiation

Science.gov (United States)

The utilization of green chemistry techniques is dramatically reducing chemical waste and reaction times as has recently been proven in several organic syntheses and chemical transformations. To illustrate these advantages in the synthesis of bio-active heterocycles, we have stud...
Recent advances in the research of heterocyclic compounds as antitubercular agents.

Science.gov (United States)

Yan, Mi; Ma, Shutao

2012-12-01

Tuberculosis (TB) is a major health problem, with approximately one-third of the world's population infected with Mycobacterium tuberculosis, eight million people in the active disease state, and two million dying annually. Furthermore, the prevalence of TB/HIV co-infection, and the emergence of multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) have further aggravated the spread of this disease and thus mortality by it. There is an urgent need for novel antitubercular agents with improved properties, such as lower toxicity, shortened duration of therapy, rapid bactericidal action, and enhanced activity against MDR strains. Fortunately, a number of new potential antitubercular candidate drugs with heterocyclic rings, which are most likely to be effective against resistant strains, have entered clinical trials in recent years. This review highlights recent advances in the research of novel heterocyclic compounds, with particular focus on their antimycobacterial activity, mechanisms of action, toxicity, and structure-activity relationships (SARs). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Formation and ecotoxicity of N-heterocyclic compounds on ammoxidation of mono- and polysaccharides.

Science.gov (United States)

Klinger, Karl Michael; Liebner, Falk; Fritz, Ines; Potthast, Antje; Rosenau, Thomas

2013-09-25

Ammoxidation of technical lignins under mild conditions is a suitable approach to artificial humic substances. However, carbohydrates as common minor constituents of technical lignins have been demonstrated to be a potential source of N-heterocyclic ecotoxic compounds. Ethyl acetate extracts of ammoxidation mixtures of the monosaccharides glucose and xylose exhibited considerable growth inhibiting activity in the OECD 201 test, with 4-methyl-1H-imidazole, 4-(hydroxymethyl)-1H-imidazole, and 3-hydroxypyridine being the most active compounds. The amount of N-heterocyclic compounds formed at moderate ammoxidation conditions (70 °C, 0.2 MPa O2, 3 h) was significantly lower for the polysaccharides cellulose and xylan (16-30 μg/g of educt) compared to glucose (15.4 mg). Ammoxidation at higher temperature is not recommendable for carbohydrate-rich materials as much higher amounts of N-heterocyclic compounds were formed from both monosaccharides (100 °C: 122.4-160.5 mg/g of educt) and polysaccharides (140 °C: 5.52-16.03 mg/g of educt).
Effects of nitro-heterocyclic derivatives against Leishmania (Leishmania) infantum promastigotes and intracellular amastigotes.

Science.gov (United States)

Petri e Silva, Simone Carolina Soares; Palace-Berl, Fanny; Tavares, Leoberto Costa; Soares, Sandra Regina Castro; Lindoso, José Angelo Lauletta

2016-04-01

Leishmaniasis is an overlooked tropical disease affecting approximately 1 million people in several countries. Clinical manifestation depends on the interaction between Leishmania and the host's immune response. Currently available treatment options for leishmaniasis are limited and induce severe side effects. In this research, we tested nitro-heterocyclic compounds (BSF series) as a new alternative against Leishmania. Its activity was measured in Leishmania (Leishmania) infantum promastigotes and intracellular amastigotes using MTT colorimetric assay. Additionally, we assessed the phosphatidylserine exposure by promastigotes, measured by flow cytometry, as well as nitric oxide production, measured by Griess' method. The nitro-heterocyclic compounds (BSF series) showed activity against L. (L.) infantum promastigotes, inducting the phosphatidylserine exposition by promastigotes, decreasing intracellular amastigotes and increasing oxide nitric production. The selectivity index was more prominent to Leishmania than to macrophages. Compared to amphotericin b, our compounds presented higher IC50, however the selectivity index was more specific to parasite than to amphotericin b. In conclusion, these nitro-heterocyclic compounds showed to be promising as an anti-Leishmania drug, in in vitro studies. Copyright © 2016 Elsevier Inc. All rights reserved.
Alkynylation of heterocyclic compounds using hypervalent iodine reagent.

Science.gov (United States)

Kamlar, M; Císařová, I; Veselý, J

2015-03-14

The alkynylation of various nitrogen- and/or sulphur-containing heterocyclic compounds using hypervalent iodine TMS-EBX by utilization of tertiary amines under mild conditions is described. The developed metal-free methodology furnishes the corresponding alkynylated heterocycles bearing quaternary carbon in high yields.
Palladium-catalyzed allylation of tautomerizable heterocycles with alkynes.

Science.gov (United States)

Lu, Chuan-Jun; Chen, Dong-Kai; Chen, Hong; Wang, Hong; Jin, Hongwei; Huang, Xifu; Gao, Jianrong

2017-07-21

A method for the allylic amidation of tautomerizable heterocycles was developed by a palladium catalyzed allylation reaction with 100% atom economy. A series of structurally diverse N-allylic substituted heterocycles can be synthesized in good yields with high chemo-, regio-, and stereoselectivities under mild conditions.
Sulfur-Kβ /sub emission studies on sulfur-bearing heterocycles

International Nuclear Information System (INIS)

Phillips, D.R.; Andermann, G.G.; Fujiwara, F.

1986-01-01

Sulfur-K/β /sub x-ray fluorescence spectroscopy (XFS) has been used to study the electronic structure and bonding in sulfur-bearing heterocycles. XFS not only has the capability of experimentally measuring valence electron energies in molecular species, but can also provide intensity data which can help define the nature of the molecular orbitals defined by the electrons. This report discusses the feasibility of using XFS as an analytical tool for the determination of total and specific sulfur heterocycle content in samples. A variety of compounds were studied. These include thiophene, thiophene derivatives, tetranydrothiophene, several more complex saturated and unsaturated sulfur heterocycles, and heterocycles containing both sulfur and nitrogen. The sulfur-K/β /sub spectra were obtained using a double crystal spectrometer which provided an instrumental resolution of about 0.7 eV
Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review

International Nuclear Information System (INIS)

Xue Weiling; Warshawsky, David

2005-01-01

Polycyclic aromatic hydrocarbons (PAHs) and heterocyclic aromatic compounds (HACs) constitute a major class of chemical carcinogens present in the environment. These compounds require activation to electrophilic metabolites to exert their mutagenic or carcinogenic effects. There are three principal pathways currently proposed for metabolic activation of PAH and HAC: the pathway via bay region dihydrodiol epoxide by cytochrome P450 enzymes (CYPs), the pathway via radical cation by one-electron oxidation, and the ortho-quinone pathway by dihydrodiol dehydrogenase (DD). In addition to these major pathways, a brief description of a minor metabolic activation pathway, sulfonation, for PAHs that contain a primary benzylic alcoholic group or secondary hydroxyl group(s) is included in this review. The DNA damages caused through the reactive metabolites of PAH/HAC are described involving the DNA covalent binding to form stable or depurinating adducts, the formation of apurinic sites, and the oxidative damage. The review emphasizes the chemical/biochemical reactions involved in the metabolic processes and the chemical structures of metabolites and DNA adducts

New Gold(I) Organometallic Compounds with Biological Activity in Cancer Cells

NARCIS (Netherlands)

Bertrand, Benoit; de Almeida, Andreia; van der Burgt, Evelien P. M.; Picquet, Michel; Citta, Anna; Folda, Alessandra; Rigobello, Maria Pia; Le Gendre, Pierre; Bodio, Ewen; Casini, Angela

N-Heterocyclic carbene gold(I) complexes bearing a fluorescent coumarin ligand were synthesized and characterized by various techniques. The compounds were examined for their antiproliferative effects in normal and tumor cells in vitro; they demonstrated moderate activity and a certain degree of
Synthesis and antibacterial activity of novel Pyrazolo [3, 4-B] quinoline based heterocyclic azo compounds and their dyeing performance

International Nuclear Information System (INIS)

Thaokar, Sanjay F.; Patel, Dinesh M.; Patel, Manish P.; Patel, Ranjan G.

2007-01-01

3-Amino-6-methyl-1H- pyrazolo [3, 4-B] quinoline was synthesized in good yield. Monoazo compounds were prepared using this intermediate as diazo component with various heterocyclic coupling components. All the azo compounds were characterized by their percentage yield, melting point, elemental analysis, UV-visible spectra, IR-spectra and dyeing performance on nylon and polyester fibres and by their antibacterial activity against gram positive and gram negative bacteria. (author)
Synthesis of a molecularly defined single-active site heterogeneous catalyst for selective oxidation of N-heterocycles.

Science.gov (United States)

Zhang, Yujing; Pang, Shaofeng; Wei, Zhihong; Jiao, Haijun; Dai, Xingchao; Wang, Hongli; Shi, Feng

2018-04-13

Generally, a homogeneous catalyst exhibits good activity and defined active sites but it is difficult to recycle. Meanwhile, a heterogeneous catalyst can easily be reused but its active site is difficult to reveal. It is interesting to bridge the gap between homogeneous and heterogeneous catalysis via controllable construction of a heterogeneous catalyst containing defined active sites. Here, we report that a molecularly defined, single-active site heterogeneous catalyst has been designed and prepared via the oxidative polymerization of maleimide derivatives. These polymaleimide derivatives can be active catalysts for the selective oxidation of heterocyclic compounds to quinoline and indole via the recycling of -C=O and -C-OH groups, which was confirmed by tracing the reaction with GC-MS using maleimide as the catalyst and by FT-IR analysis with polymaleimide as the catalyst. These results might promote the development of heterogeneous catalysts with molecularly defined single active sites exhibiting a comparable activity to homogeneous catalysts.
Effect of cooking time and temperature on the heterocyclic amine content of fried beef patties.

Science.gov (United States)

Knize, M G; Dolbeare, F A; Carroll, K L; Moore, D H; Felton, J S

1994-07-01

The mutagenic heterocyclic amines 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), 2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (DiMeIQx) were measured in ground-beef patties fried at 150, 190 and 230 degrees C for 2-10 min on each side. Heterocyclic amines were purified using solid-phase extraction and analysed by HPLC. Recovery-corrected amounts of each heterocyclic amine were determined by the method of standard addition based on spiked samples with recoveries ranging from 40 to 70%. Mutagenic activity measured by the Ames/Salmonella test was determined for each sample. The amounts of MeIQx, PhIP, DiMeIQx and IQ increased with time and temperature of cooking. 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1), 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) and 2-amino-9H-pyrido[2,3-b]indole (A alpha C) were not detected in any sample. The mutagenic activity response measured for the meat extracts (TA98 revertants) was similar to the mutagenic activity calculated from the mass of heterocyclic amines present. The rate of formation of PhIP in a model system containing creatinine and phenylalanine heated in 80% diethylene glycol was compared with PhIP formation during meat frying. The apparent heats of activation were 6.5 kcal/mol in the model system compared with 6.0 kcal/mol in the fried meat patties. The increase in PhIP and MeIQx formation fitted an exponential function over the range 0 to 11 min and from 150 to 230 degrees C. This report shows clearly that increases in cooking temperature and time can have a profound effect on the amounts of heterocyclic amines generated and subsequently consumed in the diet.
Photometabolism of Heterocyclic Aromatic Compounds by Rhodopseudomonas palustris OU 11

Science.gov (United States)

Sasikala, C.; Ramana, C. V.; Rao, P. Raghuveer

1994-01-01

Rhodopseudomonas palustris OU 11 (ATCC 51186; DSM 7375) isolated from a pond of chemical industry effluent could anaerobically photometabolize heterocyclic aromatic compounds belonging to the pyridine and pyrazine groups only after a period of adaptation on pyrazinoic acid of 5 to 6 weeks. Growth on heterocyclic compounds was light dependent. The effects of various concentrations of heterocyclic compounds on growth suggest that higher concentrations of these compounds inhibit growth and are toxic. PMID:16349307
Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c] coumarin and pyrazolo[4,3-c] coumarin frameworks.

Science.gov (United States)

El-Dean, Adel M Kamal; Zaki, Remon M; Geies, Ahmed A; Radwan, Shaban M; Tolba, Mahmoud S

2013-01-01

Reaction of 4-chlorocoumarin-3-carbonitrile with ethyl thioglycolate and ethyl glycinate hydrochloride leads to a series of title products. Hydrazinolysis of amino thienocoumarin carboxylate afforded the hydrazine derivative which underwent various reactions to build new heterocyclic rings containing thienocoumarin moiety. Chloro acetylation of aminoester compound afforded the chloro acetyl amino which underwent nucleophilic substitution reactions various amines. The following treatment with formaldehyde under Mannich conditions afforded the corresponding imidazo derivatives. Reaction of Ghloroacetylamino with potassium thiocyanate yielded ethylpyrimidothieno coumarin sulfanylacetate which was used as a versatile precursor for synthesis of other heterocycles. On the other hand, reaction of chloro coumarin carbo nitrile with hydrazine gave the aminopyrazolocoumaine which reacted with bifunctionally compounds to give the substituted pyrimido derivatives. Diazotization and coupling of aminopyrazole with ethylcyanoacetate yielded ethylaminotriazinopyrazolocoumarine carboxylate. Several of the compounds obtained demonstrated considerable antifungal and antibacterial activity in the in vitro test systems.
METHODS OF SYNTHESIS EIGHT-TELLURIUM-CONTAINING HETEROCYCLES WITH MORE HETEROATOMS

Directory of Open Access Journals (Sweden)

G. M. Abakarov

2013-01-01

Full Text Available In this article systematized and summarized data on the synthesis of neweight-embered tellurium-containing heterocycles and new preparative methods described above produce heterocyclic tellurium.
Synthesis of Heterocycles through a Ruthenium‐Catalyzed Tandem Ring‐Closing Metathesis/Isomerization/N‐Acyliminium Cyclization Sequence

DEFF Research Database (Denmark)

Ascic, Erhad; Jensen, Jakob Feldthusen; Nielsen, Thomas Eiland

2011-01-01

Tandem bicycle: In the title reaction double bonds created during ring-closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting hete...... heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic natural product harmicine....
Structural mechanisms of photoeffect in polyimide structures containing heterocyclic fragments

International Nuclear Information System (INIS)

Aleksandrova, E. L.

2006-01-01

Trends in the variation in the quantum yields of charge-carrier photogeneration in polyimide structures containing heterocyclic fragments are studied. It is shown that the efficiency of sensitization of polyimides depends on the donor and acceptor properties of the fragments of monomeric units of the polyimide. It is established that the range of spectral sensitivity for heterocyclic fragments representing intramolecular complexes with charge transport is wider than that for heterocycles that do not represent such complexes
Blue Chitin columns for the extraction of heterocyclic amines from urine samples

DEFF Research Database (Denmark)

Bang, J.; Frandsen, Henrik Lauritz; Skog, K.

2004-01-01

During normal cooking of meat, a class of mutagenic/carcinogenic compounds called heterocyclic amines is formed. Heterocyclic amines are rapidly absorbed and metabolised in the human body, and for estimation of the intake of heterocyclic amines, it is useful to determinate their levels in the uri...
Solid-phase synthesis of compounds of europium and terbium with nitrogen-containing heterocyclic compounds under mechanical activation

International Nuclear Information System (INIS)

Kalinovskaya, I.V.; Karasev, V.E.

2000-01-01

Effect of solvents and parameters of mechanical treatment on basic regularities of synthesis of rare earth compounds with nitrogen-containing heterocyclic compounds is studied. It is shown that interaction on europium (3) and terbium (3) nitrates with nitrogen-containing heterocyclic compounds leads to formation of compounds of Ln(NO 3 )·2D composition, where Ln=Eu, Tb; D=2,2-dipyridyl, 1,10-phenanthroline, diphenylguanidine. Effect of conditions of mechanical treatment and different additions on process and yield of products is studied. Compounds prepared are characterized by the methods of chemical element analysis, IR spectroscopy and luminescent spectroscopy [ru
A multi-target caffeine derived rhodium(i) N-heterocyclic carbene complex: evaluation of the mechanism of action.

Science.gov (United States)

Zhang, Jing-Jing; Muenzner, Julienne K; Abu El Maaty, Mohamed A; Karge, Bianka; Schobert, Rainer; Wölfl, Stefan; Ott, Ingo

2016-08-16

A rhodium(i) and a ruthenium(ii) complex with a caffeine derived N-heterocyclic carbene (NHC) ligand were biologically investigated as organometallic conjugates consisting of a metal center and a naturally occurring moiety. While the ruthenium(ii) complex was largely inactive, the rhodium(i) NHC complex displayed selective cytotoxicity and significant anti-metastatic and in vivo anti-vascular activities and acted as both a mammalian and an E. coli thioredoxin reductase inhibitor. In HCT-116 cells it increased the reactive oxygen species level, leading to DNA damage, and it induced cell cycle arrest, decreased the mitochondrial membrane potential, and triggered apoptosis. This rhodium(i) NHC derivative thus represents a multi-target compound with promising anti-cancer potential.
2-Aminothiophene scaffolds: Diverse biological and pharmacological attributes in medicinal chemistry.

Science.gov (United States)

Bozorov, Khurshed; Nie, Li Fei; Zhao, Jiangyu; Aisa, Haji A

2017-11-10

2-Aminothiophenes are important five-membered heterocyclic building blocks in organic synthesis, and the chemistry of these small molecules is still developing based on the discovery of cyclization by Gewald. Another attractive feature of 2-aminothiophene scaffolds is their ability to act as synthons for the synthesis of biological active thiophene-containing heterocycles, conjugates and hybrids. Currently, the biological actions of 2-aminothiophenes or their 2-N-substituted analogues are still being investigated because of their various mechanisms of action (e.g., pharmacophore and pharmacokinetic properties). Likewise, the 2-aminothiophene family is used as diverse promising selective inhibitors, receptors, and modulators in medicinal chemistry, and these compounds even exhibit effective pharmacological properties in the various clinical phases of appropriate diseases. In this review, major biological and pharmacological reports on 2-aminothiophenes and related compounds have been highlighted; most perspective drug-candidate hits were selected for discussion and described, along with additional synthetic pathways. In addition, we focused on the literature dedicated to 2-aminothiophenes and 2-N-substituted derivatives, which have been published from 2010 to 2017. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Synthesis of heterocycles via transition-metal-catalyzed hydroarylation of alkynes.

Science.gov (United States)

Yamamoto, Yoshihiko

2014-03-07

Transition-metal (TM)-catalyzed hydroarylation reactions of alkynes have received much attention, because they enable the net insertion of alkyne C-C triple bonds into C-H bonds of aromatic precursors, resulting in regio- and stereo-selective formation of synthetically useful arylalkenes. Taking advantage of this feature, TM-catalyzed alkyne hydroarylations have been successfully used for the synthesis of heterocycles. TM-catalyzed alkyne hydroarylations can be classified into three major categories depending on the type of reaction and precursors involved: (1) palladium-catalyzed reductive Heck reactions of alkynes with aryl halides, (2) TM-catalyzed conjugate arylation reactions of activated alkynes with arylboronic acids, and (3) TM-catalyzed aromatic C-H alkenylations with alkynes. This review surveys heterocycle synthesis via TM-catalyzed hydroarylation of alkynes according to the above classification, with an emphasis on the scope and limitations, as well as the underlying mechanisms.
Heterocyclic Schiff bases as non toxic antioxidants: Solvent effect, structure activity relationship and mechanism of action

Science.gov (United States)

Shanty, Angamaly Antony; Mohanan, Puzhavoorparambil Velayudhan

2018-03-01

Phenolic heterocyclic imine based Schiff bases from Thiophene-2-carboxaldehyde and Pyrrole-2-carboxaldehyde were synthesized and characterized as novel antioxidants. The solvent effects of these Schiff bases were determined and compared with standard antioxidants, BHA employing DPPH assay and ABTS assay. Fixed reaction time and Steady state measurement were used for study. IC50 and EC50 were calculated. Structure-activity relationship revealed that the electron donating group in the phenolic ring increases the activity where as the electron withdrawing moiety decreases the activity. The Schiff base derivatives showed antioxidant property by two different pathways namely SPLET and HAT mechanisms in DPPH assay. While in ABTS method, the reaction between ABTS radical and Schiff bases involves electron transfer followed by proton transfer (ET-PT) mechanism. The cytotoxicity of these compounds has been evaluated by MTT assay. The results showed that all these compounds are non toxic in nature.
Heterocyclic aramid nanoparticle-assisted graphene exfoliation for fabrication of pristine graphene-based composite paper

Energy Technology Data Exchange (ETDEWEB)

Mo, Yao; Liu, Qi; Fan, Jinchen, E-mail: Jinchen.fan@shiep.edu.cn; Shi, Penghui; Min, Yulin, E-mail: ahaqmylin@126.com; Xu, Qunjie [Shanghai University of Electric Power, Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, College of Environmental and Chemical Engineering (China)

2015-07-15

Mechanically strong, electrically conductive, and flexible pristine graphene-based composite paper was prepared based on heterocyclic aramid nanoparticle-assisted liquid-phase exfoliation of graphite. The macroscopic heterocyclic aramid yarns were split and assembled into heterocyclic aramid nanoparticles with the size of ∼30 nm by deprotonation in dimethylsulfoxide in the presence of potassium hydroxide. The obtained heterocyclic aramid nanoparticles dimethylsulfoxide dispersion was used as good medium solvent for highly efficiency liquid-phase exfoliation of graphite. The results demonstrated that the concentration of exfoliated graphene can facile reaches ∼2.72 mg/mL after direct sonication of 7 h with assist of heterocyclic aramid nanoparticles. After exfoliation, the self-assembled pristine graphene-based composite paper was fabricated by vacuum-assisted filtration. Due to the introduction of heterocyclic aramid nanoparticles, the self-assembled pristine graphene/heterocyclic aramid nanoparticles composite paper exhibited good mechanical property with tensile strength of ∼129.7 MPa, meantime, has a high electrical conductivity of ∼1.42 × 10{sup 4} S/m.
Heterocyclic aramid nanoparticle-assisted graphene exfoliation for fabrication of pristine graphene-based composite paper

International Nuclear Information System (INIS)

Mo, Yao; Liu, Qi; Fan, Jinchen; Shi, Penghui; Min, Yulin; Xu, Qunjie

2015-01-01

Mechanically strong, electrically conductive, and flexible pristine graphene-based composite paper was prepared based on heterocyclic aramid nanoparticle-assisted liquid-phase exfoliation of graphite. The macroscopic heterocyclic aramid yarns were split and assembled into heterocyclic aramid nanoparticles with the size of ∼30 nm by deprotonation in dimethylsulfoxide in the presence of potassium hydroxide. The obtained heterocyclic aramid nanoparticles dimethylsulfoxide dispersion was used as good medium solvent for highly efficiency liquid-phase exfoliation of graphite. The results demonstrated that the concentration of exfoliated graphene can facile reaches ∼2.72 mg/mL after direct sonication of 7 h with assist of heterocyclic aramid nanoparticles. After exfoliation, the self-assembled pristine graphene-based composite paper was fabricated by vacuum-assisted filtration. Due to the introduction of heterocyclic aramid nanoparticles, the self-assembled pristine graphene/heterocyclic aramid nanoparticles composite paper exhibited good mechanical property with tensile strength of ∼129.7 MPa, meantime, has a high electrical conductivity of ∼1.42 × 10 4 S/m.
Petroleum geochemistry of the Potwar Basin, Pakistan: II – Oil classification based on heterocyclic and polycyclic aromatic hydrocarbons

International Nuclear Information System (INIS)

Asif, Muhammad; Fazeelat, Tahira

2012-01-01

In a previous study, oils in the Potwar Basin (Upper Indus) of Pakistan were correlated based on the dissimilarity of source and depositional environment of organic matter (OM) using biomarkers and bulk stable isotopes. This study is aimed at supporting the classification of Potwar Basin oils into three groups (A, B and C) using the distribution of alkylnaphthalenes, alkylphenanthrenes, alkyldibenzothiophenes, alkyldibenzofurans, alkylfluorenes, alkylbiphenyls, triaromatic steroids, methyl triaromatic steroids, retene, methyl retenes and cadalene. The higher relative abundance of specific methyl isomers of naphthalene and phenanthrene and the presence of diagnostic aromatic biomarkers clearly indicate the terrigenous and oxic depositional environment of OM for group A oil. Group B and C oils are of marine origin and the aforementioned heterocyclic and polycyclic aromatic hydrocarbons (HCs) differentiate them clearly into two different groups. The relative percentages of heterocyclic aromatic HCs reveal that the distribution of these compounds is controlled by the depositional environment of the OM. Sulfur-containing heterocyclic aromatic HCs are higher in crude oils generated from source rocks deposited in suboxic depositional environments, while oxygen-containing heterocyclic aromatic HCs in combination with alkylfluorenes are higher in marine oxic and deltaic oils. Biomarker and aromatic HC parameters do not indicate significant differences in the thermal maturity of Potwar Basin oils. Triaromatic and methyl triaromatic steroids support the division of Potwar Basin oils into the three groups and their relative abundances are related to source OM rather than thermal maturity. Significantly higher amounts of C 20 and C 21 triaromtic steroids and the presence or absence of long chain triaromatic steroids (C 25 , C 26 , C 27 , and C 28 ) indicates that these compounds are probably formed from different biological precursors in each group. Different isomers of methyl
Insight into eukaryotic topoisomerase II-inhibiting fused heterocyclic compounds in human cancer cell lines by molecular docking.

Science.gov (United States)

Taskin, T; Yilmaz, S; Yildiz, I; Yalcin, I; Aki, E

2012-01-01

Etoposide is effective as an anti-tumour drug by inhibiting eukaryotic DNA topoisomerase II via establishing a covalent complex with DNA. Unfortunately, its wide therapeutic application is often hindered by multidrug resistance (MDR), low water solubility and toxicity. In our previous study, new derivatives of benzoxazoles, benzimidazoles and related fused heterocyclic compounds, which exhibited significant eukaryotic DNA topoisomerase II inhibitory activity, were synthesized and exhibited better inhibitory activity compared with the drug etoposide itself. To expose the binding interactions between the eukaryotic topoisomerase II and the active heterocyclic compounds, docking studies were performed, using the software Discovery Studio 2.1, based on the crystal structure of the Topo IIA-bound G-segment DNA (PDB ID: 2RGR). The research was conducted on a selected set of 31 fused heterocyclic compounds with variation in structure and activity. The structural analyses indicate coordinate and hydrogen bonding interactions, van der Waals interactions and hydrophobic interactions between ligands and the protein, as Topo IIA-bound G-segment DNA are responsible for the preference of inhibition and potency. Collectively, the results demonstrate that the compounds 1a, 1c, 3b, 3c, 3e and 4a are significant anti-tumour drug candidates that should be further studied.
Thiosemicarbazides in the synthesis of five- and six-membered heterocyclic compounds

International Nuclear Information System (INIS)

Gazieva, Galina A; Kravchenko, Angelina N

2012-01-01

Data on key chemical transformations of thiosemicarbazides resulting in heterocyclic compounds are generalized and described systematically. Methods for the synthesis of five- and six-membered heterocycles with two and three heteroatoms are considered. The bibliography includes 190 references.

Sulforaphane Analogues with Heterocyclic Moieties: Syntheses and Inhibitory Activities against Cancer Cell Lines

Directory of Open Access Journals (Sweden)

Ye-Hui Shi

2016-04-01

Full Text Available Recent studies have shown that sulforaphane (SFN selectively inhibits the growth of ALDH+ breast cancer stem-like cells.Herein, a series of SFN analogues were synthesized and evaluated against breast cancer cell lines MCF-7 and SUM-159, and the leukemia stem cell-like cell line KG-1a. These SFN analogues were characterized by the replacement of the methyl group with heterocyclic moieties, and the replacement of the sulfoxide group with sulfide or sulfone. A growth inhibitory assay indicated that the tetrazole analogs 3d, 8d and 9d were significantly more potent than SFN against the three cancer cell lines. Compound 14c, the water soluble derivative of tetrazole sulfide 3d, demonstrated higher potency against KG-1a cell line than 3d. SFN, 3d and 14c significantly induced the activation of caspase-3, and reduced the ALDH+ subpopulation in the SUM159 cell line, while the marketed drug doxrubicin(DOX increased the ALDH+ subpopulation.
Computer prediction of biological activity of 2-methyl(phenyl-6,9-epoksybenzo[g]quinoline-4,5,10-Trion and 5-methyl-(1,2,4-triazolo[4,3-a] quinoline

Directory of Open Access Journals (Sweden)

Yu. V. Karpenko

2015-04-01

Full Text Available , One of the priority measures, which are evaluated in the creation of new effective medicines, is their high selective effect and lack of side effects. A considerable interest is the possibility of combining several structures of heterocycles in one molecule, such as quinoline and furan, which may cause an increase in biological activity of these combined compounds or an emergence of new properties. It is known that derivatives of 1,2,4-triazolo[4,3-a]quinoline have anticonvulsant effect and treat the syndrome of disorders with the nervous system. The aim of research. The main purpose of this work was an establishment of combinatorial library of bioregulators, which combines structures 5,8-dioksoquinoline and furan (1-8, quinoline and triazole (9-12, using computer program PASS (Prediction Activitity Spectra for Substances. Virtual screening of heterocycles derivatives was conducted to determine the direction of their bioactivity researches. Materials and methods. The virtual screening of compounds was performed by using the computer program PASS (Prediction Activity Spectra for Substances. For the specific activity the increase of Pa quantity and the decrease of the Pi quantity, helps to get the greater chance to detect this activity in the experiment. Predicting the probability of substance manifestation of specific types of biological activity determines which tests are the most appropriate for studying the biological activity of specific chemical substances and which substances of those that are available to the researcher likely will show the desired effect. With theoretical prediction the most likely basic structures of new compounds with desired biological effect, which best suits the task will be selected. Results. Analysis of computer prediction demonstrates the promising search of antineoplastic, antibiotic, analgesic and other types of activity in some of these compounds. An important instant of prediction of these substances is
Masked N-Heterocyclic Carbene-Catalyzed Alkylation of Phenols with Organic Carbonates.

Science.gov (United States)

Lui, Matthew Y; Yuen, Alexander K L; Masters, Anthony F; Maschmeyer, Thomas

2016-09-08

An easily prepared masked N-heterocyclic carbene, 1,3-dimethylimidazolium-2-carboxylate (DMI-CO2 ), was investigated as a "green" and inexpensive organocatalyst for the alkylation of phenols. The process made use of various low-toxicity and renewable alkylating agents, such as dimethyl- and diethyl carbonate, in a focused microwave reactor. DMI-CO2 was found to be a very active catalyst and excellent yields of a range of aryl alkyl ethers were obtained under relatively benign conditions. The observed difference in the conversion behavior of phenol methylation, in the presence of either the carbene or 1,8-diazabicycloundec-7-ene (DBU) catalyst, was rationalized on the basis of mechanistic investigations. The primary mode of action for the N-heterocyclic carbene is nucleophilic catalysis. Activation of the dialkyl carbonate electrophile results in concomitant evolution of an organo-soluble alkoxide, which deprotonates the phenolic starting material. In contrast, DBU is initially protonated by the phenol and thus consumed. Subsequent regeneration and participation in nucleophilic catalysis only becomes significant after some phenolate alkylation occurs. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Reactions of 3-Formylchromone with Active Methylene and Methyl Compounds and Some Subsequent Reactions of the Resulting Condensation Products

Directory of Open Access Journals (Sweden)

M. LÃƒÂ¡cova

2005-08-01

Full Text Available This review presents a survey of the condensations of 3-formylchromone with various active methylene and methyl compounds, e.g. malonic or barbituric acid derivatives, five-membered heterocycles, etc. The utilisation of the condensation products for the synthesis of different heterocyclic systems, which is based on the ability of the ÃŽÂ³-pyrone ring to be opened by the nucleophilic attack is also reviewed. Finally, the applications of microwave irradiation as an unconventional method of reaction activation in the synthesis of condensation products is described and the biological activity of some chromone derivatives is noted.
Carbon-14 labelled nitrogen heterocycles; the syntheses of three phosphodiesterase inhibitors

International Nuclear Information System (INIS)

Lawrie, K.W.M.; Novelli, C.E.A.; Saunders, David

1995-01-01

The syntheses of three heterocyclic phosphodiesterase inhibitors are described from a common radiolabelled precursor, namely 2-propoxybenzo[cyano- 14 C] nitrile. Conversion of the nitrile to the corresponding methyl ketone or amidine allows elaboration of the heterocycles radiolabelled within the ring systems. (Author)
Synthesis of novel 3-cyclohexylpropanoic acid-derived nitrogen heterocyclic compounds and their evaluation for tuberculostatic activity.

Science.gov (United States)

Gobis, Katarzyna; Foks, Henryk; Bojanowski, Krzysztof; Augustynowicz-Kopeć, Ewa; Napiórkowska, Agnieszka

2012-01-01

A series of novel 3-cyclohexylpropanoic acid derivatives and 3-cyclohexylpropanoic acid-derived nitrogen heterocyclic compounds (1-8) have been synthesized and evaluated for tuberculostatic activity. Compounds 1a, 1c, 1e and 1f bearing benzimidazole or benzimidazole-like systems showed the most potent tuberculostatic activity against Mycobacterium tuberculosis strains with MIC values ranging from 1.5 to 12.5μg/mL. More importantly 1a (6-chloro-2-(2-cyclohexylethyl)-4-nitro-1H-benzo[d]imidazole) and 1f (2-(2-cyclohexylethyl)-1H-imidazo[4,5-b]phenazine) appeared selective for M. tuberculosis as compared with eukaryotic cells (human fibroblasts), and other antimicrobial strains. These compounds may thus represent a novel, selective class of antitubercular agents. Additionally compound 1a stimulated type I collagen output by fibroblasts, in vitro. Copyright © 2011 Elsevier Ltd. All rights reserved.
α-Diazo oxime ethers for N-heterocycle synthesis.

Science.gov (United States)

Choi, Subin; Ha, Sujin; Park, Cheol-Min

2017-06-01

This Feature Article introduces the preparation and synthetic utility of α-diazo oxime ethers. α-Oximino carbenes are useful synthons for N-heterocycles, and can be easily prepared from α-diazo oxime ethers as precursors. We begin with the preparation of α-diazo oxime ethers and their application in [3+2] cycloaddition. It turns out that the nature of metals bound to carbenes plays a crucial role in modulating the reactivity of α-oximino carbenes, in which copper carbenes smoothly react with enamines, whereas the less reactive enol ethers and nitriles require gold carbenes. In Section 3.2, a discussion on N-O and C-H bond activation is presented. Carbenes derived from diazo oxime ethers show unique reactivity towards N-O and C-H bond activation, in which the proximity of the two functionalities, carbene and oxime ether, dictates the preferred reaction pathways toward pyridines, pyrroles, and 2H-azirines. In Section 3.3, the development of tandem reactions based on α-diazo oxime ethers is discussed. The nature of carbenes in which whether free carbenes or metal complexes are involved dissects the pathway and forms different types of 2H-azirines. The 2H-azirine formation turned out to be an excellent platform for the tandem synthesis of N-heterocycles including pyrroles and pyridines. In the last section, we describe the electrophilic activation of 2H-azirines with vinyl carbenes and oximino carbenes. The resulting azirinium species undergo rapid ring expansion rearrangements to form pyridines and pyrazines.
Carbon-14 labelled nitrogen heterocycles; the syntheses of three phosphodiesterase inhibitors

Energy Technology Data Exchange (ETDEWEB)

Lawrie, K.W.M.; Novelli, C.E.A.; Saunders, David [SmithKline Beecham Pharmaceuticals Research and Development, Harlow (United Kingdom). Synthetic Isotope Chemistry Dept.; Coates, W.J. [SmithKline Beecham Pharmaceuticals Research and Development, Welwyn (United Kingdom)

1995-09-01

The syntheses of three heterocyclic phosphodiesterase inhibitors are described from a common radiolabelled precursor, namely 2-propoxybenzo[cyano-{sup 14}C] nitrile. Conversion of the nitrile to the corresponding methyl ketone or amidine allows elaboration of the heterocycles radiolabelled within the ring systems. (Author).
Auranofin and N-heterocyclic carbene gold-analogs are potent inhibitors of the bacteria Helicobacter pylori.

Science.gov (United States)

Owings, Joshua P; McNair, Nina N; Mui, Yiu Fung; Gustafsson, Tomas N; Holmgren, Arne; Contel, Maria; Goldberg, Joanna B; Mead, Jan R

2016-07-01

Auranofin is an FDA-approved gold-containing compound used for the treatment of rheumatoid arthritis. Recent reports of antimicrobial activity against protozoa and bacteria indicate that auranofin targets the reductive enzyme thioredoxin reductase (TrxR). We evaluated auranofin as well as five auranofin analogs containing N-heterocyclic carbenes (instead of the triethylphosphane present in auranofin) and five gold-carbene controls for their ability to inhibit or kill Helicobacter pylori in vitro Auranofin completely inhibited bacterial growth at 1.2 μM. Purified H. pylori TrxR was inhibited by auranofin in a cell-free assay (IC50 ∼88 nM). The most active gold(I)-N-heterocyclic carbene compounds exhibited MICs comparable to auranofin against H. pylori (2 μM), while also exhibiting lower toxicities for human embryonic kidney cells (HEK-293T cells). Median toxic concentrations (TC50) were 13-20-fold higher compared to auranofin indicating that they were less cytotoxic. The N-heterocyclic carbene analogs maybe well tolerated, but further evaluation is needed in vivo Finally, auranofin was synergistic with the antibiotic amoxicillin, suggesting that targeting both the reductive enzyme TrxR and cell wall synthesis may be effective against H. pylori infections. © FEMS 2016. All rights reserved. For permissions, please e-mail: journals.permissions@oup.com.
Synthesis and characterization of new N-heterocyclic carbene ligands: 1,3-Bis(acetamide)imidazol-3-ium bromide and 3-(acetamide)-1-(3-aminopropyl)-1H-imidazol-3-ium bromide

Science.gov (United States)

Turkyilmaz, Murat; Uluçam, Gühergül; Aktaş, Şaban; Okan, S. Erol

2017-05-01

Two new pincer type N-heterocyclic carbene ligands were synthesized. The compounds were characterized by FTIR, NMR (1H, 13C) GC-MS and elemental analyses. They were also both modelled by DFT calculations as the crystal structure of 1,3-bis(acetamide)imidazol-3-ium bromide was determined by XRD which is an orthorhombic system with space group P21212. The structural analyses in gas phase were realized by comparing the experimental NMR and IR spectra with those of the theoretical calculations. In vitro biological activities of the molecules were determined and found that one of them exhibits significant cytotoxic activity.
Synthesis of pyridine and isoquinoline labelled with 14C on the nitrogen heterocycle

International Nuclear Information System (INIS)

Robveille, Jacques

1985-01-01

This research thesis addresses the synthesis of derivatives of pyridine and isoquinoline labelled with carbon 14 ( 14 C) in the nitrogenated heterocycle as these compounds are of biological and pharmacological interest. The author aimed at developing rather general synthesis schemes which could be easily applied to the synthesis of radioactive compounds, and could produce, through a given synthesis way, the largest as possible family of differently substituted compounds. Different sources for labelled pyridine and isoquinoline have been used: dioxo-1,5 or their corresponding dioxins, substituted pentadienoic acids, derivatives of acrylic acid, and derivatives of cinnamic acid. Thus, three different synthesis processes have been developed to obtain 14 C labelled pyridine, and one of them is applied to the preparation of 14 C labelled isoquinoline. These synthesis processes can have a very general application, and allow different 14 C labelling positions to be envisaged. The possibility to obtain the same compounds but labelled with tritium can also be envisaged to obtain much higher specific activities [fr
Azomesogens with a heterocyclic moiety

Indian Academy of Sciences (India)

Unknown

Azomesogens with a heterocyclic moiety. †. JAYRANG S DAVE and MEERA MENON*. Department of Applied Chemistry, Faculty of Technology and Engineering, MS University of Baroda,. Baroda 390 001, India. Abstract. Azobenzene derivatives were among the first ten liquid crystalline compounds. But there have been.
Combinatorial synthesis of oxazol-thiazole bis-heterocyclic compounds.

Science.gov (United States)

Murru, Siva; Nefzi, Adel

2014-01-13

A combinatorial library of novel oxazol-thiazole bis-heterocycles was synthesized in good to excellent overall yields with high purity using a solution and solid-phase parallel synthesis approach. Oxazole amino acids, prepared from serine methyl ester and amino acids via coupling and cyclodehydration, were treated with Fmoc-NCS and α-haloketones for the parallel synthesis of diverse bis-heterocycles. Fmoc-isothiocyanate is used as a traceless reagent for thiazole formation. Oxazole diversity can be achieved by using variety of amino acids, whereas thiazole diversity is produced with various haloketones.
Synthesis, characterization and antimicrobial activities of novel silver(I) complexes with coumarin substituted N-heterocyclic carbene ligands.

Science.gov (United States)

Karataş, Mert Olgun; Olgundeniz, Begüm; Günal, Selami; Özdemir, İlknur; Alıcı, Bülent; Çetinkaya, Engin

2016-02-15

Eight new coumarin substituted silver(I) N-heterocyclic carbene (NHC) complexes were synthesized by the interaction of the corresponding imidazolium or benzimidazolium chlorides and Ag2O in dichloromethane at room temperature. Structures of these complexes were established on the basis of elemental analysis, (1)H NMR, (13)C NMR, IR and mass spectroscopic techniques. The antimicrobial activities of carbene precursors and silver NHC complexes were tested against standard strains: Enterococcus faecalis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and the fungi Candida albicans and Candida tropicalis. Results showed that all the compounds inhibited the growth of the all bacteria and fungi strains and some complexes performed good activities against different microorganisms. Among all the compounds, the most lipophilic complex bis[1-(4-methylene-6,8-dimethyl-2H-chromen-2-one)-3-(naphthalene-2-ylmethyl)benzimidazol-2-ylidene]silver(I) dichloro argentate (5e) was found out as the most active one. Copyright © 2015 Elsevier Ltd. All rights reserved.
Recent Advances in the Synthesis and Anticancer Activity of Some Molecules Other Than Nitrogen Containing Heterocyclic Moeities.

Science.gov (United States)

Akhtar, Md Jawaid; Yar, M Shahar; Khan, Ahsan Ahmed; Ali, Zulphikar; Haider, Md Rafi

2017-01-01

The present review article presented a detailed account of the design strategies and the structure activity relationship of different derivatives apart from the nitrogen containing ring. These scaffolds play an important part in the drug discovery which showed anticancer activity against different human cancer cell lines through apoptosis, cell cycle arrest, inhibiting kinases, angiogenesis, disruption of cell migration, modulation of nuclear receptor responsiveness and others. Naphthalenes amides/amidines, furan, podophyllotoxin, platinum compounds, steroids, and urea, which forms the core part or along with other N-heterocyclic rings are enclosed. Some of these compounds e.g. podophyllotoxin and platinum based drugs displayed anticancer activity at nanomolar range. Various substitutions from the earlier and latest information are prerequisite in the drug synthesis process. The review focused on the recent development of these derivatives, design and anticancer properties, thus providing with the most profound knowledge for the development of targeted based anticancer drugs. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.
Quantum-chemical investigation of the 1,2-proton shift in protonated five-membered aromatic heterocycles

International Nuclear Information System (INIS)

Abronin, I.A.; Gorb, L.G.; Litvinov, V.P.

1985-01-01

Calculations of the energetics of the 1,2-proton shift in protonated five-membered aromatic heterocycles - pyrrole, furan, and thiophene - have been carried out by the SCF MO LCAO method in the MINDO/3 approximation and nonempirically on the OST-3GF (OST-3GF) basis. The general features of this process, and also the influence of solvation and of taking into account the vacant d-AOs of the sulfur atom in the protonated form of thiophene on the results of the calculation are considered. The results obtained have been used for a discussion of the activity and selectivity of the heterocycles considered in aromatic electrophilic substitution reactions
Synthesis, Structural Analysis and Antimicrobial Activities of Novel Water Soluble Ionic Liquids Derived from N-Heterocyclic Carbene Salts

Directory of Open Access Journals (Sweden)

Ahmet Kunduracıoğlu

2016-06-01

Full Text Available Six N-heterocyclic Carbene based Ionic Liquids (ILs have been synthesized by conventional methods. The ILs were spectroscopically characterized by NMR and FT-IR techniques. Their in vitro antimicrobial activities were determined towards gram-positive and gram-negative bacterias and yeast strains using minimum inhibition concentration (MIC assay. The best inhibition performances were obtained with compound 1 due to its more hydrophilic nature compared with the others. It exhibited 1 mg L–1 MIC value against to the most bacteria while the others showed 4 mg L–1. This work is licensed under a Creative Commons Attribution 4.0 International License.
Partitioning-separation of metal ions using heterocyclic ligands

International Nuclear Information System (INIS)

Hudson, M.J.; Drew, M.G.B.; Iveson, P.B.; Russell, M.L.

2001-01-01

Some guidelines are proposed for the effective design of heterocyclic ligands for partitioning because there is no doubt that the correct design of a molecular extractant is required for the effective separation of metal ions such as actinides(III) from lanthanides(III). Heterocyclic ligands with aromatic ring systems have a rich chemistry, which is only now becoming sufficiently well understood in relation to the partitioning process. The synthesis, characterisation and structures of some chosen molecules will be introduced in order to illustrate some important features. For example, the molecule N-carboxy-butyl-2-amino-4,6-di (2-pyridyl)-1,3,5-triazine (BADPTZ), which is an effective solvent extraction reagent for actinides and lanthanides, has been synthesised, characterised and its interaction with lanthanide ions studied. The interesting and important features of this molecule will be compared with those of other heterocyclic molecules such as 2,6-bis(5-butyl-1,2,4-triazole-3-yl) pyridine (DBTZP), which is a candidate molecule for the commercial separation of actinides and lanthanide elements. (author)
Summary of diamino pyrazoles derived and study their biological activities

International Nuclear Information System (INIS)

Hagui, Marwa

2016-01-01

The work involves the synthesis of new heterocyclic structures diamino pyrazoles derivatives that are present in many natural products and products of pharmacological and therapeutic interests and study their biological activities. In order to develop a radiotracer interest and use in diagnostic nuclear medicine, we are interested to synthesis a pyrazole derivative with the precursor [Re(CO)5Br] and studying the antibacterial and antifungal activity of 3.5-diamino pyrazole and even thioamide complex rhenium. The objectives of our workout: 1/ Synthesis of molecules 3,5-diamino pyrazole and thioamide. 2/ Synthesis of 3,5-diamino pyrazole-rhenium complex. 3/ The in vitro study: Bacteriological Tests (Study of antibacterial and antifungal activity of 3,5-diamino pyrazole and thioamide). The first part of this work concerns the chemical synthesis of molecules such as: thioamide, Amp z1 Ampz2 and then we had synthesized the complex 3,5-diamino pyrazole-rhenium. Similarly we determined the physicochemical characteristics of the compounds synthesized by CLHP, CCM and RMN ( 1 H, 13 C). The second part is devoted to the study in vitro of biological activities of the synthesized molecules and complex 3,5 diaminopyrazole-rhenium with concentration 1 mg/mL and 2 mg/mL. The results allow us to say that the thioamide and Ampz2 have antibacterial activity against S. enterica and Ampz2 has low activity against S. aureus and P. aeruginossa. Other pyrazole derivatives have no significant antibacterial and antifungal activity. The results also show that the synthesized compounds of concentration 2 mg/mL in relation to the inhibition zones of amoxicillin and DMSO: 1/ Escherichia coli, there is antibacterial activity for thioamide, and the Amp z1-Re Ampz2 compound. 2/ Staphylococcus aureus, the complex Ampz 1-Re and the thioamide have significant antibacterial activity. 3/ Salmonella, we observe that the thioamide molecules, Ampz2 and Amp z1-Re have significant antibacterial activity
Synthesis, Antiproliferative, and Multidrug Resistance Reversal Activities of Heterocyclic α,β-Unsaturated Carbonyl Compounds.

Science.gov (United States)

Sun, Ju-Feng; Hou, Gui-Ge; Zhao, Feng; Cong, Wei; Li, Hong-Juan; Liu, Wen-Shuai; Wang, Chunhua

2016-10-01

A series of heterocyclic α,β-unsaturated carbonyl compounds (1a-1d, 2a-2d, 3a-3d, 4a-3d, and 5a-5d) with 1,5-diaryl-3-oxo-1,4-pentadienyl pharmacophore were synthesized for the development of anticancer and multidrug resistance reverting agents. The antiproliferative activities were tested against nine human cancer cell lines. Approximately 73% of the IC50 values were below 5 μm, while 35% of these figures were submicromolar, and compounds 3a-3d with 4-trifluoro methyl in the arylidene benzene rings were the most potent, since their IC50 values are between 0.06 and 3.09 μm against all cancer cell lines employed. Meanwhile, their multidrug resistance reversal properties and cellular uptake were further examined. The data displayed that all of these compounds could reverse multidrug resistance, particularly, compounds 3a and 4a demonstrated both potent multidrug resistance reverting properties and strong antiproliferative activities, which can be taken as leading molecules for further research of dual effect agents in tumor chemotherapy. © 2016 John Wiley & Sons A/S.

NEW DERIVATIVES OF 2-R1-N-(5-R-1,3,4-THIADIAZOL-2-YL-BENZOLSULFONAMIDES: SYNTHESIS, PHYSICOCHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITY PREDICTION

Directory of Open Access Journals (Sweden)

Sych I.V.

2015-12-01

Full Text Available Introduction: The analysis of modern literature, including overseas one, showed that a lot of the scientific researches is devoted to finding and creating biologically active compounds on base 1,3,4-thiadiazole. Derivatives of 1,3,4-thiadiazole are the large group of heterocyclic compounds with high rates of antimicrobial, antituberculosis, antidiabetic, antineoplastic and anticonvulsant activity. Material and methods: The purpose of this study was the expansion of sulfone derivatives substituted nitrogen-containing heterocyclic systems through the synthesis of 2-R1-N (5-R-1,3,4-thiadiazol-2-ilbenzolsulfonamides and prediction their pharmacological activity for future planning pharmacological screening. Synthesis of semi-products 2-amino-5-R-1,3,4-thiadiazoles was carried out by cyclization thiosemicarbazide and substituted derivatives of carboxylic acids in the presence of concentrated sulfuric acid. The synthesis of target compounds 2-R1-N(5-R-1,3,4-thiadiazol-2-ylbenzolsulfon-amides was carried out by N-acylation of 2-amino-5R-1,3,4-thiadiazole substituted benzolsul-fochlorides in the presence of anhydrous pyridine. The reaction proceeds by the classic SN2-mechanism. The resulting compounds are white crystalline substances, soluble in alcohol, chloroform and acetone, difficult to dissolve in water. Yields of obtained compounds was satisfactory (76-84%. The purity of the obtained compounds was determined by TLC. The structure of the obtained compounds was proved by elemental analysis, IR methods and 1H NMR spectroscopy. NMR 1H spectra were recorded at Bruker WM spectrometer (200 MHz; solvent DMSO-d6; chemical shifts were in ppm, internal standard (TMS (tetramethylsilane was used. The prognosis of biological activity for obtained compounds were carried out using the program PASS (Prediction of Activity Spectra for Substances in order to plan the further pharmacological screening. The program PASS predicts more than 500 kinds of biological
The reactions of anthronylidene carbene with some heterocyclic compounds

International Nuclear Information System (INIS)

Divisia, Bernadette

1970-01-01

The action of the anthronylidene carbene, generated by photochemical decomposition of 9-diazo 10-anthron, on four heterocyclic compounds (furan, thiophene, 1-methyl-pyrrole and 2,5-dihydrofuran) has been examined. Two classical carbene reactions have been observed: the addition on double bond (furan, thiophene, 1-methylpyrrole) and hydrogen atom abstraction of the heterocyclic compound (2,5-dihydrofuran). In the case of furan and thiophene, the cyclo-propanic compound resulting from the addition is spontaneously transformed into an ethylenic derivative by valence isomerization. The furan derivative undergoes a cis-trans isomerization, while the thiophene one undergoes an extra carbene attack. In the case of 1-methylpyrrole, the corresponding cyclo-propanic compound undergoes a ring cleavage, followed by a hydrogen atom migration leading to the formation of a substituted anthron. Only an allylic hydrogen atom selective abstraction of heterocyclic compound takes place in the reaction of anthronylidene carbene with 2,5-dihydrofuran. The asymmetrical coupling of radicals so obtained yields the corresponding substituted anthron. (author) [fr
Investigations on organogermanium compounds; III. N-tributylgermyl-substituted aliphatic and heterocyclic amines

NARCIS (Netherlands)

Rijkens, F.; Janssen, M.J.; Kerk, G.J.M. van der

1965-01-01

A series of new organogermanium compounds containing a germanium‐nitrogen bond, in many of which the nitrogen atom forms part of an heterocyclic ring, are prepared, in some cases by new methods: transamination reactions and reactions of germoxanes with heterocyclic amines. Striking differences in
Recent advances in novel heterocyclic scaffolds for the treatment of drug-resistant malaria.

Science.gov (United States)

Kumar, Sahil; Singh, Rajesh K; Patial, Babita; Goyal, Sachin; Bhardwaj, T R

2016-01-01

Malaria is a major public health problem all over the world, particularly in tropical and subtropical countries due to the development of resistance and most deadly infection is caused by Plasmodium falciparum. There is a direct need for the discovery of new drugs with unique structures and mechanism of action to treat sensitive and drug-resistant strains of various plasmodia for radical cure of this disease. Traditional compounds such as quinine and related derivatives represent a major source for the development of new drugs. This review presents recent modifications of 4-aminoquinoline and 8-aminoquinolone rings as leads to novel active molecules which are under clinical trials. The review also encompasses the other heterocyclic compounds emerged as potential antimalarial agents with promising results such as acridinediones and acridinone analogues, pyridines and quinolones as antimalarials. Miscellaneous heterocyclics such as tetroxane derivatives, indole derivatives, imidazolopiperazine derivatives, biscationic choline-based compounds and polymer-linked combined antimalarial drugs are also discussed. At last brief introduction to heterocyclics in natural products is also reviewed. Most of them have been under clinical trials and found to be promising in the treatment of drug-resistant strains of Plasmodium and others can be explored for the same purpose.
Activity of Antifungal Organobismuth(III Compounds Derived from Alkyl Aryl Ketones against S. cerevisiae: Comparison with a Heterocyclic Bismuth Scaffold Consisting of a Diphenyl Sulfone

Directory of Open Access Journals (Sweden)

Toshihiro Murafuji

2014-07-01

Full Text Available A series of hypervalent organobismuth(III compounds derived from alkyl aryl ketones [XBi(5-R'C6H3-2-COR(Ar] was synthesized to investigate the effect of the compounds’ structural features on their antifungal activity against the yeast Saccharomyces cerevisiae. In contrast to bismuth heterocycles [XBi(5-RC6H3-2-SO2C6H4-1'-] derived from diphenyl sulfones, a systematic quantitative structure-activity relationship study was possible. The activity depended on the Ar group and increased for heavier X atoms, whereas lengthening the alkyl chain (R or introducing a substituent (R' reduced the activity. IBi(C6H4-2-COCH3(4-FC6H4 was the most active. Its activity was superior to that of the related acyclic analogues ClBi[C6H4-2-CH2N(CH32](Ar and ClBi(C6H4-2-SO2 tert-Bu(Ar and also comparable to that of heterocyclic ClBi(C6H4-2-SO2C6H4-1'-, which was the most active compound in our previous studies. Density function theory calculations suggested that hypervalent bismuthanes undergo nucleophilic addition with a biomolecule at the bismuth atom to give an intermediate ate complex. For higher antifungal activity, adjusting the lipophilicity-hydrophilicity balance, modeling the three-dimensional molecular structure around the bismuth atom, and stabilizing the ate complex appear to be more important than tuning the Lewis acidity at the bismuth atom.
Reactions of carbonyl compounds with α,β-unsaturated nitriles as a convenient pathway to carbo- and heterocycles

International Nuclear Information System (INIS)

Sharanin, Yu A; Goncharenko, M P; Litvinov, Victor P

1998-01-01

Published data on the methods for synthesis of carbo- and heterocyclic compounds based on reactions of α,β-unsaturated nitriles with carbonyl compounds and activated phenols are surveyed. It is demonstrated that all these reactions occur via nucleophilic addition of the carbanion generated from a carbonyl compound to the double bond of an unsaturated nitrile (the Michael reaction). The main routes of transformation of the adducts into carbo- and heterocyclic compounds are considered. The methods for regioselective preparation of fused 4H-pyrans or 1,4-dihydropyridines by varying conditions of cyclisation of Michael adducts are discussed. The bibliography includes 249 references.
Alkyne hydroarylation with Au N-heterocyclic carbene catalysts

Directory of Open Access Journals (Sweden)

Cristina Tubaro

2013-02-01

Full Text Available Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3. Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.
Synthesis of heterocycle-attached methylidenebenzenesulfonohydrazones as antifungal agents.

Science.gov (United States)

Gao, Zhinan; Lv, Min; Li, Qin; Xu, Hui

2015-11-15

A series of heterocycle-attached methylidenebenzenesulfonohydrazone derivatives were synthesized and evaluated for their antifungal activities against seven phytopathogenic fungi such as Fusarium graminearum, Alternaria solani, Valsa mali, Phytophthora capsici, Fusarium solani, Botrytis cinerea, and Glomerella cingulata. Compounds 7b, 8d, 9a, 9b and 9d exhibited a good and broad-spectrum of antifungal activities against at least five phytopathogenic fungi at the concentration of 100 μg/mL. It demonstrated that addition of one double bond between the phenylsulfonylhydrazone fragment and the furan ring of 6a,b,d could afford more active compounds 9a,b,d; however, introduction of the nitro group on the phenyl ring of 6a-9a gave less potent compounds 6e-9e. Copyright © 2015 Elsevier Ltd. All rights reserved.
Triazole nucleoside derivatives bearing aryl functionalities on the nucleobases show antiviral and anticancer activity.

Science.gov (United States)

Xia, Yi; Qu, Fanqi; Peng, Ling

2010-08-01

Synthetic nucleoside mimics are important candidates in the searing for antiviral and anticancer drugs. Ribavirin, the first antiviral nucleoside drug, is unique in its antiviral activity with mutilple modes of action, which are mainly due to its special triazole heterocycle as nucleobase. Additionally, introducing aromatic functionalities to the nucleobase is able to confer novel mechanisms of action for nucleoside mimics. With the aim to combine the special characteristics of unnatural triazole heterocycles with those of the appended aromatic groups on the nucleobases, novel 1,2,4-triazole nucleoside analogs bearing aromatic moieties were designed and developed. The present short review summarizes the molecular design, chemical synthesis and biological activity of these triazole nucleoside analogs. Indeed, the discovery of antiviral and anticancer activities shown by these triazole nucleosides as well as the new mechanism underlying the biological activity by one of the anticancer leads has validated the rationale for molecular design and impacted us to further explore the concept with the aim of developing structurally novel nucleoside drug candidates with new modes of action.
Microwave-Assisted Multicomponent Synthesis of Heterocycles

NARCIS (Netherlands)

Kruithof, A.; Ruijter, E.; Orru, R.V.A.

2011-01-01

Multicomponent reactions are valuable tools for the generation of diverse heterocycles. As in many fields or organic chemistry, microwave irradiation is rapidly replacing conventional heating methods in multicomponent chemistry. In this review, we present an overview of recent applications of the
Synthesis of heterocycles: Indolo (2,1-a) isoquinolines, renewables, and aptamer ligands for cellular imaging

Energy Technology Data Exchange (ETDEWEB)

Beasley, Jonathan [Ames Laboratory (AMES), Ames, IA (United States)

2013-01-01

In this thesis, we explore both total syntheses and methodologies of several aromatic heterocyclic molecules. Extensions of the Kraus indole synthesis toward 2-substituted and 2,3-disubstituted indoles, as well as biologically attractive indolo[2,1-a]isoquinolines are described. Recent renewable efforts directed to commodity maleic acid and the first reported furan-based ionic liquids are described. Our total synthesis of mRNA aptamer ligand PDC-Gly, and its dye coupled forms, plus aminoglycoside dye coupled ligands used in molecular imaging, are described.
New heterocyclic compounds: Synthesis and antitrypanosomal properties.

Science.gov (United States)

Pomel, S; Dubar, F; Forge, D; Loiseau, P M; Biot, C

2015-08-15

Three new series of quinoline, quinolone, and benzimidazole derivatives were synthesized and evaluated in vitro against Trypanosoma brucei gambiense. In the quinoline series, the metallo antimalarial drug candidate (ferroquine, FQ) and its ruthenium analogue (ruthenoquine, RQ, compound 13) showed the highest in vitro activities with IC50 values around 0.1 μM. Unfortunately, both compounds failed to cure Trypanosoma brucei brucei infected mice in vivo. The other heterocyclic compounds were active in vitro with IC50 values varying from 0.8 to 34 μM. One of the most interesting results was a fluoroquinolone derivative (compound 2) that was able to offer a survival time of 8 days after a treatment at the single dose of 100 μmol/kg by intraperitoneal route. Although no clear-cut structure-activity relationships emerged, further pharmacomodulations are worth to be developed in this series. Copyright © 2015 Elsevier Ltd. All rights reserved.
Dietary exposure to heterocyclic amines in high-temperature cooked meat and fish in Malaysia.

Science.gov (United States)

Jahurul, M H A; Jinap, S; Ang, S J; Abdul-Hamid, A; Hajeb, P; Lioe, H N; Zaidul, I S M

2010-08-01

The intake of heterocyclic amines is influenced by the amount and type of meat and fish ingested, frequency of consumption, cooking methods, cooking temperature, and duration of cooking. In this study, the dietary intake of heterocyclic amines in Malaysia and their main sources were investigated. Forty-two samples of meat and fish were analysed by high-performance liquid chromatography with photodiode array detector to determine the concentration of the six predominant heterocyclic amines, namely: 2-amino-3-methylimidazo[4,5-f] quinoline (IQ), 2-amino-3,4-dimethylimidazo[4,5-f] quinoline(MeIQ), 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline (MeIQx), 2-amino-3,4,8-trimethylimidazo[4,5-f] quinoxaline (4,8-DiMeIQx), 2-amino-3,7,8-trimethylimidazo[4,5-f] quinoxaline (7,8-DiMeIQx), and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP). Dietary intake data were obtained using a food-frequency questionnaire when interviewing 600 Malaysian respondents. The level of total heterocyclic amines in food samples studies ranged from not detected to 38.7 ng g(-1). The average daily intake level of heterocyclic amine was 553.7 ng per capita day(-1). The intake of PhIP was the highest, followed by MeIQx and MeIQ. The results reveal that fried and grilled chicken were the major dietary source of heterocyclic amines in Malaysia. However, the heterocyclic amine intake by the Malaysian population was lower than those reported from other regions.
Synthesis of heterocycles through transition-metal-catalyzed isomerization reactions

DEFF Research Database (Denmark)

Ishøy, Mette; Nielsen, Thomas Eiland

2014-01-01

of structurally complex and diverse heterocycles. In this Concept article, we attempt to cover this area of research through a selection of recent versatile examples. A sea of opportunities! Transition-metal-catalyzed isomerization of N- and O-allylic compounds provides a mild, selective and synthetically...... versatile method to form iminium and oxocarbenium ions. Given the number of reactions involving these highly electrophilic intermediates, this concept provides a sea of opportunities for heterocycle synthesis, (see scheme; Nu=nucleophile). © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim....
Inorganic heterocycles with two manganes or rhenium carbonyl units

International Nuclear Information System (INIS)

Kuellmer, V.; Vahrenkamp, H.

1977-01-01

From the reactive complexes [(CO) 4 M-E-Sn(CH 3 ) 3 ] 2 (M = Mn,Re; E = S,Se) with (CH 3 ) 2 PCl via the non-isolable four-membered ring intermediates [(CO) 4 M-E-P(CH 3 ) 2 ] 2 the six-membered heterocycles[-(CO) 4 M-P(CH 3 ) 2 -E-] 2 are formed. By use of (CH 3 ) 2 AsCl both the four-membered ring intermediates and the six-membered ring products can be isolated. The six-membered heterocycles can be opened by trimethylphosphine. (orig./HK) [de
Synthesis and Characterization of a New Heterocyclic Azo Pigment

International Nuclear Information System (INIS)

Asniza, M.; Issam, A.M.; Khalil, H.P.S.A.

2011-01-01

A new heterocyclic coupling agent has been produced from the reaction of maleic anhydride and p-aminophenol, namely N-(4-hexahydrophenol)maleimide. The coupling agent underwent azo coupling reaction with aromatic amine, which is p-aminophenol to produce a new heterocyclic azo pigment. The pigment was then subjected to solubility, hiding power and light fastness test. Fourier Transform Infrared Spectroscopy (FTIR), Ultraviolet/ Visible (UV/Vis) Spectroscopy, and Nuclear Magnetic Resonance Spectroscopy ( 1 H-NMR, 13 C-NMR) were used to obtain the characteristics and structural features of the pigment. (author)
An exploration on the synthesis and bio-applications of derivatives ...

African Journals Online (AJOL)

Keeping in view of the importance of this organic moiety in the field of medicine and biology here an attempt has been made to review the synthesis and biological importance of heterocyclic Mannich base derivatives. Keywords: Amines, β-amino carbonyl compounds, Biological activity, Heterocyclic Mannich base derivative ...
Isoxazole-type derivatives related to combretastatin A-4, synthesis and biological evaluation.

Science.gov (United States)

Kaffy, Julia; Pontikis, Renée; Carrez, Danièle; Croisy, Alain; Monneret, Claude; Florent, Jean-Claude

2006-06-15

Novel combretastatin analogues bearing various five-membered heterocycles with consecutive oxygen and nitrogen atoms, in place of the olefinic bridge of CA4, have been synthesized (isoxazole, isoxazoline, oxadiazole, etc). These compounds have been evaluated for cytotoxicity and their ability to inhibit the tubulin assembly. On the basis of the relative position of the aromatic A- and B-rings on the heterocyclic moiety, they could be split in two classes, the alpha,gamma- or alpha,beta-diaryl heterocyclic derivatives. In the first series, the 3,5-diaryloxadiazole 9a displayed comparable antitubulin activity to that of CA4, but was devoid of cytotoxic effects. Among the alpha,beta-diaryl heterocyclic derivatives, the 4,5-diarylisoxazole 35 exhibited greater antitubulin activity than that of CA4 (0.75 vs 1.2 microM), but modest antiproliferative activity. These data showed that minor alteration in the chemical structure of the heterocyclic ring and its relative orientation with regard to the two phenyl rings of CA4 could dramatically influence the tubulin binding properties.
Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

Science.gov (United States)

2016-01-01

Summary Multicomponent reactions (MCRs) are one of the most important processes for the preparation of highly functionalized organic compounds in modern synthetic chemistry. As shown in this review, they play an important role in organophosphorus chemistry where phosphorus reagents are used as substrates for the synthesis of a wide range of phosphorylated heterocycles. In this article, an overview about multicomponent reactions used for the synthesis of heterocyclic compounds bearing a phosphonate group on the ring is given. PMID:27559377
Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities.

Science.gov (United States)

Shafi, Syed; Alam, Mohammad Mahboob; Mulakayala, Naveen; Mulakayala, Chaitanya; Vanaja, G; Kalle, Arunasree M; Pallu, Reddanna; Alam, M S

2012-03-01

A focused library of novel bis-heterocycles encompassing 2-mercapto benzothiazole and 1,2,3-triazoles were synthesized using click chemistry approach. The synthesized compounds have been tested for their anti-inflammatory activity by using biochemical cyclooxygenase (COX) activity assays and carrageenan-induced hind paw edema. Among the tested compounds, compound 4d demonstrated a potent selective COX-2 inhibition with COX-2/COX-1 ratio of 0.44. Results from carrageenan-induced hind paw edema showed that compounds 4a, 4d, 4e and 4f posses significant anti-inflammatory activity as compared to the standard drug Ibuprofen. The compounds showing significant activity were further subjected to anti-nociceptive activity by writhing test. These four compounds have shown comparable activity with the standard Ibuprofen. Further ulcerogenic studies shows that none of these compounds causing gastric ulceration. Copyright Â© 2012 Elsevier Masson SAS. All rights reserved.

Novel synthesis and antitumor evaluation of polyfunctionally substituted heterocyclic compounds derived from 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide.

Science.gov (United States)

Shams, Hoda Z; Mohareb, Rafat M; Helal, Maher H; Mahmoud, Amira E

2010-12-27

The reaction of 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene with ethyl cyanoacetate gave 2-cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide. The latter was used to synthesize different heterocyclic derivatives comprising thiophene, thiazole, pyrazole, pyridine, pyrimidine, and coumarin rings. The mechanistic and synthetic pathways depended on regioselective attack and/or cyclization by the cyanoacetamido moiety in the key precursor on various chemical reagents. The competition of the reaction pathways including dipolar cyclization, dinucleophilic-bielectrophilic attack, β-attack, Gewald-type attack, and condensation reactions led to the diversity of the synthesized products. The antitumor activities of the synthesized products were studied and evaluated. Most of the compounds revealed high inhibitory effects when screened in vitro for their antiproliferative activity. Three human cancer cell lines, namely, breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were used in the screening tests. The simplicity of the synthetic procedures which mainly involved one-pot reactions under mild reaction conditions, the convenience of yield production and the diversity of the reactive sites in the produced systems play a valuable role for further heterocyclic transformations and further biological investigations.
Synthesis and catalytic activity of N-heterocyclic silylene (NHSi) cobalt hydride for Kumada coupling reactions.

Science.gov (United States)

Qi, Xinghao; Sun, Hongjian; Li, Xiaoyan; Fuhr, Olaf; Fenske, Dieter

2018-02-20

The electron-rich silylene Co(i) chloride 5 was obtained through the reaction of CoCl(PMe 3 ) 3 with chlorosilylene. Complex 5 reacted with 1,3-siladiazole HSiMe(NCH 2 PPh 2 ) 2 C 6 H 4 to give the silylene Co(iii) hydride 6 through chelate-assisted Si-H activation. To the best of our knowledge, complex 6 is the first example of Co(iii) hydride supported by N-heterocyclic silylene. Complexes 5 and 6 were fully characterized by spectroscopic methods and X-ray diffraction analysis. Complex 6 was used as an efficient precatalyst for Kumada cross-coupling reactions. Compared with the related complex 3 supported by only trimethylphosphine, complex 6 as a catalyst supported by both chlorosilylene and trimethylphosphine exhibits a more efficient performance for the Kumada cross-coupling reactions. A novel catalytic radical mechanism was suggested and experimentally verified. As an intermediate silylene cobalt(ii) chloride 6d was isolated and structurally characterized.
Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes.

Science.gov (United States)

Liu, Tao; Chen, Ling-yan; Sun, Zhihua

2015-11-20

N-heterocyclic carbene borane (NHC-borane) based on a triazole core is demonstrated for the first time to be efficient for reduction of a variety of tert-butanesulfinyl ketimines. Up to 95% yield and up to >99% diastereomeric excess were achieved. NHC-borane exhibited excellent activities that are more efficient than or comparable to commonly used reductive reagents such as NaBH4, NaBH3CN, l-selectride, Ru catalyst, or BH3-THF.
Synthesis and Studies of Sulfur-Containing Heterocyclic Molecules for Molecular Electronics

DEFF Research Database (Denmark)

Mazzanti, Virginia

This work describes the synthesis and studies of sulfur containing π conjugated heterocycles, which are considered interesting motifs in the field of molecular electronics. The first project, which is covered in Chapter 1, concerns the functionalization of tetracycle dibenzo[bc,fg][1,4]dithiapent......This work describes the synthesis and studies of sulfur containing π conjugated heterocycles, which are considered interesting motifs in the field of molecular electronics. The first project, which is covered in Chapter 1, concerns the functionalization of tetracycle dibenzo[bc,fg][1......,4]dithiapentalene (DDP). Attempts to prepare the S-O analog are also discussed. Chapter 2, focuses upon the studies performed on DDP and other sulfur containing π conjugated organic molecules. Organic Field Effect Transistor devices were fabricated and their performances were evaluated. Chapter 3 entails...... the synthesis of dimeric structures of redox active system tetrathiafulvalene (TTF). Molecules with different conjugation pathways bridging two TTFs were synthesized and studied using CV and DPV in order to probe the electronic interaction between these two redox units. The last aspect of this thesis, which...
Heterocyclic cyclohexanone monocarbonyl analogs of curcumin can inhibit the activity of ATP-binding cassette transporters in cancer multidrug resistance.

Science.gov (United States)

Revalde, Jezrael L; Li, Yan; Hawkins, Bill C; Rosengren, Rhonda J; Paxton, James W

2015-02-01

Curcumin (CUR) is a phytochemical that inhibits the xenobiotic ABC efflux transporters implicated in cancer multidrug resistance (MDR), such as P-glycoprotein (P-gp), breast cancer resistance protein (BCRP) and multidrug resistance-associated proteins 1 and 5 (MRP1 and MRP5). The use of CUR in the clinic however, is complicated by its instability and poor pharmacokinetic profile. Monocarbonyl analogs of CUR (MACs) are compounds without CUR's unstable β-diketone moiety and were reported to have improved stability and in vivo disposition. Whether the MACs can be used as MDR reversal agents is less clear, as the absence of a β-diketone may negatively impact transporter inhibition. In this study, we investigated 23 heterocyclic cyclohexanone MACs for inhibitory effects against P-gp, BCRP, MRP1 and MRP5. Using flow cytometry and resistance reversal assays, we found that many of these compounds inhibited the transport activity of the ABC transporters investigated, often with much greater potency than CUR. Overall the analogs were most effective at inhibiting BCRP and we identified three compounds, A12 (2,6-bis((E)-2,5-dimethoxy-benzylidene)cyclohexanone), A13 (2,6-bis((E)-4-hydroxyl-3-methoxybenzylidene)-cyclohexanone) and B11 (3,5-bis((E)-2-fluoro-4,5-dimethoxybenzylidene)-1-methylpiperidin-4-one), as the most promising BCRP inhibitors. These compounds inhibited BCRP activity in a non-cell line, non-substrate-specific manner. Their inhibition occurred by direct transporter interaction rather than modulating protein or cell surface expression. From these results, we concluded that MACs, such as the heterocyclic cyclohexanone analogs in this study, also have potential as MDR reversal agents and may be superior alternatives to the unstable parent compound, CUR. Copyright © 2014 Elsevier Inc. All rights reserved.
Nucleobases in Space: Laboratory Studies of Polycyclic Aromatic Nitrogen Heterocycles

Science.gov (United States)

Elsila, Jamie; Mattioda, Andy; Bernstein, Max; Sandford, Scott; Hudgins, Doug

2005-01-01

Polycyclic Aromatic Nitrogen Heterocycles (PANHs) are heterocyclic aromatics Le., PAHs with carbon atoms replaced by a nitrogen atom. These molecules have been detected in meteorite extracts, and in general these nitrogen heterocycles are of astrobiological interest since this class of molecules include nucleobases, basic components of our nucleic acids. These compounds are predicted to be present in the interstellar medium and in Titan tholin, but have received relatively little attention. We will present spectra and reactions of PANHs, frozen in solid H2O at 12 K, conditions germane to astronomical observations. In contrast to simple PAHs, that do not interact strongly with solid H2O, the nitrogen atoms in PANHs are potentially capable of hydrogen bonding with H20 changing their spectra, complicating their remote detection on the surfaces of icy bodies. Moreover, we have studied the photo-chemistry of these interesting compounds under astrophysical conditions and will use our lab studies to assess a potential interstellar heritage of these compounds in carbonaceous chondrites.
Co(II) and Cd(II) Complexes Derived from Heterocyclic Schiff-Bases: Synthesis, Structural Characterisation, and Biological Activity

Science.gov (United States)

Ahmed, Riyadh M.; Yousif, Enaam I.; Al-Jeboori, Mohamad J.

2013-01-01

New monomeric cobalt and cadmium complexes with Schiff-bases, namely, N′-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]furan-2-carbohydrazide (L1) and N′-[(E)-(3-hydroxy-4-methoxyphenyl)methylidene]thiophene-2-carbohydrazide (L2) are reported. Schiff-base ligands L1 and L2 were derived from condensation of 3-hydroxy-4-methoxybenzaldehyde (iso-vanillin) with furan-2-carboxylic acid hydrazide and thiophene-2-carboxylic acid hydrazide, respectively. Complexes of the general formula [M(L)2]Cl2 (where M = Co(II) or Cd(II), L = L1 or L2) have been obtained from the reaction of the corresponding metal chloride with the ligands. The ligands and their metal complexes were characterised by spectroscopic methods (FTIR, UV-Vis, 1H, and 13C NMR spectra), elemental analysis, metal content, magnetic measurement, and conductance. These studies revealed the formation of four-coordinate complexes in which the geometry about metal ion is tetrahedral. Biological activity of the ligands and their metal complexes against gram positive bacterial strain Bacillus (G+) and gram negative bacteria Pseudomonas (G−) revealed that the metal complexes become less resistive to the microbial activities as compared to the free ligands. PMID:24027449
New heterocyclic compounds from Ranunculus ternatus Thunb.

Science.gov (United States)

Feng, Zi-Ming; Zhan, Zhi-Lai; Yang, Ya-Nan; Jiang, Jian-Shuang; Zhang, Pei-Cheng

2017-10-01

Five new heterocyclic compounds, 5-α-d-fructofuranosylmethyl-furfural (1), 5-β-d-fructofuranosylmethyl-furfural (2), 5-β-d-fructopyranosylmethyl-furfural (3), 4-(2-((2S-2,3-dihydroxypropoxy)methyl)-5-formyl-1H-pyrrol-1-yl)butanoic acid (4), and 3S,4S-4,5,8-trihydroxy-3-(prop-1-en-2-yl)isochroman-1-one (5), were obtained from the root of Ranunculus ternatus Thunb., which is a traditional Chinese anti-tuberculosis medicine. Their structures were elucidated by UV, IR, HRESIMS, NMR data, and the comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Notably, compounds 1-3 are rarely occurring furfural fructosides in natural sources. These heterocyclic compounds could be further studied for the synthetic chemists and pharmacologists due to the source and structural properties. Copyright © 2017 Elsevier Inc. All rights reserved.
Complexes of Th(IV) perchlorates, nitrates and thiocyanates with some heterocyclic bases

International Nuclear Information System (INIS)

Agarwal, R.K.; Srivastava, A.K.; Srivastava, M.; Bhakru, N.; Srivastava, T.N.

1980-01-01

Some Th(IV) perchlorate complexes of heterocyclic bases have been reported previously. Adducts of Th(IV) nitrates and thiocyanates with some heterocyclic N-oxides have been prepared and physico-chemical properties investigated. Comparatively little is known about the complexes of Th(IV) ion with the ligands containing nitrogen atom acting as electron donating centres. In view of this, the adducts of Th(IV) ion with certain nitrogen heterocyclic bases such as pyridine (Py), α-picoline (Pic), 2-amino pyridine (NH 2 Py), 2:4-lutidine (2,4LN), 2:6-lutidine, (2,6LN), quinoline (Q), isoquinoline (Isoq), 2,2'-bipyridine (Bipy) and 1,10-phenanthroline (Phen) were synthesised and characterised by analysis and IR absorption spectra. The results are presented and discussed. (author)
Study of molecular mechanisms of proapoptotic action of novel heterocyclic 4-thiazolidone derivatives

Directory of Open Access Journals (Sweden)

Lesyk R. B.

2012-04-01

Full Text Available Aim. Mechanisms of induction of apoptosis signaling pathways in mammalian tumor cells treated by novel heterocyclic 4-thiazolidones with different side groups were studied. Methods. Annexin V/propidium iodide and DAPI (4',6-diamidino-2-phenylindole staining of cells, Western-blot analysis of specific proteins. Results. 4-Thiazolidone derivatives of various structure possess similar cytotoxic activity in vitro (²Ñ50 = 5 µM, and induce apoptosis in both leukemia (Jurkat, CCRF-CEM and carcinoma (MCF-7, MDA-MD-231 cells. Western-blot analysis of the expression of several proteins of apoptosis signaling showed that the structure of lateral groups of 4-thiazolidones may directly affect biological activity of these proteins in leukemia cells. In particular, compounds Les-3120 (pyrazoline-substituted thiazolidinone and Les-3166 (thiazolidinone-benzothiazole conjugate induced receptor-mediated apoptosis in Jurkat T-leukemia cells. 4-Iminothiazolidinone Les-3372 caused mitochondrial type apoptosis, mediated by AIF protein. Conclusions. Structure-functional relationships between the presence of specific side groups in novel 4-thiazolidones and the signaling apoptotic pathways induced by these compounds have been established. The obtained results allow designing new, «hybrid» compounds which can simultaneously induce more than one apoptotic pathway in tumor cells.
The Depolymerization of Poly(Ethylene Terephthalate) (PET) Using N-Heterocyclic Carbenes from Ionic Liquids

Science.gov (United States)

Kamber, Nahrain E.; Tsujii, Yasuhito; Keets, Kate; Waymouth, Robert M.; Pratt, Russell C.; Nyce, Gregory W.; Hedrick, James L.

2010-01-01

The depolymerization of the plastic polyethylene terephthalate (PET or PETE) is described in this laboratory procedure. The transesterification reaction used to depolymerize PET employs a highly efficient N-heterocyclic carbene catalyst derived from a commercially available imidazolium ionic liquid. N-heterocyclic carbenes are potent nucleophilic…
Removal of selected nitrogenous heterocyclic compounds in biologically pretreated coal gasification wastewater (BPCGW) using the catalytic ozonation process combined with the two-stage membrane bioreactor (MBR).

Science.gov (United States)

Zhu, Hao; Han, Yuxing; Ma, Wencheng; Han, Hongjun; Ma, Weiwei

2017-12-01

Three identical anoxic-aerobic membrane bioreactors (MBRs) were operated in parallel for 300 consecutive days for raw (R 1 ), ozonated (R 2 ) and catalytic ozonated (R 3 ) biologically pretreated coal gasification wastewater (BPCGW) treatment. The results demonstrated that catalytic ozonation process (COP) applied asa pretreatment remarkably improved the performance of the unsatisfactory single MBR. The overall removal efficiencies of COD, NH 3 -N and TN in R 3 were 92.7%, 95.6% and 80.6%, respectively. In addition, typical nitrogenous heterocyclic compounds (NHCs) of quinoline, pyridine and indole were completely removed in the integrated process. Moreover, COP could alter sludge properties and reshape microbial community structure, thus delaying the occurrence of membrane fouling. Finally, the total cost for this integrated process was estimated to be lower than that of single MBR. The results of this study suggest that COP is a good option to enhance pollutants removal and alleviate membrane fouling in the MBR for BPCGW treatment. Copyright © 2017 Elsevier Ltd. All rights reserved.
[Distribution and sources of oxygen and sulfur heterocyclic aromatic compounds in surface soil of Beijing, China].

Science.gov (United States)

He, Guang-Xiu; Zhang, Zhi-Huan; Peng, Xu-Yang; Zhu, Lei; Lu, Ling

2011-11-01

62 surface soil samples were collected from different environmental function zones in Beijing. Sulfur and oxygen heterocyclic aromatic compounds were detected by GC/MS. The objectives of this study were to identify the composition and distribution of these compounds, and discuss their sources. The results showed that the oxygen and sulfur heterocyclic aromatic compounds in the surface soils mainly contained dibenzofuran, methyl- and C2-dibenzofuran series, dibenzothiophene, methyl-, C2- and C3-dibenzothiophene series and benzonaphthothiophene series. The composition and distribution of the oxygen and sulfur heterocyclic aromatic compounds in the surface soil samples varied in the different environmental function zones, of which some factories and the urban area received oxygen and sulfur heterocyclic aromatic compounds most seriously. In Beijing, the degree of contamination by oxygen and sulfur heterocyclic aromatic compounds in the north surface soil was higher than that in the south. There were preferable linear correlations between the concentration of dibenzofuran series and fluorene series, as well as the concentration of dibenzothiophene series and dibenzofuran series. The oxygen and sulfur heterocyclic aromatic compounds in the surface soil were mainly derived from combustion products of oil and coal and direct input of mineral oil, etc. There were some variations in pollution sources of different environmental function zones.
Heterocycles by Transition Metals Catalyzed Intramolecular Cyclization of Acetylene Compounds

International Nuclear Information System (INIS)

Vizer, S.A.; Yerzhanov, K.B.; Dedeshko, E.C.

2003-01-01

Review shows the new strategies in the synthesis of heterocycles, having nitrogen, oxygen and sulfur atoms, via transition metals catalyzed intramolecular cyclization of acetylenic compounds on the data published at the last 30 years, Unsaturated heterocyclic compounds (pyrroles and pyrroline, furans, dihydro furans and benzofurans, indoles and iso-indoles, isoquinolines and isoquinolinones, aurones, iso coumarins and oxazolinone, lactams and lactones with various substitutes in heterocycles) are formed by transition metals, those salts [PdCl 2 , Pd(OAc) 2 , HgCl 2 , Hg(OAc) 2 , Hg(OCOCF 3 ) 2 , AuCl 3 ·2H 2 O, NaAuCl 4 ·2H 2 O, CuI, CuCl], oxides (HgO) and complexes [Pd(OAc) 2 (PPh 3 )2, Pd(PPh 3 ) 4 , PdCl 2 (MeCN) 2 , Pd(OAc ) 2 /TPPTS] catalyzed intramolecular cyclization of acetylenic amines, amides, ethers, alcohols, acids, ketones and βdiketones. More complex hetero polycyclic systems typical for natural alkaloids can to obtain similar. Proposed mechanisms of pyrroles, isoquinolines, iso indoles and indoles, benzofurans and iso coumarins, thiazolopyrimidinones formation are considered. (author)
Sulfamides in the synthesis of heterocyclic compounds

International Nuclear Information System (INIS)

Gazieva, Galina A; Kravchenko, Angelina N; Lebedev, Oleg V

2000-01-01

A comparative analysis of the structures and physicochemical properties of sulfamides and ureas has been performed. New procedures for the synthesis of heterocyclic compounds containing the sulfamide fragment are surveyed and the properties of the resulting compounds are described. The bibliography includes 112 references.
C-N Bond Activation and Ring Opening of a Saturated N-Heterocyclic Carbene by Lateral Alkali-Metal-Mediated Metalation.

Science.gov (United States)

Hernán-Gómez, Alberto; Kennedy, Alan R; Hevia, Eva

2017-06-01

Combining alkali-metal-mediated metalation (AMMM) and N-heterocyclic carbene (NHC) chemistry, a novel C-N bond activation and ring-opening process is described for these increasingly important NHC molecules, which are generally considered robust ancillary ligands. Here, mechanistic investigations on reactions of saturated NHC SIMes (SIMes=[:C{N(2,4,6-Me 3 C 6 H 2 )CH 2 } 2 ]) with Group 1 alkyl bases suggest this destructive process is triggered by lateral metalation of the carbene. Exploiting co-complexation and trans-metal-trapping strategies with lower polarity organometallic reagents (Mg(CH 2 SiMe 3 ) 2 and Al(TMP)iBu 2 ), key intermediates in this process have been isolated and structurally defined. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
-Heterocyclic Carbene Complexes of Mineral Acids

KAUST Repository

Brill, Marcel; Nahra, Fady; Gó mez-Herrera, Alberto; Zinser, Caroline; Cordes, David B.; Slawin, Alexandra M. Z.; Nolan, Steven P.

2016-01-01

We have synthesized and characterized new gold-N-heterocyclic carbene (NHC) complexes derived from the deprotonation of mineral acids. The use of sulfuric acid was a particularly interesting case. These complexes were tested in known gold-catalyzed reactions, such as the hydration of alkynes and the Meyer–Schuster rearrangement. They proved to be highly efficient in both reactions.
-Heterocyclic Carbene Complexes of Mineral Acids

KAUST Repository

Brill, Marcel

2016-11-08

We have synthesized and characterized new gold-N-heterocyclic carbene (NHC) complexes derived from the deprotonation of mineral acids. The use of sulfuric acid was a particularly interesting case. These complexes were tested in known gold-catalyzed reactions, such as the hydration of alkynes and the Meyer–Schuster rearrangement. They proved to be highly efficient in both reactions.
Synthesis and Antibacterial Evaluation of Novel Heterocyclic Compounds Containing a Sulfonamido Moiety

Directory of Open Access Journals (Sweden)

Eman A. El-Bordany

2013-01-01

Full Text Available Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-ylsulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine derivatives to give pyrazole and oxazole derivatives was studied. On the other hand, treatment of the same precursor with urea, thiourea and/or guanidine hydrochloride furnished pyrimidine and thiazine derivatives, respectively. The newly synthesized compounds were tested for antibacterial activity, whereby eight compounds were found to have high activities.
Synthesis and structure-activity relationships of carbohydrazides and 1,3,4-oxadiazole derivatives bearing imidazolidine moiety against the yellow fever and dengue vector, Aedes aegypti

Science.gov (United States)

BACKGROUND: 1,3,4-oxadiazole and imidazolidine rings are important heterocyclic compounds exhibiting a variety of biological activities. In this study, novel compounds with oxadiazole and imidazolidine rings were synthesized from 3-(methylsulfonyl)-2-oxoimidazolidine-1-carbonyl chloride and screened...

Water purification by reverse osmosis using heterocyclic polymer membranes

Science.gov (United States)

Scott, H.

1972-01-01

Pyrrone (polyimidazopyrrolone) polymers are a new class of thermally stable, radiation and chemical resistant aromatic-heterocyclic polymers featuring a greater chemical and mechanical durability than cellulose acetate.
New Approaches for the Synthesis, Cytotoxicity and Toxicity of Heterocyclic Compounds Derived from 2-Cyanomethylbenzo[c]imidazole.

Science.gov (United States)

Mohareb, Rafat M; Mohamed, Abeer A; Abdallah, Amira E M

2016-01-01

The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.
The GR-value deviation from the additivity rule for irradiated systems containing heterocyclic compounds

International Nuclear Information System (INIS)

Nanobashvili, H.M.; Shanidze, G.V.; Khidesheli, G.I.; Panchvidze, M.V.

1988-01-01

The investigation of the low temperature radiolysis of binary systems containing heterocyclic compounds has been carried out. In the systems under study the G R -value deviation from the additivity rule is observed due to the energy transfer processes from matrix molecules. It is shown that heterocyclic compounds are good radioprotectors. (author)
Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications.

Science.gov (United States)

Stępień, Marcin; Gońka, Elżbieta; Żyła, Marika; Sprutta, Natasza

2017-02-22

Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.
Weathering trend characterization of medium-molecular weight polycyclic aromatic disulfur heterocycles by Fourier transform ion cyclotron resonance mass spectrometry.

Science.gov (United States)

Hegazi, Abdelrahman H; Fathalla, Eiman M; Andersson, Jan T

2014-09-01

Different weathering factors act to change petroleum composition once it is spilled into the environment. n-Alkanes, biomarkers, low-molecular weight polyaromatic hydrocarbons and sulfur heterocycles compositional changing in the environment have been extensively studied by different researchers and many parameters have been used for oil source identification and monitoring of weathering and biological degradation processes. In this work, we studied the fate of medium-molecular weight polycyclic aromatic disulfur heterocycles (PAS2Hs), up to ca. 900Da, of artificially weathered Flotta North Sea crude oil by ultra high-resolution Fourier transform ion cyclotron resonance mass spectrometry. It was found that PAS2Hs in studied crude oil having double bond equivalents (DBE) from 5 to 8 with a mass range from ca 316 to 582Da were less influenced even after six months artificial weathering experiment. However, compounds having DBEs 12, 11 and 10 were depleted after two, four and six months weathering, respectively. In addition, DBE 9 series was more susceptible to weathering than those of DBE 7 and 8. Copyright © 2014 Elsevier Ltd. All rights reserved.
GREENER SYNTHESIS OF HETEROCYCLIC COMPOUNDS USING MICROWAVE IRRADIATION

Science.gov (United States)

An introduction of our interest in the microwave-assisted greener synthesis of a variety of heterocyclic compounds will be presented. It involves microwave (MW) exposure of neat reactants (undiluted) catalyzed by the surfaces of recyclable mineral supports, such as alumina, sili...
MICROBIAL DEGRADATION OF NITROGEN, OXYGEN AND SULFUR HETEROCYCLIC COMPOUNDS UNDER ANAEROBIC CONDITIONS: STUDIES WITH AQUIFER SAMPLES

Science.gov (United States)

The potential for anaerobic biodegradation of 12 heterocyclic model compounds was studied. Nine of the model compounds were biotransformed in aquifer slurries under sulfate-reducing or methanogenic conditions. The nitrogen and oxygen heterocyclic compounds were more susceptible t...
Ruthenium sulfoxides structure and reactivity with nitrogen heterocyclic bases

International Nuclear Information System (INIS)

Oliveira, Denise de.

1990-01-01

Ruthenium (II) sulfoxides are compounds of great interest in oxidative catalysis and in chemotherapy. In order to contribute for the understanding of the chemistry and electronic structure of this class of compounds, it has been studied a series of [Ru Cl 2 (S-DMSO) 2 L x ] complexes, where x = 1 (polymeric compounds) or 2 (monomers) and L N-heterocyclic ligands (pyridine, pyrazine and imidazole derivatives). The nature of N-heterocyclic ligand and their coordination are of great relevance to the stability, spectroscopic and electrochemical characteristics of the complexes. The trans-interactions are extremely important in this series, influencing the strength of the Ru(II)-> S-DMSO and Ru(II)-> L π-back donation. The DMSO and L ligands are π-acceptors. The metal-> ligand π-back donation is strengthened when the ligand is trans to chloride, which is π-donor, due to trans-cooperative interactions of the type: π-donor -> Ru(II) π-acceptor. Another interesting aspect in the series of [Ru Cl 2 (S-DMSO) 2 L 2 ] complexes is the occurrence of dissociative equilibria in the solution, due to the existence of three types of ligands. It was observed that the trans-N isomer of 2,6-dimethyl pyrazine derivative undergoes thermal substitution, with preferential liabilization of the N-heterocyclic ligand. Chloride ion is the most inert ligand in this complex. (author). 145 refs., 76 figs., 21 tabs
Greener Synthetic Alternatives to Heterocycles, Nanomaterials and Nanocomposites

Science.gov (United States)

Microwave (MW) expedited reaction of neat reactants or catalyzed by mineral support surfaces, such as alumina, silica, clay, or their ‘doped’ versions, for the rapid one-pot assembly of heterocyclic compounds from in situ generated reactive intermediates via enamines or using hyp...
Synthesis and properties of heterocyclic type I photoinitiators

International Nuclear Information System (INIS)

Liska, R.; Knaus, S.; Wendrinsky, J.

1999-01-01

The synthesis and properties of a series of new heterocyclic hydroxyalkylphenone-analogous photoinitiators (PIs) is described. The PIs are obtained by reaction of aromatic organolithium compounds with nitriles or by Friedel-Craft's-acylation. Preliminary photocalorimetric tests and UV absorption data are included
New heterocycles having double characters; as antimicrobial and surface active agents.

Directory of Open Access Journals (Sweden)

El-Sayed, R.

2004-12-01

Full Text Available Fatty acids isothiocyanate (1 was used as a starting material to synthesize some important heterocycles such as triazoles, oxazoles, thiazoles, benzoxazoles and quinazolines by treating with different types of nucleophiles such as nitrogen nucleophiles, oxygen nucleophiles, and sulfur nucleophiles. The produced compounds were subjected to propylene oxide in different moles (n = 3, 5 and 7 to produce novel groups of nonionic compounds having the double function as antimicrobial and surface active agents which can be used in the manufacturing of drugs, cosmetics, pesticides or can be used as antibacterial and/or antifungal. The physical properties as surface and interfacial tension, cloud point, foaming height, wetting time, emulsification power and the critical micelle concentration (CMC were determined, antimicrobial and biodegradability were also determined.Isocianatos de acidos grasos se utilizaron como material de partida para la síntesis de importantes heterociclos tales como triazoles, oxazoles, thoazoles, benzoxazoles y quinazolinas mediante el tratamiento de los mismos con diferentes tipos de nucleofilos tales como nucleofilos nitrogenados, oxigenados, o azufrados. Los compuestos producidos se trataron con oxido de propileno a diferentes concentraciones molares (n = 3, 5 y 7 para producir nuevos grupos de compuestos no iónicos que tuvieran la doble función de ser compuestos antimicrobianos y agentes de superficie, que se pudieran usar en la fabricación de medicinas, cosméticos, pesticidas o como antibacterianos o antifúngicos. Se determinaron sus propiedades tales como tensión superficial e interfacial, punto de turbidez, altura de espuma, tiempo de mojado, poder de emulsificación y concentración micelar crítica (CMC, asi como sus propiedades antimicrobianas y de degradabilidad.
Structural and spectral comparisons between isomeric benzisothiazole and benzothiazole based aromatic heterocyclic dyes

Science.gov (United States)

Wang, Yin-Ge; Wang, Yue-Hua; Tao, Tao; Qian, Hui-Fen; Huang, Wei

2015-09-01

A pair of isomeric heterocyclic compounds, namely 3-amino-5-nitro-[2,1]-benzisothiazole and 2-amino-6-nitrobenzothiazole, are used as the diazonium components to couple with two N-substituted 4-aminobenzene derivatives. As a result, two pairs of isomeric aromatic heterocyclic azo dyes have been produced and they are structurally and spectrally characterized and compared including single-crystal structures, electronic spectra, solvatochromism and reversible acid-base discoloration, thermal stability and theoretically calculations. It is concluded that both benzisothiazole and benzothiazole based dyes show planar molecular structures and offset π-π stacking interactions, solvatochromism and reversible acid-base discoloration. Furthermore, benzisothiazole based aromatic heterocyclic dyes exhibit higher thermal stability, larger solvatochromic effects and maximum absorption wavelengths than corresponding benzothiazole based ones, which can be explained successfully by the differences of their calculated isomerization energy, dipole moment and molecular band gaps.
Rh(I)-Catalyzed Arylation of Heterocycles via C-H Bond Activation: Expanded Scope Through Mechanistic Insight

Energy Technology Data Exchange (ETDEWEB)

Lewis, Jared; Berman, Ashley; Bergman, Robert; Ellman, Jonathan

2007-07-18

A practical, functional group tolerant method for the Rh-catalyzed direct arylation of a variety of pharmaceutically important azoles with aryl bromides is described. Many of the successful azole and aryl bromide coupling partners are not compatible with methods for the direct arylation of heterocycles using Pd(0) or Cu(I) catalysts. The readily prepared, low molecular weight ligand, Z-1-tert-butyl-2,3,6,7-tetrahydrophosphepine, which coordinates to Rh in a bidentate P-olefin fashion to provide a highly active yet thermally stable arylation catalyst, is essential to the success of this method. By using the tetrafluoroborate salt of the corresponding phosphonium, the reactions can be assembled outside of a glove box without purification of reagents or solvent. The reactions are also conducted in THF or dioxane, which greatly simplifies product isolation relative to most other methods for direct arylation of azoles employing high-boiling amide solvents. The reactions are performed with heating in a microwave reactor to obtain excellent product yields in two hours.
Self-association and infrared spectres of some heterocyclic compounds based on pyrrol in solid state

International Nuclear Information System (INIS)

Mulloev, N.; Nurulloev, M.; Narziev, B.N.

1993-01-01

Present article is devoted to self-association and infrared spectres of some heterocyclic compounds based on pyrrol in solid state. The study results of self-association specified by molecular hydrogen bonds of some heterocyclic compounds based on pyrrol on spectres of infrared absorption of stretching vibrations of N-H group were considered.
Regiospecificity in the heterocyclization of b-oxonitriles to 5-substituted 4-oxothiazolidine derivatives

Directory of Open Access Journals (Sweden)

PETER STEEL

2003-05-01

Full Text Available A study on the regiospecificity of the base-catalyzed reaction of activated b-oxonitriles 1 with diethyl mercaptosuccinate affording the title compounds 3 is reported. Other competitive heterocyclic products, that is 4-oxo-1,3-thiazinanes 4, derivatives of tetrahydrothiophene 5 and/or thiacyclohexane 6 which on the grounds of mechanistic considerations could be formed, were not observed. Spectroscopic and experimental evidence, together with theoretical considerations, provides a reasonable explanation for the observed regiospecificity.
Synthesis and anticancer activity of silver(I)-N-heterocyclic carbene complexes derived from the natural xanthine products caffeine, theophylline and theobromine.

Science.gov (United States)

Mohamed, Heba A; Lake, Benjamin R M; Laing, Thomas; Phillips, Roger M; Willans, Charlotte E

2015-04-28

A new library of silver(I)-N-heterocyclic carbene complexes prepared from the natural products caffeine, theophylline and theobromine is reported. The complexes have been fully characterised using a combination of NMR spectroscopy, mass spectrometry, elemental analysis and X-ray diffraction analysis. Furthermore, the hydrophobicity of the complexes has been measured. The silver(I)-N-heterocyclic carbenes have been evaluated for their antiproliferative properties against a range of cancer cell lines of different histological types, and compared to cisplatin. The data shows different profiles of response when compared to cisplatin in the same panel of cells, indicating a different mechanism of action. Furthermore, it appears that the steric effect of the ligand and the hydrophobicity of the complex both play a role in the chemosensitivity of these compounds, with greater steric bulk and greater hydrophilicity delivering higher cytotoxicity.
Flexible Enantioselectivity of Tryptophanase Attributable to Benzene Ring in Heterocyclic Moiety of D-Tryptophan

Directory of Open Access Journals (Sweden)

Akihiko Shimada

2012-05-01

Full Text Available The invariance principle of enzyme enantioselectivity must be absolute because it is absolutely essential to the homochiral biological world. Most enzymes are strictly enantioselective, and tryptophanase is one of the enzymes with extreme absolute enantioselectivity for L-tryptophan. Contrary to conventional knowledge about the principle, tryptophanase becomes flexible to catalyze D-tryptophan in the presence of diammonium hydrogenphosphate. Since D-amino acids are ordinarily inert or function as inhibitors even though they are bound to the active site, the inhibition behavior of D-tryptophan and several inhibitors involved in this process was examined in terms of kinetics to explain the reason for this flexible enantioselectivity in the presence of diammonium hydrogenphosphate. Diammonium hydrogenphosphate gave tryptophanase a small conformational change so that D-tryptophan could work as a substrate. As opposed to other D-amino acids, D-tryptophan is a very bulky amino acid with a benzene ring in its heterocyclic moiety, and so we suggest that this structural feature makes the catalysis of D-tryptophan degradation possible, consequently leading to the flexible enantioselectivity. The present results not only help to understand the mechanism of enzyme enantioselectivity, but also shed light on the origin of homochirality.
On the radioprotective properties of heterocyclic nitrogenous compounds

International Nuclear Information System (INIS)

Rinaldi, R.; Bernard, Y.

1964-01-01

Continuing their study of the possible radioprotective properties of heterocyclic nitrogenous compounds, the authors study certain derivatives of imidazole and other compounds of similar structure. The results obtained showed: 1 - that the derivatives resulting from the presence in the imidazole ring of the mercapto, methyl, carbonyl, or benzyl groups are inactive: these substitutions appear to destroy the significant radioprotective activity of the imidazole, 2 - that benzimidazole, on the contrary, seems to possess highly interesting properties. The percentage of survivals obtained with mice treated with benzimidazole and exposed to lethal irradiation has encouraged the authors to undertake careful study of this substance, with a view to define optimum activity conditions, and to determine the mechanism responsible for its radioprotective action. Further on and so as to of clarify certain points that might give useful data concerning the mechanisms of action of radioprotective chemicals, in respect of each of the products the authors have studied: a - the action of these bodies on the internal temperature of mice, b - their radioprotective activity in vitro, in a solution of irradiated hemin. (authors) [fr
Comprehensive database of Manufactured Gas Plant tars. Part C. Heterocyclic and hydroxylated polycyclic aromatic hydrocarbons.

Science.gov (United States)

Gallacher, Christopher; Thomas, Russell; Lord, Richard; Kalin, Robert M; Taylor, Chris

2017-08-15

Coal tars are a mixture of organic and inorganic compounds that were by-products from the manufactured gas and coke making industries. The tar compositions varied depending on many factors such as the temperature of production and the type of retort used. For this reason a comprehensive database of the compounds found in different tar types is of value to understand both how their compositions differ and what potential chemical hazards are present. This study focuses on the heterocyclic and hydroxylated compounds present in a database produced from 16 different tars from five different production processes. Samples of coal tar were extracted using accelerated solvent extraction (ASE) and derivatized post-extraction using N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) with 1% trimethylchlorosilane (TMCS). The derivatized samples were analysed using two-dimensional gas chromatography combined with time-of-flight mass spectrometry (GCxGC/TOFMS). A total of 865 heterocyclic compounds and 359 hydroxylated polycyclic aromatic hydrocarbons (PAHs) were detected in 16 tar samples produced by five different processes. The contents of both heterocyclic and hydroxylated PAHs varied greatly with the production process used, with the heterocyclic compounds giving information about the feedstock used. Of the 359 hydroxylated PAHs detected the majority would not have been be detected without the use of derivatization. Coal tars produced using different production processes and feedstocks yielded tars with significantly different heterocyclic and hydroxylated contents. The concentrations of the individual heterocyclic compounds varied greatly even within the different production processes and provided information about the feedstock used to produce the tars. The hydroxylated PAH content of the samples provided important analytical information that would otherwise not have been obtained without the use of derivatization and GCxGC/TOFMS. Copyright © 2017 John Wiley & Sons, Ltd.
A study of ruthenium complexes of some biologically relevant a-N ...

Indian Academy of Sciences (India)

Home; Journals; Journal of Chemical Sciences; Volume 112; Issue 3. A study of ruthenium complexes of some biologically relevant ∙ -N-heterocyclic ... Author Affiliations. P Sengupta1 S Ghosh1. Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta 700 032, India ...

Extended mechanistic aspects on photoinitiated polymerization of 1,6-hexanediol diacrylate by hexaarylbisimidazoles and heterocyclic mercapto compounds.

Science.gov (United States)

Berdzinski, Stefan; Strehmel, Nadine; Lindauer, Heike; Strehmel, Veronika; Strehmel, Bernd

2014-05-01

Chlorine substituted hexaarylbisimidazole (o-Cl-HABI) efficiently initiates radical polymerization of multifunctional acrylic esters in the presence of a heterocyclic mercapto compound if the latter can form its tautomeric thione. Exposure of o-Cl-HABI results in lophyl radicals, which efficiently add to the thione in the first step while the second step releases a highly reactive thiyl radical from this intermediate. LC-MS and CID-MS measurements support this reaction scheme. Furthermore, photo-DSC experiments applying UV light between 320 and 380 nm showed that mercaptotriazole and phenylmercaptotriazole exhibited the best reactivity in the monomer 1,6-hexanediol diacrylate (HDDA) while alkyl substituted mercaptotriazoles showed less reactivity. Change of the triazole heterocycle by mercaptoimidazole resulted in a significant decrease of photoinitiation efficiency. This heterocycle does not form the corresponding thione in HDDA as shown by NMR measurements. Replacement of mercaptotriazole by an alkylthiol leads to a system showing the lowest photoinitiation efficiency in this series. Formation of thione structure in the case of heterocyclic mercapto compounds may cause higher reactivity of the heterocyclic mercapto compounds with the lophyl radical in the monomer chosen.
One-Pot Two-Step Multicomponent Process of Indole and Other Nitrogenous Heterocycles or Amines toward α-Oxo-acetamidines.

Science.gov (United States)

Martinez-Ariza, Guillermo; McConnell, Nicholas; Hulme, Christopher

2016-04-15

A cesium carbonate promoted three-component reaction of N-H containing heterocycles, primary or secondary amines, arylglyoxaldehydes, and anilines is reported. The key step involves a tandem sequence of N-1 addition of a heterocycle or an amine to preformed α-iminoketones, followed by an air- or oxygen-mediated oxidation to form α-oxo-acetamidines. The scope of the reaction is enticingly broad, and this novel methodology is applied toward the synthesis of various polycyclic heterocycles.
Rational Design and Synthesis of Biologically Active Disubstituted 2(3H) Furanones and Pyrrolone Derivatives as Potent and Safer Non Steroidal Anti-inflammatory Agents.

Science.gov (United States)

Khokra, S L; Khan, S A; Choudhary, D; Hasan, S M; Ahmad, A; Husain, Asif

2016-01-01

Furanone and pyrrolone heterocyclic ring system represent important and interesting classes of bioactive compounds. Medicinal chemists use these heterocycyclic moieties as scaffolds in drug design and discovery. A series of 3-arylidene-5-(naphthalene-2-yl)-furan-2(3H)-ones (2a-j) were synthesized by incorporating pharmacophore of COX-2 inhibitor rofecoxib and naphthyl ring of naproxen as potential non steroidal anti-inflammatory agents. These furanone derivatives were subsequently reacted with dry ammonia gas and benzylamine to furnish corresponding 3-arylidene-5-(naphthlen-2-yl)-1H-pyrrol-2(3H)-ones (3a-e) and 3-arylidene-1-benzyl-5- (naphthalene-2-yl)-1H-pyrrol-2(3H)-ones (4a-e), respectively. The newly prepared heterocyclics were screened for their expected in-vivo biological activities including anti-inflammatory, analgesic and ulcerogenic actions in rodents. The COX-2 inhibitory behavior of synthesized compounds was also assessed via automated docking studies. The chemical structure of the synthesized compounds was characterized by using modern spectroscopic techniques. Result of in-vivo pharmacological studies demonstrated that almost all N-Benzyl-pyrrol-2(3H)-ones (4a-e) showed better anti-inflammatory and analgesic activities in comparison with the other two series of furan-2(3H)-ones and pyrrol- 2(3H)-ones. The moldock score value of the tested compounds was found in the range of -116.66 to -170.328 and was better than the standard drug. Among all the synthesized compounds, only nine compounds (2d, 2g, 2h, 3d, 4a, 4b, 4c, 4d and 4e) exhibited potent anti-inflammatory and analgesic activities with significantly reduced gastrointestinal toxicity in various animal models in comparison to standard drug, diclofenac. Therefore, it is recommended to explore the potential of the synthesized compounds as lead candidates for the development of new therapeutic agents.
Dapson in heterocyclic chemistry, part VIII: synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biologically active 1,3-dihydropyridine, chromene and chromenopyridine moieties

Directory of Open Access Journals (Sweden)

Al-Said Mansour S

2012-07-01

Full Text Available Abstract Several new sulfonebiscompounds having a biologically active 1,2-dihydropyridine-2-one 3–19, acrylamide 20, chromene 21, 22 and chromenopyridine 23, 24 moieties were synthesized and evaluated as potential anticancer agents. The structures of the products were confirmed via elemental analyses and spectral data. The screening tests showed that many of the biscompounds obtained exhibited good anticancer activity against human breast cell line (MCF7 comparable to doxorubicin which was used as reference drug. Compounds 11, 17 and 24 showed IC50 values 35.40 μM, 29.86 μM and 30.99 μM, respectively. In order to elucidate the mechanism of action of the synthesized compounds as anticancer agents, docking on the active site of farnesyltransferase and arginine methyltransferase was also performed and good results were obtained.
How does the addition of steric hindrance to a typical N-heterocyclic carbene ligand affect catalytic activity in olefin metathesis?

KAUST Repository

Poater, Albert; Falivene, Laura; Urbina-Blanco, Cé sar A.; Manzini, Simone; Nolan, Steven P.; Cavallo, Luigi

2013-01-01

Density functional theory (DFT) calculations were used to predict and rationalize the effect of the modification of the structure of the prototype 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) N-heterocyclic carbene (NHC) ligand. The modification consists in the substitution of the methyl groups of ortho isopropyl substituent with phenyl groups, and here we plan to describe how such significant changes affect the metal environment and therefore the related catalytic behaviour. Bearing in mind that there is a significant structural difference between both ligands in different olefin metathesis reactions, here by means of DFT we characterize where the NHC ligand plays a more active role and where it is a simple spectator, or at least its modification does not significantly change its catalytic role/performance. © 2013 The Royal Society of Chemistry.
Mn(III)-initiated facile oxygenation of heterocyclic 1,3-dicarbonyl compounds.

Science.gov (United States)

Rahman, Md Taifur; Haque, Md Aminul; Igarashi, Hikaru; Nishino, Hiroshi

2011-11-16

The Mn(III)-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corresponding hydroperoxides and the 10 alcohols, their characterization, and the limitations of the procedure are described. In addition, the mechanism of the hydroperoxidation and the redox decomposition of the hydroperoxides are discussed.
Preparation methods, reactivity and biological importance of 4-thiazolidinones; Metodos de obtencao, reatividade e importancia biologica de 4-tiazolidinonas

Energy Technology Data Exchange (ETDEWEB)

Liesen, Andre P.; Aquino, Thiago M. de; Goes, Alexandre J.S. [Universidade Federal de Pernambuco (UFPE)e, PE (Brazil). Dept. de Antibioticos]. E-mail: ajsg@ufpe.br; Lima, Jose G. de; Faria, Antonio R. de; Alves, Antonio J. [Universidade Federal de Pernambuco (UFPE)e, PE (Brazil). Dept. de Ciencias Farmaceuticas

2008-07-01

Molecules containing the 4-thiazolidinone ring are known to possess a wide range of biological properties including antimicrobial and antiinflammatory activities among others. These compounds can be synthesized by cyclization reactions involving alpha-haloacetic acid or alpha-mercaptoacetic acid and employed in several chemoselective reactions. Comprehensive reviews have been written on 4-thiazolidinones in 1961 by Brown and in 1980 by Singh et al. In the recent literature, some new synthesis methods for 4-thiazolidinone derivatives and several reactions have been reported. These advances warrant to review the chemical and biological properties of compounds with this important heterocycle employed in synthetic organic chemistry and medicinal chemistry (author)
Photoactivation of heterocyclic change-transfer complexes-electrolytes

International Nuclear Information System (INIS)

Studzinskij, O.P.; Ponomareva, R.P.; Proskuryakova, T.V.

1999-01-01

Effect of light on the systems containing of five- or six-number nitrogen-containing heterocycles, molecular iodine and different-nature organic solvents, has been studied by the methods of absorption spectroscopy and electric conductivity measurement. It has been ascertained that in proton-donor solvents the complexes of 1:1 composition are formed with charge transfer, their electric conductivity increasing essentially with photoactivation [ru
Sulfur ylides in the synthesis of heterocyclic and carbocyclic compounds

International Nuclear Information System (INIS)

Lakeev, Sergei N; Maydanova, Irina O; Galin, Fanur Z; Tolstikov, Genrikh A

2001-01-01

Data on the use of sulfonium ylides in the synthesis of carbocyclic and heterocyclic compounds published over the last 15 years are analysed, systematised and generalised. The bibliography includes 139 references.
N,S,O-Heterocycles in Aged Champagne Reserve Wines and Correlation with Free Amino Acid Concentrations.

Science.gov (United States)

Le Menn, Nicolas; Marchand, Stephanie; de Revel, Gilles; Demarville, Dominique; Laborde, Delphine; Marchal, Richard

2017-03-22

Champagne regulations allow winegrowers to stock still wines to compensate for quality shifts in vintages, mainly due to climate variations. According to their technical requirements and house style, Champagne producers use these stored wines in their blends to enhance complexity. The presence of lees and aging at low pH (2.95-3.15), as in Champagne wines, lead to several modifications in wine composition. These conditions, combined with extended aging, result in the required environment for the Maillard chemical reaction, involving aromatic molecules, including sulfur, oxygen, and nitrogen heterocycles (such as thiazole, furan, and pyrazine derivatives), which may have a sensory impact on wine. Some aromatic heterocycles in 50 monovarietal wines aged from 1 to 27 years provided by Veuve Clicquot Ponsardin Champagne house were determined by the SPME-GC-MS method. The most interesting result highlighted a strong correlation between certain heterocycle concentrations and wine age. The second revealed a correlation between heterocyclic compound and free amino acid concentrations measured in the wines, suggesting that these compounds are potential aromatic precursors when wine is aged on lees and, thus, potential key compounds in the bouquet of aged Champagnes. The principal outcome of these assays was to reveal, for the first time, that aromatic heterocycle concentrations in Champagne base wines are correlated with wine age.
Theoretical study of ionization and one-electron oxidation potentials of N-heterocyclic compounds.

Science.gov (United States)

Sviatenko, Liudmyla K; Gorb, Leonid; Hill, Frances C; Leszczynski, Jerzy

2013-05-15

A number of density functionals was utilized to predict gas-phase adiabatic ionization potentials (IPs) for nitrogen-rich heterocyclic compounds. Various solvation models were applied to the calculation of difference in free energies of solvation of oxidized and reduced forms of heterocyclic compounds in acetonitrile (AN) for correct reproduction of their standard oxidation potentials. We developed generally applicable protocols that could successfully predict the gas-phase adiabatic ionization potentials of nitrogen-rich heterocyclic compounds and their standard oxidation potentials in AN. This approach is supported by a MPW1K/6-31+G(d) level of theory which uses SMD(UA0) approximation for estimation of solvation energy of neutral molecules and PCM(UA0) model for ionized ones. The mean absolute derivation (MAD) and root mean square error (RMSE) of the current theoretical models for IP are equal to 0.22 V and 0.26, respectively, and for oxidation potentials MAD = 0.13 V and RMSE = 0.17. Copyright © 2013 Wiley Periodicals, Inc.
Advances in heterocycle synthesis via [3+m]-cycloaddition reactions involving an azaoxyallyl cation as the key intermediate.

Science.gov (United States)

Xuan, Jun; Cao, Xia; Cheng, Xiao

2018-05-17

Heterocyclic compounds are widely found in many natural isolates and medicinally relevant compounds, as well as some fine chemicals. The development of general and efficient methods for the construction of heterocyclic compounds is one of the most important tasks in synthetic organic chemistry. Along these lines, [3+m]-cycloaddition reactions involving in situ generated azaoxyallyl cations as the 3-atom units have emerged as a powerful method for the synthesis of nitrogen-containing heterocycles. In this feature article, we highlight recent advances in this rapidly growing area, mainly focusing on the reaction design as well as the reaction mechanism.
Nitrogen, oxygen or sulfur containing heterocyclic compounds as analgesic drugs used as modulators of the nitroxidative stress.

Science.gov (United States)

Salat, Kinga; Moniczewski, Andrzej; Librowski, Tadeusz

2013-03-01

Numerous lines of evidence suggest that heterocyclic compounds used as analgesic, anti-inflammatory and anti-migraine agents can be potent regulators of the nitroxidative stress and targeting free nitrogen and oxygen radicals is a very promising strategy for future pain management. Both classical analgesics (nonsteroidal anti-inflammatory drugs, opioid drugs) and many analgesic adjuvants, including desipramine, duloxetine, fluoxetine, paroxetine, escitalopram, phenytoin or carbamazepine and α-lipoic acid can modulate the balance between pro-oxidant and antioxidant processes in the mammalian tissues and these properties of drugs such as indomethacin, meloxicam, tenoxicam, valdecoxib or some metabolites of analgesic drugs formed by the activity of tissue peroxidases may contribute to their clinical efficacy and drug-related toxic effects, including gastrointestinal ulcers, hepatic failure, agranulocytosis, aplastic anemia, neutropenia, opiate-induced hyperalgesia and tolerance. The antioxidant capacities of novel heterocyclic compounds, including the compounds acting either by prevention of formation or catalyzed decomposition of peroxynitrite anion (ONOO-), namely the peroxynitrite decomposition catalysts or as superoxide (O2 •-)-scavengers which are the functional mimetics of superoxide dismutase (SOD) enzymes (SODm), as well as the derivatives of 6-nitro-3,4-methylenedioxyphenyl-Nacylhydrazone (LASSBio-881) or γ-butyrolactone (LPP1, BM113, BM113A, BM138 and BM138A) are also discussed as potent and promising future heterocyclic analgesics.
Publishing activities improves undergraduate biology education.

Science.gov (United States)

Smith, Michelle K

2018-06-01

To improve undergraduate biology education, there is an urgent need for biology instructors to publish their innovative active-learning instructional materials in peer-reviewed journals. To do this, instructors can measure student knowledge about a variety of biology concepts, iteratively design activities, explore student learning outcomes and publish the results. Creating a set of well-vetted activities, searchable through a journal interface, saves other instructors time and encourages the use of active-learning instructional practices. For authors, these publications offer new opportunities to collaborate and can provide evidence of a commitment to using active-learning instructional techniques in the classroom.
Mn(III-Initiated Facile Oxygenation of Heterocyclic 1,3-Dicarbonyl Compounds

Directory of Open Access Journals (Sweden)

Md. Aminul Haque

2011-11-01

Full Text Available The Mn(III-initiated aerobic oxidation of heterocyclic 1,3-dicarbonyl compounds, such as 4-alkyl-1,2-diphenylpyrazolidine-3,5-diones, 1,3-dialkylpyrrolidine-2,4-diones, 3-alkyl-1,5-dimethylbarbituric acids, and 3-butyl-4-hydroxy-2-quinolinone gave excellent to good yields of the corresponding hydroperoxides, which were gradually degraded by exposure to the metal initiator after the reaction to afford the corresponding alcohols. The synthesis of 30 heterocyclic 1,3-dicarbonyl compounds, the corresponding hydroperoxides and the 10 alcohols, their characterization, and the limitations of the procedure are described. In addition, the mechanism of the hydroperoxidation and the redox decomposition of the hydroperoxides are discussed.
Nitrogen-rich heterocycles as reactivity retardants in shocked insensitive explosives.

Science.gov (United States)

Manaa, M Riad; Reed, Evan J; Fried, Laurence E; Goldman, Nir

2009-04-22

We report the first quantum-based multiscale simulations to study the reactivity of shocked perfect crystals of the insensitive energetic material triaminotrinitrobenzene (TATB). Tracking chemical transformations of TATB experiencing overdriven shock speeds of 9 km/s for up to 0.43 ns and 10 km/s for up to 0.2 ns reveal high concentrations of nitrogen-rich heterocyclic clusters. Further reactivity of TATB toward the final decomposition products of fluid N(2) and solid carbon is inhibited due to the formation of these heterocycles. Our results thus suggest a new mechanism for carbon-rich explosive materials that precedes the slow diffusion-limited process of forming the bulk solid from carbon clusters and provide fundamental insight at the atomistic level into the long reaction zone of shocked TATB.
Asymmetric Hydrogenation of Seven-Membered C=N-containing Heterocycles and Rationalization of the Enantioselectivity.

Science.gov (United States)

Balakrishna, Bugga; Bauzá, Antonio; Frontera, Antonio; Vidal-Ferran, Anton

2016-07-18

Iridium(I) complexes with phosphine-phosphite ligands efficiently catalyze the enantioselective hydrogenation of diverse seven-membered C=N-containing heterocyclic compounds (eleven examples; up to 97 % ee). The P-OP ligand L3, which incorporates an ortho-diphenyl substituted octahydrobinol phosphite fragment, provided the highest enantioselectivities in the hydrogenation of most of the heterocyclic compounds studied. The observed stereoselection was rationalized by means of DFT calculations. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Greener Alternatives to Expedient Synthesis of Heterocycles and Nanomaterial

Science.gov (United States)

A brief account of reactions involving microwave (MW) exposure of neat reactants or catalyzed by mineral support surfaces, such as alumina, silica, clay, or their ‘doped’ versions, for the rapid one-pot assembly of heterocyclic compounds [1] from in situ generated reactive interm...
Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents.

Science.gov (United States)

Zhao, Shizhen; Zhang, Xiangqian; Wei, Peng; Su, Xin; Zhao, Liyu; Wu, Mengya; Hao, Chenzhou; Liu, Chunchi; Zhao, Dongmei; Cheng, Maosheng

2017-09-08

To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for improving the activity against Aspergillus spp. Among these compounds, 2-F substituted analogues 23g and 23h displayed the most remarkable in vitro activity against Candida spp., C. neoformans, A. fumigatus and fluconazole-resistant C.alb. strains, which is superior or comparable to the activity of the reference drugs fluconazole and voriconazole. Notably, the compounds 23g and 23h exhibited low inhibition profiles for various isoforms of human cytochrome P450 and excellent blood plasma stability. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Preparation, one- and two-photon properties of carbazole derivatives containing nitrogen heterocyclic ring

Science.gov (United States)

Zhang, Yichi; Wang, Ping; Li, Liang; Chen, Zhimin; He, Chunying; Wu, Yiqun

Preparation of recording materials with high two-photon absorption activities is one of the important issues to superhigh- density two-photon absorption (TPA) three-dimensional (3D) optical data storage. In this paper, three new carbazole derivatives containing nitrogen heterocyclic ring with symmetric and asymmetric structures are prepared using ethylene as the π bridge between the carbazole unit and nitrogen heterocyclic ring, namely, 9-butyl-3-(2-(1,8- naphthyridin)vinyl)-carbazole (material 1), 9-butyl-3,6-bis(2-(1,8-naphthyl)vinyl)-carbazole (material 2) and 9-butyl-3,6- bis(2-(quinolin)vinyl)-carbazole (material 3). Their one photon properties including linear absorption spectra, fluorescence emission spectra, and fluorescence quantum yields are studied. The fluorescence excited by 120 fs pulse at 800 nm Ti: sapphire laser operating at 1 kHz repetition rate with different incident powers of 9-butyl-3-(2-(quinolin) vinyl)-carbazole (material 3) was investigated, and two-photon absorption cross-sections has been obtained. It is shown that material 3 containing quinoline rings as electron acceptor with symmetric structure exhibit high two-photon absorption activity. The result implies that material 3 (9-butyl-3-(2-(quinolin) vinyl)-carbazole) is a good candidate as a promising recording material for super-high-density two-photon absorption (TPA) three-dimensional (3D) optical data storage. The influence of chemical structure of the materials on the optical properties is discussed.

Selective Access to Heterocyclic Sulfonamides and Sulfonyl Fluorides via a Parallel Medicinal Chemistry Enabled Method.

Science.gov (United States)

Tucker, Joseph W; Chenard, Lois; Young, Joseph M

2015-11-09

A sulfur-functionalized aminoacrolein derivative is used for the efficient and selective synthesis of heterocyclic sulfonyl chlorides, sulfonyl fluorides, and sulfonamides. The development of a 3-step parallel medicinal chemistry (PMC) protocol for the synthesis of pyrazole-4-sulfonamides effectively demonstrates the utility of this reagent. This reactivity was expanded to provide rapid access to other heterocyclic sulfonyl fluorides, including pyrimidines and pyridines, whose corresponding sulfonyl chlorides lack suitable chemical stability.
Pyrolysis of high-ash sewage sludge in a circulating fluidized bed reactor for production of liquids rich in heterocyclic nitrogenated compounds.

Science.gov (United States)

Zuo, Wu; Jin, Baosheng; Huang, Yaji; Sun, Yu; Li, Rui; Jia, Jiqiang

2013-01-01

A circulating fluidized bed reactor was used for pyrolyzing sewage sludge with a high ash content to produce liquids rich in heterocyclic nitrogenated compounds. GC/MS and FTIR analyses showed that heterocyclic nitrogenated compounds and hydrocarbons made up 38.5-61.21% and 2.24-17.48% of the pyrolysis liquids, respectively. A fluidized gas velocity of 1.13 m/s, a sludge feed rate of 10.78 kg/h and a particle size of 1-2mm promoted heterocyclic nitrogenated compound production. Utilizing heterocyclic nitrogenated compounds as chemical feedstock could be a way for offsetting the cost of sewage sludge treatment. Copyright © 2012 Elsevier Ltd. All rights reserved.
Biological Activities of Hydrazone Derivatives

Directory of Open Access Journals (Sweden)

S. GÃƒÂ¼niz KÃƒÂ¼ÃƒÂ§ÃƒÂ¼kgÃƒÂ¼zel

2007-08-01

Full Text Available There has been considerable interest in the development of novel compounds with anticonvulsant, antidepressant, analgesic, antiinflammatory, antiplatelet, antimalarial, antimicrobial, antimycobacterial, antitumoral, vasodilator, antiviral and antischistosomiasis activities. Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as target structures and evaluated their biological activities. These observations have been guiding for the development of new hydrazones that possess varied biological activities.
N-Heterocyclic Carbene-Catalyzed Olefination of Aldehydes with Vinyliodonium Salts To Generate α,β-Unsaturated Ketones.

Science.gov (United States)

Rajkiewicz, Adam A; Kalek, Marcin

2018-04-06

An organocatalyzed metal-free, direct olefination of aldehydes with vinyliodonium salts has been achieved by an N-heterocyclic carbene-promoted C-H bond activation. The reaction proceeds under very mild conditions, delivering a range of (hetero)aryl-vinyl ketones in good yields. The retention of the double bond configuration is uniformly observed, and the application of 2-methoxyphenyl auxiliary group in iodonium salts secures a complete selectivity of the vinyl transfer.
New synthesis of photocurable silanes and polysiloxanes bearing heterocyclic or olefinic functions

International Nuclear Information System (INIS)

Youssef, B.; Lecamp, L.; Garin, S.; Bunel, C.

1999-01-01

In this work, we described the synthesis of silanes and polysiloxanes bearing cationic photopolymerizable groups. Two new methods were used. The first one is the reaction between 3-mercapto-propyl-1-triethoxysilane (1) and chloromethylated olefins by a phase transfer catalysis. The second one is the radical addition of (1) or poly(dimethylsiloxane-co-methylmercaptopropylsiloxane) (9) to allyl or vinyl substituted heterocyclic monomers. These methods led to the expected adducts with an excellent yield. The polysiloxanes bearing heterocyclic functional groups linked through thioether bonds were photocurable by cationic route. Under UV light intensity of 17.5 mW/cm 2 , these polymers harden after 15 or 20 s
Far IR spectra of Th(IV) halide complexes of some heterocyclic bases

International Nuclear Information System (INIS)

Srivastava, A.K.; Agarwal, R.K.; Srivastava, M.; Kapoor, V.; Srivastava, T.N.

1981-01-01

The synthesis and IR spectra of Th(IV) perchlorato, nitrato and thiocyanato complexes of some heterocyclic bases have been reported. Halogens are common ligands in coordination chemistry forming coordinate bonds with metals readily. Metal halogen (M-X) stretching bands show a strong absorption in the far-IR region. Very little information is available on Th-X stretching frequencies. In the present communication, adducts of Th(IV) halide with certain nitrogen heterocyclic bases such as pyridine, α-picoline, 2-amino pyridine, 2:4-lutidine, 2:6-lutidine, quinoline, 2,2'-bipyridine and 1,10-phenanthroline were synthesised and characterised. Experimental details are given. Results are presented and discussed. (author)
Structure of radicals produced by γ radiolysis. Part 4. Adamantane matrices doped with various 5-membered heterocyclic molecules

International Nuclear Information System (INIS)

Winters, D.L.; Ling, A.C.

1976-01-01

The effects of γ-radiolysis at room temperature on adamantane and adamantane-d 16 matrices doped with 5-membered heterocyclic molecules has been examined by X-band electron spin resonance (esr) spectrometry. Radical structures formed from heterocyclic solute molecules are discussed and tentative assignments made. Discussion of possible radical structures derived from selected heterocyclic compounds is included, but unambiguous assignmens of structure cannot be made for these compounds from the esr data obtained. It was noted that perdeuterated adamantane matrices provided superior resolution for esr spectra derived from radicals with a delocalized spin center such as allyl or allenyl species. (author)
Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes

KAUST Repository

Zhao, Changgui; Guo, Donghui; Munkerup, Kristin; Huang, Kuo-Wei; Li, Fangyi; Wang, Jian

2018-01-01

on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a
Basic deuteroexchange in transition metal complexes with nitrogen-containing aromatic heterocycles

International Nuclear Information System (INIS)

Tupitsyn, I.F.

1986-01-01

Kinetics of deuteroexchange in the methyl group of nitrate complexes of a metal - nickel (2) - with different methyl-substituted aromatic heterocycles and isostructural complexes of a ligand - 2 - methyl quinoline - with different central metal atoms (Mn(2), Ni(2), Cu(2), Zn(2)) is studied. Series for influence of ligand structure on deuteroexchange rate in complexes doesn't correspond qualitatively to series for deuteroexchange rate increase in noncoordinated ligands. Deuteroexchange rate is weakly subjected to influence of exchange in metal-complexing agent. Deuteroexchange mechanism is suggested and discussed. According to this mechanism the structure developed in the course of the exchange process with electron density transfer from the heterocyclic ligand to a metal ion is a transition state of the reaction
Positron annihilation lifetime studies of changes in free volume on some biorelevant nitrogen heterocyclic compounds and their S-glycosylation

International Nuclear Information System (INIS)

Mahmoud, K.R.; Khodair, A.I.; Shaban, S.Y.

2015-01-01

A series of N-heterocyclic compounds was investigated by positron annihilation lifetime spectroscopy as well as Doppler broadening of annihilation radiation (DBAR) at room temperature. The results showed that the formation probability and life time of ortho-positronium in this series are structure and electron-donation character dependent, and can give more information about the structure. The DBAR provides direct information about the change of core and valance electrons as well as the number of defect types present in these compounds. - Highlights: • N-heterocyclic compounds were studied by PALS and DBAR at room temperature. • These compounds contain thiohydantoins which have wide applications as anticarcinogenic, antiviral, human immunodeficiency virus (HIV) and antimicrobial activity. • The DBAR provides direct information about the change of core and valance electrons as well as the number of defect types present in these compounds.
Bent Shaped 1,3,4-Oxadiazole/Thiadiazole heterocyclic rings ...

Indian Academy of Sciences (India)

Two series of bent shaped 1,3,4-oxadiazole/thiadiazole heterocyclic ring containing liquid crystalline (LC) compounds were synthesized and characterized by FT-IR, 1H, 13C-NMR and ESI-Mass spectro-scopic techniques. Liquid crystal properties were investigated by polarized optical microscopy and differential scanning ...
Synthesis, characterization and applications of some novel mordent and heterocyclic disperse dyes on polyester and wool fibers

Directory of Open Access Journals (Sweden)

Hitendra Mangubhai Patel

2012-10-01

Full Text Available The novel mordent and disperse heterocyclic dyes were prepared by coupling of various diazo solution of aromatic amines with 1-[(2-butyl-2,3-dihydrobenzofuran-3-yl]-1-(4-hydroxyphenylmethanone. The resultant mordent and disperse heterocyclic dyes were characterized by elemental analyses, IR and 1H-NMR and 13C-NMR spectral studies. The UV-visible spectral data have also been discussed in terms of structural property relationship. The dyeing assessment of all the mordent and disperse heterocyclic dyes was evaluated on wool and polyester textile fibers. The results of antibacterial studies of chrome pretreated fabrics revealed that the toxicity of mordented dyes against Escherichia coli, Staphylococcus aureus, Salmonella typhi, Bacillus subtilis bacteria was fairly good.
Theoretical NMR spectroscopy of N-heterocyclic carbenes and their metal complexes

KAUST Repository

Falivene, Laura; Cavallo, Luigi

2016-01-01

Recent theoretical analysis of the NMR properties of free N-heterocyclic carbenes (NHC) and Metal-NHC complexes has complemented experiments, allowing the establishment of structure/property relationships and the rationalization of otherwise
Impact of environmental exposures on the mutagenicity/carcinogenicity of heterocyclic amines

Energy Technology Data Exchange (ETDEWEB)

Felton, James S; Knize, Mark G; Bennett, L Michelle; Malfatti, Michael A; Colvin, Michael E; Kulp, Kristen S

2004-05-20

Carcinogenic heterocyclic amines are produced from overcooked foods and are highly mutagenic in most short-term test systems. One of the most abundant of these amines, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), induces breast, colon and prostate tumors in rats. Human dietary epidemiology studies suggest a strong correlation between either meat consumption or well-done muscle meat consumption and cancers of the colon, breast, stomach, lung and esophagus. For over 20 years our laboratory has helped define the human exposure to these dietary carcinogens. In this report we describe how various environmental exposures may modulate the risk from exposure to heterocyclic amines, especially PhIP. To assess the impact of foods on PhIP metabolism in humans, we developed an LC/MS/MS method to analyze the four major PhIP urinary metabolites following the consumption of a single portion of grilled chicken. Adding broccoli to the volunteers' diet altered the kinetics of PhIP metabolism. At the cellular level we have found that PhIP itself stimulates a significant estrogenic response in MCF-7 cells, but even more interestingly, co-incubation of the cells with herbal teas appear to enhance the response. Numerous environmental chemicals found in food or the atmosphere can impact the exposure, metabolism, and cell proliferation response of heterocyclic amines.
Impact of environmental exposures on the mutagenicity/carcinogenicity of heterocyclic amines

International Nuclear Information System (INIS)

Felton, James S.; Knize, Mark G.; Bennett, L. Michelle; Malfatti, Michael A.; Colvin, Michael E.; Kulp, Kristen S.

2004-01-01

Carcinogenic heterocyclic amines are produced from overcooked foods and are highly mutagenic in most short-term test systems. One of the most abundant of these amines, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), induces breast, colon and prostate tumors in rats. Human dietary epidemiology studies suggest a strong correlation between either meat consumption or well-done muscle meat consumption and cancers of the colon, breast, stomach, lung and esophagus. For over 20 years our laboratory has helped define the human exposure to these dietary carcinogens. In this report we describe how various environmental exposures may modulate the risk from exposure to heterocyclic amines, especially PhIP. To assess the impact of foods on PhIP metabolism in humans, we developed an LC/MS/MS method to analyze the four major PhIP urinary metabolites following the consumption of a single portion of grilled chicken. Adding broccoli to the volunteers' diet altered the kinetics of PhIP metabolism. At the cellular level we have found that PhIP itself stimulates a significant estrogenic response in MCF-7 cells, but even more interestingly, co-incubation of the cells with herbal teas appear to enhance the response. Numerous environmental chemicals found in food or the atmosphere can impact the exposure, metabolism, and cell proliferation response of heterocyclic amines
Latent ruthenium–indenylidene catalysts bearing a N-heterocyclic carbene and a bidentate picolinate ligand

Directory of Open Access Journals (Sweden)

Thibault E. Schmid

2015-09-01

Full Text Available A silver-free methodology was developed for the synthesis of unprecedented N-heterocyclic carbene ruthenium indenylidene complexes bearing a bidentate picolinate ligand. The highly stable (SIPr(picolinateRuCl(indenylidene complex 4a (SIPr = 1,3-bis(2-6-diisopropylphenylimidazolidin-2-ylidene demonstrated excellent latent behaviour in ring closing metathesis (RCM reaction and could be activated in the presence of a Brønsted acid. The versatility of the catalyst 4a was subsequently demonstrated in RCM, cross-metathesis (CM and enyne metathesis reactions.
An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

Directory of Open Access Journals (Sweden)

Nikzad Nikbin

2011-04-01

Full Text Available This review presents a comprehensive overview on selected synthetic routes towards commercial drug compounds as published in both journal and patent literature. Owing to the vast number of potential structures, we have concentrated only on those drugs containing five-membered heterocycles and focused principally on the assembly of the heterocyclic core. In order to target the most representative chemical entities the examples discussed have been selected from the top 200 best selling drugs of recent years.
Interpretation of electronic spectra of ruthenium nitroso complexes with N-heterocyclic ligands

International Nuclear Information System (INIS)

Sizova, O.V.; Ivanova, N.V.; Lyubimova, O.O.; Nikol'skij, A.B.

2004-01-01

Relaying on ab initio and semiempirical CINDO/CI calculations of free ligands L and complexes trans-[Ru(NO)(NH 3 ) 4 (L)] 3+ (L=pyridine, pyrazine, nicotinamide, l-histidine, imidazole), electronic absorption spectra of nitroso complexes with nitrogen-containing heterocyclic ligands L have been analyzed. Spectral manifestations of strong covalent bond Ru-NO was pointed out and the conclusion was made about advisability of presentation of Ru and NO oxidation states in grouping RuNO 3+ as Ru(III) and NO 0 . Introduction of nitroso group into inner coordination sphere of Ru(II) complexes with nitrogen-containing heterocyclic ligands results in essential rearrangement of the entire structure and deprives ligands L of their ability to manifest chromophore properties [ru
Genetically modified CHO cells for studying the genotoxicity of heterocyclic amines from cooked foods

International Nuclear Information System (INIS)

Thompson, L.H.; Wu, R.W.; Felton, J.S.

1995-07-01

We have developed metabolically competent CHO cells to evaluate the genotoxicity associated with heterocyclic amines, such as those that are present in cooked foods. Into repair-deficient UV5 cells we introduced cDNAs for expressing cytochrome P450IA2 and acetyltransferases. We then genetically reverted these transformed lines to obtain matched metabolically competent repair-deficient/proficient lines. For a high mutagenic response, we find a requirement for acetyltransferase with IQ but not with PhIP. This system allows for both quantifying mutagenesis and analyzing the mutational spectra produced by heterocyclic amines
A comprehensive evaluation of the toxicology of cigarette ingredients: heterocyclic nitrogen compounds.

Science.gov (United States)

Coggins, Christopher R E; Merski, Jerome A; Oldham, Michael J

2011-06-01

Three heterocyclic nitrogen compounds, 2,3-diethylpyrazine (DEP), 2,3,5,6-tetramethylpyrazine (TMP), and 2-acetyl pyridine (AP), are naturally present in tobacco and are also added to tobacco as flavor ingredients. A battery of tests was used to compare the toxicity of mainstream smoke from experimental cigarettes containing the three heterocyclic nitrogen compounds added individually at three different levels. The lowest target inclusion level of the ingredient was 10 ppm, and the highest was 10,000 ppm. Smoke from experimental and control cigarettes was evaluated in analytical smoke chemistry, in vitro cytotoxicity, and mutagenicity assays. The cigarettes with added DEP produced some minor (approximately 10%) changes in smoke chemistry when compared with the cigarettes containing no DEP. Smoke chemistry was effectively unchanged by the addition of either AP or TMP. Cytotoxicity, assessed by the neutral red uptake assay using both gas-vapor and particulate phases of smoke, was unaffected by the addition of any of the test ingredients. Mutagenicity, assessed in five strains of Salmonella treated with mainstream cigarette smoke condensate, also was unaffected by any of the test ingredients. Despite the exaggerated ingredient levels relative to commercial-use levels, there was a lack of a toxicological response for the three heterocyclic nitrogen compounds in the test systems used.

Anticancer Properties of an Important Drug Lead Podophyllotoxin Can Be Efficiently Mimicked by Diverse Heterocyclic Scaffolds Accessible via One-Step Synthesis

Science.gov (United States)

Magedov, Igor V.; Frolova, Liliya; Manpadi, Madhuri; Bhoga, Uma devi; Tang, Hong; Evdokimov, Nikolai M.; George, Olivia; Georgiou, Kathy Hadje; Renner, Steffen; Getlic, Matthäus; Kinnibrugh, Tiffany L.; Fernandes, Manuel A.; Van slambrouck, Severine; Steelant, Wim F. A.; Shuster, Charles B.; Rogelj, Snezna; van Otterlo, Willem A. L.; Kornienko, Alexander

2011-01-01

Structural simplification of an antimitotic natural product podophyllotoxin with mimetic heterocyclic scaffolds constructed using multicomponent reactions led to the identification of compounds exhibiting low nanomolar antiproliferative and apoptosis-inducing properties. The most potent compounds were found in the dihydropyridopyrazole, dihydropyridonaphthalene, dihydropyridoindole and dihydropyridopyrimidine scaffold series. Biochemical mechanistic studies performed with dihydropyridopyrazole compounds showed that these heterocycles inhibit in vitro tubulin polymerization and disrupt the formation of mitotic spindles in dividing cells at low nanomolar concentrations, in a manner similar to podophyllotoxin itself. Separation of a racemic dihydropyridonaphthalene into individual enantiomers demonstrated that only the optical antipode matching the absolute configuration of podophyllotoxin possessed potent anticancer activity. Computer modeling, performed using the podophyllotoxin binding site on beta-tubulin, provided a theoretical understanding of these successful experimental findings. PMID:21615090
Biological activities of Lavandula angustifolia essential oil

OpenAIRE

Bílková, Zuzana

2013-01-01

Zuzana Bílková, Biological activities of Lavandula angustifolia essential oil, Thesis, Charles University in Prague, Faculty of Pharmacy in Hradec Králové, thesis author: PharmDr. Jan Martin, PhD., Hradec Králové, 2013, 72 pages. The thesis called "Biological activities of Lavandula angustifolia essential oil" is interested in biological activities of Lavandula angustifolia essential oil, specifically antifungal, antioxidant, anti-inflammatory, cytotoxicity, nematicidal and repellency activit...
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

2015-12-10

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.
Synthesis, pharmacological activity evaluation and molecular modeling of new polynuclear heterocyclic compounds containing benzimidazole derivatives.

Science.gov (United States)

Bassyouni, Fatma A; Saleh, Tamer S; ElHefnawi, Mahmoud M; Abd El-Moez, Sherein I; El-Senousy, Waled M; Abdel-Rehim, Mohamed E

2012-12-01

Novel heterocyclic compounds containing benzimidazole derivatives were synthesized from 2-(1H-benzimidazol-2-yl) acetonitrile (1) and arylhydrazononitrile derivative 2 was obtained via coupling of 1 with 4-methyl phenyldiazonium salt, which was then reacted with hydroxylamine hydrochloride to give amidooxime derivative 3. This product was cyclized into the corresponding oxadiazole derivative 4 upon reflux in acetic anhydride. Compound 4 was refluxed in DMF in the presence of triethylamine to give the corresponding 5-(1H-benzimidazol-2-yl)-2-p-tolyl-2H-1,2,3-triazol-4-amine 6. Treatment of compound 6 with ethyl chloroformate afforded 2,6-dihydro-2-(4-methylphenyl)-1,2,3-triazolo[4",5"-4',5']pyrimido[1,6-a]benzimidazole-5(4H)-one (8). 1,2-bis(2-cyanomethyl-1H-benzimidazol-1-yl)ethane-1,2-dione (10) was synthesized via the condensation reaction of 2-(1H-benzimidazol-2-yl) acetonitrile (1) and diethyloxalate. The reactivity of compound 10 towards some diamine reagents was studied. The in vitro antimicrobial activity of the synthesized compounds was investigated against several pathogenic bacterial strains such as Escherichia coli O157, Salmonella typhimurium, E. coli O119, S. paratyphi, Pseudomonas aeruginosa, Staphylococcus aureus, Listeria monocytogenes and Bacillus cereus. The results of MIC revealed that compounds 12a-c showed the most effective antimicrobial activity against tested strains. On the other hand, compounds 12a, b exhibited high activity against rotavirus Wa strain while compounds 12b, c exhibited high activity against adenovirus type 7. In silico target prediction, docking and validation of the compounds 12a-c were performed. The dialkylglycine decarboxylase bacterial enzyme was predicted as a potential bacterial target receptor using pharmacophore-based correspondence with previous leads; giving the highest normalized scores and a high correlation docking score with mean inhibition concentrations. A novel binding mechanism was predicted after docking
Synthesis and characterization of nitrile functionalized silver(I)-N-heterocyclic carbene complexes: DNA binding, cleavage studies, antibacterial properties and mosquitocidal activity against the dengue vector, Aedes albopictus.

Science.gov (United States)

Asekunowo, Patrick O; Haque, Rosenani A; Razali, Mohd R; Avicor, Silas W; Wajidi, Mustafa F F

2018-04-25

A series of four benzimidazolium based nitrile-functionalized mononuclear-Ag(I)-N-heterocyclic carbene and binuclear-Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) hexafluorophosphate complexes (5b-8b) were synthesized by reacting the corresponding hexafluorophosphate salts (1b-4b) with Ag 2 O in acetonitrile, respectively. These compounds were characterized by 1 H NMR, 13 C NMR, IR, UV-visible spectroscopic techniques, elemental analyses and molar conductivity. Additionally, 8b was structurally characterized by single crystal X-ray diffraction technique. Preliminary in vitro antibacterial evaluation was conducted for all the compounds against two standard bacteria; gram-positive (Staphylococcus aureus) and gram-negative (Escherichia coli) bacterial strains. Most of the Ag(I)-NHC complexes (5b-8b) showed moderate to good antibacterial activity with MIC values in the range of 12.5-100 μg/mL. Especially, compound 8b exhibited promising anti-Staphylococcus aureus activity with a low MIC value (12.5 μg/mL). However, all the hexafluorophosphate salts (1b-4b) were inactive against the bacteria strains. The preliminary interactive investigation revealed that the most active compound, 8b, could effectively intercalate into DNA to form 8b-DNA complex which shows a better binding ability for DNA (K b  = 3.627 × 10 6 ) than the complexes 5b-7b (2.177 × 10 6 , 8.672 × 10 5 and 6.665 × 10 5 , respectively). Nuclease activity of the complexes on plasmid DNA and Aedes albopictus genomic DNA was time-dependent, although minimal. The complexes were larvicidal to the mosquito, with 5b, 6b and 8b being highly active. Developmental progression from the larval to the adult stage was affected by the complexes, progressively being toxic to the insect's development with increasing concentration. These indicate the potential use of these complexes as control agents against bacteria and the dengue mosquito Ae. albopictus. Copyright © 2018 Elsevier Masson SAS. All
N-heterocyclic carbene metal complexes as bio-organometallic antimicrobial and anticancer drugs.

Science.gov (United States)

Patil, Siddappa A; Patil, Shivaputra A; Patil, Renukadevi; Keri, Rangappa S; Budagumpi, Srinivasa; Balakrishna, Geetha R; Tacke, Matthias

2015-01-01

Late transition metal complexes that bear N-heterocyclic carbene (NHC) ligands have seen a speedy growth in their use as both, metal-based drug candidates and potentially active homogeneous catalysts in a plethora of C-C and C-N bond forming reactions. This review article focuses on the recent developments and advances in preparation and characterization of NHC-metal complexes (metal: silver, gold, copper, palladium, nickel and ruthenium) and their biomedical applications. Their design, syntheses and characterization have been reviewed and correlated to their antimicrobial and anticancer efficacies. All these initial discoveries help validate the great potential of NHC-metal derivatives as a class of effective antimicrobial and anticancer agents.
Studies of effect of heterocyclic dyes in photogalvanic cells for solar ...

Indian Academy of Sciences (India)

Unknown

Studies of effect of heterocyclic dyes in photogalvanic cells for solar ... observed and current–voltage characteristics of the cell studied, and a mechanism has been proposed for the generation ... dye work effectively in the strong alkaline range.
Elution behavior of N-heterocyclic derivatives of mixed ruthenium(II)-sulfoxide complexes in reversed-phase high-performance liquid chromatography

International Nuclear Information System (INIS)

Toma, H.E.; Silva, D.O.

1991-01-01

The elution behaviour of a series of dichlorobis-(dimethylsulfoxide)bis(N-heterocyclic) ruthenium(II) complexes has been investigated using reversed-phase HPLC. Similar trends as those displayed by the free N-heterocyclic bases have been observed for the complexes, essentially reflecting the hydrophobic properties of the aromatic ligands. (orig.)
High intake of heterocyclic amines from meat is associated with oxidative stress.

Science.gov (United States)

Carvalho, A M; Miranda, A M; Santos, F A; Loureiro, A P M; Fisberg, R M; Marchioni, D M

2015-04-28

High meat intake has been related to chronic diseases such as cancer and CVD. One hypothesis is that heterocyclic amines (HCA), which are formed during the cooking process of meat, can generate reactive species. These compounds can cause oxidation of lipids, proteins and DNA, resulting in oxidative stress, cell damage and loss of biological function. This association has been seen in vitro; however, it remains unclear in vivo. The aim of the present study was to investigate the association between oxidative stress and HCA intake, and oxidative stress and meat intake. Data were from the Health Survey for Sao Paulo--ISA-Capital (561 adult and elderly). Food intake was estimated by one 24-h dietary recall (24HR) complemented by a detailed FFQ with preferences of cooking methods and level of doneness for meat. HCA intake was estimated linking the meat from the 24HR to a database of HCA. Oxidative stress was estimated by malondialdehyde (MDA) concentration in the plasma, after derivatisation with thiobarbituric acid and quantification by HPLC/diode array. Analyses were performed using multivariate logistic regressions adjusted for smoking, sex, age, BMI, skin colour, energy intake, fruit and vegetable intake, and physical activity. A positive association between HCA intake and MDA concentration (OR 1·17; 95% CI 1·01, 1·38) was observed, showing that HCA from meat may contribute to increase oxidative stress, and may consequently increase the risk of chronic diseases.
Brassinosteroids: synthesis and biological activities

Czech Academy of Sciences Publication Activity Database

Oklešťková, Jana; Rárová, Lucie; Kvasnica, Miroslav; Strnad, Miroslav

2015-01-01

Roč. 14, č. 6 (2015), s. 1053-1072 ISSN 1568-7767 R&D Projects: GA MŠk(CZ) LO1204 Institutional support: RVO:61389030 Keywords : Brassinosteroids * Chemical synthesis * Plant biological activity Subject RIV: EB - Genetics ; Molecular Biology Impact factor: 2.686, year: 2015
Toxicity of six heterocyclic nitrogen compounds to Daphnia pulex

Science.gov (United States)

Perry, Cynthia M.; Smith, Stephen B.

1988-01-01

We determined the relative toxicities to the aquatic crustacean Daphniz pulex of six heterocyclic nitrogen compunds. These compounds were selected because they were detected in lake trout or walleyes and were commercially available. Stress to the daphnid populations may affect forage fish populations that depend either directly or indirectly on zooplankton as a food source in the Great Lakes.
N-Heterocyclic carbene functionalized goup 7-9 transition metal

NARCIS (Netherlands)

Aktas, H.; Slootweg, J.C.; Ehlers, A.W.; Lutz, M.; Spek, A.L.; Lammertsma, K.

2009-01-01

The N-heterocyclic carbene (NHC) functionalized phosphinidene complexes [(pCy)(IiPr2Me2)- RudPMes*] (4), [(pCy)(IiPr2Me2)OsdPMes*] (6), and [(Cp*)(IiPr2Me2)RhdPMes*] (7) were generated by a double-dehydrohalogenation-ligation sequence of the corresponding primary phosphine complexes with 3 equiv of
A review exploring biological activities of hydrazones

Directory of Open Access Journals (Sweden)

Garima Verma

2014-01-01

Full Text Available The development of novel compounds, hydrazones has shown that they possess a wide variety of biological activities viz. antimicrobial, anticonvulsant, antidepressant, anti-inflammatory, analgesic, antiplatelet, antimalarial, anticancer, antifungal, antitubercular, antiviral, cardio protective etc., Hydrazones/azomethines/imines possess-NHN = CH- and constitute an important class of compounds for new drug development. A number of researchers have synthesized and evaluated the biological activities of hydrazones. This review aims at highlighting the diverse biological activities of hydrazones.
Synthesis and properties of nitrogenous heterocycles containing a spiro-fused cyclopropane fragment

International Nuclear Information System (INIS)

Tomilov, Yury V; Nefedov, Oleg M; Kostyuchenko, Irina V

2000-01-01

The published data on the methods of synthesis and chemical transformations of nitrogenous heterocyclic compounds spiro-fused with a cyclopropane fragment are described systematically and generalised. The bibliography includes 146 references.
New chiral zwitterionic phosphorus heterocycles: synthesis, structure, properties and application as chiral solvating agents.

Science.gov (United States)

Sheshenev, Andrey E; Boltukhina, Ekaterina V; Grishina, Anastasiya A; Cisařova, Ivana; Lyapkalo, Ilya M; Hii, King Kuok Mimi

2013-06-17

A family of new chiral zwitterionic phosphorus-containing heterocycles (zPHC) have been derived from methylene-bridged bis(imidazolines). These structures were unambiguously determined, including single-crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor-acceptor complexes formed were established by NMR titration methods. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Recyclisation of carbo- and heterocyclic compounds involving malononitrile and its derivatives

International Nuclear Information System (INIS)

Litvinov, Victor P

1999-01-01

Published data on recyclisation reactions of carbo- and heterocycles with participation of malononitrile and recyclisation of compounds containing a malononitrile fragment or fragments with malononitrile as a synthon are surveyed, described systematically and analysed. The bibliography includes 206 references.
Genus Pouteria: chemistry and biological activity

Directory of Open Access Journals (Sweden)

Cíntia A. M. Silva

Full Text Available The genus Pouteria belongs to the family Sapotaceae and can be widely found around the World. These plants have been used as building material, as food, because the eatable fruits, as well as remedies in folk medicine. Some biological activities have been reported to species of this genus such as antioxidant, anti-inflammatory, antibacterial and antifungal. However, the real potential of this genus as source of new drugs or phytomedicines remains unknown. Therefore, a review of the so far known chemical composition and biological activities of this genus is presented to stimulate new studies about the species already reported moreover that species have no reference about chemistry or biological activities could be found until now.
General and efficient one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones from sugar terminal alkynes by Sonogashira/tetra-n- butylammonium permanganate oxidation.

Science.gov (United States)

Zhang, Fuyi; Wu, Xiaopei; Wang, Liming; Liu, Hong; Zhao, Yufen

2015-11-19

A new approach for one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones has been achieved by the reaction of various sugar terminal alkynes with heterocyclic(aryl) iodides at room temperature. This one-pot protocol includes Sonogashira coupling and mild n-Bu4NMnO4 oxidation reaction. This method is mild, general and efficient. Fifty-six examples have been given and the sugar/heterocyclic(aryl) 1,2-diketones were obtained in 71-94% yields. The sugar terminal alkynes include 9 structurally different sugars in pyranose, furanose, and acyclic form which have various protecting groups, sensitive groups, and sterically bulky substituents. The heterocyclic(aryl) iodides include sterically bulky heterocyclic compounds and iodobenzenes with electron-donating, electron-neutral, and electron-withdrawing substituents. Copyright © 2015 Elsevier Ltd. All rights reserved.
Enantioselective [3+3] atroposelective annulation catalyzed by N-heterocyclic carbenes

KAUST Repository

Zhao, Changgui

2018-02-05

Axially chiral molecules are among the most valuable substrates in organic synthesis. They are typically used as chiral ligands or catalysts in asymmetric reactions. Recent progress for the construction of these chiral molecules is mainly focused on the transition-metal-catalyzed transformations. Here, we report the enantioselective NHC-catalyzed (NHC: N-heterocyclic carbenes) atroposelective annulation of cyclic 1,3-diones with ynals. In the presence of NHC precatalyst, base, Lewis acid and oxidant, a catalytic C–C bond formation occurs, providing axially chiral α-pyrone−aryls in moderate to good yields and with high enantioselectivities. Control experiments indicated that alkynyl acyl azoliums, acting as active intermediates, are employed to atroposelectively assemble chiral biaryls and such a methodology may be creatively applied to other useful NHC-catalyzed asymmetric transformations.
Synthesis of boron-containing heterocyclic compounds

International Nuclear Information System (INIS)

Azev, Yuri; Slepukhina, Irina; Gabel, Detlef

2004-01-01

The synthesis of boron-containing 1,3,5-triazines and 1,2,4-triazines is described. Derivatives of 1,3,5-triazine containing the o-carborane cluster have been obtained by reacting the corresponding propargyl derivatives with B 10 H 14 . Derivatives of 1,2,4-triazine containing the B 12 H 12 2- cluster have been obtained by nucleophilic substitution of ethylsulfone derivatives with B 12 H 11 SH 2- . They have been isolated in their ring-protonated form. Reaction of RNH 2 -B 8 H 11 NH-R with stericly demanding heterocycles failed, either for steric or for solubility reasons

Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes.

Science.gov (United States)

Liu, Kai; Zhu, Chenghao; Min, Junxiang; Peng, Shiyong; Xu, Guangyang; Sun, Jiangtao

2015-10-26

A stereodivergent synthesis of five-membered N-heterocycles, such as 2,3-dihydropyrroles, and 2-methylene and 3-methylene pyrrolidines, has been developed through a tandem annulation of amino alkynes with diazo compounds and involves the trapping of in situ formed intermediates. Mechanistic investigations indicate that the copper-catalyzed tandem annulations proceed by allenoate formation and subsequent intramolecular hydroamination. In contrast, the rhodium-catalyzed protocol features a carbenoid insertion into the NH bond and subsequent Conia-ene cyclization. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Ruthenium(III) Complexes of Heterocyclic Tridentate (ONN) Schiff Base: Synthesis, Characterization and its Biological Properties as an Antiradical and Antiproliferative Agent

Science.gov (United States)

Ejidike, Ikechukwu P.; Ajibade, Peter A.

2016-01-01

The current work reports the synthesis, spectroscopic studies, antiradical and antiproliferative properties of four ruthenium(III) complexes of heterocyclic tridentate Schiff base bearing a simple 2′,4′-dihydroxyacetophenone functionality and ethylenediamine as the bridging ligand with RCHO moiety. The reaction of the tridentate ligands with RuCl3·3H2O lead to the formation of neutral complexes of the type [Ru(L)Cl2(H2O)] (where L = tridentate NNO ligands). The compounds were characterized by elemental analysis, UV-vis, conductivity measurements, FTIR spectroscopy and confirmed the proposed octahedral geometry around the Ru ion. The Ru(III) compounds showed antiradical potentials against 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radicals, with DPPH scavenging capability in the order: [(PAEBOD)RuCl2] > [(BZEBOD)RuCl2] > [(MOABOD)RuCl2] > [Vit. C] > [rutin] > [(METBOD)RuCl2], and ABTS radical in the order: [(PAEBOD)RuCl2] < [(MOABOD)RuCl2] < [(BZEBOD)RuCl2] < [(METBOD)RuCl2]. Furthermore, in vitro anti-proliferative activity was investigated against three human cancer cell lines: renal cancer cell (TK-10), melanoma cancer cell (UACC-62) and breast cancer cell (MCF-7) by SRB assay. PMID:26742030
Ruthenium(III Complexes of Heterocyclic Tridentate (ONN Schiff Base: Synthesis, Characterization and its Biological Properties as an Antiradical and Antiproliferative Agent

Directory of Open Access Journals (Sweden)

Ikechukwu P. Ejidike

2016-01-01

Full Text Available The current work reports the synthesis, spectroscopic studies, antiradical and antiproliferative properties of four ruthenium(III complexes of heterocyclic tridentate Schiff base bearing a simple 2′,4′-dihydroxyacetophenone functionality and ethylenediamine as the bridging ligand with RCHO moiety. The reaction of the tridentate ligands with RuCl3·3H2O lead to the formation of neutral complexes of the type [Ru(LCl2(H2O] (where L = tridentate NNO ligands. The compounds were characterized by elemental analysis, UV-vis, conductivity measurements, FTIR spectroscopy and confirmed the proposed octahedral geometry around the Ru ion. The Ru(III compounds showed antiradical potentials against 2,2-Diphenyl-1-Picrylhydrazyl (DPPH and 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid (ABTS radicals, with DPPH scavenging capability in the order: [(PAEBODRuCl2] > [(BZEBODRuCl2] > [(MOABODRuCl2] > [Vit. C] > [rutin] > [(METBODRuCl2], and ABTS radical in the order: [(PAEBODRuCl2] < [(MOABODRuCl2] < [(BZEBODRuCl2] < [(METBODRuCl2]. Furthermore, in vitro anti-proliferative activity was investigated against three human cancer cell lines: renal cancer cell (TK-10, melanoma cancer cell (UACC-62 and breast cancer cell (MCF-7 by SRB assay.
Cyclobutane-Containing Alkaloids: Origin, Synthesis, and Biological Activities

OpenAIRE

Sergeiko, Anastasia; Poroikov, Vladimir V; Hanuš, Lumir O; Dembitsky, Valery M

2008-01-01

Present review describes research on novel natural cyclobutane-containing alkaloids isolated from terrestrial and marine species. More than 60 biological active compounds have been confirmed to have antimicrobial, antibacterial, antitumor, and other activities. The structures, synthesis, origins, and biological activities of a selection of cyclobutane-containing alkaloids are reviewed. With the computer program PASS some additional biological activities are also predicted, which point toward ...
Bis-ligated Ti and Zr complexes of chelating N-heterocyclic carbenes

KAUST Repository

El-Batta, Amer; Waltman, Andrew W.; Grubbs, Robert H.

2011-01-01

In this communication we report the synthesis of novel titanium and zirconium complexes ligated by bidentate "salicylaldimine-like" N-heterocyclic carbenes (NHC). Double addition of the NHC chelate to either TiCl4(thf)2 or ZrCl4 forms bis
Quenching of excited uranyl ion during its photochemical reduction with triphenyl-phosphine : Part IV - effect of heterocyclic molecules

International Nuclear Information System (INIS)

Sidhu, M.S.; Bhatia, P.V.K.

1994-01-01

The presence of heterocyclic compounds triggers off a competition between photophysical and photochemical annihilation of excited uranyl ion during its photochemical reduction with triphenylphosphine. This competition is used to measure Stern-Volmer constant using UV visible spectrophotometer for quenching the uranyl ion luminescence with a number of heterocyclic molecules viz., pyridine, thiophene bipyridyl, tetrahydrofuran and piperidine. (author). 7 refs., 2 figs., 1 tab
Synthesis, characterization and dyeing behavior of heterocyclic acid dyes and mordent acid dyes on wool and silk fabrics

Directory of Open Access Journals (Sweden)

Patel Hitendra M.

2012-01-01

Full Text Available Novel heterocyclic acid and mordent acid dyes were synthesized by the coupling of diazonium salt solution of different aromatic amines with 2- butyl-3-(4-hydroxybenzoylbenzofuran. The resulting heterocyclic acid dyes were characterized by spectral techniques, i.e., elemental analysis, IR, 1HNMR, 13C-NMR spectral studies and UV- visible spectroscopy. The dyeing performance of all the heterocyclic acid dyes was evaluated on wool and silk fabrics. The dyeing of chrome pre treated wool and silk fabrics showed better hues on mordented fabrics. Dyeing of wool and silk fabrics resulted in pinkish blue to red shades with very good depth and levelness. The dyed fabrics showed excellent to very good light, washing, perspiration, sublimation and rubbing fastness.
Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds.

Science.gov (United States)

Nihemaiti, Maolida; Le Roux, Julien; Hoppe-Jones, Christiane; Reckhow, David A; Croué, Jean-Philippe

2017-01-03

The potential formation of nitrogenous disinfection byproducts (N-DBPs) was investigated from the chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production yields. Resorcinol, a major precursor of chloroform, also formed di/trichloroacetonitrile, di/trichloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and fragmentation patterns from electronic impact and positive chemical ionization modes, several products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were structurally similar to the heterocyclic compounds formed during chlorination, such as the highly mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic compounds is reported from chloramination process. The formation of these nitrogenous byproducts during chloramination might be of concern considering their potential toxicity.
Two food-borne heterocyclic amines: Metabolism and DNA adduct formation of amino-alpha-carbolines

DEFF Research Database (Denmark)

Frederiksen, Hanne

2005-01-01

or proteins of animal or vegetable origin, furthermore they are found in many cooked foods, such as fish, meat, and chicken. The specific mutagenicity of the amino-a-carbolines are lower in the Ames Salmonella assay than other heterocyclic amines, but in rodent studies the carcinogenicity of the aminoa, alpha......The amino-alpha-carbolines 2-amino-9H-pyrido[2,3-b]indole (A alpha C) and 2-amino-3-methyl-9H-pyrido-[2,3-b]indole (MeA alpha C) are two mutagenic and carcinogenic heterocyclic amines formed during ordinary cooking. Amino-alpha-carbolines can be formed in model systems by pyrolyzing tryptophan...
Highly selective deuteration of pharmaceutically relevant nitrogen-containing heterocycles: a flow chemistry approach.

Science.gov (United States)

Ötvös, Sándor B; Mándity, István M; Fülöp, Ferenc

2011-08-01

A simple and efficient flow-based technique is reported for the catalytic deuteration of several model nitrogen-containing heterocyclic compounds which are important building blocks of pharmacologically active materials. A continuous flow reactor was used in combination with on-demand pressure-controlled electrolytic D(2) production. The D(2) source was D(2)O, the consumption of which was very low. The experimental set-up allows the fine-tuning of pressure, temperature, and flow rate so as to determine the optimal conditions for the deuteration reactions. The described procedure lacks most of the drawbacks of the conventional batch deuteration techniques, and additionally is highly selective and reproducible.
MICROWAVE IRRADIATION IN BENIGN SYNTHESIS OF HETEROCYCLES, NOBLE NANOMETALS AND NANOCOMPOSITES

Science.gov (United States)

A brief historic account of reactions involving microwave (MW) exposure of neat reactants or catalyzed by mineral support surfaces, such as alumina, silica, clay, or their ‘doped’ versions, for the rapid one-pot assembly of heterocyclic compounds [1] from in situ generated reacti...
Expedient Access to an N -phenylpyrrolidin-2-yl Heterocycle via a ...

African Journals Online (AJOL)

Expedient Access to an N -phenylpyrrolidin-2-yl Heterocycle via a Base-Induced Intramolecular aza -Michael Reaction. ... in good overall yield when employing a stoichiometric amount of base to facilitate the intramolecular aza-Michael reaction. Keywords: aza Michael, intramolecular, catalysed, piperidine, pyrrolidine, base ...
Inhibitory activity of Asian spices on heterocyclic amines formation in cooked beef patties.

Science.gov (United States)

Puangsombat, Kanithaporn; Jirapakkul, Wannee; Smith, J Scott

2011-10-01

Heterocyclic amines (HCAs) are mutagenic compounds formed when foods are cooked at high temperatures. Numerous reports have shown that natural antioxidants from spices, fruits, chocolate, and tea can inhibit formation. In this study, we evaluated HCA formation in the presence of 5 of Asian spices: galangal (Alpinia galangal), fingerroot (Boesenbergia pandurata), turmeric (Curcuma longa), cumin (Cuminum cyminum), and coriander seeds (Coriandrum sativum). HCA levels were compared to patties containing rosemary (Rosmarinus officinalis), of which the inhibitory effect is well documented. Inhibition of HCA formation by the spices was evaluated in beef patties cooked at 204 °C (400 °F) for 10 min. All spices were mixed into patties at 0.2% before cooking, and HCAs levels were measured in the final product. All patties, including the control, contained 2-amino-3,8-dimethylimidazo [4,5-f]quinoxaline (MeIQx) and 2-amino-1-methyl -6-phenylimidazo [4,5-b]pyridine (PhIP). The average HCA content of the control patties was 7 ng/g MeIQx and 6.53 ng/g PhIP. Turmeric (39.2% inhibition), fingerroot (33.5% inhibition), and galangal (18.4% inhibition) significantly decreased HCAs compared with the control. But, only turmeric and fingerroot were as effective as rosemary in preventing HCA formation. The HCA inhibition in patties containing spices was significantly correlated to the total phenolic content (R(2) = 0.80) and the scavenging activity (R(2) = 0.84) of the spices as measured by the 2,2-diphenyl-β-picrylhydrazyl assay. Results of this study suggest that addition of Asian spices can be an important factor in decreasing the levels of HCAs in fried beef patties. © 2011 Institute of Food Technologists®
Synthesis and Biological Activity of 3-[Phenyl(1,3-thiazol-2-yl-amino]propanoic Acids and Their Derivatives

Directory of Open Access Journals (Sweden)

Vytautas Mickevičius

2013-12-01

Full Text Available New N,N-disubstituted β-amino acids and their derivatives with thiazole, aromatic, and heterocyclic substituents were synthesized from N-phenyl-N-thiocarbamoyl-β-alanine by the Hantzsch method; derivatives with hydrazone fragments were also obtained. Some of the synthesized compounds exhibited discrete antimicrobial activity, and 3-[(4-oxo-4,5-dihydro-1,3-thiazol-2-yl(phenylamino]propanoic acid was found to promote rapeseed growth and to increase seed yield and oil content.
Fluoroalkyl Amino Reagents (FARs: A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents

Directory of Open Access Journals (Sweden)

Bruno Commare

2017-06-01

Full Text Available Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS onto heterocycles. In this context, fluoroalkyl amino reagents (FARs—a class of chemicals that was slightly forgotten over the last decades—has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (heteroaromatic derivatives.
Fluoroalkyl Amino Reagents (FARs): A General Approach towards the Synthesis of Heterocyclic Compounds Bearing Emergent Fluorinated Substituents.

Science.gov (United States)

Commare, Bruno; Schmitt, Etienne; Aribi, Fallia; Panossian, Armen; Vors, Jean-Pierre; Pazenok, Sergiy; Leroux, Frédéric R

2017-06-12

Fluorinated heterocycles are important building blocks in pharmaceutical, agrochemical and material sciences. Therefore, organofluorine chemistry has witnessed high interest in the development of efficient methods for the introduction of emergent fluorinated substituents (EFS) onto heterocycles. In this context, fluoroalkyl amino reagents (FARs)-a class of chemicals that was slightly forgotten over the last decades-has emerged again recently and proved to be a powerful tool for the introduction of various fluorinated groups onto (hetero)aromatic derivatives.
Kappa-receptor selective binding of opioid ligands with a heterocyclic bicyclo[3.3.1]nonan-9-one structure.

Science.gov (United States)

Benyhe, S; Márki, A; Nachtsheim, Corina; Holzgrabe, Ulrike; Borsodi, Anna

2003-01-01

Previous pharmacological results have suggested that members of the heterocyclic bicyclo[3.3.1]nonan-9-one-like compounds are potent kappa-opioid receptor specific agonists. One lead molecule of this series. called compound 1 (dimethyl 7-methyl-2,4-di-2-pyridyl-3.7-diazabicyclo[3.3.1]nonan-9-one-1,5-dicarboxylate) exhibited high affinity for [3H]ethylketocyclazocine and [3H]U-69.593 binding sites in guinea pig cerebellar membranes which known to be a good source for kappa1 receptors. It was shown by molecular modelling that heterocyclic bicyclo[3.3.1]nonan-9-ones fit very well with the structure of ketazocine, a prototypic kappa-selective benzomorphan compound; when compared to the arylacetamide structure of U-69.593, a specific kappa1-receptor agonist, a similar geometry was found with a slightly different distribution of the charges. It is postulated, that the essential structural skeleton involved in the opioid activity is an aryl-propyl-amine element distributed along the N7-C6-C5-C4-aryl bonds.
Thermally Stable Heterocyclic Imines as New Potential Nonlinear Optical Materials

Science.gov (United States)

Nesterov, Volodymyr V.; Antipin, Mikhail Y.; Nesterov, Vladimir N.; Moore, Craig E.; Cardelino, Beatriz H.; Timofeeva, Tatiana V.

2004-01-01

In the course of a search for new thermostable acentric nonlinear optical crystalline materials, several heterocyclic imine derivatives were designed, with the general structure D-pi-A(D'). Introduction of a donor amino group (D') into the acceptor moiety was expected to bring H-bonds into their crystal structures, and so to elevate their melting points and assist in an acentric molecular packing. Six heterocycle-containing compounds of this type were prepared, single crystals were grown for five of them, and these crystals were characterized by X-ray analysis. A significant melting temperature elevation was found for all of the synthesized compounds. Three of the compounds were also found to crystallize in acentric space groups. One of the acentric compounds is built as a three-dimensional H-bonded molecular network. In the other two compounds, with very similar molecular structure, the molecules form one-dimensional H-bonded head-to-head associates (chains). These chains are parallel in two different crystallographic directions and form very unusual interpenetrating chain patterns in an acentric crystal. Two of the compounds crystallized with centrosymmetric molecular packing.
Analysis of heterocyclic amines in hair by on-line in-tube solid-phase microextraction coupled with liquid chromatography−tandem mass spectrometry

International Nuclear Information System (INIS)

Kataoka, Hiroyuki; Inoue, Tsutomu; Saito, Keita; Kato, Hisato; Masuda, Kazufumi

2013-01-01

Graphical abstract: Mutagenic and carcinogenic heterocyclic amines are accumulated in the hair of smoker. -- Highlights: •On-line in-tube solid-phase microextraction of heterocyclic amines was optimized. •Fourteen heterocyclic amines were simultaneously determined by LC–MS/MS. •Pico gram levels of heterocyclic amines could be easily analyzed within 15 min. •Heterocyclic amines could be quantitatively analyzed from several milligrams of hair. •The method is useful for the assessment of long-term exposure to heterocyclic amines. -- Abstract: Mutagenic and carcinogenic heterocyclic amines (HCAs) are formed during heating of various proteinaceous foods, but human exposure to HCAs has not yet been elucidated in detail. To assess long-term exposure to HCAs, we developed a simple and sensitive method for measuring HCAs in hair by automated on-line in-tube solid-phase microextraction (SPME) coupled with liquid chromatography–tandem mass spectrometry (LC–MS/MS). Using a Zorbax Eclipse XDB-C8 column, 16 HCAs were analyzed within 15 min. The optimum in-tube SPME conditions were 20 draw/eject cycles of 40 μL sample at a flow rate of 200 μL min −1 using a Supel-Q PLOT capillary column as an extraction device. The extracted HCAs were easily desorbed from the column by passage of the mobile phase, with no carryover observed. This in-tube SPME LC–MS/MS method showed good linearity for HCAs in the range of 10–2000 pg mL −1 , with correlation coefficients above 0.9989 (n = 18), using stable isotope-labeled HCA internal standards. The detection limits (S/N = 3) of 14 HCAs except for MeAαC and Glu-P-1 were 0.10–0.79 pg mL −1 . This method was successfully utilized to analyze 14 HCAs in hair samples without any interference peaks, with quantitative limits (S/N = 10) of about 0.17–1.32 pg mg −1 hair. Using this method, we evaluated the exposure to HCAs in cigarette smoke and the suitability of using hair HCAs as exposure biomarkers
Basic deuteroexchange in complexes of transition metals with nitrogen-containing aromatic heterocycles

International Nuclear Information System (INIS)

Tupitsyn, I.F.

1986-01-01

A study was made of the kinetics of deuteroexchange in the methyl group in complexes of one metal [nickel(II)] with different methyl-substituted aromatic heterocycles and in isostructural complexes of one ligand (2-methylquinoline) with different central metal atoms (Mn 2+ , Ni 2+ , Cu 2+ , Zn 2+ ). The order in which the structures of the ligands influence the rate of deuteroexchange in the complexes does not correspond qualitatively with the order of increase in the rate of deuteroexchange in the noncoordinated ligands. The rate of deuteroexchange is only weakly influenced by change in the identity of the metal complex former. A deuteroexchange mechanism is proposed and discussed. A structure arising in the course of the exchange process with transfer of electron density from the heterocyclic ligand to the metal ion forms the transition state of the reaction

Photolysis of Heterocyclic Lactones in Cryogenic Inert Matrices

International Nuclear Information System (INIS)

Kus, N.

2008-01-01

Heterocyclic lactones receive important uses in organic synthesis and are important biologically active compounds. Their weak toxicity and easy synthesis have made these compounds the subject of great interest and extensive investigation. Since long ago, lactones have been shown to possess an interesting photochemistry. Some representative six- and five-membered conjugated lactones [α-pyrone and some of its derivatives, including coumarin and 3-acetamido coumarin, 2(5H)-furanone] were recently investigated by infrared spectroscopy using the matrix isolation technique and quantum chemical calculations in our laboratories. Two main competitive photochemical reaction pathways could be identified: (i) ring-opening, leading to formation of the isomeric aldehyde-ketene, and (ii) ring-contraction leading to the corresponding Dewar isomers. For α-pyrone and 2(5H)-furanone, the ring-opening process dominates over the ring-contraction reaction, the same occurring for derivatives of these compounds bearing a voluminous substituent at position 3. In 2(5H)-furanone, the ring-opening reaction requires the simultaneous occurrence of a [1,2]-hydrogen atom migration, which was found to occur upon excitation at λ> 235 nm. Under the identical UV-irradiation (λ> 235 nm) of the six-membered analogues, the ring-opening reaction was more efficient in α-pyrone than in coumarin, and factors explaining this observation will be discussed. In turn, the Dewar forms of the studied compounds, resulting from the ring-contraction photoreaction, were found to undergo subsequent photo-elimination of CO 2 , with formation of the corresponding cycloalkenes. In the matrices, CO 2 and the simultaneously formed cycloalkenes were predicted by calculations to exist as associates, in which the CO 2 molecule is preferentially placed over the cycloalkene ring in a stacked-type geometry. For coumarin, a third photoreaction channel was observed, leading to formation of benzofurane and CO. This additional
[Cycloferon biological activity characteristics].

Science.gov (United States)

Utkina, T M; Potekhina, L P; Kartashova, O L; Vasilchenko, A S

2014-01-01

Study the effect of cycloferon in experimental and clinical conditions on persistence properties of aurococci as well as features of their morpho-functional reaction by atomic force microscopy. The study was carried out in 12 Staphylococcus aureus clones isolated from mucous membrane of nose anterior part of a resident carrier. The effect of cycloferon in vivo was evaluated in 26 resident staphylococci carriers under the control of anti-carnosine activity of staphylococci. Anti-carnosine activity was determined by O.V. Bukharin et al. (1999), biofilm formation -by G.A. O'Toole et al. (2000). Staphylococci treated with cycloferon were studied by atomic force microscopy in contact mode using scanning probe SMM-2000 microscope. The decrease of persistence properties of staphylococci under the effect of cycloferon in vitro and in vivo may be examined as one of the mechanisms of biological activity of the preparation. A significant increase of S. aureus surface roughness and changes in their morphology under the effect of cycloferon allow stating the disorder of barrier functions in the aurococci cell wall. The data obtained expand the understanding of cycloferon biological activity mechanisms.
Development and validation of method for heterocyclic compounds in wine: optimization of HS-SPME conditions applying a response surface methodology.

Science.gov (United States)

Burin, Vívian Maria; Marchand, Stéphanie; de Revel, Gilles; Bordignon-Luiz, Marilde T

2013-12-15

Considering the importance of the heterocyclic compounds in terms of wine flavor, this study aims to propose a new rapid and solvent free method to quantify different classes of heterocyclic compounds, such as furans, thiophenes, thiazols and pyrazines, which are products of the Maillard reaction, in wines. The use of a central composite design and the response surface methodology to determine the best conditions allows the optimum combination of analytical variables (pH, NaCl and extraction time) to be identified. The validation was carried out using several types of wine as matrices. The method shows satisfactory repeatability (2.7%heterocyclic compounds were determined, mainly for red wines. © 2013 Elsevier B.V. All rights reserved.
The effect of heterocyclic S,S-ligands on the electrochemical properties of some cobalt(III complexes in acid

Directory of Open Access Journals (Sweden)

V. M. JOVANOVIC

2005-02-01

Full Text Available Eight mixed-ligand cobalt(III complexes with the macrocyclic amine 1,4,8,11-tetraazacyclotetradecane (cyclam and a heterocyclic dithiocarbamate (Rdtc- i.e., morpholine- (Morphdtc, thiomorpholine- (Timdtc, piperazine- (Pzdtc, N-methylpiperazine-(Mepzdtc, piperidine- (Pipdtc, 2-, 3- or 4-methylpiperidine- (2-, 3- and 4-Mepipdtc carbodithionato-S,S ions, of the general formula [Co(cyclamRdtc](ClO42, were investigated in deoxygenated 0.1MHClO4 solutions. Cyclic voltammetry data at a glassy carbon (GC electrode demonstrate a redox reaction of cobalt(III from the complexes at potentials strongly influenced by the presence of different heterocyclic Rdtc- ligands. In this respect, the complexes were separated into two groups: the first, with a heteroatom O, S or N in the heterocyclic ring, and the second, with a methyl group on the piperidine ring of the Rdtc- ligand. Anodic polarization of an Fe electrode in the presence of the complexes shows their influence not only on the dissolution of iron but also on the hydrogen evolution reactions and on this basis complexes the complexes could be divided into the same two groups. It was found that the weaker the inhibiting effect of the free heterocyclic amines is, the significantly higher is the efficiency of the corresponding complexes.
Biotransformation of heterocyclic dinitriles by Rhodococcus erythropolis and fungal nitrilases

Czech Academy of Sciences Publication Activity Database

Vejvoda, Vojtěch; Šveda, Ondřej; Kaplan, Ondřej; Přikrylová, Věra; Elišáková, Veronika; Himl, Michal; Kubáč, David; Pelantová, Helena; Kuzma, Marek; Křen, Vladimír; Martínková, Ludmila

2007-01-01

Roč. 29, č. 7 (2007), s. 1119-1124 ISSN 0141-5492 R&D Projects: GA AV ČR IAA500200708; GA MŠk LC06010; GA MŠk OC D25.001 Institutional research plan: CEZ:AV0Z50200510 Keywords : amidase * arpegillus nniger * heterocyclic Subject RIV: EE - Microbiology, Virology Impact factor: 1.222, year: 2007
Prediction model of biocrude yield and nitrogen heterocyclic compounds analysis by hydrothermal liquefaction of microalgae with model compounds.

Science.gov (United States)

Sheng, Lili; Wang, Xin; Yang, Xiaoyi

2018-01-01

The model of biocrude yield and the nitrogen heterocyclic compounds in biocrude of microalgae hydrothermal liquefaction are two of the most concerned issues in this field at present. This study explored a hydrothermal liquefaction biocrude yield model involved in the interaction among biochemical compounds in microalgae and analysed nitrogen heterocyclic compounds in biocrude. The model compound (castor oil, soya protein and glucose) and Nanochloropsis were liquefied at 280°C for 1h. The products were analyzed by GC-MS, element analysis and FTIR. The results suggested that interactions among different components in microalgae enhanced biocrude yield. The biocrude yield prediction model involved cross-interactions performed more accurate than previous models.When the ratio of protein and carbohydrate around 3, the cross-interaction and nitrogen heterocyclic compounds in biocrude would both reach the highest extent. Copyright © 2017. Published by Elsevier Ltd.
Synthesis and Antibacterial Activity of New Spiro[thiadiazoline-(pyrazolo[3,4-d]pyrimidine] Derivatives

Directory of Open Access Journals (Sweden)

Mohammed El Fal

2015-01-01

Full Text Available New heterocyclic compounds spiroderivatives of allopurinol of biological interest were prepared from allopurinol via thionation and 1,3-dipolar cycloaddition and were produced in high to excellent yields. These compounds were characterized on the basis of spectral and spectroscopic data (1H NMR, 13C, IR, and MS. The antibacterial activity of the synthesized products was studied using bacterial strains: Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, and Pseudomonas aeruginosa. Compounds having an ethyl group showed the best activity with MIC value of 31.25 µg/mL against Staphylococcus aureus and Streptococcus fasciens.
Abiotic synthesis of purines and other heterocyclic compounds by the action of electrical discharges

Science.gov (United States)

Yuasa, S.; Flory, D.; Basile, B.; Oro, J.

1984-01-01

The synthesis of purines and pyrimidines using Oparin-Urey-type primitive earth atmospheres has been demonstrated by reacting methane, ethane, and ammonia in electrical discharges. Adenine, guaine, 4-aminoimidazole-5-carboxamide (AICA), and isocytosine have been identified by UV spectrometry and paper chromatography as the products of the reaction. The total yields of the identified heterocyclic compounds are 0.0023 percent. It is concluded that adenine synthesis occurs at a much lower concentration of hydrogen cyanide than has been shown by earlier studies. Pathways for the synthesis of purines from hydrogen cyanide are discussed, and a comparison of the heterocyclic compounds that have been identified in meteorites and in prebiotic reactions is presented.
Copper- and copper–N-heterocyclic carbene-catalyzed C─H activating carboxylation of terminal alkynes with CO2 at ambient conditions

Science.gov (United States)

Yu, Dingyi; Zhang, Yugen

2010-01-01

The use of carbon dioxide as a renewable and environmentally friendly source of carbon in organic synthesis is a highly attractive approach, but its real world applications remain a great challenge. The major obstacles for commercialization of most current protocols are their low catalytic performances, harsh reaction conditions, and limited substrate scope. It is important to develop new reactions and new protocols for CO2 transformations at mild conditions and in cost-efficient ways. Herein, a copper-catalyzed and copper–N-heterocyclic carbene-cocatalyzed transformation of CO2 to carboxylic acids via C─H bond activation of terminal alkynes with or without base additives is reported. Various propiolic acids were synthesized in good to excellent yields under ambient conditions without consumption of any organometallic or organic reagent additives. This system has a wide scope of substrates and functional group tolerances and provides a powerful tool for the synthesis of highly functionalized propiolic acids. This catalytic system is a simple and economically viable protocol with great potential in practical applications. PMID:21059950
Differential specificity in the glomerular response profiles for alicyclic, bicyclic and heterocyclic odorants

Science.gov (United States)

Johnson, Brett A.; Xu, Zhe; Pancoast, Paige; Kwok, Jennifer; Ong, Joan; Leon, Michael

2008-01-01

As part of our ongoing effort to relate stimulus to response in the olfactory system, we tested the hypothesis that the unique chemical structures and odors of various cyclic odorants would be associated with unique spatial response patterns in the glomerular layer of the rat olfactory bulb. To this end, rats were exposed to sets of odorants including monocyclic hydrocarbons, bicyclic compounds, and various heterocyclic structures containing oxygen or nitrogen in the ring. Relative activity across the entire layer was assessed by mapping uptake of 2-deoxyglucose into anatomically standardized data matrices. Whereas monocyclic hydrocarbons evoked patterns similar to those evoked by open-chained hydrocarbon odorants, a set of bicyclic compounds with structures and odors similar to camphor evoked uptake in paired ventral domains not previously associated with any other odorant chemical structures. Despite their unique odors as judged by humans, heterocyclic odorants either evoked uptake in previously characterized areas corresponding to their functional groups or stimulated weak or patchy patterns involving isolated glomeruli. While the patchiness of the patterns may be partly related to the rigidity of the compounds, which would be expected to restrict their interactions to only a few receptors, the weakness of the patterns suggests the possibility of species-specific odorant representations. We conclude that whereas some of the novel cyclic structures indeed were represented by unique patterns in the rat bulb, other unique structures were poorly represented, even when they evoked intense and unique odors in humans. PMID:16958095
Exploring the novel heterocyclic derivatives as lead molecules for design and development of potent anticancer agents.

Science.gov (United States)

Azad, Iqbal; Nasibullah, Malik; Khan, Tahmeena; Hassan, Firoj; Akhter, Yusuf

2018-05-01

This paper deals with in silico evaluation of newly proposed heterocyclic derivatives in search of potential anticancer activity. Best possible drug candidates have been proposed using a rational approach employing a pipeline of computational techniques namely MetaPrint2D prediction, molinspiration, cheminformatics, Osiris Data warrior, AutoDock and iGEMDOCK. Lazar toxicity prediction, AdmetSAR predictions, and targeted docking studies were also performed. 27 heterocyclic derivatives were selected for bioactivity prediction and drug likeness score on the basis of Lipinski's rule, Viber rule, Ghose filter, leadlikeness and Pan Assay Interference Compounds (PAINS) rule. Bufuralol, Sunitinib, and Doxorubicin were selected as reference standard drug for the comparison of molecular descriptors and docking. Bufuralol is a known non-selective adreno-receptor blocking agent. Studies showed that beta blockers are also used against different types of cancers. Sunitinib is well known Food and Drug administration (FDA) approved pyrrole containing tyrosine kinase inhibitor and our proposed molecules possess similarities with both drug and doxorubicin is another moiety having anticancer activity. All heterocyclic derivatives were found to obey the drug filters except standard drug Doxorubicin. Bioactivity score of the compounds was predicted for drug targets including enzymes, nuclear receptors, kinase inhibitors, G protein-coupled receptor (GPCR) ligands and ion channel modulators. Absorption, distribution, metabolism and toxicity (ADMET) prediction of all proposed compound showed good Blood-brain barrier (BBB) penetration, Human intestinal absorption (HIA), Caco-2 cell permeability except compound-11 and was found to have no AdmetSAR toxicity as well as carcinogenic effect. Compounds 1-9 were slightly mutagenic while compound 2, 11, 20 and 21 showed carcinogenic effect according to Lazar toxicity prediction. Rests of the compounds were predicted to have no side effect
Design, synthesis, and biological testing of thiosalicylamides as a novel class of calcium channel blockers.

Science.gov (United States)

Mehanna, Ahmed S; Kim, Jin Yung

2005-07-01

The current research aimed to investigate the importance of the heterocyclic ring system in the structure of the cardiovascular drug diltiazem for its calcium channel blocking activity. The manuscript describes the design, synthesis, and biological testing of a total of 10 S-(p-methoxybenzyl), N-substituted thiosalicylamides as a series of non-cyclic compounds derived from diltiazem's structure. The new compounds maintained all diltiazem pharmacophores except the thiazepine ring system. In vitro evaluation of the new series for calcium channel blocking effects revealed moderate activities with IC50 values in the range of 4.8-56.0 microM. The data suggest that the ring system is not essential for activity; however, its absence leads to a considerable drop of activity relative to that of diltiazem (IC50=0.3 microM). Compounds of the current series showed optimum activity when the aliphatic alkyl chain on the salicylamide nitrogen is part of a piperidine or piperazine ring system substituted at the terminal nitrogen with a benzyl group.
Synthesis, anticancer activity and molecular docking studies on a series of heterocyclic trans-cyanocombretastatin analogues as antitubulin agents.

Science.gov (United States)

Penthala, Narsimha Reddy; Zong, Hongliang; Ketkar, Amit; Madadi, Nikhil Reddy; Janganati, Venumadav; Eoff, Robert L; Guzman, Monica L; Crooks, Peter A

2015-03-06

A series of heterocyclic combretastatin analogues have been synthesized and evaluated for their anticancer activity against a panel of 60 human cancer cell lines. The most potent compounds were two 3,4,5-trimethoxy phenyl analogues containing either an (Z)-indol-2-yl (8) or (Z)-benzo[b]furan-2-yl (12) moiety; these compounds exhibited GI50 values of Compounds 8, and 12 and two previously reported compounds in the same structural class, i.e. 29 and 31, also showed potent anti-leukemic activity against leukemia MV4-11 cell lines with LD50 values = 44 nM, 47 nM, 18 nM, and 180 nM, respectively. From the NCI anti-cancer screening results and the data from the in vitro toxicity screening on cultured AML cells, seven compounds: 8, 12, 21, 23, 25, 29 and 31 were screened for their in vitro inhibitory activity on tubulin polymerization in MV4-11 AML cells; at 50 nM, 8 and 29 inhibited polymerization of tubulin by >50%. The binding modes of the three most active compounds (8, 12 and 29) to tubulin were also investigated utilizing molecular docking studies. All three molecules were observed to bind in the same hydrophobic pocket at the interface of α- and β-tubulin that is occupied by colchicine, and were stabilized by van der Waals' interactions with surrounding tubulin residues. The results from the tubulin polymerization and molecular docking studies indicate that compounds 8 and 29 are the most potent anti-leukemic compounds in this structural class, and are considered lead compounds for further development as anti-leukemic drugs. Copyright © 2015 Elsevier Masson SAS. All rights reserved.
Componentes voláteis do café torrado. Parte I: compostos heterocíclicos Volatile components in roasted coffee. Part I: heterocyclic compounds

Directory of Open Access Journals (Sweden)

Carlos Alberto Bastos De Maria

1999-04-01

Full Text Available A review of heterocyclic compounds in roasted coffee is presented. The contents, precursors and sensorial properties of furans, pyrroles, oxazoles, thiazoles, thiophenes, pyrazines and pyridines are discussed. The impact heterocyclic compounds of coffee aroma are described.
Polar and non-polar heterocyclic amines in cooked fish and meat products and their corresponding pan residues.

Science.gov (United States)

Skog, K; Augustsson, K; Steineck, G; Stenberg, M; Jägerstad, M

1997-06-01

Fourteen cooked dishes with their corresponding pan residues were analysed for polar and non-polar heterocyclic amines using HPLC. The choice of foods, including beef, pork, poultry, game, fish, egg and sausages, was based on an investigation of an elderly population in Stockholm participating in an analytical epidemiological case-control study on cancer risks after intake of heterocyclic amines. The food items were prepared using normal household cooking practices, and to reflect the wide range of surface browning of the cooked dishes that would be encountered in this population, four cooking temperatures were used in the range 150-225 degrees C. For all food samples, the total amount of heterocyclic amines formed at 150 degrees C was less than 1 ng/g cooked product, and at 175 degrees C less than 2 ng/g. The highest concentrations of heterocyclic amines were detected in fillet of pork, reindeer meat and chicken breast fried at 200 and 225 degrees C and their corresponding pan residues. The total sum of 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline, 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine was about 1 microgram per 100 g portion (including pan residues) for reindeer meat and chicken breast, and between 1.9 and 6.3 micrograms per 100-g portion for fillet of pork. PhIP was the most abundant heterocyclic amine, identified in 73 of 84 samples, and the highest concentration of PhIP, 32.0 ng/g, was found in the pan residue from fillet of pork cooked at 225 degrees C. The non-polar heterocyclic amines 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole and 3-amino-1-methyl-5H-pyrido[4,3-b]indole were detected in the range of 0.5-7.4 ng/g in most foods cooked at 225 degrees C, and also in meat sauce prepared at 200 and 175 degrees C. The other heterocyclic amines tested for: 2-amino-3-methylimidazo-[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, 2-amino-6-methyl-pyrido-[1,2-a:3',2'-d]-imidazole and 2
Greener Synthesis of N-Heterocycles via Sustainable Applications of Nano-Catalysts

Science.gov (United States)

A brief historic account of reactions involving microwave (MW) exposure of neat reactants or catalysis by mineral surfaces, such as alumina, silica, clay, or their ‘doped’ versions, for the rapid one-pot assembly of heterocyclic compounds from in situ generated reactive intermedi...
Reaction of vanadocene and its monochloride with salts of nitrogen-containing heterocycles

International Nuclear Information System (INIS)

Gordetsov, A.S.; Pereshein, V.V.; Lyatyaeva, V.N.; Mar'in, V.P.; Rukevich, OS.; Zakharova, E.S.

1985-01-01

The reaction of bis(eta 5 -cyclopentadienyl) vanadium (Cp 2 V) and its monochloride with diallyl isocyanurates of Ag and alkali metals and with Ag salt of succinimide is used for preparing almost inaccessible Cp 2 V-substituted nitrogen-containing heterocycles. The reactions have been performed in toluene in an evacuated ampoule at room temperature and at 120-130 deg C in case of diallyl isocyanurates of alkali metals. Reaction yields element analysis data, DTA, IR spectra and ESR spectra. Cp 2 V easily reduces Ag from its salts with nitrogen-containing heterocycles oxidizing with production of V(3) sandwich derivatives In exchange reactions of Cp 2 VCl with diallyl isocyanurate salts of alkali metals and silver Cp 2 V-diallyl isocyanurate with an oxo-structure is prosduced as well. The produced AgCl subsequently oxidizers Cp 2 VCl up to Cp 2 VCl 2
Sorption of Heterocyclic Organic Compounds to Multiwalled Carbon Nanotubes.

Science.gov (United States)

Metzelder, Florian; Funck, Matin; Schmidt, Torsten C

2018-01-16

Sorption is an important natural and technical process. Sorption coefficients are typically determined in batch experiments, but this may be challenging for weakly sorbing compounds. An alternative method enabling analysis of those compounds is column chromatography. A column packed with the sorbent is used and sorption data are determined by relating sorbate retention to that of a nonretarded tracer. In this study, column chromatography was applied for the first time to study sorption of previously hardly investigated heterocyclic organic compounds to multiwalled carbon nanotubes (MWCNTs). Sorption data for these compounds are very limited in literature, and weak sorption is expected from predictions. Deuterium oxide was used as nonretarded tracer. Sorption isotherms were well described by the Freundlich model and data showed reasonable agreement with predicted values. Sorption was exothermic and physisorption was observed. H-bonding may contribute to overall sorption, which is supported by reduced sorption with increasing ionic strength due to blocking of functional groups. Lowering pH reduced sorption of ionizable compounds, due to electrostatic repulsion at pH 3 where sorbent as well as sorbates were positively charged. Overall, column chromatography was successfully used to study sorption of heterocyclic compounds to MWCNTs and could be applied for other carbon-based sorbents.
N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II-PYRIDINE (PEPPSI COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION

Directory of Open Access Journals (Sweden)

Rukiye Fırıncı

2016-08-01

Full Text Available A series of N-butyl substituted imidazolium salts, (1a-c and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI themed palladium N-heterocyclic carbene complexes (2a-c were synthesized and characterized. Pd-NHC complexes were fully determined by elemental analysis and spectroscopic. The synthesized complexes were tested in Suzuki-Miyaura cross-coupling reaction. These complexes were found to be efficient catalysts for the Suzuki-Miyaura reaction of phenylboronic acid with aryl bromides.
Synthesis and structure-activity relationships of constrained heterocyclic analogues of combretastatin A4.

Science.gov (United States)

Arthuis, Martin; Pontikis, Renée; Chabot, Guy G; Seguin, Johanne; Quentin, Lionel; Bourg, Stéphane; Morin-Allory, Luc; Florent, Jean-Claude

2011-09-05

A series of combretastatin A4 (CA4) analogues with a lactam or lactone ring fused to the trimethoxyphenyl or the B-phenyl moiety were synthesized in an efficient and stereoselective manner by using a domino Heck-Suzuki-Miyaura coupling reaction. The vascular-disrupting potential of these conformationally restricted CA4 analogues was assessed by various in vitro assays: inhibition of tubulin polymerization, modification of endothelial cell morphology, and disruption of endothelial cell cords. Compounds were also evaluated for their growth inhibitory effects against murine and human tumor cells. B-ring-constrained derivatives that contain an oxindole ring (in contrast to compounds with a benzofuranone ring) as well as analogues bearing a six-membered lactone core fused to the trimethoxyphenyl ring are endowed with significant biological activity. The most potent compound of this series (oxindole 9 b) is of particular interest, as it combines chemical stability and a biological activity profile characteristic of a vascular-disrupting agent. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Cationic bis-N-heterocyclic carbene (NHC) ruthenium complex: Structure and application as latent catalyst in olefin metathesis

KAUST Repository

Rouen, Mathieu

2014-09-11

An unexpected cationic bis-N-heterocyclic carbene (NHC) benzylidene ether based ruthenium complex (2 a) was prepared through the double incorporation of an unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligand that bore an N-substituted cyclododecyl side chain. The isolation and full characterization (including X-ray diffraction studies) of key synthetic intermediates along with theoretical calculations allowed us to understand the mechanism of the overall cationization process. Finally, the newly developed complex 2 a displayed interesting latent behavior during ring-closing metathesis, which could be "switched on" under acidic conditions.
Conductive Supramolecular Architecture Constructed from Polyoxovanadate Cluster and Heterocyclic Surfactant

Directory of Open Access Journals (Sweden)

Toshiyuki Misawa

2018-01-01

Full Text Available Proton-conductive solid electrolytes are significant for fuel-cell battery technology. Especially for use in motor vehicles, proton conductors which work at intermediate temperatures (373–673 K under an anhydrous atmosphere are desired to improve the fuel cell stability and efficiency. Inorganic–organic hybrid supramolecular architectures are a promising option for the realization of highly conductive proton conductors. Here, a hybrid layered crystal was synthesized for the first time by using an proton-containing decavanadate (V10 anion and a heterocyclic surfactant cation. A simple ion-exchange reaction led to the formation of an inorganic–organic hybrid of V10 by using dodecylpyridazinium (C12pda as the heterocyclic surfactant. Single crystal X-ray analyses revealed that four C12pda cations were associated with one V10 anion, which was a diprotonated species forming a one-dimensional infinite chain structure through hydrogen bonds. Anhydrous proton conductivity was investigated by alternating current (AC impedance spectroscopy in the range of 313–393 K, exhibiting a maximum value of 1.7 × 10−5 S cm−1 at 373 K.
Inhibitory effects of pomegranate seed extract on the formation of heterocyclic aromatic amines in beef and chicken meatballs after cooking by four different methods.

Science.gov (United States)

Keşkekoğlu, Hasan; Uren, Ali

2014-04-01

Beef and chicken meatballs with a 0.5% (w/w) pomegranate seed extract were cooked using four different cooking methods (oven roasting, pan cooking, charcoal-barbecue, and deep-fat frying) and six heterocyclic aromatic amines; IQ, MeIQx, 4,8-DiMeIQx, PhIP, norharman, and harman were observed. In the beef meatballs, the highest inhibitory effects of pomegranate seed extract on heterocyclic aromatic amines formation were 68% for PhIP, 24% for norharman, 18% for harman, 45% for IQ, and 57% for MeIQx. Total heterocyclic aromatic amine formation was reduced by 39% and 46% in beef meatballs cooked by charcoal-barbecue and deep-fat frying, respectively. In the chicken meatballs, the highest inhibitory effects were 75% for PhIP, 57% for norharman, 28% for harman, 46% for IQ, and 49% for MeIQx. When the pomegranate seed extract was added to the chicken meatballs cooked by deep-fat frying, the total heterocyclic aromatic amine formation was inhibited by 49%, in contrast the total heterocyclic aromatic amine contents after oven roasting increased by 70%. Copyright © 2013 Elsevier Ltd. All rights reserved.
Synthesis, chemical and biological properties of the new mono- and bis-derivatives of imidazoles

Directory of Open Access Journals (Sweden)

E. V. Welchinska

2014-12-01

Full Text Available The aim of research. The problem of finding effective antitumour medical preparation with low toxicity is an important issue of medical and pharmaceutical chemistry. Knowledge of cancer cell features and its metabolism enables to predict the direction of chemical and biological research, to conduct a targeted synthesis of potential drugs, and to assess their applicability in oncological practice as antitumor agents. The purpose of work is to explain preformed heterocycles as purines, its synthesis and investigation of chemical and biological properties. After construction of the potential active structures we proposed the new method of original derivatives synthesis which are received on the base of imidazole, from one side, and fluorocontaining common anesthetic halothane (2-bromo-1,1,1-trifluoro-2-chloroethane from other side. Molecular complex of more perspective biologically active bis-imidazole with antitumour bacterial lectine has been received. With the purpose to synthesize potential antitumour compounds on the base of halothane and imidazole, new convenient methods for the preparation of original heterocyclic derivatives of imidazole have been described. The structure and composition of synthesized compound has been confirmed by the methods of elemental analysis, IR- and NMRІН-spectra. Materials and methods. The majority of the absolute organic solvents (benzene, dimethylformamide, ethyl ester employed in the present studies were distilled before their use. Organic solvents were dried over anhydrous magnesium sulfate or metallic sodium. Gas-liquid chromatography was carried out by Perkin Elmer chromatograph with UV-detector ("Perkin", Germany. IR spectra were recorded in a UR-20 spectrometer ("Charles Ceise Hena", Germany. The 1HNMR spectra were recorded in DMSO-d6 on a 200 MHz BrakerWP-200 ("Braker", Switzerland or Varian T-60 spectrometer ("Varian", USA. Investigation of critical toxicity of new compounds was carried out at
Structure and evaluation of antibacterial and antitubercular properties of new basic and heterocyclic 3-formylrifamycin SV derivatives obtained via 'click chemistry' approach.

Science.gov (United States)

Pyta, Krystian; Klich, Katarzyna; Domagalska, Joanna; Przybylski, Piotr

2014-09-12

Thirty four novel derivatives of 3-formylrifamycin SV were synthesized via reductive alkylation and copper(I)-catalysed azide-alkyne cycloaddition. According to the obtained results, 'click chemistry' can be successfully applied for modification of structurally complex antibiotics such as rifamycins, with the formation of desired 1,2,3-triazole products. However, when azide-alkyne cycloaddition on 3-formylrifamycin SV derivatives demanded higher amount of catalyst, lower temperature and longer reaction time because of the high volatility of substrates, an unexpected intramolecular condensation with the formation of 3,4-dihydrobenzo[g]quinazoline heterocyclic system took place. Structures of new derivatives in solution were determined using one- and two-dimensional NMR methods and FT-IR spectroscopy. Computational DFT and PM6 methods were employed to correlate their conformation and acid-base properties to biological activity and establish SAR of the novel compounds. Microbiological, physico-chemical (logP, solubility) and structural studies of newly synthesised rifamycins indicated that for the presence of relatively high antibacterial (MIC ~0.01 nmol/mL) and antitubercular (MIC ~0.006 nmol/mL) activities, a rigid and basic substituent at C(3) arm, containing a protonated nitrogen atom "open" toward intermolecular interactions, is required. Copyright © 2014 Elsevier Masson SAS. All rights reserved.
Studies on the cytotoxicity and anticancer performance of heterocyclic hypervalent organobismuth(III) compounds.

Science.gov (United States)

Liu, Yong-Ping; Lei, Jian; Tang, Li-Wen; Peng, Yao; Au, Chak-Tong; Chen, Yi; Yin, Shuang-Feng

2017-10-20

Novel organobismuth(III) complex of 5H-dibenzo[c,f][1,5]oxabismocin-12(7H)-yl nitrate (C2) was synthesized and characterized by spectral and elemental analysis. It was compared with other five C,E,C-chelating (E = N, O, S) organobismuth(III) complexes against human adenocarcinoma alveolar basal epithelial cells (A549), human liver cancer cell line (SMCC7721), human gastric cancer cell line (SGC-7901), human colon adenocarcinoma cell line (SW480) and healthy human bronchial cell line (16HBE14o-) in vitro. It was found that C2 exhibited the best anticancer activity. Further mechanistic investigation indicated that toxicological activity of C2 was ascribable to apoptosis rather than anti-proliferative activity. Apoptosis was induced through up-regulating the level of Bcl-2/Bax as well as the activation of caspase-3. The results demonstrate that heterocyclic organobismuth(III) complexes of this type have great potential in the treatment of cancer. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Enaminone in heterocyclic synthesis: synthesis of new pyrazolopyrazole, pyrazolothienooxazine and pyrazolothienopyridine derivatives

International Nuclear Information System (INIS)

Hafiz, I.S.; Rahim, M.A.M.A.

2014-01-01

The chemical reactivity of enaminone 2 toward some nucleophilic and electrophilic reagents was investigated. Enaminone 2 was used as a key precursor for the synthesis of many important heterocyclic compounds. The synthesized compounds were characterized by IR, 1H-NMR, MS spectral and elemental analysis. (author)
Cyclodepsipeptides and other O-containing heterocyclic metabolites from Beauveria felina EN-135, a marine-derived entomopathogenic fungus.

Science.gov (United States)

Du, Feng-Yu; Li, Xiao-Ming; Zhang, Peng; Li, Chun-Shun; Wang, Bin-Gui

2014-05-13

Bioassay-guided fractionation of a culture extract of Beauveria felina EN-135, an entomopathogenic fungus isolated from a marine bryozoan, led to the isolation of a new cyclodepsipeptide, iso-isariin D (1); two new O-containing heterocyclic compounds that we have named felinones A and B (2 and 3); and four known cyclodepsipeptides (4-7). The structures were elucidated via spectroscopic analysis, and the absolute configurations of 1 and 2 were determined using single-crystal X-ray diffraction and CD, respectively. All isolated compounds were evaluated for antimicrobial activity and brine-shrimp (Artemia salina) lethality.
Oxidation of methyl heterocyclic compounds on vanadium oxide catalysts

International Nuclear Information System (INIS)

Shimanskaya, M.V.; Lejtis, L.A.; Iovel', I.G.; Gol'dberg, Yu.Sh.; Skolmejstere, R.A.; Golender, L.O.

1985-01-01

Data on vapor-phase oxidation of methyl derivatives of thiophene, Δ 2 - thiazo line, pyridine, pyrazine and pyramidine on oxide vanadium-molybdenum catalysts to corresponding heterylaldehydes are generalized. The dependence of catalytic properties of oxide vanadium-molybdenum systems in oxidation reactions of methylheterocyclic compounds on V:Mo ratio in the catalyst is revealed. It is shown that heterocyclic compounds are coordinated by a heteroatom on Lewis centres of V-Mo-O-catalyst primarily with partially reduced vanadium ions
Dehydrogenative Synthesis of Imines from Alcohols and Amines Catalyzed by a Ruthenium N-Heterocyclic Carbene Complex

DEFF Research Database (Denmark)

Maggi, Agnese; Madsen, Robert

2012-01-01

A new method for the direct synthesis of imines from alcohols and amines is described where hydrogen gas is liberated. The reaction is catalyzed by the ruthenium N-heterocyclic carbene complex [RuCl2(IiPr)(p-cymene)] in the presence of the ligand DABCO and molecular sieves. The imination can...... be applied to a variety of primary alcohols and amines and can be combined with a subsequent addition reaction. A deuterium labeling experiment indicates that the catalytically active species is a ruthenium dihydride. The reaction is believed to proceed by initial dehydrogenation of the alcohol...
Anticancer Gold N-Heterocyclic Carbene Complexes: A Comparative in vitro and ex vivo Study.

Science.gov (United States)

Estrada-Ortiz, Natalia; Guarra, Federica; de Graaf, Inge A M; Marchetti, Lorella; de Jager, Marina H; Groothuis, Geny M M; Gabbiani, Chiara; Casini, Angela

2017-09-07

A series of organometallic Au I N-heterocyclic carbene (NHC) complexes was synthesized and characterized for anticancer activity in four human cancer cell lines. The compounds' toxicity in healthy tissue was determined using precision-cut kidney slices (PCKS) as a tool to determine the potential selectivity of the gold complexes ex vivo. All evaluated compounds presented cytotoxic activity toward the cancer cells in the nano- or low micromolar range. The mixed Au I NHC complex, (tert-butylethynyl)-1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene gold(I), bearing an alkynyl moiety as ancillary ligand, showed high cytotoxicity in cancer cells in vitro, while being barely toxic in healthy rat kidney tissues. The obtained results open new perspectives toward the design of mixed NHC-alkynyl gold complexes for cancer therapy. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
The Biological Activities of Sesterterpenoid-Type Ophiobolins

Directory of Open Access Journals (Sweden)

Wei Tian

2017-07-01

Full Text Available Ophiobolins (Ophs are a group of tricarbocyclic sesterterpenoids whose structures contain a tricyclic 5-8-5 carbotricyclic skeleton. Thus far, 49 natural Ophs have been reported and assigned into A–W subgroups in order of discovery. While these sesterterpenoids were first characterized as highly effective phytotoxins, later investigations demonstrated that they display a broad spectrum of biological and pharmacological characteristics such as phytotoxic, antimicrobial, nematocidal, cytotoxic, anti-influenza and inflammation-promoting activities. These bioactive molecules are promising drug candidates due to the developments of their anti-proliferative activities against a vast number of cancer cell lines, multidrug resistance (MDR cells and cancer stem cells (CSCs. Despite numerous studies on the biological functions of Ophs, their pharmacological mechanism still requires further research. This review summarizes the chemical structures, sources, and biological activities of the oph family and discusses its mechanisms and structure–activity relationship to lay the foundation for the future developments and applications of these promising molecules.
The Biological Activities of Sesterterpenoid-Type Ophiobolins.

Science.gov (United States)

Tian, Wei; Deng, Zixin; Hong, Kui

2017-07-18

Ophiobolins (Ophs) are a group of tricarbocyclic sesterterpenoids whose structures contain a tricyclic 5-8-5 carbotricyclic skeleton. Thus far, 49 natural Ophs have been reported and assigned into A-W subgroups in order of discovery. While these sesterterpenoids were first characterized as highly effective phytotoxins, later investigations demonstrated that they display a broad spectrum of biological and pharmacological characteristics such as phytotoxic, antimicrobial, nematocidal, cytotoxic, anti-influenza and inflammation-promoting activities. These bioactive molecules are promising drug candidates due to the developments of their anti-proliferative activities against a vast number of cancer cell lines, multidrug resistance (MDR) cells and cancer stem cells (CSCs). Despite numerous studies on the biological functions of Ophs, their pharmacological mechanism still requires further research. This review summarizes the chemical structures, sources, and biological activities of the oph family and discusses its mechanisms and structure-activity relationship to lay the foundation for the future developments and applications of these promising molecules.
Synthesis and Reactions of Five-Membered Heterocycles Using Phase Transfer Catalyst (PTC Techniques

Directory of Open Access Journals (Sweden)

Ahmed M. El-Sayed

2014-01-01

Full Text Available Phase transfer catalysts (PTCs have been widely used for the synthesis of organic compounds particularly in both liquid-liquid and solid-liquid heterogeneous reaction mixtures. They are known to accelerate reaction rates by facilitating formation of interphase transfer of species and making reactions between reagents in two immiscible phases possible. Application of PTC instead of traditional technologies for industrial processes of organic synthesis provides substantial benefits for the environment. On the basis of numerous reports it is evident that phase-transfer catalysis is the most efficient way for generation and reactions of many active intermediates. In this review we report various uses of PTC in syntheses and reactions of five-membered heterocycles compounds and their multifused rings.
Can creatine supplementation form carcinogenic heterocyclic amines in humans?

Science.gov (United States)

Pereira, Renato Tavares dos Santos; Dörr, Felipe Augusto; Pinto, Ernani; Solis, Marina Yazigi; Artioli, Guilherme Giannini; Fernandes, Alan Lins; Murai, Igor Hisashi; Dantas, Wagner Silva; Seguro, Antônio Carlos; Santinho, Mirela Aparecida Rodrigues; Roschel, Hamilton; Carpentier, Alain; Poortmans, Jacques Remi; Gualano, Bruno

2015-01-01

Abstract Creatine supplementation has been associated with increased cancer risk. In fact, there is evidence indicating that creatine and/or creatinine are important precursors of carcinogenic heterocyclic amines (HCAs). The present study aimed to investigate the acute and chronic effects of low- and high-dose creatine supplementation on the production of HCAs in healthy humans (i.e. 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (8-MeIQx), 2-amino-(1,6-dimethylfuro[3,2-e]imidazo[4,5-b])pyridine (IFP) and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4,8-DiMeIQx)). This was a non-counterbalanced single-blind crossover study divided into two phases, in which low- and high-dose creatine protocols were tested. After acute (1 day) and chronic supplementation (30 days), the HCAs PhIP, 8-MeIQx, IFP and 4,8-DiMeIQx were assessed through a newly developed HPLC–MS/MS method. Dietary HCA intake and blood and urinary creatinine were also evaluated. Out of 576 assessments performed (from 149 urine samples), only nine (3 from creatine and 6 from placebo) showed quantifiable levels of HCAs (8-MeIQx: n = 3; 4,8-DiMeIQx: n = 2; PhIP: n = 4). Individual analyses revealed that diet rather than creatine supplementation was the main responsible factor for HCA formation in these cases. This study provides compelling evidence that both low and high doses of creatine supplementation, given either acutely or chronically, did not cause increases in the carcinogenic HCAs PhIP, 8-MeIQx, IFP and 4,8-DiMeIQx in healthy subjects. These findings challenge the long-existing notion that creatine supplementation could potentially increase the risk of cancer by stimulating the formation of these mutagens. Key points There is a long-standing concern that creatine supplementation could be associated with cancer, possibly by facilitating the formation of carcinogenic heterocyclic amines (HCAs). This study provides compelling evidence
Pd(OAc)2/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles.

Science.gov (United States)

Kellner, Dominik; Weger, Maximilian; Gini, Andrea; Mancheño, Olga García

2017-01-01

The palladium-catalyzed dimerization of isoprene is a practical approach of synthesizing monoterpenes. Though several highly selective methods have been reported, most of them still required pressure or costly ligands for attaining the active system and desired selectivity. Herein, we present a simple and economical procedure towards the tail-to-tail dimer using readily available Pd(OAc) 2 and inexpensive triphenylphosphine as ligand. Furthermore, simple screw cap vials are employed, allowing carrying out the reaction at low pressure. In addition, the potential of the dimer as a chemical platform for the preparation of heterocyclic terpenes by subsequent (hetero)-Diels-Alder or [4 + 1]-cycloadditions with nitrenes is also depicted.
STRUCTURES AND BIOLOGICAL ACTIVITY OF CUPROPHYLLINS

Directory of Open Access Journals (Sweden)

Martynov A.V.

2017-06-01

Full Text Available Chlorophylls (a, b are the porphyrin compounds and most common chemical in the plant’s world. In fact, these compounds are an obligatory intermediate product both in energy metabolism and in plant catabolism. At the same time, currently there are few pharmaceutical preparations on the pharmaceutical market based on chlorophylls. Dyes based on hydrolyzed chlorophyll are successfully used in the food industry. Commercial chlorophylline is a copper complex of hydrolyzed chlorophylls. As shown earlier in TLC, the chlorophyllin mixture contains a large number of different compounds. It is like water-soluble saponified derivatives in the form of sodium-magnesium complexes, and similar structures in the form of a complex with copper. The latter are more brightly colored, soluble in water and widely used as coloring agents in cooking. In this case, if the initial chlorophyll was not found to have a pronounced biological activity, the substituted derivatives in the form of copper complexes possessed a number of new unique biological properties. Non-hydrolyzed hydrophobic cuprophylline obtained from eucalyptus leaves possessed high antimicrobial activity to most strains of staphylococci, inclusion resistant to antimicrobials and multiresistant strains. This drug is called Chlorophyllipt, it is allowed to be used as a medicinal product and is one of the oldest antibacterial drugs from plants on the market. It is marketed as ethanoic and oily solutions for topical use, and as an alcohol solution for intravenous injections. Its main purpose is the fight against staphylococcal infections. Recently, found that the oral administration of chlorophyllipt activates cellular immunity and indirectly exhibits antiviral activity. Another compound of cuprophyllin is water-soluble chlorophyllin. Some authors show the variability of the structure and biological activity of cuprophyllins. Different derivatives of chlorophyll have different biological activity
Application of heterocyclic aldehydes as components in Ugi–Smiles couplings

Directory of Open Access Journals (Sweden)

Katelynn M. Mason

2016-09-01

Full Text Available Efficient one-pot Ugi–Smiles couplings are reported for the use of furyl-substituted aldehyde components. In the presence of these heterocyclic aldehydes, reactions tolerated variations in amine components and led to either isolated N-arylamide Ugi–Smiles adducts or N-arylepoxyisoindolines, products of tandem Ugi–Smiles Diels–Alder cyclizations, in moderate yields. A thienyl-substituted aldehyde was also a competent component for Ugi–Smiles adduct formation.
Oxidative N-Heterocyclic Carbene-Catalyzed γ-Carbon Addition of Enals to Imines: Mechanistic Studies and Access to Antimicrobial Compounds.

Science.gov (United States)

Zheng, Peng-Cheng; Cheng, Jiajia; Su, Shihu; Jin, Zhichao; Wang, Yu-Huang; Yang, Song; Jin, Lin-Hong; Song, Bao-An; Chi, Yonggui Robin

2015-07-06

The reaction mechanism of the γ-carbon addition of enal to imine under oxidative N-heterocyclic carbene catalysis is studied experimentally. The oxidation, γ-carbon deprotonation, and nucleophilic addition of γ-carbon to imine were found to be facile steps. The results of our study also provide highly enantioselective access to tricyclic sulfonyl amides that exhibit interesting antimicrobial activities against X. oryzae, a bacterium that causes bacterial disease in rice growing. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

Directory of Open Access Journals (Sweden)

Louis P. Sandjo

2015-09-01

Full Text Available This review focuses on pyridoacridine-related metabolites as one biologically interesting group of alkaloids identified from marine sources. They are produced by marine sponges, ascidians and tunicates, and they are structurally comprised of four to eight fused rings including heterocycles. Acridine, acridone, dihydroacridine, and quinolone cores are features regularly found in these alkaloid skeletons. The lack of hydrogen atoms next to quaternary carbon atoms for two or three rings makes the chemical shift assignment a difficult task. In this regard, one of the aims of this review is the compilation of previously reported, pyridoacridine 13C NMR data. Observations have been made on the delocalization of electrons and the presence of some functional groups that lead to changes in the chemical shift of some carbon resonances. The lack of mass spectra information for these alkaloids due to the compactness of their structures is further discussed. Moreover, the biosynthetic pathways of some of these metabolites have been shown since they could inspire biomimetic synthesis. The synthesis routes used to prepare members of these marine alkaloids (as well as their analogues, which are synthesized for biological purposes are also discussed. Pyridoacridines were found to have a large spectrum of bioactivity and this review highlights and compares the pharmacophores that are responsible for the observed bioactivity.

Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles

Directory of Open Access Journals (Sweden)

Pavol Jakubec

2012-04-01

Full Text Available A versatile nitro-Mannich/lactamisation cascade for the direct stereoselective synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles has been developed. A highly enantioenriched substituted 5-nitropiperidin-2-one was synthesised in a four component one-pot reaction combining an enantioselective organocatalytic Michael addition with the diastereoselective nitro-Mannich/lactamisation cascade. Protodenitration and chemoselective reductive manipulation of the heterocycles was used to install contiguous and fully substituted stereocentres in the synthesis of substituted piperidines.
Condensed heterocycles with a thiazole ring. 13. Azinothiazoloquinoxalinium salts

International Nuclear Information System (INIS)

Nesterenko, Yu.A.; Romanov, N.N.

1987-01-01

The condensation of 2,3-dichloroquinoxaline with 2-mercaptopyridines and 2-mercaptoquinolines gave the corresponding derivatives of new heterocyclic systems, viz., azino[1',2':3,2]thaizolo[4,5-b]quinoxalinium salts, which can be used for the synthesis of cyanine dyes. The electronic spectra of solutions of the compounds were obtained with an SF-8 spectrophotometer. The PMR spectra of solutions of CF 3 COOD were recorded with a BS-467 spectrometer (60 MHz) with hexamethyldisiloxane (HMDS) as the external standard
Theoretical NMR spectroscopy of N-heterocyclic carbenes and their metal complexes

KAUST Repository

Falivene, Laura

2016-12-26

Recent theoretical analysis of the NMR properties of free N-heterocyclic carbenes (NHC) and Metal-NHC complexes has complemented experiments, allowing the establishment of structure/property relationships and the rationalization of otherwise surprising experimental results. In this review, the main conclusions from recent literature are discussed, with the aim to offer a vision of the potential of theoretical analyses of NMR properties.
Complexes of uranyl with N-oxides of heterocyclic amines. Electron-vibrational absorption spectra

International Nuclear Information System (INIS)

Jezowska-Trzebiatowska, B.; Wieczorek, M.

1977-01-01

A number of coordination compounds formed by uranyl chloride and nitrate with N-oxides of heterocyclic amines have been prepared and characterized by spectral measurements in the absorption region 20000-50000 cm -1 . The electrons and vibronic transitions have been determined and discussed. (author)
N,N'-diamidoketenimines via coupling of isocyanides to an N-heterocyclic carbene.

Science.gov (United States)

Hudnall, Todd W; Moorhead, Eric J; Gusev, Dmitry G; Bielawski, Christopher W

2010-04-16

Treatment of an N-heterocyclic carbene that features two amide groups N-bound to the carbene nucleus with various organic isocyanides afforded a new class of ketenimines in yields of up to 96% (isolated). DFT analyses revealed that the carbene exhibits a unique, low-lying LUMO, which may explain the atypical reactivity observed.
Multifunctional and biologically active matrices from multicomponent polymeric solutions

Science.gov (United States)

Kiick, Kristi L. (Inventor); Yamaguchi, Nori (Inventor)

2010-01-01

The present invention relates to a biologically active functionalized electrospun matrix to permit immobilization and long-term delivery of biologically active agents. In particular the invention relates to a functionalized polymer matrix comprising a matrix polymer, a compatibilizing polymer and a biomolecule or other small functioning molecule. In certain aspects the electrospun polymer fibers comprise at least one biologically active molecule functionalized with low molecular weight heparin. Examples of active molecules that may be used with the multicomponent polymer of the invention include, for example, a drug, a biopolymer, for example a growth factor, a protein, a peptide, a nucleotide, a polysaccharide, a biological macromolecule or the like. The invention is further directed to the formation of functionalized crosslinked matrices, such as hydrogels, that include at least one functionalized compatibilizing polymer capable of assembly.
Role of Muramyl Dipeptide in Lipopolysaccharide-Mediated Biological Activity and Osteoclast Activity

Directory of Open Access Journals (Sweden)

Hideki Kitaura

2018-01-01

Full Text Available Lipopolysaccharide (LPS is an endotoxin and bacterial cell wall component that is capable of inducing inflammation and immunological activity. Muramyl dipeptide (MDP, the minimal essential structural unit responsible for the immunological activity of peptidoglycans, is another inflammation-inducing molecule that is ubiquitously expressed by bacteria. Several studies have shown that inflammation-related biological activities were synergistically induced by interactions between LPS and MDP. MDP synergistically enhances production of proinflammatory cytokines that are induced by LPS exposure. Injection of MDP induces lethal shock in mice challenged with LPS. LPS also induces osteoclast formation and pathological bone resorption; MDP enhances LPS induction of both processes. Furthermore, MDP enhances the LPS-induced receptor activator of NF-κB ligand (RANKL expression and toll-like receptor 4 (TLR4 expression both in vivo and in vitro. Additionally, MDP enhances LPS-induced mitogen-activated protein kinase (MAPK signaling in stromal cells. Taken together, these findings suggest that MDP plays an important role in LPS-induced biological activities. This review discusses the role of MDP in LPS-mediated biological activities, primarily in relation to osteoclastogenesis.
Cyclometalated N-heterocyclic carbene iridium(iii) complexes with naphthalimide chromophores: a novel class of phosphorescent heteroleptic compounds.

Science.gov (United States)

Lanoë, Pierre-Henri; Chan, Jonny; Groué, Antoine; Gontard, Geoffrey; Jutand, Anny; Rager, Marie-Noelle; Armaroli, Nicola; Monti, Filippo; Barbieri, Andrea; Amouri, Hani

2018-03-06

A series of cyclometalated N-heterocyclic carbene complexes of the general formula [Ir(C^N) 2 (C^C:)] has been prepared. Two sets of compounds were designed, those where (C^C:) represents a bidentate naphthalimide-substituted imidazolylidene ligand and (C^N) = ppy (3a), F2ppy (4a), bzq (5a) and those where (C^C:) represents a naphthalimide-substituted benzimidazolylidene ligand and (C^N) = ppy (3b), F2ppy (4b), bzq (5b). The naphthalimide-imidazole and naphthalimide-benzimidazole ligands 1a,b and the related imidazolium and benzimidazolium salts 2a,b were also prepared and fully characterized. The N-heterocyclic carbene Ir(iii) complexes have been characterized by NMR spectroscopy, cyclic voltammetry and elemental analysis. Moreover, the molecular structures of one imidazolium salt and four Ir(iii) complexes were determined by single-crystal X-ray diffraction. The structures provide us with valuable information, most notably the orientation of the naphthalimide chromophore with respect to the N-heterocyclic carbene moiety. All compounds are luminescent at room temperature and in a frozen solvent at 77 K, exhibiting a broad emission band that extends beyond 700 nm. The presence of the naphthalimide moiety changes the character of the lowest excited state from 3 MLCT to 3 LC, as corroborated by DFT and TD-DFT calculations. Remarkably, replacing imidazole with a benzimidazole unit improves the quantum yields of these compounds by decreasing the k nr values which is an important feature for optimized emission performance. These studies provide valuable insights about a novel class of N-heterocyclic carbene-based luminescent complexes containing organic chromophores and affording metal complexes emitting across the red-NIR range.
African Journal of Science and Technology (AJST) REACTIONS OF ...

African Journals Online (AJOL)

opiyo

Acetylenic amines have been used in the synthesis of potential biologically active heterocyclic compounds. Recently the anticonvulsant activity of some acetylenic quinazolinone derivatives have been evaluated and most of them exhibited significant activity in the seizure threshold test with subcutaneous pentylenetetrazole.
Adsorption Characteristics of DNA Nucleobases, Aromatic Amino Acids and Heterocyclic Molecules on Silicene and Germanene Monolayers

KAUST Repository

Hussain, Tanveer

2017-09-14

Binding of DNA/RNA nucleobases, aromatic amino acids and heterocyclic molecules on two-dimensional silicene and germanene sheets have been investigated for the application of sensing of biomolecules using first principle density functional theory calculations. Binding energy range for nucleobases, amino acids and heterocyclic molecules with both the sheets have been found to be (0.43-1.16eV), (0.70-1.58eV) and (0.22-0.96eV) respectively, which along with the binding distances show that these molecules bind to both sheets by physisorption and chemisorption process. The exchange of electric charges between the monolayers and the incident molecules has been examined by means of Bader charge analysis. It has been observed that the introduction of DNA/RNA nucleobases, aromatic amino acids and heterocyclic molecules alters the electronic properties of both silicene and germanene nano sheets as studied by plotting the total (TDOS) and partial (PDOS) density of states. The DOS plots reveal the variation in the band gaps of both silicene and germanene caused by the introduction of studied molecules. Based on the obtained results we suggest that both silicene and germanene monolayers in their pristine form could be useful for sensing of biomolecules.
Synthesis of 2-arylidenebenzocycloalkanones containing N-donor heterocyclic rings

Energy Technology Data Exchange (ETDEWEB)

Sun, S.-W., E-mail: sunsw0819@163.com [Yuncheng University, Department of Applied Chemistry (China); Zhang, X., E-mail: zhangx@hit.edu.cn [Harbin Institute of Technology, Academy of Fundamental and Interdisciplinary Science (China); Wang, G.-F. [Yuncheng University, Department of Applied Chemistry (China)

2016-12-15

A series of 2-arylidenebenzocycloalkanones containing heterocyclic rings 1–8 were prepared and characterized by IR, {sup 1}H NMR and elemental analyses. X-ray diffraction study of 6 reveals that the cyclohexyl ring of the 3,4-dihydronaphthalen-1(2H)-one adopts a chair conformation with a maximum deviation of 0.547(3) Å and makes dihedral angles of 52.24(17)° and 11.23(16)°, respectively, with the benzene plane and the mean plane of the benzimidazole ring.
Regioselective Aziridination of Silyl Allenes and Application for the Synthesis of New Heterocycles

Science.gov (United States)

Burke, Eileen Grace

Rhodium catalyzed aziridination of homoallenic sulfamates has proven to be a successful first step in the synthesis of a diverse array of complex nitrogenated motifs. Previously, however, the resultant methyleneaziridine was limited to the exocyclic isomer. In this work, a reliable direction strategy for the formation of the endocyclic isomer was identified. Placement of a silicon group on the allene so that its C - Si bond is co-planar to the distal pi-bond allowed for stabilization of the developing positive charge during aziridination, and therefore selective activation to form the endocyclic methyleneaziridine. This strategy proved robust, and endocyclic methyleneaziridines were formed in high yields with exclusive formation of the desired isomer regardless of the substitution of the allene. With the endocyclic isomer now readily available, its reactivity could be explored. First, the endocyclic methyleneaziridine was applied to the synthesis of densely functionalized, nitrogen containing motifs. In comparison with their exocyclic counterparts, the endocyclic methyleneaziridines were found to have differing reactivity. The olefin could be epoxidized using meta-chloroperoxybenzoic acid (mCPBA), and the resulting spirocyclic intermediate rapidly rearranged to an azetidin-3-one. This synthesis of the highly substituted fourmembered heterocycle represented a novel approach to these motifs, and was found to be both flexible, and to selectively form a single diastereomer. Additional derivatization of these scaffolds gave a diverse array of complex products. Further use of the endocyclic methyleneaziridine focused not on the complexity of the product motif but rather on its utility. The remaining silyl group could be eliminated upon reaction with a fluoride source, triggering the formation of an alkyne and resultant opening of the aziridine. This strained heterocyclic alkyne and its synthesis represent a new addition to the field of strained alkyne synthesis. Uniquely
Mechanistic Investigation of the Ruthenium–N-Heterocyclic-Carbene-Catalyzed Amidation of Alcohols and Amines

DEFF Research Database (Denmark)

Makarov, Ilya; Fristrup, Peter; Madsen, Robert

2012-01-01

The mechanism of the ruthenium–N-heterocyclic-carbene-catalyzed formation of amides from alcohols and amines was investigated by experimental techniques (Hammett studies, kinetic isotope effects) and by a computational study by using dispersion-corrected density functional theory (DFT/ M06...
Cyclodepsipeptides and Other O-Containing Heterocyclic Metabolites from Beauveria felina EN-135, a Marine-Derived Entomopathogenic Fungus

Directory of Open Access Journals (Sweden)

Feng-Yu Du

2014-05-01

Full Text Available Bioassay-guided fractionation of a culture extract of Beauveria felina EN-135, an entomopathogenic fungus isolated from a marine bryozoan, led to the isolation of a new cyclodepsipeptide, iso-isariin D (1; two new O-containing heterocyclic compounds that we have named felinones A and B (2 and 3; and four known cyclodepsipeptides (4–7. The structures were elucidated via spectroscopic analysis, and the absolute configurations of 1 and 2 were determined using single-crystal X-ray diffraction and CD, respectively. All isolated compounds were evaluated for antimicrobial activity and brine-shrimp (Artemia salina lethality.
Ethnobotanical and biological activities of Leptadenia pyrotechnica ...

African Journals Online (AJOL)

Conclusion: This review includes the substance of different ethnobotanical uses, phytochemistry and exclusive capability of this plant in the field of anti-microbial and human disease activities. Key words: Leptadenia pyrotechnica, Biological activities, Desert plant, Ethnobotanical, Phytochemical activity, phytochemistry.
Bone Scan in Detection of Biological Activity in Nonhypertrophic Fracture Nonunion

OpenAIRE

Gandhi, Sunny J.; Rabadiya, Bhavdeep

2017-01-01

Biological activity of the fracture site is very important factor in treatment planning of fracture nonunion. If no biological activity is detected, then an autologous bone graft can be supplemented or osteogenic supplementations, such as bone morphogenetic protein is given. If biological activity is present, then secure fixation is sufficient to achieve bony union. Biological activity of nonunions is usually assessed by conventional radiographs. The presence of callus formation is usually as...
Pulse gas chromatographic study of adsorption of substituted aromatics and heterocyclic molecules on MIL-47 at zero coverage.

Science.gov (United States)

Duerinck, Tim; Couck, Sarah; Vermoortele, Frederik; De Vos, Dirk E; Baron, Gino V; Denayer, Joeri F M

2012-10-02

The low coverage adsorptive properties of the MIL-47 metal organic framework toward aromatic and heterocyclic molecules are reported in this paper. The effect of molecular functionality and size on Henry adsorption constants and adsorption enthalpies of alkyl and heteroatom functionalized benzene derivates and heterocyclic molecules was studied using pulse gas chromatography. By means of statistical analysis, experimental data was analyzed and modeled using principal component analysis and partial least-squares regression. Structure-property relationships were established, revealing and confirming several trends. Among the molecular properties governing the adsorption process, vapor pressure, mean polarizability, and dipole moment play a determining role.
Mixed-ligand complexes of copper (II with ditiolfenols and heterocyclic diamines

Directory of Open Access Journals (Sweden)

K. A. Kuliev

2017-01-01

Full Text Available By the methods spectrophotometric methods was investigated complex formation of copper with 2,6-ditiolphenol and its derivatives (2,6-ditiol-4-methylphenol, 2,6-ditiol-4-ethylphenol and 2,6-ditiol-4-tert-buthylphenol in the presence of heterocyclic diamines. As heterocyclic diamines phenantroline (Fen, batophenantroline and dipyridile were used. It was established, that mixedligand complex were formed in weak acidic medium (pHop=6,0-8,5. Maximum of light absorption observed at (=522–550 nm. Molar coefficient of light absorption was ( = (3.08–4.92?104. The stoichiometry of complexes had been discovered using shift the equilibrium and relative yield methods. During the extraction of copper(II complexes with ditiol-phenols with the presence of heterocyclic diamines there was discovered that there is no chlorophorm molecules in the composition of the extracted complexes. IR spectra shows that hydroxyl group is involved to the formation of a bond with the metal and that phenantroline is included in the composition of the copper complex. In the organic phase mixed-ligand complexes have the monomeric form and can’t polymerize; that fact can be proved by calculations. By dint of spectrophotometric, IR-spectroscopic, thermogravimetric experiments and some published data we were able to determine the structural formula of complexes. Also had been determined main spectrophotometric characteristics of copper(II mixed-ligand complexes: pH of the beginning of the deposition, optimal pH, detection limit and sensivity. For separation and finding copper, we studied the effect of interfering foreign ions: alkali, alkaline earth and rare earth elements, as well as acid anions selected masking reagents. On the base of the results was offered photometric method for determination of copper in steel different trade-marks and in food. This method characterized by good reproduction (relatively standard deviation no more 0.05 and low limit of discovery.
Decisive Interactions between the Heterocyclic Moiety and the Cluster Observed in Polyoxometalate-Surfactant Hybrid Crystals

Directory of Open Access Journals (Sweden)

Saki Otobe

2015-04-01

Full Text Available Inorganic-organic hybrid crystals were successfully obtained as single crystals by using polyoxotungstate anion and cationic dodecylpyridazinium (C12pda and dodecylpyridinium (C12py surfactants. The decatungstate (W10 anion was used as the inorganic component, and the crystal structures were compared. In the crystal comprising C12pda (C12pda-W10, the heterocyclic moiety directly interacted with W10, which contributed to a build-up of the crystal structure. On the other hand, the crystal consisting of C12py (C12py-W10 had similar crystal packing and molecular arrangement to those in the W10 crystal hybridized with other pyridinium surfactants. These results indicate the significance of the heterocyclic moiety of the surfactant to construct hybrid crystals with polyoxometalate anions.
Titanocene–Gold Complexes Containing N-Heterocyclic Carbene Ligands Inhibit Growth of Prostate, Renal, and Colon Cancers in Vitro

Science.gov (United States)

2016-01-01

We report on the synthesis, characterization, and stability studies of new titanocene complexes containing a methyl group and a carboxylate ligand (mba = −OC(O)-p-C6H4-S−) bound to gold(I)–N-heterocyclic carbene fragments through the thiolate group: [(η5-C5H5)2TiMe(μ-mba)Au(NHC)]. The cytotoxicities of the heterometallic compounds along with those of novel monometallic gold–N-heterocyclic carbene precursors [(NHC)Au(mbaH)] have been evaluated against renal, prostate, colon, and breast cancer cell lines. The highest activity and selectivity and a synergistic effect of the resulting heterometallic species was found for the prostate and colon cancer cell lines. The colocalization of both titanium and gold metals (1:1 ratio) in PC3 prostate cancer cells was demonstrated for the selected compound 5a, indicating the robustness of the heterometallic compound in vitro. We describe here preliminary mechanistic data involving studies on the interaction of selected mono- and bimetallic compounds with plasmid (pBR322) used as a model nucleic acid and the inhibition of thioredoxin reductase in PC3 prostate cancer cells. The heterometallic compounds, which are highly apoptotic, exhibit strong antimigratory effects on the prostate cancer cell line PC3. PMID:27182101

Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis

Science.gov (United States)

Chen, Ming Z.; Micalizio, Glenn C.

2009-01-01

A two-step process is described for the union of aromatic imines, conjugated alkynes and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings. PMID:19817447
Pd(OAc2/Ph3P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

Directory of Open Access Journals (Sweden)

Dominik Kellner

2017-08-01

Full Text Available The palladium-catalyzed dimerization of isoprene is a practical approach of synthesizing monoterpenes. Though several highly selective methods have been reported, most of them still required pressure or costly ligands for attaining the active system and desired selectivity. Herein, we present a simple and economical procedure towards the tail-to-tail dimer using readily available Pd(OAc2 and inexpensive triphenylphosphine as ligand. Furthermore, simple screw cap vials are employed, allowing carrying out the reaction at low pressure. In addition, the potential of the dimer as a chemical platform for the preparation of heterocyclic terpenes by subsequent (hetero-Diels–Alder or [4 + 1]-cycloadditions with nitrenes is also depicted.
Solid-phase synthesis of complex and pharmacologically interesting heterocycles

DEFF Research Database (Denmark)

Nielsen, Thomas Eiland

2009-01-01

Efficient routes for the creation of heterocycles continue to be one of the primary goals for solid-phase synthesis. Recent advances in this field rely most notably on transition-metal-catalysis and N-acyliminium chemistry to mediate a range of cyclization processes for the generation of compounds...... with significant structural complexity and diversity. This review describes some of the most systematic solid-phase approaches that are potentially suited for pharmaceutical applications, that is, the methods described are useful for the synthesis of compound collections, and exhibit tunable stereochemistry...
Physical activity and biological maturation: a systematic review

Directory of Open Access Journals (Sweden)

Eliane Denise Araújo Bacil

2015-03-01

Full Text Available OBJECTIVE: To analyze the association between physical activity (PA and biological maturation in children and adolescents. DATA SOURCE: We performed a systematic review in April 2013 in the electronic databases of PubMed/MEDLINE, SportDiscus, Web of Science and LILACS without time restrictions. A total of 628 potentially relevant articles were identified and 10 met the inclusion criteria for this review: cross-sectional or longitudinal studies, published in Portuguese, English or Spanish, with schoolchildren aged 9-15 years old of both genders. DATA SYNTHESIS: Despite the heterogeneity of the studies, there was an inverse association between PA and biological maturation. PA decreases with increased biological and chronological age in both genders. Boys tend to be more physically active than girls; however, when controlling for biological age, the gender differences disappear. The association between PA and timing of maturation varies between the genders. Variation in the timing of biological maturation affects the tracking of PA in early adolescent girls. This review suggests that mediators (BMI, depression, low self-esteem, and concerns about body weight can explain the association between PA and biological maturation. CONCLUSIONS: There is an association between PA and biological maturation. PA decreases with increasing biological age with no differences between genders. As for the timing of biological maturation, this association varies between genders.
Gold(I-catalyzed domino cyclization for the synthesis of polyaromatic heterocycles

Directory of Open Access Journals (Sweden)

Mathieu Morin

2013-11-01

Full Text Available Gold(I complexes have emerged as powerful and useful catalysts for the formation of new C–C, C–O and C–N bonds. Taking advantage of the specificity of [IPrAuNCMe][SbF6] complexes to favor the 5-exo-dig cyclization over the 6-endo-dig pathway, we report a high yielding and efficient method to generate substituted polyaromatic heterocycles under remarkably mild reaction conditions.
Loranthus micranthus Linn.: Biological Activities and Phytochemistry

Directory of Open Access Journals (Sweden)

Soheil Zorofchian Moghadamtousi

2013-01-01

Full Text Available Loranthus micranthus Linn. is a medicinal plant from the Loranthaceae family commonly known as an eastern Nigeria species of the African mistletoe and is widely used in folkloric medicine to cure various ailments and diseases. It is semiparasitic plant because of growing on various host trees and shrubs and absorbing mineral nutrition and water from respective host. Hence, the phytochemicals and biological activities of L. micranthus demonstrated strong host and harvesting period dependency. The leaves have been proved to possess immunomodulatory, antidiabetic, antimicrobial, antihypertensive, antioxidant, antidiarrhoeal, and hypolipidemic activities. This review summarizes the information and findings concerning the current knowledge on the biological activities, pharmacological properties, toxicity, and chemical constituents of Loranthus micranthus.
The formation of electronically excited fragments by the electron impact of furan and related five-membered heterocycles

International Nuclear Information System (INIS)

Tokue, Ikuo; Ikarashi, Masami; Takizawa, Sadachika; Ito, Yoshio

1983-01-01

In the wavelength region of 200-600 nm, photoemissions from electronically excited H, CH, C 2 , and CS (only from thiophene and tetrahydrothiophene) were observed when furan, tetrahydrofuran, thiophene, and tetrahydrothiophene were excited by electron impact (0-70 eV). Hydrogen atoms (n = 4) and CH(A 2 Δ) radicals were produced from these five-membered heterocycles via single collision excitations, while CS(A 1 PI) radicals from thiophene and tetrahydrothiophene were partly formed in secondary processes. The appearance potentials for the hydrogen Balmer β and the CH(A 2 Δ-X 2 PI) bands from these five-membered heterocycles are determined, and the dissociation processes forming H(n = 4) and CH(A) are discussed. (author)
Polysaccharides from Traditional Chinese Medicines: Extraction, Purification, Modification, and Biological Activity.

Science.gov (United States)

Chen, Yun; Yao, Fangke; Ming, Ke; Wang, Deyun; Hu, Yuanliang; Liu, Jiaguo

2016-12-13

Traditional Chinese Medicine (TCM) has been used to treat diseases in China for thousands of years. TCM compositions are complex, using as their various sources plants, animals, fungi, and minerals. Polysaccharides are one of the active and important ingredients of TCMs. Polysaccharides from TCMs exhibit a wide range of biological activities in terms of immunity- modifying, antiviral, anti-inflammatory, anti-oxidative, and anti-tumor properties. With their widespread biological activities, polysaccharides consistently attract scientist's interests, and the studies often concentrate on the extraction, purification, and biological activity of TCM polysaccharides. Currently, numerous studies have shown that the modification of polysaccharides can heighten or change the biological activities, which is a new angle of polysaccharide research. This review highlights the current knowledge of TCM polysaccharides, including their extraction, purification, modification, and biological activity, which will hopefully provide profound insights facilitating further research and development.
Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

KAUST Repository

Queval, Pierre

2013-12-04

A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93 %) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand. A low-cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl- imidazolium salts in good yields and excellent selectivities, is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron-donor ability, high steric discrimination, and modular steric demand. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Enantioselective N-Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium.

Science.gov (United States)

Gillard, Rachel M; Fernando, Jared E M; Lupton, David W

2018-04-16

Herein we report the enantioselective N-heterocyclic carbene catalyzed (4+2) annulation of the dienyl acyl azolium with enolates. The reaction exploits readily accessible acyl fluorides and TMS enol ethers to give a range of highly enantio- and diastereo-enriched cyclohexenes (most >97:3 er and >20:1 dr). The reaction was found to require high nucleophilicity NHC catalysts with mechanistic studies supporting a stepwise 1,6-addition/β-lactonization. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Synthesis and Biological Activity of 2',3'-iso-Aryl-abscisic Acid Analogs.

Science.gov (United States)

Wan, Chuan; Wang, Mingan; Yang, Dongyan; Han, Xiaoqiang; Che, Chuanliang; Ding, Shanshan; Xiao, Yumei; Qin, Zhaohai

2017-12-15

2',3'- iso -Benzoabscisic acid ( iso -PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, including the substitution of phenyl ring and replacing the ring with heterocycles. Thus, 16 novel analogs of iso -PhABA were synthesized and screened with three bioassays, Arabidopsis and lettuce seed germination and rice seedling elongation. Some of them, i.e., 2',3'- iso -pyridoabscisic acid ( iso -PyABA) and 2',3'- iso -franoabscisic acid ( iso -FrABA), displayed good bioactivities that closed to iso -PhABA and natural (+)-ABA. Some others, for instance, substituted- iso -PhABA, exhibited certain selectivity to different physiological process when compared to iso -PhABA or (+)-ABA. These analogs not only provided new candidates of ABA-like synthetic plant growth regulators (PGRs) for practical application, but also new potential selective agonist/antagonist for probing the specific function of ABA receptors.
The Effect of Novel Heterocyclic Compounds on Cryptococcal Biofilm

Science.gov (United States)

Korem, Maya; Kagan, Sarah

2017-01-01

Biofilm formation by microorganisms depends on their communication by quorum sensing, which is mediated by small diffusible signaling molecules that accumulate in the extracellular environment. During human infection, the pathogenic yeast Cryptococcus neoformans can form biofilm on medical devices, which protects the organism and increases its resistance to antifungal agents. The aim of this study was to test two novel heterocyclic compounds, S-8 (thiazolidinedione derivative, TZD) and NA-8 (succinimide derivative, SI), for their anti-biofilm activity against strains of Cryptococcus neoformans and Cryptococcus gattii. Biofilms were formed in a defined medium in 96-well polystyrene plates and 8-well micro-slides. The effect of sub-inhibitory concentrations of S-8 and NA-8 on biofilm formation was measured after 48 h by a metabolic reduction assay and by confocal laser microscopy analysis using fluorescent staining. The formation and development of cryptococcal biofilms was inhibited significantly by these compounds in concentrations below the minimum inhibitory concentration (MIC) values. These compounds may have a potential role in preventing fungal biofilm development on indwelling medical devices or even as a therapeutic measure after the establishment of biofilm. PMID:29371559
The pH-influenced PET processes between pyronine and different heterocycles.

Science.gov (United States)

Yang, Ling; Niu, Jin-Yun; Sun, Ru; Xu, Yu-Jie; Ge, Jian-Feng

2017-10-11

The OFF-ON and ON-OFF type pH probes based on rosamine were designed by using the relative electron densities between pyronine and various linked heterocycles. Probe 1a with an indole-pyronine skeleton gave an OFF-ON pH response (pK a = 1.41) with decreasing pH, and the relative fluorescence intensity increased 15-fold, while probe 1b with an imidazole-pyronine skeleton did not give an ON-OFF response to different pH values. When pyronine was connected with a quinolinyl group, i.e., probes 1c-d, the red emission (around 575-800 nm) gave a monotonous ON-OFF pH response (pK a = 3.26 and 2.62, respectively) with decreasing pH. The relative fluorescence intensities decreased 263- and 46-fold, respectively. Changes in the electron donating abilities of the nitrogen containing heterocycles were used to explain variations in PET processes within the probes, and their pH-dependent PET mechanisms were verified using time-dependent density functional theory calculations. Confocal fluorescence imaging was also used to evaluate the potential biomedical application of probes 1a-d. Ultimately, probe 1d with an appropriate pK a value and good biocompatibility showed lysosome targeting ability.
O-heterocyclic derivatives with antibacterial properties from marine bacterium Bacillus subtilis associated with seaweed, Sargassum myriocystum.

Science.gov (United States)

Chakraborty, Kajal; Thilakan, Bini; Chakraborty, Rekha Devi; Raola, Vamshi Krishna; Joy, Minju

2017-01-01

The brown seaweed, Sargassum myriocystum associated with heterotrophic bacterium, Bacillus subtilis MTCC 10407 (JF834075) exhibited broad-spectra of potent antibacterial activities against pathogenic bacteria Aeromonas hydrophila, Vibrio vulnificus, and Vibrio parahaemolyticus. B. subtilis MTCC 10407 was found to be positive for polyketide synthetase (pks) gene, and therefore, was considered to characterize secondary metabolites bearing polyketide backbone. Using bioassay-guided fractionation, two new antibacterial O-heterocyclic compounds belonging to pyranyl benzoate analogs of polyketide origin, with activity against pathogenic bacteria, have been isolated from the ethyl acetate extract of B. subtilis MTCC 10407. In the present study, the secondary metabolites of B. subtilis MTCC 10407 with potent antibacterial action against bacterial pathogens was recognized to represent the platform of pks-1 gene-encoded products. Two homologous compounds 3 (3-(methoxycarbonyl)-4-(5-(2-ethylbutyl)-5,6-dihydro-3-methyl-2H-pyran-2-yl)-butyl benzoate) and 4 [2-(8-butyl-3-ethyl-3,4,4a,5,6,8a-hexahydro-2H-chromen-6-yl)-ethyl benzoate] also have been isolated from the ethyl acetate extract of host seaweed S. myriocystum. The two compounds isolated from ethyl acetate extract of S. myriocystum with lesser antibacterial properties shared similar structures with the compounds purified from B. subtilis that suggested the ecological and metabolic relationship between these compounds in seaweed-bacterial relationship. Tetrahydropyran-2-one moiety of the tetrahydropyrano-[3,2b]-pyran-2(3H)-one system of 1 might be cleaved by the metabolic pool of seaweeds to afford methyl 3-(dihydro-3-methyl-2H-pyranyl)-propanoate moiety of 3, which was found to have no significant antibacterial activity. It is therefore imperative that the presence of dihydro-methyl-2H-pyran-2-yl propanoate system is essentially required to impart the greater activity. The direct involvement of polarisability (Pl) with
Replacement of the double bond of antitubulin chalcones with triazoles and tetrazoles: Synthesis and biological evaluation.

Science.gov (United States)

Mesenzani, Ornella; Massarotti, Alberto; Giustiniano, Mariateresa; Pirali, Tracey; Bevilacqua, Valentina; Caldarelli, Antonio; Canonico, Pierluigi; Sorba, Giovanni; Novellino, Ettore; Genazzani, Armando A; Tron, Gian Cesare

2011-01-15

In the chalcone scaffold, it is thought that the double bond is an important structural linker but it is likely not essential for the interaction with tubulin. Yet, it may be a potential site of metabolic degradation and interaction with biological nucleophiles. In this letter, we have replaced this olefinic portion of chalcones with two metabolically stable and chemically inert heterocyclic rings, namely triazole or tetrazole. Yet, our biologic data suggest that, unlike in other antitubulinic structures, the olephinic ring might not be merely a structural linker. Copyright Â© 2010 Elsevier Ltd. All rights reserved.
Polysaccharides from Traditional Chinese Medicines: Extraction, Purification, Modification, and Biological Activity

Directory of Open Access Journals (Sweden)

Yun Chen

2016-12-01

Full Text Available Traditional Chinese Medicine (TCM has been used to treat diseases in China for thousands of years. TCM compositions are complex, using as their various sources plants, animals, fungi, and minerals. Polysaccharides are one of the active and important ingredients of TCMs. Polysaccharides from TCMs exhibit a wide range of biological activities in terms of immunity- modifying, antiviral, anti-inflammatory, anti-oxidative, and anti-tumor properties. With their widespread biological activities, polysaccharides consistently attract scientist's interests, and the studies often concentrate on the extraction, purification, and biological activity of TCM polysaccharides. Currently, numerous studies have shown that the modification of polysaccharides can heighten or change the biological activities, which is a new angle of polysaccharide research. This review highlights the current knowledge of TCM polysaccharides, including their extraction, purification, modification, and biological activity, which will hopefully provide profound insights facilitating further research and development.
SYNTHESIS AND STUDY OF HALOGENATED BENZYLAMIDES OF SOME ISOCYCLIC AND HETEROCYCLIC ACIDS AS POTENTIAL ANTICONVULSANTS.

Science.gov (United States)

Strupińska, Marzanna; Rostafińska-Suchar, Grażyna; Pirianowicz-Chaber, Elżbieta; Grabczuk, Mateusz; Józwenko, Magdalena; Kowalczyk, Hubert; Szuba, Joanna; Wójcicka, Monika; Chen, Tracy; Mazurek, Aleksander P

2015-01-01

A series of potential anticonvulsants have been synthesized. There are eight fluorobenzylamides and three chlorobenzylamides of isocyclic or heterocyclic acids. Two not halogenated benzylamides were also synthesized to compare the effect of halogenation. The aim of the research performed was to evaluate whether halogenation of the mother structure is able to improve its anticonvulsant activity. The compounds were tested in Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH. Compound 1 showed MES ED50 = 80.32 mg/kg, PI = 3.16. Compound 7 showed CKM ED50 = 56.72 mg/kg. Compound 8 showed MES ED50 = 34.23 mg/kg and scPTZ ED50 > 300 mg/kg, PI = 8.53.Compound 13 showed 6Hz ED50 = 78.96, PI = 3.37. The results indicate that fluorination does not improve activity, whereas chlorination in our experiment even reduces it.
Adsorption Characteristics of DNA Nucleobases, Aromatic Amino Acids and Heterocyclic Molecules on Silicene and Germanene Monolayers

KAUST Repository

Hussain, Tanveer; Vovusha, Hakkim; Kaewmaraya, Thanayut; Amornkitbamrung, Vittaya; Ahuja, Rajeev

2017-01-01

Binding of DNA/RNA nucleobases, aromatic amino acids and heterocyclic molecules on two-dimensional silicene and germanene sheets have been investigated for the application of sensing of biomolecules using first principle density functional theory
Correlations between electrochemical and spectrochemical parameters of ruthenium sulfoxides series with N-heterocyclic

International Nuclear Information System (INIS)

Oliveira, D. de; Toma, H.E.

1990-01-01

A systematic study of Ru Cl sub(2) (DMSO) sub(2) L sub(2) derivates, where L = N-heterocyclic base is described, contributing for a best understanding of chemical behaviour and electronic structure of the ruthenium sulfoxides. The correlations between the electrochemical and the spectroscopical parameters of the serie are presented with more emphasis. (author)
Amide Synthesis from Alcohols and Amines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes

DEFF Research Database (Denmark)

Dam, Johan Hygum; Osztrovszky, Gyorgyi; Nordstrøm, Lars Ulrik Rubæk

2010-01-01

The direct synthesis of amides from alcohols and amines is described with the simultaneous liberation of dihydrogen. The reaction does not require any stoichiometric additives or hydrogen acceptors and is catalyzed by ruthenium N-heterocyclic carbene complexes. Three different catalyst systems...... are presented that all employ 1,3-diisopropylimidazol-2-ylidene (IiPr) as the carbene ligand. In addition, potassium tert-butoxide and a tricycloalkylphosphine are required for the amidation to proceed. In the first system, the active catalyst is generated in situ from [RuCl2(cod)] (cod = 1,5-cyclooctadiene), 1...... chloride and base. A range of different primary alcohols and amines have been coupled in the presence of the three catalyst systems to afford the corresponding amides in moderate to excellent yields. The best results are obtained with sterically unhindered alcohols and amines. The three catalyst systems do...

Improving cytotoxic properties of ferrocenes by incorporation of saturated N-heterocycles

Czech Academy of Sciences Publication Activity Database

Hodík, Tomáš; Lamač, Martin; Červenková Šťastná, Lucie; Cuřínová, Petra; Karban, Jindřich; Skoupilová, H.; Hrstka, R.; Císařová, I.; Gyepes, Robert; Pinkas, Jiří

2017-01-01

Roč. 846, OCT 2017 (2017), s. 141-151 ISSN 0022-328X R&D Projects: GA ČR(CZ) GAP207/12/2368; GA ČR(CZ) GA17-05838S Institutional support: RVO:61388955 ; RVO:67985858 Keywords : metallodrugs * ferrocene derrivatives * N-heterocycles Subject RIV: CF - Physical ; Theoretical Chemistry; CF - Physical ; Theoretical Chemistry (UCHP-M) OBOR OECD: Inorganic and nuclear chemistry; Physical chemistry (UCHP-M) Impact factor: 2.184, year: 2016
Effect of gamma irradiation on biological activity of thyrotropin

Energy Technology Data Exchange (ETDEWEB)

Strbak, V; Macho, L; Sedlak, J; Hromadova, M

1976-03-01

The biological activity of thyrotropin (TSH) was tested after sterilization by 0.5 and 12.5 Mrad of gamma irradiation. It was found that the biological activity (McKenzie's assay) of TSH irradiated in dry state was not affected during the first month after sterilization by doses of 0.5 and 2.5 Mrad. However, substantial decrease of TSH biological activity was observed 3 to 5 months after the irradiation, the lower activity being after the former dose. The irradiation of TSH by 12.5 Mrad in dry state and by 0.5 and 2.5 Mrad in solution resulted in a decrease of biological activity already during first month. The structural changes in the molecule of TSH were apparently not very extensive, since a decrease of disulfide bonds from 0.96 to 0.77 M per 1M of TSH was found immediately after the irradiation, while uv absorbancy and electrophoretic mobility on polyacrylamide gel electrophoresis were unaffected. These changes were followed by the decrease of TSH stability during storage in dry state. It is hypothesized that TSH molecule may be affected in ..beta.. subunit or in its connection with ..cap alpha...
Effect of gamma irradiation on biological activity of thyrotropin

International Nuclear Information System (INIS)

Strbak, V.; Macho, L.; Sedlak, J.; Hromadova, M.

1976-01-01

The biological activity of thyrotropin (TSH) was tested after sterilization by 0.5 and 12.5 Mrad of gamma radiation. It was found that the biological activity (McKenzie's assay) of TSH irradiated in dry state was not affected during the first month after sterilization by doses of 0.5 and 2.5 Mrad. However, substantial decrease of TSH biological activity was observed 3 to 5 months after the irradiation, the lower activity after the 0.5 Mrad dose. The irradiation of TSH by 12.5 Mrad in dry state and by 0.5 and 2.5 Mrad in solution resulted in decreased biological activity already during the first month. The structural changes in the TSH molecule were apparently not very extensive, as a decrease of disulfide bonds from 0.96 to 0.77 M per 1 M of TSH was found immediately after the irradiation, while UV absorbancy and electrophoretic mobility on polyacrylamide gel electrophoresis were unaffected. These changes were followed by a decrease of TSH stability during storage in dry state. It is hypothesized that a TSH molecule may be affected in a β subunit or in its connection with α. (author)
Quantum chemical modeling of the inhibition mechanism of monoamine oxidase by oxazolidinone and analogous heterocyclic compounds.

Science.gov (United States)

Erdem, Safiye Sağ; Özpınar, Gül Altınbaş; Boz, Ümüt

2014-02-01

Monoamine oxidase (MAO, EC 1.4.3.4) is responsible from the oxidation of a variety of amine neurotransmitters. MAO inhibitors are used for the treatment of depression or Parkinson's disease. They also inhibit the catabolism of dietary amines. According to one hypothesis, inactivation results from the formation of a covalent adduct to a cysteine residue in the enzyme. If the adduct is stable enough, the enzyme is inhibited for a long time. After a while, enzyme can turn to its active form as a result of adduct breakdown by β-elimination. In this study, the proposed inactivation mechanism was modeled and tested by quantum chemical calculations. Eight heterocyclic methylthioamine derivatives were selected to represent the proposed covalent adducts. Activation energies related to their β-elimination reactions were calculated using ab initio and density functional theory methods. Calculated activation energies were in good agreement with the relative stabilities of the hypothetical adducts predicted in the literature by enzyme inactivation measurements.
Identification of the Eight-Membered Heterocycles Hicksoanes A-C from the Gorgonian Subergorgia hicksoni

Czech Academy of Sciences Publication Activity Database

Řezanka, Tomáš; Hanuš, L. O.; Dembitsky, V. M.; Sigler, Karel

2008-01-01

Roč. 2008, č. 7 (2008), s. 1265-1270 ISSN 1434-193X R&D Projects: GA MŠk 1P05OC073 Institutional research plan: CEZ:AV0Z50200510 Keywords : gorgonians * nitrogen heterocycles * natural products Subject RIV: EE - Microbiology, Virology Impact factor: 3.016, year: 2008
New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis, Structure, Properties and Application as Chiral Solvating Agents

Czech Academy of Sciences Publication Activity Database

Sheshenev, A. E.; Boltukhina, E. V.; Grishina, Anastasia; Císařová, I.; Lyapkalo, Ilya; Hii, K. K.

2013-01-01

Roč. 19, č. 25 (2013), s. 8136-8143 ISSN 0947-6539 Grant - others:7th European Community Framework Programme(XE) FP7-252247 Institutional support: RVO:61388963 Keywords : binding constants * chirality * enantioselectivity * NMR spectroscopy * phosphorus heterocycles * zwitterions Subject RIV: CC - Organic Chemistry Impact factor: 5.696, year: 2013
Investigation of the structure and properties of heterocyclic compounds and their complexes

International Nuclear Information System (INIS)

Shejnker, V.N.; Troilina, V.S.; Merinova, E.G.; Garnovskij, A.D.; Osipov, O.A.

1988-01-01

Complexing of acetyl derivatives of azoles with iodine and bromine iodide is investigated using UV-spectroscopy and dipole moment methods. In bimolecular complexes σ-acceptor coordination occurs by heterocycle pyridine type nitrogen atom and is not accompanied by the ligand conformation change. The complex stability increases in agreement with azole basicity. For N-acetyltriazole ligand, conformation reversal occurs in its trimolecular complex with IBr
Bimacrocyclic concave N-heterocyclic carbenes (NHCs): synthesis, structure, and application in catalyses

OpenAIRE

Lüning , Ulrich; Winkelmann , Ole

2009-01-01

Abstract Imidazolinium moieties have been incorporated into bimacrocycles to generate precursors for concave N-heterocyclic carbenes (NHCs). Starting from 2-nitroresorcinol and alkenols, symmetric concave imidazolinium salts 1 were obtained. Bimacrocyclization was achieved via ring closing metathesis (RCM). In an analogous fashion, axially chiral concave imidazolinium salts 2 were obtained by using a naphthalene bridgehead devoid of local C2-symmetry. The concave NHCs derived from ...
Transport of biologically active material in laser cutting.

Science.gov (United States)

Frenz, M; Mathezloic, F; Stoffel, M H; Zweig, A D; Romano, V; Weber, H P

1988-01-01

The transport of biologically active material during laser cutting with CO2 and Er lasers is demonstrated. This transport mechanism removes particles from the surface of gelatin, agar, and liver samples into the depth of the laser-formed craters. The transport phenomenon is explained by a contraction and condensation of enclosed hot water vapor. We show by cultivating transported bacteria in agar that biological particles can survive the shock of the transport. Determination of the numbers of active cells evidences a more pronounced activity of the cultivated bacteria after impact with an Er laser than with a CO2 laser.
Systems Biology Graphical Notation: Activity Flow language Level 1 Version 1.2.

Science.gov (United States)

Mi, Huaiyu; Schreiber, Falk; Moodie, Stuart; Czauderna, Tobias; Demir, Emek; Haw, Robin; Luna, Augustin; Le Novère, Nicolas; Sorokin, Anatoly; Villéger, Alice

2015-09-04

The Systems Biological Graphical Notation (SBGN) is an international community effort for standardized graphical representations of biological pathways and networks. The goal of SBGN is to provide unambiguous pathway and network maps for readers with different scientific backgrounds as well as to support efficient and accurate exchange of biological knowledge between different research communities, industry, and other players in systems biology. Three SBGN languages, Process Description (PD), Entity Relationship (ER) and Activity Flow (AF), allow for the representation of different aspects of biological and biochemical systems at different levels of detail. The SBGN Activity Flow language represents the influences of activities among various entities within a network. Unlike SBGN PD and ER that focus on the entities and their relationships with others, SBGN AF puts the emphasis on the functions (or activities) performed by the entities, and their effects to the functions of the same or other entities. The nodes (elements) describe the biological activities of the entities, such as protein kinase activity, binding activity or receptor activity, which can be easily mapped to Gene Ontology molecular function terms. The edges (connections) provide descriptions of relationships (or influences) between the activities, e.g., positive influence and negative influence. Among all three languages of SBGN, AF is the closest to signaling pathways in biological literature and textbooks, but its well-defined semantics offer a superior precision in expressing biological knowledge.
N-heterocyclic carbene copper(I) catalysed N-methylation of amines using CO2

KAUST Repository

Santoro, Orlando

2015-09-30

The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.
N-heterocyclic carbene copper(I) catalysed N-methylation of amines using CO2

KAUST Repository

Santoro, Orlando; Lazreg, Faï ma; Minenkov, Yury; Cavallo, Luigi; Cazin, Catherine S. J.

2015-01-01

The N-methylation of amines using CO2 and PhSiH3 as source of CH3 was efficiently performed using a N-heterocyclic carbene copper(I) complex. The methodology was found compatible with aromatic and aliphatic primary and secondary amines. Synthetic and computational studies have been carried out to support the proposed reaction mechanism for this transformation.
Biological Activity of Curcuminoids Isolated from Curcuma longa

Directory of Open Access Journals (Sweden)

Simay Çıkrıkçı

2008-04-01

Full Text Available Curcumin is the most important fraction of turmeric which is responsible for its biological activity. In this study, isolation and biological assessment of turmeric and curcumin have been discussed against standard bacterial and mycobacterial strains such as E.coli , S.aureus, E.feacalis, P.aeuroginosa, M.smegmatis, M.simiae, M.kansasii, M. terrae, M.szulgai and the fungi Candida albicans. The antioxidant activity of curcumin and turmeric were also determined by the CUPRAC method.
Anaerobic biodegradation of halogenated and nonhalogenated N-, s-, and o-heterocyclic compounds in aquifer slurries

Science.gov (United States)

Adrian, Neal R.; Suflita, Joseph M.

1994-01-01

The fate of several halogenated and nonhalogenated heterocyclic compounds in anoxic aquifer slurries was investigated Substrate depletion and methane formation were monitored in serum bottle incubations by HPLC and GC, respectively Pyridine, pyrimidine, thiophene, and furan were not mineralized following an 11-month incubation, but the corresponding carboxylated or oxygenated compounds were That is, >74% of the theoretically expected amount of methane was recovered from nicotinic acid, uracil, or 2-furoic acid Chlorinated derivatives, like 2 chloro- or 6-chloronicotinic acid, as well as 4 chloro- and 5-chlorouracil resisted mineralization However, 5-bromouracil was reductively dehalogenated to stoichiometric amounts of uracil, whereas 2-chloropyrimidine was metabolized to a more polar unidentified compound that resisted further anaerobic biodegradation Microorganisms acclimated to 5-bromouracil were unable to transform 4 chloro or 5 chlorouracil These findings illustrate how the structure of heterocyclic contaminants influences their susceptibility to anaerobic decay
Fusion of heterocyclic polymerogenic units onto a central ring: a fruitful approach to the investigation and specific tailoring of the dependence of electrical properties on monomer structure in conductive polyheterocycles

Energy Technology Data Exchange (ETDEWEB)

Berlin, A.; Brenna, E.; Pagani, G.A.; Sannicolo, F. (Dipt. di Chimica Organica e Industriale, Univ. di Milano (Italy) Centro CNR Speciali Sistemi Organici, Milan (Italy)); Zotti, G.; Schiavon, G. (CNR, Ist. di Polarografia ed Elettrochimica Preparativa, Padua (Italy))

1992-09-01

In this review the ''spacer'' strategy is described and evaluated in detail. According to this principle, the monomer contains, as terminal units, two polymerogenic rings (pyrrole or thiophene) linked to a central [pi]-conjugatively-active frame; as spacers, we have investigated ethenylic, sulphide, and aromatic moieties. In this way the redox potentials, E[sup 0], of the polymers derived from such monomers can be calibrated by the substituent effect exerted by the spacer. This control is beneficial because it is possible to increase the E[sup 0] value of polypyrrole-type systems and decrease the E[sup 0] value of polythiophene-type systems. Also, the ''spacer'' may be further functionalised and, being remote from the polymerisation site, cannot alter the conductivity characteristics typical of the polymer derived from the parent heterocycle (pyrrole or thiophene): such a functionalisation may provide the final, tailored, conductive polymer with special properties (e.g., solubility). If the central ring, acting as a ''spacer'', is formed linking two positions of a di-heterocycle with a saturated chain, it is possible partially to control the twist angle between the heterocyclic units. Crystal and molecular structures have shown that dipyrrole units, further linked through the nitrogen atoms, are quite sensitive to the central ring size. With regard to the conductivity of unsubstituted polypyrrole, the conductivity of the polymers derived from such monomers is dependent upon the twist angle between the rings. This result is relevant to a description of conjugation conditions between the heterocyclic units of a monomer required to produce a conductive polymer on doping. (orig.).
Using Active Learning to Teach Concepts and Methods in Quantitative Biology.

Science.gov (United States)

Waldrop, Lindsay D; Adolph, Stephen C; Diniz Behn, Cecilia G; Braley, Emily; Drew, Joshua A; Full, Robert J; Gross, Louis J; Jungck, John A; Kohler, Brynja; Prairie, Jennifer C; Shtylla, Blerta; Miller, Laura A

2015-11-01

This article provides a summary of the ideas discussed at the 2015 Annual Meeting of the Society for Integrative and Comparative Biology society-wide symposium on Leading Students and Faculty to Quantitative Biology through Active Learning. It also includes a brief review of the recent advancements in incorporating active learning approaches into quantitative biology classrooms. We begin with an overview of recent literature that shows that active learning can improve students' outcomes in Science, Technology, Engineering and Math Education disciplines. We then discuss how this approach can be particularly useful when teaching topics in quantitative biology. Next, we describe some of the recent initiatives to develop hands-on activities in quantitative biology at both the graduate and the undergraduate levels. Throughout the article we provide resources for educators who wish to integrate active learning and technology into their classrooms. © The Author 2015. Published by Oxford University Press on behalf of the Society for Integrative and Comparative Biology. All rights reserved. For permissions please email: journals.permissions@oup.com.
Ficus carica L. (Moraceae: Phytochemistry, Traditional Uses and Biological Activities

Directory of Open Access Journals (Sweden)

Shukranul Mawa

2013-01-01

Full Text Available This paper describes the botanical features of Ficus carica L. (Moraceae, its wide variety of chemical constituents, its use in traditional medicine as remedies for many health problems, and its biological activities. The plant has been used traditionally to treat various ailments such as gastric problems, inflammation, and cancer. Phytochemical studies on the leaves and fruits of the plant have shown that they are rich in phenolics, organic acids, and volatile compounds. However, there is little information on the phytochemicals present in the stem and root. Reports on the biological activities of the plant are mainly on its crude extracts which have been proven to possess many biological activities. Some of the most interesting therapeutic effects include anticancer, hepatoprotective, hypoglycemic, hypolipidemic, and antimicrobial activities. Thus, studies related to identification of the bioactive compounds and correlating them to their biological activities are very useful for further research to explore the potential of F. carica as a source of therapeutic agents.
Basic nitrogen-heterocyclic compounds in the Murchison meteorite

International Nuclear Information System (INIS)

Stoks, P.G.; Schwartz, A.W.

1982-01-01

A fragment of the Murchison (C2) carbonaceous meteorite was analyzed for basic, N-heterocyclic compounds, by dual detector capillary gas chromatography as well as capillary gas chromatography/mass spectrometry, using two columns of different polarity. In the formic acid extract 2,4,6-trimethylpyridine, quinoline, isoquinoline, 2-methylquinoline and 4-methylquinoline were positively identified. In addition, a suite of alkylpyridines and quinolines and/or isoquinolines was tentatively identified from their mass spectra. The (iso)quinolines were found to contain methyl substituents exclusively. The distribution of the pyridines observed reveals a similarity to that observed from catalytic reactions of ammonia and simple aldehydes under conditions similar to those applied in Fischer-Tropsch type reactions. (author)
Synthesis, electrochemical, structural and theoretical study of new derivatives of OABAN and OABAO heterocycles

Czech Academy of Sciences Publication Activity Database

Mikysek, T.; Kvapilová, Hana; Doušová, H.; Josefík, F.; Šimůnek, P.; Růžičková, Z.; Ludvík, Jiří

2017-01-01

Roč. 455, č. 2 (2017), s. 465-472 ISSN 0020-1693 R&D Projects: GA MŠk LD14129 Institutional support: RVO:61388955 Keywords : boron heterocycles * synthesis * electrochemistry Subject RIV: CG - Electrochemistry OBOR OECD: Electrochemistry (dry cells, batteries, fuel cells, corrosion metals, electrolysis) Impact factor: 2.002, year: 2016
Antibacterial and DNA cleavage activity of carbonyl functionalized N-heterocyclic carbene-silver(I) and selenium compounds

Science.gov (United States)

Haque, Rosenani A.; Iqbal, Muhammad Adnan; Mohamad, Faisal; Razali, Mohd R.

2018-03-01

The article describes syntheses and characterizations of carbonyl functionalized benzimidazolium salts, I-IV. While salts I-III are unstable at room temperature, salt IV remained stable and was further utilised to form N-heterocyclic carbene (NHC) compounds of silver(I), V and VI, and selenium compound, VII respectively. Compounds IV-VII were tested for their antibacterial potential against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). Salt IV shows a very low inhibition potential (minimum inhibitory concentration, MIC 500 μg/mL) compared to the respective silver(I)-NHC, V and VI (MIC 31.25 μg/mL against both, E. coli and S. aureus) and selenium compound, VII (MIC 125 μg/mL against E. coli and 62.50 μg/mL against S. aureus). In DNA cleavage abilities, all the test compounds cleave DNA in which the VII cleaves the DNA at the faster rate. Meanwhile, the silver(I)-NHC complexes V and VI act at the same mode and pattern of DNA cleavage while VII is similar to IV.

A Conceptual Framework for Organizing Active Learning Experiences in Biology Instruction

Science.gov (United States)

Gardner, Joel; Belland, Brian R.

2012-01-01

Introductory biology courses form a cornerstone of undergraduate instruction. However, the predominantly used lecture approach fails to produce higher-order biology learning. Research shows that active learning strategies can increase student learning, yet few biology instructors use all identified active learning strategies. In this paper, we…
Kinetics of molybdenum(6) complexation with o,o'-dihydroxyazo compounds or heterocyclic azo compounds in the presence of hydroxylamine

International Nuclear Information System (INIS)

Kochelaeva, G.A.; Degtyarev, M.Yu.; Ivanov, V.M.; Prokhorova, G.V.; Figurovskaya, V.N.

1999-01-01

The kinetics of complexation in the system molybdenum(6)-azo compound-hydroxylamine was studied. Azo compounds of the types o,o'-dihydroxyazo compounds, such as Lyumogallion IREA and Magneson IREA, and heterocyclic azo compounds, such as 4-(2-pyridylazo)resorcinol and 2-(5-bromo-2-pyridylazo)-5-diethylaminophenol, were studied. The formation of mixed-ligand complexes with the ratio of component 1 : 1 : 1 was detected. Rate constants, activation energies, and stability constants of the forming compounds were evaluated. It was concluded that the reagents under study are promising for the analytical chemistry of molybdenum [ru
Synthesis, structure, antioxidant activity, and water solubility of trolox ion conjugates

Directory of Open Access Journals (Sweden)

Yuliya V. Yushkova

2018-01-01

Full Text Available The interaction of trolox with ammonia, alkylamines of different classes, and amino derivatives of heterocyclic compounds, including nitroxyl radicals and alkaloids, led to the production of ammonium salts called ion conjugates (ICs. Five ICs were characterised by X-ray diffraction. This is the first time a wide range of ICs were made from trolox with amines, and ESI-MS data demonstrated they have the potential to generate pseudomolecular [(A−B+ + H]+ ions. For all obtained trolox ICs, a significant increase (1–3 orders of magnitude in water solubility was achieved while retaining high antioxidant activity. ICs synthesised from two biologically active fragments may be used to create polyfunctional agents with varying solubility and bioavailability. Keywords: Trolox, Amines, Ion conjugates, Antioxidants, Mass-spectrometry
AUTHOR INDEX

Indian Academy of Sciences (India)

Administrator

711. Ansari K F. Synthesis and biological activity of some heterocyclic .... π–π stacking interactions: Hydrothermal syntheses ... Synthesis and characterization of CdS and CdSe nanoparticles prepared from novel intramolecularly stabilized ...
Half -sand wish ruthenium complexes of heterocyclic-dithio carboxylato ligands

International Nuclear Information System (INIS)

El-khateeb, M.; Al-Noaimi, M.; Harb, M.; Gorls, H.; Weigand, W.

2008-01-01

The heterocyclic-dithio carboxylato complexes Cp Ru(PPh 3 )(κ 2 S,S-S 2 C-h et) [h et= 2-C 4 H 3 O (1), 2-C 4 H 3 S (2), 1-C 4 H 8 N (3)] are obtained by the reaction of the ruthenium chloride, Cp Ru(PPh 3 ) 2 CI, with the anions, h et-CS 2 . The X-ray structure of Cp Ru(PPh 3 )(κ 2 S, S-S 2 C-1- C 4 H 8 N) (3) is determined by single crystal X-ray diffraction.
Electrochemical oxidation of nitrogen-heterocyclic compounds at boron-doped diamond electrode.

Science.gov (United States)

Xing, Xuan; Zhu, Xiuping; Li, Hongna; Jiang, Yi; Ni, Jinren

2012-01-01

Nitrogen-heterocyclic compounds (NHCs) are toxic and bio-refractory contaminants widely spread in environment. This study investigated electrochemical degradation of NHCs at boron-doped diamond (BDD) anode with particular attention to the effect of different number and position of nitrogen atoms in molecular structure. Five classical NHCs with similar structures including indole (ID), quinoline (QL), isoquinoline (IQL), benzotriazole (BT) and benzimidazole (BM) were selected as the target compounds. Results of bulk electrolysis showed that degradation of all NHCs was fit to a pseudo first-order equation. The five compounds were degraded with the following sequence: ID>QL>IQL>BT>BM in terms of their rates of oxidation. Quantum chemical calculation was combined with experimental results to describe the degradation character of NHCs at BDD anode. A linear relationship between degradation rate and delocalization energy was observed, which demonstrated that electronic charge was redistributed through the conjugation system and accumulated at the active sites under the attack of hydroxyl radicals produced at BDD anode. Moreover, atom charge was calculated by semi empirical PM3 method and active sites of NHCs were identified respectively. Analysis of intermediates by GC-MS showed agreement with calculation results. Copyright © 2011 Elsevier Ltd. All rights reserved.
Biological activities of some Xylooligosaccharides from ...

African Journals Online (AJOL)

Xylooligosaccharides (XOS's) exhibited considerable biological activities and be incorporated into many food products and in pharmaceutical and drug industry. XOS's were produced from xylose-containing polysaccharides (XPS's) obtained from natural, xylan-rich, agro-industrial wastes, i.e., corncobs and sugarcane ...
Reduction of the Work Function of Gold by N-Heterocyclic Carbenes

KAUST Repository

Kim, Hye Kyung

2017-04-12

N-Heterocyclic carbenes (NHCs) bind strongly to gold and other metals. This work experimentally probes the effect of NHCs on the work function (WF) of gold for the first time, theoretically analyzes the origin of this effect, and examines the effectiveness of NHC-modified gold as an electron-injecting electrode. UV photoelectron spectroscopy shows the WF of planar gold is reduced by nearly 2 eV to values of 3.3–3.5 eV. This effect is seen for NHCs with various heterocyclic cores, and with either small or large N,N′-substituents. DFT calculations indicate the WF reduction results from both the interface dipole formed between the NHC and the gold and from the NHC molecular dipole. For N,N′-diisopropyl-NHCs, an important contributor to the former is charge transfer associated with coordination of the carbene carbon atom to gold. In contrast, the carbene carbon of N,N′-2,6-diisopropylphenyl-NHCs is not covalently bound to gold, resulting in a lower interface dipole; however, a larger molecular dipole partially compensates for this. Single-layer C60 diodes with NHC-modified gold as the bottom electrode demonstrate high rectification ratios and show that these electrodes can act as effective electron-injecting contacts, suggesting they may be useful for a variety of materials applications.
Reduction of the Work Function of Gold by N-Heterocyclic Carbenes

KAUST Repository

Kim, Hye Kyung; Hyla, Alexander; Winget, Paul; Li, Hong; Wyss, Chelsea M.; Jordan, Abraham J.; Larrain, Felipe A.; Sadighi, Joseph P.; Fuentes-Hernandez, Canek; Kippelen, Bernard; Bredas, Jean-Luc; Barlow, Stephen; Marder, Seth R.

2017-01-01

N-Heterocyclic carbenes (NHCs) bind strongly to gold and other metals. This work experimentally probes the effect of NHCs on the work function (WF) of gold for the first time, theoretically analyzes the origin of this effect, and examines the effectiveness of NHC-modified gold as an electron-injecting electrode. UV photoelectron spectroscopy shows the WF of planar gold is reduced by nearly 2 eV to values of 3.3–3.5 eV. This effect is seen for NHCs with various heterocyclic cores, and with either small or large N,N′-substituents. DFT calculations indicate the WF reduction results from both the interface dipole formed between the NHC and the gold and from the NHC molecular dipole. For N,N′-diisopropyl-NHCs, an important contributor to the former is charge transfer associated with coordination of the carbene carbon atom to gold. In contrast, the carbene carbon of N,N′-2,6-diisopropylphenyl-NHCs is not covalently bound to gold, resulting in a lower interface dipole; however, a larger molecular dipole partially compensates for this. Single-layer C60 diodes with NHC-modified gold as the bottom electrode demonstrate high rectification ratios and show that these electrodes can act as effective electron-injecting contacts, suggesting they may be useful for a variety of materials applications.
Synthesis, characterization, and reactivity of furan- and thiophene-functionalized bis(n-heterocyclic carbene) complexes of iron(II)

KAUST Repository

Rieb, Julia; Raba, Andreas; Haslinger, Stefan; Kaspar, Manuel; Pö thig, Alexander; Cokoja, Mirza; Basset, Jean-Marie; Kü hn, Fritz

2014-01-01

The synthesis of iron(II) complexes bearing new heteroatom-functionalized methylene-bridged bis(N-heterocyclic carbene) ligands is reported. All complexes are characterized by single-crystal X-ray diffraction (SC-XRD), nuclear magnetic resonance
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.
Biological activity of SV40 DNA

International Nuclear Information System (INIS)

Abrahams, P.J.

1978-01-01

This thesis deals with a study on the biological activity of SV40 DNA. The transforming activity of SV40 DNA and DNA fragments is investigated in order to define as precisely as possible the area of the viral genome that is involved in the transformation. The infectivity of SV40 DNA is used to study the defective repair mechanisms of radiation damages of human xeroderma pigmentosum cells. (C.F.)
A Review of the Secondary Metabolites and Biological Activities of ...

African Journals Online (AJOL)

Review Article. A Review of the Secondary Metabolites and Biological. Activities of Tinospora crispa ... triterpenes have been isolated, some of which have also shown corresponding biological activities. The current review is an update on the .... were found to exhibit higher antioxidative potency than the synthetic antioxidant.
Fused Heterocyclic Compounds as Potent Indoleamine-2,3-dioxygenase 1 Inhibitors.

Science.gov (United States)

Panda, Subhankar; Roy, Ashalata; Deka, Suman Jyoti; Trivedi, Vishal; Manna, Debasis

2016-12-08

Uncontrolled metabolism of l-tryptophan (l-Trp) in the immune system has been recognized as a critical cellular process in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) enzyme plays an important role in the metabolism of a local l-Trp through the kynurenine pathway in the immune systems. In this regard, IDO1 has emerged as a therapeutic target for the treatment of diseases that are associated with immune suppression like chronic infections, cancer, and others. In this study, we synthesized a series of pyridopyrimidine, pyrazolopyranopyrimidine, and dipyrazolopyran derivatives. Further lead optimizations directed to the identification of potent compounds, 4j and 4l (IC 50 = 260 and 151 nM, respectively). These compounds also exhibited IDO1 inhibitory activities in the low nanomolar range in MDA-MB-231 cells with very low cytotoxicity. Stronger selectivity for the IDO1 enzyme (>300-fold) over tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. Hence, these fused heterocyclic compounds are attractive candidates for the advanced study of IDO1-dependent cellular function and immunotherapeutic applications.
Heterocyclic amines content of meat and fish cooked by Brazilian methods

OpenAIRE

Iwasaki, Motoki; Kataoka, Hiroyuki; Ishihara, Junko; Takachi, Ribeka; Hamada, Gerson Shigeaki; Sharma, Sangita; Le Marchand, Loïc; Tsugane, Shoichiro

2010-01-01

Heterocyclic amine (HCA) concentrations were measured in meat and fish samples cooked by pan-frying, grilling and churrasco (Brazilian barbecue) to various levels of doneness in accordance with the cooking methods most commonly used in Brazil. HCAs were extracted by the Blue-rayon absorption method and measured by liquid chromatography–mass spectrometry. 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), and 2-amino-3,4,8-trimethylim...
Study of physicochemical properties of zinc(II) butyrate complex compounds with some heterocyclic ligands

Czech Academy of Sciences Publication Activity Database

Szakácsová, M.; Györová, K.; Szunyogová, E.; Kovářová, Jana

2002-01-01

Roč. 96, - (2002), s. 383 ISSN 0009-2770. [Meeting of Chemical Societies /54./. 30.06.2002-04.07.2002, Brno] R&D Projects: GA AV ČR KSK4050111; GA MŠk VEGA 1/9247/02; GA MŠk VEGA 047/074 Keywords : butyrate complex compounds * heterocyclic ligands Subject RIV: CD - Macromolecular Chemistry
Synthesis and biological investigation of PIM mimics carrying biotin or a fluorescent label for cellular imaging.

Science.gov (United States)

Front, Sophie; Bourigault, Marie-Laure; Rose, Stéphanie; Noria, Ségueni; Quesniaux, Valérie F J; Martin, Olivier R

2013-01-16

Phosphatidyl inositol mannosides (PIMs) are constituents of the mycobacterial cell wall; these glycolipids are known to exhibit potent inhibitory activity toward the LPS-induced production of cytokines by macrophages, and therefore have potential as anti-inflammatory agents. Recently, heterocyclic analogues of PIMs in which the inositol is replaced by a piperidine (aza-PIM mimics) or a tetrahydropyran moiety (oxa-PIM mimics) have been prepared by short synthetic sequences and shown to retain the biological activity of the parent PIM structures. In this investigation, the aza-PIM analogue was used as a convenient scaffold to link biotin or a fluorescent label (tetramethyl-rhodamine) by way of an aminocaproyl spacer, with the goal of using these conjugates for intracellular localization and for the study of the mechanism of their antiinflammatory action. The synthesis of these compounds is reported, as well as the evaluation of their activities as inhibitors of LPS-induced cytokine production by macrophages (TNFα, IL12p40); preliminary investigations by FACS and confocal microscopy indicated that PIM-biotin conjugate binds to macrophage membranes with rapid kinetics.
Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst.

Science.gov (United States)

Wendlandt, Alison E; Stahl, Shannon S

2014-01-08

Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.
Cyclopentadienyl molybdenum(II/VI) N-heterocyclic carbene complexes: Synthesis, structure, and reactivity under oxidative conditions

KAUST Repository

Li, Shenyu; Kee, Choonwee; Huang, Kuo-Wei; Hor, Andy Sum Andy; Zhao, Jin

2010-01-01

A series of N-heterocyclic carbene (NHC) complexes CpMo(CO) 2(NHC)X (NHC = IMe = 1,3-dimethylimidazol-2-ylidene, X = Br, 1; NHC = 1,3-dipropylimidazol-2-ylidene, X = Br, 2; NHC = IMes = 1,3-bis(2,4,6- trimethylphenyl)imidazol-2-ylidene, X = Br, 3
N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

KAUST Repository

Wang, Ying; Du, Guang Fen; Xing, Fen; Huang, Kuo-Wei; Dai, Bin; He, Lin

2015-01-01

N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

N-Heterocyclic-Carbene-Catalysed Diastereoselective Vinylogous Mukaiyama/Michael Reaction of 2-(Trimethylsilyloxy)furan and Enones

KAUST Repository

Wang, Ying

2015-10-15

N-heterocyclic carbenes have been utilised as highly efficient nucleophilic organocatalysts to mediate vinylogous Mukaiyama/Michael reactions of 2-(trimethylsilyloxy)furan with enones to afford γ-substituted butenolides in 44-99% yield with 3:1-32:1 diastereoselectivity. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Solid‐Phase Synthesis of Structurally Diverse Heterocycles by an Amide–Ketone Condensation/N‐Acyliminium Pictet–Spengler Sequence

DEFF Research Database (Denmark)

Komnatnyy, Vitaly V.; Givskov, Michael Christian; Nielsen, Thomas Eiland

2012-01-01

An efficient approach for the solid‐phase synthesis of structurally diverse heterocyclic compounds is presented. Under acidic reaction conditions, peptidic levulinamides undergo intramolecular ketone–amide condensation reactions to form cyclic N‐acyliminium intermediates. In the presence...
Neutron activation analysis of biological substances

International Nuclear Information System (INIS)

Ordogh, M.

1978-08-01

A Bowen cabbage sample was used as a reference material for the neutron activation studies, and the method was checked by the analysis of other biological substances (blood or serum etc.). For nondestructive measurements also some non-trace elements were determined in order to decide whether the activation analysis is a useful means for such measurements. The new activation analysis procedure was used for biomedical studies as, e.g., for trace element determination in body fluids, and for the analysis of inorganic components in air samples. (R.P.)
Amides with nitrogenous heterocyclic substituent, their manufacturing process and their use to draw out selectively Actinium series (III) and to separate them in particular from Lanthanides (III)

International Nuclear Information System (INIS)

Cuillerdier, C.; Musikas, C.

1993-01-01

Present invention is concerned with new amides with nitrogenous heterocyclic substituent utilizable to separate trivalent actinium series from trivalent lanthanides. In these molecules, it is possible to obtain particularly covalent liaison which has more affinity with 5f series, that is to say actinium series; included a manufacturing process for these amides with nitrogenous heterocyclic substituent
Radical Addition to Iminium Ions and Cationic Heterocycles

Directory of Open Access Journals (Sweden)

Johannes Tauber

2014-10-01

Full Text Available Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical’s SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra- and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species.
Meat Consumption, Heterocyclic Amines, and Colorectal Cancer Risk: The Multiethnic Cohort Study

OpenAIRE

Ollberding, Nicholas J.; Wilkens, Lynne R.; Henderson, Brian E.; Kolonel, Laurence N.; Le Marchand, Loïc

2012-01-01

Greater consumption of red and processed meat has been associated with an increased risk of colorectal cancer in several recent meta-analyses. Heterocyclic amines (HCAs) have been hypothesized to underlie this association. In this prospective analysis conducted within the Multiethnic Cohort Study, we examined whether greater consumption of total, red, or processed meat was associated with the risk of colorectal cancer among 165,717 participants who completed a detailed food frequency question...
Pyridynes and indolynes as building blocks for functionalized heterocycles and natural products.

Science.gov (United States)

Goetz, Adam E; Shah, Tejas K; Garg, Neil K

2015-01-04

Heterocyclic arynes, or hetarynes, have been studied for over 100 years. However, challenges associated with observing these reactive species, as well as developing synthetically useful methods for their generation and trapping, have limited their use. This review provides a brief historical perspective on the field of hetarynes, in addition to a discussion of pyridyne and indolyne methodologies. Moreover, this review highlights the use of pyridynes, indolynes, and related strained intermediates in natural product synthesis.
SYNTHESIS AND ANTIMICROBIAL ACTIVITIES OF NEW 1,2,4- TRIAZOLES, MANNICH BASES, CONAZOLES, AND FLUOROQUINOLONES

Directory of Open Access Journals (Sweden)

Şule CEYLAN

2016-09-01

Full Text Available Abstract: Triazoles are heterocyclic compounds which have been of interest in the development of novel compounds with antidepressant, anti-inflammatory, analgesic, antibacterial, antimycobacterial, antifungal, antiviral, anticancer, and other activities. In this article, a series of fluorine- and piperazine-containing some novel biologically active 1,2,4-triazole-3-one derivatives were synthesized by the Mannich reaction of triazole intermediates. The structures for novel synthesized compounds were elucidated using elemental analysis and FT IR, 13C NMR, 1H NMR, EI MS techniques. These compounds were investigated in vitro for their antimicrobial properties and several compounds have fungicidal activity against Candida albicans and Saccharomyces cerevisiae. And also some of the compounds exhibited excellent activity on Mycobacterium smegmatis, a nonpigmented fast-rising mycobacterium, at the concentration of <1 μg/mL is better than standard drug streptomycin.
Mixed-ligand complexes of zirconium (IV) and uranium with salicylaldehyde and some heterocyclic azopyrazolones

International Nuclear Information System (INIS)

Amrallahi, A.H.

1994-01-01

Mixed-ligand complexes of Zr(IV) and U(IV) with salicylaldehyde (SA) and some heterocyclic azopyrazolenes have been studied spectrophotometrically. All formed chelates have ratio 1:1:1. The stoichiometry and stability of the binary mixed chelates been evaluated. Elemental analysis, molar conductance and IR spectra have been used for identification of solid mixed complexes. (author)
Heterocyclization reaction of 4-(2-Methylaziridin-1-yl)-3-ureidobenzotrifluorides under appel's conditions

International Nuclear Information System (INIS)

Cho, Hyun In; Lee, Kee Jung

2003-01-01

The reaction of 4-(2-Methylaziridin-1-yl)-3-ureidobenzotrifluorides 4 with triphenylphosphine, carbon tetrachloride, and triethylamine (Appel's condition) led to the corresponding carbodiimides 5, which underwent intramolecular cycloaddition reaction with aziridine under the reaction condition to give the benzimidazole-fused heterocycles, 2.3-dihydro-1H-imidazo(1,2-a)benzimidazoles 8 and 12,13-dihydro-5H-benzimidazo(2,3-b)(1,3)benzodizzepines 9
Synthesis of new 4,6-disubstituted-1,3-oxazinan-2-one analogues

Indian Academy of Sciences (India)

1,3-Oxazinan-2-one analogues are important heterocyclic compounds having significant biologi- cal activities. This study reports ... reaction of aldehyde, allyltrimethylsilane and benzyl carbamate in presence of iodine as catalyst. In the next step ... reaction of activated diazoketone catalysed by metal triflates was reported by ...
Variation of the Sterical Properties of the N-Heterocyclic Carbene Coligand in Thermally Triggerable Ruthenium-Based Olefin Metathesis Precatalysts/Initiators

KAUST Repository

Pump, Eva

2015-11-09

A series of ruthenium complexes based on the κ(C,N)-(2-(benzo[h]quinolin-10-yl)methylidene ruthenium dichloride fragment featuring different neutral coligands L (L = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene (SIPr), 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene (SIMes), 1,3-bis(2,4-dimethylphenyl)-4,5-dihydroimidazol-2-ylidene (SIXyl), and 1,3-bis(2-methylphenyl)-4,5-dihydroimidazol-2-ylidene (SITol)) was prepared, characterized, and tested in the thermally induced ring-opening metathesis polymerization of dicyclopentadiene. In addition, the corresponding tricyclohexylphosphine derivative was investigated for comparison. All compounds were isolated as their trans-dichloro isomers. NMR spectroscopic features as well as structural features are, particularly within the NHC-bearing complexes, very similar, but their polymerization activity at elevated temperatures is distinctly different. While the SIMes derivative shows the desired properties, i.e., latency at room temperature and pronounced polymerization activity at elevated temperature, all other preinitiators do not. The preinitiator featuring the SIPr coligand is the most latent one, needing temperatures > 140 °C to show moderate activity in the polymerization of dicyclopentadiene. Compounds bearing the smaller N-heterocyclic carbene congeners are stable and latent at room temperature, but decompose upon heating, diminishing the polymerization activity at elevated temperatures. Density functional calculations show that the SIMes derivative is the easiest to activate and yields the most stable 14-electron intermediate. Finally calculations reveal a distinct influence of the nature of the N-heterocyclic carbene ligand on the position of the equilibrium of cis- and trans-dichloro isomers of the complexes. While the SIPr and the SIMes derivatives prefer the cis-configuration, all other derivatives favor, at least in solvents with low dielectric constants, the trans
The investigation of hydrogens bonds between sulphur-bearing heterocyclic and proton-donor compounds by IR absorption spectra

International Nuclear Information System (INIS)

Narziev, B.N.; Nurulloev, M.; Makhkambaev, D.

1982-01-01

In this article the results of intermolecular interaction study of sulfur-containing heterocyclic (thiophene, thiophane) and proton-donar (water, alcohol, carbonic acids, chlorophon) molecules for measuring of IR spectrum absorption of protondonar compounds in soluted shape are presented
A Review on Phytoconstituents and Biological activities of Cuscuta species.

Science.gov (United States)

Ahmad, Ateeque; Tandon, Sudeep; Xuan, Tran Dang; Nooreen, Zulfa

2017-08-01

The genus Cuscuta belonging to the Cuscutaceae family comprises of about 100-170 species spread around the world. Although several species have been studied for their phytochemical characterization and biological activities but still many species are yet unexplored till date. Cuscuta are parasitic plants generally of yellow, orange, red or rarely green color. The Cuscuta species were reported rich in flavonoid and glycosidic constituents along with alkaloids, fatty acids, fixed oil, minerals, essential oil and others phytomolecules also etc. Flavonoids and other molecules of Cuscuta species were reported for different types of biological activities such as antiproliferative activity, antioxidant activity, anti-inflammatory, hepatoprotective, antimicrobial and anxiolytic activity, while some other flavonoids have exhibited potential antiviral and anticancer especially in ovarian and breast cancer activities. This review is an attempt to compile all the available data for the 24 different of Cuscuta species on the basis of different types of phytochemical constituents and biological studies as above. Copyright © 2017 Elsevier Masson SAS. All rights reserved.
Single-catalyst high-weight% hydrogen storage in an N-heterocycle synthesized from lignin hydrogenolysis products and ammonia.

Science.gov (United States)

Forberg, Daniel; Schwob, Tobias; Zaheer, Muhammad; Friedrich, Martin; Miyajima, Nobuyoshi; Kempe, Rhett

2016-10-20

Large-scale energy storage and the utilization of biomass as a sustainable carbon source are global challenges of this century. The reversible storage of hydrogen covalently bound in chemical compounds is a particularly promising energy storage technology. For this, compounds that can be sustainably synthesized and that permit high-weight% hydrogen storage would be highly desirable. Herein, we report that catalytically modified lignin, an indigestible, abundantly available and hitherto barely used biomass, can be harnessed to reversibly store hydrogen. A novel reusable bimetallic catalyst has been developed, which is able to hydrogenate and dehydrogenate N-heterocycles most efficiently. Furthermore, a particular N-heterocycle has been identified that can be synthesized catalytically in one step from the main lignin hydrogenolysis product and ammonia, and in which the new bimetallic catalyst allows multiple cycles of high-weight% hydrogen storage.
A simple, convenient, and one pot synthetic route for the preparation of 1,3,5-thiadiazines-2-thione heterocyclic compounds and their antifungal activity

Directory of Open Access Journals (Sweden)

Sohail Saeed

2015-12-01

Full Text Available A series of new heterocyclic 1,3,5-thiadiazines-2-thione with aroyl/aryl substituents (3a-c were synthesized by reacting isothiocyanates with N- (propan-2-ylpropan-2- amine in the presence of tetrabutylammonium bromide as phase transfer catalyst. The structures of these novel compounds were characterized by IR, mass spectrometry, and elemental analysis. The crystal structures were determined from single-crystal X-ray diffraction data. The synthesized compounds were tested in vitro against Fusarium solani, A. fumigatus, and Aspergillus flavus using standard drugs.
Cascade olefin isomerization/intramolecular Diels-Alder reaction catalyzed by N-heterocyclic carbenes.

Science.gov (United States)

Kowalczyk, Marcin; Lupton, David W

2014-05-19

The addition of an N-heterocyclic carbene to the carbonyl group of an α,β,γ,δ-unsaturated enol ester affords a hemiacetal azolium intermediate that enables a cascade olefin isomerization/Diels-Alder reaction, for which mechanistic studies implicate Lewis base catalysis. Preliminary studies into the utility of the products have been undertaken with reductive and oxidative cleavage, giving materials for potential use in complex-target synthesis. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
The half-lives of biological activity of some pesticides in water

OpenAIRE

Kyaw Myint Oo,

2001-01-01

In the absence of analytical methods, the half-lives of biological activity of pesticides can be estimated by bioassays. To determine the half-lives of biological acivity of pesticides to fish, static bioassays were conducted in the laboratory with ten different formulations of pesticides using Labeo rohita as a bio-indicator. The half-lives of biological activity for ten different pesticides in soft water at pH 7.5 and 27░C, ranged from 4.6 days to 11.8 days. The half-life of biological acti...
Assembly of Four Diverse Heterocyclic Libraries Enabled by Prins Cyclization, Au-Catalyzed Enyne Cycloisomerization, and Automated Amide Synthesis

Science.gov (United States)

Cui, Jiayue; Chai, David I.; Miller, Christopher; Hao, Jason; Thomas, Christopher; Wang, JingQi; Scheidt, Karl A.; Kozmin, Sergey A.

2013-01-01

We describe a unified synthetic strategy for efficient assembly of four new heterocyclic libraries. The synthesis began by creating a range of structurally diverse pyrrolidinones or piperidinones. Such compounds were obtained in a simple one-flask operation starting with readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters, which were rapidly assembled by our Prins cyclization protocol, enabled efficient fusion of pyran and piperidinone cores. A newly developed Au(I)-catalyzed cycloisomerization of alkyne-containing enamides further expanded heterocyclic diversity by providing rapid entry into a wide range of bicyclic and tricyclic dienamides. The final stage of the process entailed diversification of each of the initially produced carboxylic acids using a fully automated platform for amide synthesis, which delivered 1872 compounds in high diastereomeric and chemical purity. PMID:22860634
The design and synthesis of novel spirocyclic heterocyclic sulfone ROMK inhibitors as diuretics.

Science.gov (United States)

Chobanian, Harry R; Guo, Yan; Pio, Barbara; Tang, Haifeng; Teumelsan, Nardos; Clements, Matthew; Frie, Jessica; Ferguson, Ronald; Guo, Zach; Thomas-Fowlkes, Brande S; Felix, John P; Liu, Jessica; Kohler, Martin; Priest, Birgit; Hampton, Caryn; Pai, Lee-Yuh; Corona, Aaron; Metzger, Joseph; Tong, Vincent; Joshi, Elizabeth M; Xu, Ling; Owens, Karen; Maloney, Kevin; Sullivan, Kathleen; Pasternak, Alexander

2017-02-15

A spirocyclic class of ROMK inhibitors was developed containing a structurally diverse heterocyclic sulfone moiety and spirocyclic core starting from lead 1. These compounds not only displayed exquisite ROMK potency but significantly improved selectivity over hERG. The lead compounds were found to have favorable pharmacokinetic properties and displayed robust diuretic, natriuretic and blood pressure lowering effects in spontaneously hypertensive rats. Copyright © 2016 Elsevier Ltd. All rights reserved.

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues.

Science.gov (United States)

Risseeuw, Martijn; Overhand, Mark; Fleet, George W J; Simone, Michela I

2013-10-01

This compendium focuses on functionalised sugar amino acids (SAAs) and their 3- to 6-membered nitrogen heterocyclic and carbocyclic analogues. The main benefit of using SAAs and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents. These building blocks provide access to hydrophilic and hydrophobic peptide isosteres whose physical properties allow entry to a region of chemotherapeutic space which is still under-explored by medicinal chemists. These building blocks are also important in providing amino acids whose inherent conformational bias leads to predisposition to secondary structure upon oligomerisation in relatively short sequences. These foldamers, particularly those containing ω-amino acids, provide an additional opportunity to expand access to the control of structures by artificial peptides. The synthesis and biological evaluation of these building blocks in glycomimetics and peptidomimetics systems keep expanding the reach of the glycosciences to the medical sciences, provide a greater outlook onto the wide range of cellular functions of saccharides and their derivatives involved and greater insight into the nature of oligosaccharide and protein folding.
Metal–organic coordination architectures of tetrazole heterocycle ligands bearing acetate groups: Synthesis, characterization and magnetic properties

International Nuclear Information System (INIS)

Hu, Bo-Wen; Zheng, Xiang-Yu; Ding, Cheng

2015-01-01

Two new coordination complexes with tetrazole heterocycle ligands bearing acetate groups, [Co(L) 2 ] n (1) and [Co 3 (L) 4 (N 3 ) 2 ·2MeOH] n (2) (L=tetrazole-1-acetate) have been synthesized and structurally characterized. Single crystal structure analysis shows that the cobalt-complex 1 has the 3D 3,6-connected (4 2 .6) 2 (4 4 .6 2 .8 8 .10)-ant topology. By introducing azide in this system, complex 2 forms the 2D network containing the [Co 3 ] units. And the magnetic properties of 1 and 2 have been studied. - Graphical abstract: The synthesis, crystal structure, and magnetic properties of the new coordination complexes with tetrazole heterocycle ligands bearing acetate groups are reported. - Highlights: • Two novel Cobalt(II) complexes with tetrazole acetate ligands were synthesized. • The magnetic properties of two complexes were studied. • Azide as co-ligand resulted in different structures and magnetic properties. • The new coordination mode of tetrazole acetate ligand was obtained.
Physicochemical study of niobium(5) complexes with rhodanide and heterocyclic bases

International Nuclear Information System (INIS)

Lobanov, F.I.; Zatonskaya, V.M.; Gibalo, I.M.

1980-01-01

Mixed complexes of niobium rhodanide with organic heterocyclic bases-1,10-phenanthroline; 2,3-dimethyl-1,10-phenanthroline; 4,7-diphenyl-1,10 phenanthroline-bathophenanthroline; S-collidine are singled out. The composition of the compounds is established. The character of the bonds Nb-O, Nb-NCS, Nb-basis is studied using the method of IR spectroscopy. Derivatogravimetric analysis of the complexes singled out has shown the complex character of their decomposition. The measurement of electric conductivity of the mixed complexes in dimethylformamide solutions has shown that they are binary electrolytes
Radical fragmentation of six-membered oxygen-containing heterocycles

International Nuclear Information System (INIS)

Petryaev, E.P.; Kosobutskij, V.S.; Shadyro, O.I.

1982-01-01

Using chromatography, the composition and radiation-chemical yields of final products of desctruction of six-member saturated oxygen-containing heterocycles (the effect of #betta#-radiation on aqueous solutions of tetrahydropyran, 1,3-dioxane, 2,2 dimethyl-1,3 dioxane, 1,4-dioxane, paraldehyde) have been determined. It is established that the identified products are formed at the expense of decomposition of primary radicals of the initial compounds and point to the realization of the following fragmentation ways: 1) #betta#-scattering, 2) #betta#-scattering with a subsequent 1,5 migration of an H atom, 3) simultaneous rupture of two vicinal, relative to the radical center, bonds. A formation mechanism of the substances desctruction products is suggested. Material balance of the product yields of 1,3-dioxane radical synchronous decomposition is presented
Biological activity of selected plants with adaptogenic effect

Directory of Open Access Journals (Sweden)

Eva Ivanišová

2016-05-01

Full Text Available The aim of this study was to determine biological activity of plants with adaptogenic effect: Panax ginseng Mayer., Withania somnifera L., Eleuterococcus senticosus Rupr. et Maxim., Astragallus membranaceus Fisch. and Codonopsis pilosulae Franch. The antioxidant activity was detected by DPPH and phosphomolybdenum method, total polyphenol content with Folin – Ciocalteu reagent, flavonoids content by aluminium chloride method. The detection of antimicrobial activity was carried out by disc diffusion method against three species of Gram-negative bacteria: Escherichia coli CCM 3988, Salmonella enterica subsp. enterica CCM 3807, Yersinia enterocolitica CCM 5671 and two Gram-positive bacteria: Bacillus thuringiensis CCM 19, Stapylococcus aureus subsp. aureus CCM 2461. Results showed that plants with adaptogenic effect are rich for biologically active substances. The highest antioxidant activity by DPPH method was determined in the sample of Eleuterococcus senticosus (3.15 mg TEAC – Trolox equivalent antioxidant capacity per g of sample and by phosphomolybdenum method in the sample of Codonopsis pilosulae (188.79 mg TEAC per g of sample. In the sample of Panax ginseng was measured the highest content of total polyphenols (8.10 mg GAE – galic acid equivalent per g of sample and flavonoids (3.41 μg QE – quercetin equivalent per g of sample. All samples also showed strong antimicrobial activity with the best results in Panax ginseng and Withania somnifera in particular for species Yersinia enterocolitica CCM 5671 and Salmonella enterica subsp. enterica CCM 3807. The analyzed species of plant with high value of biological activity can be used more in the future, not only in food, but also in cosmetics and pharmaceutical industries.
Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds.

Science.gov (United States)

Shaker, Soheir A; Marzouk, Magda I

2016-01-29

A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, ¹H-NMR (13)C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.
Sacrificial spacer and non-covalent routes toward the molecular imprinting of 'poorly-functionalized' N-heterocycles

International Nuclear Information System (INIS)

Kirsch, N.; Alexander, C.; Davies, S.; Whitcombe, M.J.

2004-01-01

A comparison of three different methods for the imprinting of small aromatic heterocycles containing only a single nitrogen atom, for the preparation of specific analytical phases, was carried out. A conventional non-covalent approach to the imprinting of pyridine using methacrylic acid as the functional monomer was compared with two sacrificial spacer methods, in which heterocycles were imprinted as covalent template analogues. The results of binding experiments showed that discrimination based on ligand size was possible when polymers were prepared using a silyl ester-based template. The most selective polymer was able to bind pyridine in preference to quinoline or acridine which is opposite to the trend predicted by the pK HB values for the three ligands. Curve fitting of the isotherm for pyridine binding to this polymer to the Langmuir model gave an approximate K d of 1.1±0.1 mM and a binding site concentration of 57±2 mmol g -1 . Acridine binding did not show saturation behaviour and was non-specific and cooperative in nature
Optimized Syntheses of Cyclopentadienyl Nickel Chloride Compounds Containing "N"-Heterocyclic Carbene Ligands for Short Laboratory Periods

Science.gov (United States)

Cooke, Jason; Lightbody, Owen C.

2011-01-01

Experiments are described for the preparation of imidazolium chloride precursors to "N"-heterocyclic carbenes and their cyclopentadienyl nickel chloride derivatives. The syntheses have been optimized for second- and third-year undergraduate laboratories that have a maximum programmed length of three hours per week. The experiments are flexible and…
Benzofuran as a promising scaffold for the synthesis of antimicrobial and antibreast cancer agents: A review

Directory of Open Access Journals (Sweden)

Ghadamali Khodarahmi

2015-01-01

Full Text Available Benzofuran as an important heterocyclic compound is extensively found in natural products as well as synthetic materials. Since benzofuran drivatives display a diverse array of pharmacological activities, an interest in developing new biologically active agents from benzofuran is still under consideration. This review highlights recent findings on biological activities of benzofuran derivatives as antimicrobial and antibreast cancer agents and lays emphasis on the importance of benzofurans as a major source for drug design and development.
Application of activation techniques to biological analysis

International Nuclear Information System (INIS)

Bowen, H.J.M.

1981-01-01

Applications of activation analysis in the biological sciences are reviewed for the period of 1970 to 1979. The stages and characteristics of activation analysis are described, and its advantages and disadvantages enumerated. Most applications involve activation by thermal neutrons followed by either radiochemical or instrumental determination. Relatively little use has been made of activation by fast neutrons, photons, or charged particles. In vivo analyses are included, but those based on prompt gamma or x-ray emission are not. Major applications include studies of reference materials, and the elemental analysis of plants, marine biota, animal and human tissues, diets, and excreta. Relatively little use of it has been made in biochemistry, microbiology, and entomology, but it has become important in toxicology and environmental science. The elements most often determined are Ag, As, Au, Br, Ca, Cd, Cl, Co, Cr, Cs, Cu, Fe, Hg, I, K, Mn, Mo, Na, Rb, Sb, Sc, Se, and Zn, while few or no determinations of B, Be, Bi, Ga, Gd, Ge, H, In, Ir, Li, Nd, Os, Pd, Pr, Pt, Re, Rh, Ru, Te, Tl, or Y have been made in biological materials
Reactivity of N-heterocyclic carbene-pyridine palladacyclopentadiene complexes toward halogen addition. The unpredictable course of the reaction.

Science.gov (United States)

Visentin, Fabiano; Santo, Claudio; Scattolin, Thomas; Demitri, Nicola; Canovese, Luciano

2017-08-08

As an extension of a previously published work we have reacted some palladacyclopentadiene complexes stabilized by bidentate N-heterocyclic carbene-pyridine or monodentate N-heterocyclic carbene-pyridine and isocyanide ligands with the halogens I 2 and Br 2 . All the bidentate and monodentate complexes react with halogens to give at first the expected σ-coordinated butadienyl fragment. However, two of the less hindered NHC carbene-pyridine bidentate butadienyl iodo derivatives undergo a further rearrangement and novel Pd(ii) complexes characterized by a ten term coordinative ring were isolated and characterized. In the most favorable case we were able to carry out the kinetics of rearrangement and measure its reaction rate. Moreover, we have surmised a plausible mechanism on the basis of a dedicated computational approach and in one case the surprising structure characterized by the ten term coordinative ring was resolved by X-ray diffraction.
Diastereoselective Synthesis of Novel Heterocyclic Scaffolds through Tandem Petasis 3-Component/Intramolecular Diels-Alder and ROM-RCM Reactions

DEFF Research Database (Denmark)

Ishøy, Mette; Petersen, Rico; Petersen, Michael Åxman

2017-01-01

A high-yielding, stereoselective and extraordinarily complexity generatingPetasis 3-component/intramolecular Diels-Alderreaction has been developed. In combination with ROM-RCM, rapid access to complex sp3-rich heterocyclic scaffolds amenableto subsequent functionalization and library synthesis...
Domino approach to 2-aroyltrimethoxyindoles as novel heterocyclic combretastatin A4 analogues.

Science.gov (United States)

Arthuis, Martin; Pontikis, Renée; Chabot, Guy G; Quentin, Lionel; Scherman, Daniel; Florent, Jean-Claude

2011-01-01

Two series of 2-aroyltrimethoxyindoles were designed to investigate the effects of the replacement of the trimethoxyphenyl ring of phenstatin with a trimethoxyindole moiety. These compounds were efficiently prepared through a domino palladium-catalyzed sequence from 2-gem-dibromovinylanilines substituted by three methoxy groups and arylboronic acids under carbon monoxide atmosphere. These novel heterocyclic combretastatin A4 analogues were evaluated for their cell growth inhibitory properties and their ability to inhibit the tubulin polymerization. Copyright © 2010 Elsevier Masson SAS. All rights reserved.
Biological activity and photostability of biflorin micellar nanostructures.

Science.gov (United States)

Santana, Edson R B; Ferreira-Neto, João P; Yara, Ricardo; Sena, Kêsia X F R; Fontes, Adriana; Lima, Cláudia S A

2015-05-13

Capraria biflora L. is a shrub from the Scrophulariaceae family which produces in its roots a compound named biflorin, an o-naphthoquinone that shows activity against Gram-positive bacteria and fungi and also presents antitumor and antimetastatic activities. However, biflorin is hydrophobic and photosensitive. These properties make its application difficult. In this work we prepared biflorin micellar nanostructures looking for a more effective vehiculation and better preservation of the biological activity. Biflorin was obtained, purified and characterized by UV-Vis, infrared (IR) and 1H- and 13C-NMR. Micellar nanostructures of biflorin were then assembled with Tween 80®, Tween 20® and saline (0.9%) and characterized by UV-Vis spectroscopy and dynamic light scattering (DLS). The results showed that the micellar nanostructures were stable and presented an average size of 8.3 nm. Biflorin micellar nanostructures' photodegradation was evaluated in comparison with biflorin in ethanol. Results showed that the biflorin in micellar nanostructures was better protected from light than biflorin dissolved in ethanol, and also indicated that biflorin in micelles were efficient against Gram-positive bacteria and yeast species. In conclusion, the results showed that the micellar nanostructures could ensure the maintenance of the biological activity of biflorin, conferring photoprotection. Moreover, biflorin vehiculation in aqueous media was improved, favoring its applicability in biological systems.
Biological Activity and Photostability of Biflorin Micellar Nanostructures

Directory of Open Access Journals (Sweden)

Edson R. B. Santana

2015-05-01

Full Text Available Capraria biflora L. is a shrub from the Scrophulariaceae family which produces in its roots a compound named biflorin, an o-naphthoquinone that shows activity against Gram-positive bacteria and fungi and also presents antitumor and antimetastatic activities. However, biflorin is hydrophobic and photosensitive. These properties make its application difficult. In this work we prepared biflorin micellar nanostructures looking for a more effective vehiculation and better preservation of the biological activity. Biflorin was obtained, purified and characterized by UV-Vis, infrared (IR and 1H- and 13C-NMR. Micellar nanostructures of biflorin were then assembled with Tween 80®, Tween 20® and saline (0.9% and characterized by UV-Vis spectroscopy and dynamic light scattering (DLS. The results showed that the micellar nanostructures were stable and presented an average size of 8.3 nm. Biflorin micellar nanostructures’ photodegradation was evaluated in comparison with biflorin in ethanol. Results showed that the biflorin in micellar nanostructures was better protected from light than biflorin dissolved in ethanol, and also indicated that biflorin in micelles were efficient against Gram-positive bacteria and yeast species. In conclusion, the results showed that the micellar nanostructures could ensure the maintenance of the biological activity of biflorin, conferring photoprotection. Moreover, biflorin vehiculation in aqueous media was improved, favoring its applicability in biological systems.
Biological activation of carbon filters.

Science.gov (United States)

Seredyńska-Sobecka, Bozena; Tomaszewska, Maria; Janus, Magdalena; Morawski, Antoni W

2006-01-01

To prepare biological activated carbon (BAC), raw surface water was circulated through granular activated carbon (GAC) beds. Biological activity of carbon filters was initiated after about 6 months of filter operation and was confirmed by two methods: measurement of the amount of biomass attached to the carbon and by the fluorescein diacetate (FDA) test. The effect of carbon pre-washing on WG-12 carbon properties was also studied. For this purpose, the nitrogen adsorption isotherms at 77K and Fourier transform-infrared (FT-IR) spectra analyses were performed. Moreover, iodine number, decolorizing power and adsorption properties of carbon in relation to phenol were studied. Analysis of the results revealed that after WG-12 carbon pre-washing its BET surface increased a little, the pH value of the carbon water extract decreased from 11.0 to 9.4, decolorizing power remained at the same level, and the iodine number and phenol adsorption rate increased. In preliminary studies of the ozonation-biofiltration process, a model phenol solution with concentration of approximately 10mg/l was applied. During the ozonation process a dose of 1.64 mg O(3)/mg TOC (total organic carbon) was employed and the contact time was 5 min. Four empty bed contact times (EBCTs) in the range of 2.4-24.0 min were used in the biofiltration experiment. The effectiveness of purification was measured by the following parameters: chemical oxygen demand (COD(Mn)), TOC, phenol concentration and UV(254)-absorbance. The parameters were found to decrease with EBCT.
Liposomal packaging generates Wnt protein with in vivo biological activity.

Directory of Open Access Journals (Sweden)

Nathan T Morrell

2008-08-01

Full Text Available Wnt signals exercise strong cell-biological and regenerative effects of considerable therapeutic value. There are, however, no specific Wnt agonists and no method for in vivo delivery of purified Wnt proteins. Wnts contain lipid adducts that are required for activity and we exploited this lipophilicity by packaging purified Wnt3a protein into lipid vesicles. Rather than being encapsulated, Wnts are tethered to the liposomal surface, where they enhance and sustain Wnt signaling in vitro. Molecules that effectively antagonize soluble Wnt3a protein but are ineffective against the Wnt3a signal presented by a cell in a paracrine or autocrine manner are also unable to block liposomal Wnt3a activity, suggesting that liposomal packaging mimics the biological state of active Wnts. When delivered subcutaneously, Wnt3a liposomes induce hair follicle neogenesis, demonstrating their robust biological activity in a regenerative context.
Synthesis of substituted gamma-lactams through petasis-type addition of boronic acids to N-acyliminium lons

DEFF Research Database (Denmark)

Wu, Peng; Clausen, Mads Hartvig; Nielsen, Thomas Eiland

2014-01-01

Substituted g -lactams are important heterocyclic motifs found in various biologically active compounds and marketed drugs, such as glimepiride, doxapram, and levetiracetam. Among available m ethods for the synthesis of substituted g -lactams, the addition of nucleophiles to N -acyliminium ions...
[BIOLOGICAL ACTIVITY OF ANTIMICROBIAL PEPTIDES FROM CHICKENS THROMBOCYTES].

Science.gov (United States)

Sycheva, M V; Vasilchenko, A S; Rogozhin, E A; Pashkova, T M; Popova, L P; Kartashova, O L

2016-01-01

Isolation and study of biological activity of antimicrobial peptides from chickens thrombocytes. Peptides from chickens thrombocytes, obtained by reverse-phase high-performance liquid chromatography method with stepped and linear gradients of concentration increase of the organic solvent were used in the study. Their antimicrobial activity was determined by microtitration method in broth; mechanism of biological effect--by using fluorescent spectroscopy method with DNA-tropic dyes. Individual fractions of peptides were isolated from chickens thrombocytes, that possess antimicrobial activity against Staphylococcus aureus P209 and Escherichia coli K12. A disruption of integrity of barrier structures of microorganisms under the effect of thrombocyte antimicrobial peptides and predominance of cells with damaged membrane in the population of E. coli was established. The data obtained on antimicrobial activity and mechanism of bactericidal effect of the peptide fractions from chickens thrombocytes isolated for the first time expand the understanding of functional properties of chickens thrombocytes and open a perspective for their further study with the aim of use as antimicrobial means.
Marine natural flavonoids: chemistry and biological activities.

Science.gov (United States)

Martins, Beatriz T; Correia da Silva, Marta; Pinto, Madalena; Cidade, Honorina; Kijjoa, Anake

2018-05-04

As more than 70% of the world's surface is covered by oceans, marine organisms offer a rich and unlimited resource of structurally diverse bioactive compounds. These organisms have developed unique properties and bioactive compounds that are, in majority of them, unparalleled by their terrestrial counterparts due to the different surrounding ecological systems. Marine flavonoids have been extensively studied in the last decades due to a growing interest concerning their promising biological/pharmacological activities. The most common classes of marine flavonoids are flavones and flavonols, which are mostly isolated from marine plants. Although most of flavonoids are hydroxylated and methoxylated, some marine flavonoids possess an unusual substitution pattern, not commonly found in terrestrial organisms, namely the presence of sulphate, chlorine, and amino groups. This review presents, for the first time in a systematic way, the structure, natural occurrence, and biological activities of marine flavonoids.

Monitoring Biological Activity at Geothermal Power Plants

Energy Technology Data Exchange (ETDEWEB)

Peter Pryfogle

2005-09-01

The economic impact of microbial growth in geothermal power plants has been estimated to be as high as $500,000 annually for a 100 MWe plant. Many methods are available to monitor biological activity at these facilities; however, very few plants have any on-line monitoring program in place. Metal coupon, selective culturing (MPN), total organic carbon (TOC), adenosine triphosphate (ATP), respirometry, phospholipid fatty acid (PLFA), and denaturing gradient gel electrophoresis (DGGE) characterizations have been conducted using water samples collected from geothermal plants located in California and Utah. In addition, the on-line performance of a commercial electrochemical monitor, the BIoGEORGE?, has been evaluated during extended deployments at geothermal facilities. This report provides a review of these techniques, presents data on their application from laboratory and field studies, and discusses their value in characterizing and monitoring biological activities at geothermal power plants.
Effects of halogenated aromatics/aliphatics and nitrogen(N)-heterocyclic aromatics on estimating the persistence of future pharmaceutical compounds using a modified QSAR model.

Science.gov (United States)

Lim, Seung Joo; Fox, Peter

2014-02-01

The effects of halogenated aromatics/aliphatics and nitrogen(N)-heterocyclic aromatics on estimating the persistence of future pharmaceutical compounds were investigated using a modified half life equation. The potential future pharmaceutical compounds investigated were approximately 2000 pharmaceutical drugs currently undergoing the United States Food and Drug Administration (US FDA) testing. EPI Suite (BIOWIN) model estimates the fates of compounds based on the biodegradability under aerobic conditions. While BIOWIN considered the biodegradability of a compound only, the half life equation used in this study was modified by biodegradability, sorption and cometabolic oxidation. It was possible that the potential future pharmaceutical compounds were more accurately estimated using the modified half life equation. The modified half life equation considered sorption and cometabolic oxidation of halogenated aromatic/aliphatics and nitrogen(N)-heterocyclic aromatics in the sub-surface, while EPI Suite (BIOWIN) did not. Halogenated aliphatics in chemicals were more persistent than halogenated aromatics in the sub-surface. In addition, in the sub-surface environment, the fates of organic chemicals were much more affected by halogenation in chemicals than by nitrogen(N)-heterocyclic aromatics. © 2013.
Baltic cyanobacteria- A source of biologically active compounds

Digital Repository Service at National Institute of Oceanography (India)

Mazur-Marzec, H.; Błaszczyk, A.; Felczykowska, A.; Hohlfeld, N.; Kobos, J.; Toruńska-Sitarz, A.; PrabhaDevi; Montalva`o, S.; DeSouza, L.; Tammela, P.; Mikosik, A.; Bloch, S.; Nejman-Faleńczyk, B.; Węgrzyn, G.

cyanobacteria, enzyme activity, enzyme inhibitors, immunological activity, natural products, nonribosomal peptides, plant growth regulators 2 INTRODUCTION Cyanobacteria are Gram-negative bacteria which are widely distributed in many water bodies..., immunological, 4 antimicrobial and plant growth tests. The overall aim of the experiments was to identify strains showing the most promising biological activity for potential biotechnological application. MATERIALS AND METHODS Isolation, culture...
Comprehensive and Facile Synthesis of Some Functionalized Bis-Heterocyclic Compounds Containing a Thieno[2,3-b]thiophene Motif

Science.gov (United States)

Mabkhot, Yahia N.; Barakat, Assem; Al-Majid, Abdullah M.; Alshahrani, Saeed A.

2012-01-01

A comprehensive and facile method for the synthesis of new functionalized bis-heterocyclic compounds containing a thieno[2,3-b]thiophene motif is described. The hitherto unknown bis-pyrazolothieno[2,3-b]thiophene derivatives 2a–c, bis-pyridazin othieno[2,3-b]thiophene derivatives 4, bis-pyridinothieno[2,3-b]thiophene derivatives 6a,b, and to an analogous bis-pyridinothieno[2,3-b]thiophene nitrile derivatives 7 are obtained. Additionally, the novel bis-pyradazinonothieno[2,3-b]thiophene derivatives 9, and nicotinic acid derivatives 10, 11 are obtained via bis-dienamide 8. The structures of all newly synthesized compounds have been elucidated by 1H, 13C NMR, GCMS, and IR spectrometry. These compounds represent a new class of sulfur and Nitrogen containing heterocycles that should also be of interest as new materials. PMID:22408452
Assessing Student Behaviors and Motivation for Actively Learning Biology

Science.gov (United States)

Moore, Michael Edward

Vision and Change states that one of the major changes in the way we design biology courses should be a switch in approach from teacher-centered learning to student-centered learning and identifies active learning as a recommended methods. Studies show performance benefits for students taking courses that use active learning. What is unknown is why active learning is such an effective instructional tool and the limits of this instructional method’s ability to influence performance. This dissertation builds a case in three steps for why active learning is an effective instructional tool. In step one, I assessed the influence of different types of active learning (clickers, group activities, and whole class discussions) on student engagement behavior in one semester of two different introductory biology courses and found that active learning positively influenced student engagement behavior significantly more than lecture. For step two, I examined over four semesters whether student engagement behavior was a predictor of performance and found participation (engagement behavior) in the online (video watching) and in-class course activities (clicker participation) that I measure were significant predictors of performance. In the third, I assessed whether certain active learning satisfied the psychological needs that lead to students’ intrinsic motivation to participate in those activities when compared over two semesters and across two different institutions of higher learning. Findings from this last step show us that student’s perceptions of autonomy, competency, and relatedness in doing various types of active learning are significantly higher than lecture and consistent across two institutions of higher learning. Lastly, I tie everything together, discuss implications of the research, and address future directions for research on biology student motivation and behavior.
Complex-forming capacity of some biologically active imidazoles

Energy Technology Data Exchange (ETDEWEB)

Lenarcik, B; Wisniewski, M

1983-01-01

By using the potentiometric and spectrophotometric methods, formation of Co(2), Cu(2), Zn(2), Ni(2) and Cd(2) complexes of (3S-cis)-3-ethyl-dihydro-4-((1-methyl-1H-imidazol-5-yl)-methyl)-2(3H)-furanone (pilocarpine, PLC), 4,5-dihydro-2-(phenylmethyl)-1H-imidazole (tolazoline, TLZ), 2-methyl-5-nitro-1H-imidazole-1-ethanol (metronidazole, MET) and 1H-imidazole-4-ethanamine (histamine, HIST) was investigated. The stability constants, ..beta../sub n/, of these complexes were determined. It was shown that the electron-donor strength of the ligands was controlled by the heterocyclic nitrogen atom, and that the formation of the Zn(2)-PLC complex was accompanied by the change in the structure of the coordination sphere of the metal. With Cu(2), the PLC and TLZ ligands were shown to enhance the Jahn-Teller deformation.
Heterocyclic amines in meat and meat products

Directory of Open Access Journals (Sweden)

Aliye BULGAN

2013-06-01

Full Text Available Heterocyclic amines (HA are the mutagenic/carcinogenic compounds which generate as a result of cooking of red meat, poultry meat and fish fillets at high temperatures. Up to 20 different HAs were detected and classified in the researches that conducted on these types of meats cooked at high temperatures. HAs are the products of Maillard reactions and the Strecker degredation of main precursors such as creatine/creatinine, aminoacid and the polysaccharides. Many physical and chemical factors effect the formation of HAs. Thus, it was reported by many researchers that utilizing coating and marination processes in addition to using natural and synthetic antioxidants and seasonings-plant extracts were effective on inhibiting/decreasing the formation of HAs. Additionally, boiling/steaming and microwave cooking methodologies were recommended instead of barbecuing, grilling or frying to inhibit/decrease the formation of HAs. The HAs formed in meat and meat products and the factors which have effects on the formation of HAs are presented in this review.
Heterocyclic anions of astrobiological interest

International Nuclear Information System (INIS)

Cole, Callie A.; Demarais, Nicholas J.; Bierbaum, Veronica M.; Yang, Zhibo; Snow, Theodore P.

2013-01-01

As more complex organic molecules are detected in the interstellar medium, the importance of heterocyclic molecules to astrobiology and the origin of life has become evident. 2-Aminothiazole and 2-aminooxazole have recently been suggested as important nucleotide precursors, highlighting azoles as potential prebiotic molecules. This study explores the gas-phase chemistry of three deprotonated azoles: oxazole, thiazole, and isothiazole. For the first time, their gas-phase acidities are experimentally determined with bracketing and H/D exchange techniques, and their reactivity is characterized with several detected interstellar neutral molecules (N 2 O, O 2 , CO, OCS, CO 2 , and SO 2 ) and other reactive species (CS 2 , CH 3 Cl, (CH 3 ) 3 CCl, and (CH 3 ) 3 CBr). Rate constants and branching fractions for these reactions are experimentally measured using a modified commercial ion trap mass spectrometer whose kinetic data are in good accord with those of a flowing afterglow apparatus reported here. Last, we have examined the fragmentation patterns of these deprotonated azoles to elucidate their destruction mechanisms in high-energy environments. All experimental data are supported and complemented by electronic structure calculations at the B3LYP/6-311++G(d,p) and MP2(full)/aug-cc-pVDZ levels of theory.
Induction of micronuclei in V79 cells after combined treatments with heterocyclic aromatic amines.

Science.gov (United States)

Perez, C; Lopez de Cerain, A; Bello, J

2002-10-01

Heterocyclic aromatic amines (HAs) appear in foods rich in proteins when subjected to different cooking processes. These amines have been demonstrated to be mutagenic in bacteria; in eucaryotic cells, controversial results have been referred. The objective of this study is to evaluate the clastogenic and/or aneugenic capacity of three HAs--2-amino-3-methylimidazo[4,5-f]quinoline (IQ), 2-amino-3-methylimidazo[4,5-f]quinoxaline (IQx), and 2-amino-3-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)--in isolated as well as in combined treatments. The micronucleus test in vitro was used on V79 cells in the presence and absence of metabolic activation. The duration of the treatment was 2 h, and cytochalasin B was added for 21 h to stop cytokinesis; then, micronuclei (MN) were counted in binucleated cells. In the presence of metabolic activation, the three amines showed a significant increase in the number of MN with respect to the negative control. The PhIP amine presented the highest values and it also resulted slightly active in the absence of metabolic activation, although these differences have not been considered to be significant. The combined treatments of these amines have shown that the effects attributed to them when administered together are those that are expected for a possible additive effect; the effect attributed to each HA separately is not potentiated nor inhibited.
Exploring rhizosphere bacteria of Eichhornia crassipes for metal tolerance and biological activity

Digital Repository Service at National Institute of Oceanography (India)

PrabhaDevi; Gomez, S.; Ribeiro, M.; Deshpande, S.A.; Singh, K.S.; DeSouza, L.

Cl₃, They were further screened for antibiotic sensitivity and biological activity according to Kirby-Bauer disc diffusion method The MTB under metal stress condition showed significant biological activity against clinical pathogens, fouling...
Comparative study of biological activity of glutathione, sodium ...

African Journals Online (AJOL)

Glutathione (GSH) and sodium tungstate (Na2WO4) are important pharmacological agents. They provide protection to cells against cytotoxic agents and thus reduce their cytotoxicity. It was of interest to study the biological activity of these two pharmacological active agents. Different strains of bacteria were used and the ...
2-Amino-1-methyl-6-(5-hydroxy-)phenylimidazo[4,5-b]pyridine (5-OH-PhIP), a biomarker for the genotoxic dose of the heterocyclic amine, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)

DEFF Research Database (Denmark)

Frandsen, H; Frederiksen, H; Alexander, J

2002-01-01

2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) is a mutagenic and carcinogenic heterocyclic amine formed during ordinary cooking. PhIP is metabolically activated by CYP P450 mediated N-hydroxylation followed by phase II esterification. The ultimate mutagenic metabolite reacts with DNA...
Biological Activities of Royal Jelly - Review

Directory of Open Access Journals (Sweden)

Crenguţa I. Pavel

2011-10-01

Full Text Available Royal jelly is a secretion product of the cephalic glands of nurse bees that has been used for centuries for itsextraordinary properties and health effects. This bibliographic study aims to review many of the scientific findingsand research that prove many of the remarkable various actions, effects and some uses of royal jelly. There are takeninto consideration numerous biological properties and effects of royal jelly: antioxidant, neurotrophic, hipoglicemiant, hipocholesterolemiant and hepatoprotective, hypotensive and blood pressure regulatory, antitumor, antibiotic, anti-inflammatory, immunomodulatory and anti-allergic, general tonic and antiaging. Royal jelly is one ofthe most studied bee products, but there still remains much to reveal about its biochemistry and biological activity infuture research for our health and life benefit.
Biological activity of antitumoural MGBG: the structural variable.

Science.gov (United States)

Marques, M P M; Gil, F P S C; Calheiros, R; Battaglia, V; Brunati, A M; Agostinelli, E; Toninello, A

2008-05-01

The present study aims at determining the structure-activity relationships (SAR's) ruling the biological function of MGBG (methylglyoxal bis(guanylhydrazone)), a competitive inhibitor of S-adenosyl-L-methionine decarboxylase displaying anticancer activity, involved in the biosynthesis of the naturally occurring polyamines spermidine and spermine. In order to properly understand its biochemical activity, MGBG's structural preferences at physiological conditions were ascertained, by quantum mechanical (DFT) calculations.
New Palladium-Catalyzed Approaches to Heterocycles and Carbocycles

Energy Technology Data Exchange (ETDEWEB)

Huang, Qinhua [Iowa State Univ., Ames, IA (United States)

2004-12-19

The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I₂, ICl, PhSeCl, PhSCl and p-O₂NC₆H₄SCl to give the corresponding halogen-, selenium- and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. The Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes provides an efficient way to synthesize a variety of 4-(1-alkenyl)-3-arylisoquinolines in moderate to excellent yields. The introduction of an ortho-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Highly substituted naphthalenes have been synthesized by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon-carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields. Novel palladium migratiodarylation methodology for the synthesis of complex fused polycycles has been developed, in which one or more sequential Pd-catalyzed intramolecular migration processes involving C-H activation are employed. The chemistry works best with electron-rich aromatics, which is in agreement
Removal of polycyclic aromatic hydrocarbons in soil spiked with model mixtures of petroleum hydrocarbons and heterocycles using biosurfactants from Rhodococcus ruber IEGM 231.

Science.gov (United States)

Ivshina, Irina; Kostina, Ludmila; Krivoruchko, Anastasiya; Kuyukina, Maria; Peshkur, Tatyana; Anderson, Peter; Cunningham, Colin

2016-07-15

Removal of polycyclic aromatic hydrocarbons (PAHs) in soil using biosurfactants (BS) produced by Rhodococcus ruber IEGM 231 was studied in soil columns spiked with model mixtures of major petroleum constituents. A crystalline mixture of single PAHs (0.63g/kg), a crystalline mixture of PAHs (0.63g/kg) and polycyclic aromatic sulfur heterocycles (PASHs), and an artificially synthesized non-aqueous phase liquid (NAPL) containing PAHs (3.00g/kg) dissolved in alkanes C10-C19 were used for spiking. Percentage of PAH removal with BS varied from 16 to 69%. Washing activities of BS were 2.5 times greater than those of synthetic surfactant Tween 60 in NAPL-spiked soil and similar to Tween 60 in crystalline-spiked soil. At the same time, amounts of removed PAHs were equal and consisted of 0.3-0.5g/kg dry soil regardless the chemical pattern of a model mixture of petroleum hydrocarbons and heterocycles used for spiking. UV spectra for soil before and after BS treatment were obtained and their applicability for differentiated analysis of PAH and PASH concentration changes in remediated soil was shown. The ratios A254nm/A288nm revealed that BS increased biotreatability of PAH-contaminated soils. Copyright © 2016 Elsevier B.V. All rights reserved.
N-heterocycle carbene (NHC)-ligated cyclopalladated N,N-dimethylbenzylamine: a highly active, practical and versatile catalyst for the Heck-Mizoroki reaction.

Science.gov (United States)

Peh, Guang-Rong; Kantchev, Eric Assen B; Zhang, Chi; Ying, Jackie Y

2009-05-21

The wide dissemination of catalytic protocols in academic and industrial laboratories is facilitated by the development of catalysts that are not only highly active but also user-friendly, stable to moisture, air and long term storage and easy to prepare on a large scale. Herein we describe a protocol for the Heck-Mizoroki reaction mediated by cyclopalladated N,N-dimethylbenzylamine (dmba) ligated with a N-heterocyclic carbene, 1,3-bis(mesityl)imidazol-2-ylidene (IMes), that fulfils these criteria. The precatalyst can be synthesized on approximately 100 g scale by a tri-component, sequential, one-pot reaction of N,N-dimethylbenzylamine, PdCl2 and IMes.HCl in refluxing acetonitrile in air in the presence of K2CO3. This single component catalyst is stable to air, moisture and long term storage and can be conveniently dispensed as a stock solution in NMP. It mediates the Heck-Mizoroki reaction of a range of aryl- and heteroaryl bromides in reagent grade NMP at the 0.1-2 mol% range without the need for rigorous anhydrous techniques or a glovebox, and is active even in air. The catalyst is capable of achieving very high levels of catalytic activity (TON of up to 5.22 x 10(5)) for the coupling of a deactivated arylbromide, p-bromoanisole, with tBu acrylate as a benchmark substrate pair. A wide range of aryl bromides, iodides and, for the first time with a NHC-Pd catalyst, a triflate was coupled with diverse acrylate derivatives (nitrile, tert-butyl ester and amides) and styrene derivatives. The use of excess (>2 equiv.) of the aryl bromide and tert-butyl acrylate leads to mixture of tert-butyl beta,beta-diarylacrylate and tert-butyl cinnamate derivatives depending on the substitution pattern of the aryl bromide. Electron rich m- and p-substituted arylbromides give the diarylated products exclusively, whereas electron-poor aryl bromides give predominantly mono-arylated products. For o-substituted aryl bromides, no doubly arylated products could be obtained under any
Bis-ligated Ti and Zr complexes of chelating N-heterocyclic carbenes

KAUST Repository

El-Batta, Amer

2011-07-01

In this communication we report the synthesis of novel titanium and zirconium complexes ligated by bidentate "salicylaldimine-like" N-heterocyclic carbenes (NHC). Double addition of the NHC chelate to either TiCl4(thf)2 or ZrCl4 forms bis-ligated organometallic fragments with a distorted octahedral geometry. These complexes are rare examples of group IV transition-metal NHC adducts. Preliminary catalytic tests demonstrate that in the presence of methylaluminoxane (MAO) these complexes are useful initiators for the polymerization of ethylene and the copolymerization of ethylene with norbornene and 1-octene. © 2011 Elsevier B.V. All rights reserved.
Parameters of biological activity in colorectal cancer

Czech Academy of Sciences Publication Activity Database

Svobodová, Š.; Topolčan, O.; Holubec jr., L.; Levý, M.; Pecen, Ladislav; Svačina, Š.

2011-01-01

Roč. 31, č. 1 (2011), s. 373-378 ISSN 0250-7005 Institutional research plan: CEZ:AV0Z10300504 Keywords : colorectal cancer * biological activity * prognosis * tumor markers * angiogenetic factors * metalloproteinases * adhesion molecules Subject RIV: FD - Oncology ; Hematology Impact factor: 1.725, year: 2011
The role of hydrogen bonding on kinetics of rearrangement of heterocyclic aldoximes in perchloric acide

International Nuclear Information System (INIS)

Azzouz, A.S.; Abdullah, K.A.; Al-Niemi, I.

1995-01-01

Four paris of syn and anti aromatic heterocyclic aldoximes as 2-thiophenealdoxime, 2- furfuraladoxime, 2-pyridinealdoxime and 2-pyrrolealdoxime are prepared. The strcutures of these geometrical isomers are confirmed by the meaasurements of their U.V. I, R and melting points. Experiments show the existence of these aldoximers in an intramolecular hy-drogen bonding with variable strength depending on the hetero ztoms in the aldoximes. The first order rate constants of the rearrangement of syn aldoximes follow the order of hetero S>O>N, while the anti aldoximes show irregular order, Factors governing the aniti constants of the rearrangement of syn and anti aldoximes are analysed. Activation parameters are estimated and discussed on the basis of isokinetic relation-ship. The differences in physical and spectroscpic behavior of aldoximes lead to an important suggestion regarding the configuration of oxime. (author). 27 refs., 2 figs., 2 tabs

Quantitative LC–MS for water-soluble heterocyclic amines in fine aerosols (PM2.5) at Duke Forest, USA

Science.gov (United States)

In this study, a quantitative liquid chromatography-mass spectrometry (LC-MS) technique capable of measuring the concentrations of heterocyclic nitrogen compounds in ambient fine aerosols (PM2.5) has been developed. Quadrupole time-of-flight (Q-TOF) MS technology is used to provi...
MACROMOLECULAR ADDUCT FORMATION AND METABOLISM OF HETEROCYCLIC AMINES IN HUMANS AND RODENTS AT LOW DOSES. (R825280)

Science.gov (United States)

Abstract2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) are heterocyclic amines formed during the cooking of meat and fish. Both are genotoxic in a number of test systems and are carcinogen...
Advanced biological activated carbon filter for removing pharmaceutically active compounds from treated wastewater.

Science.gov (United States)

Sbardella, Luca; Comas, Joaquim; Fenu, Alessio; Rodriguez-Roda, Ignasi; Weemaes, Marjoleine

2018-04-28

Through their release of effluents, conventional wastewater treatment plants (WWTPs) represent a major pollution point sources for pharmaceutically active compounds (PhACs) in water bodies. The combination of a biological activated carbon (BAC) filter coupled with an ultrafiltration (UF) unit was evaluated as an advanced treatment for PhACs removal at pilot scale. The BAC-UF pilot plant was monitored for one year. The biological activity of the biofilm that developed on the granular activated carbon (GAC) particles and the contribution of this biofilm to the overall removal of PhACs were evaluated. Two different phases were observed during the long-term monitoring of PhACs removal. During the first 9200 bed volumes (BV; i.e., before GAC saturation), 89, 78, 83 and 79% of beta-blockers, psychiatric drugs, antibiotics and a mix of other therapeutic groups were removed, respectively. The second phase was characterized by deterioration of the overall performances during the period between 9200 and 13,800 BV. To quantify the respective contribution of adsorption and biodegradation, a lab-scale setup was operated for four months and highlighted the essential role played by GAC in biofiltration units. Physical adsorption was indeed the main removal mechanism. Nevertheless, a significant contribution due to biological activity was detected for some PhACs. The biofilm contributed to the removal of 22, 25, 30, 32 and 35% of ciprofloxacin, bezafibrate, ofloxacin, azithromycin and sulfamethoxazole, respectively. Copyright © 2018 The Authors. Published by Elsevier B.V. All rights reserved.
Biological activity of selected plants with adaptogenic effect

OpenAIRE

Eva Ivanišová; Miroslava Kačániová; Jana Petrová; Radka Staňková; Lucia Godočíková; Tomáš Krajčovič; Štefan Dráb

2016-01-01

The aim of this study was to determine biological activity of plants with adaptogenic effect: Panax ginseng Mayer., Withania somnifera L., Eleuterococcus senticosus Rupr. et Maxim., Astragallus membranaceus Fisch. and Codonopsis pilosulae Franch. The antioxidant activity was detected by DPPH and phosphomolybdenum method, total polyphenol content with Folin – Ciocalteu reagent, flavonoids content by aluminium chloride method. The detection of antimicrobial activity was carried out by disc diff...
An electrochemical procedure coupled with a Schiff base method; application to electroorganic synthesis of new nitrogen-containing heterocycles

International Nuclear Information System (INIS)

Dowlati, Bahram; Othman, Mohamed Rozali

2013-01-01

The synthesis of Nitrogen-containing heterocycles has been achieved using chemical and electrochemical methods, respectively. The direct chemical synthesis of nucleophiles proceeds through the Schiff base chemical reaction. This procedure offers an alternate reaction between dicarbonyl compounds and diamines leads to the formation of products. The results indicate that the Schiff base chemical method for synthesis of the product has successfully performed in excellent overall yield. In the electrochemical step, a series of Nitrogen-containing compounds were electrosynthesized. Various parameters such as the applied potential, pH of the electrolytic solution, cell configuration and also purification techniques, were carried out to optimize the yields of corresponding products. New Nitrogen-containing heterocycle derivatives were synthesized using an electrochemical procedure coupled with a Schiff base as a facile, efficient and practical method. The products have been characterized after purification by IR, 1 H NMR, 13 C NMR and ESI-MS 2
Trace Analysis of Mutagenic Heterocyclic Aromatic Amines in Cigarette Smoke Condensate and its Base Fractions via Silylation-GC-MS

Directory of Open Access Journals (Sweden)

Liu S

2014-12-01

Full Text Available Among the more than 5000 chemicals reported in cigarette smoke condensate (CSC, heterocyclic aromatic amines (HAAs are considered to be a contributor to observed biological activity. HAAs are non-volatile and are reported at ppb levels in CSC. A new method for HAA analysis at the trace level is reported here. N, O-Bis(trimethylsilyl trifluoroacetamide (BSTFA containing 1% trimethylchlorosilane was employed to derivatize amino groups by heating the reagent containing a sample of CSC at 80 °C for 30 min followed by analysis employing gas chromatography-mass spectroscopy (GC-MS in the selected-ion-monitoring (SIM mode. This derivatization method afforded symmetrical peak shapes on a ZB-50 stationary phase and achieved instrumental limits of quantification (LOQ at 10:1 S/N from -1 ng/mL for AαC to120 ng/mL for Glu-P-1. The chemical identity of each derivative was confirmed by comparison of retention time and mass spectra of standards. The latter were characterized by the following ions: M·+ or [M-1]+, [M-15]+, and m/z 73 (i.e., trimethylsilyl. CSC and its base sub-fractions were studied using the GC-MS method. Ten HAAs were screened and five were quantified in cigarette smoke condensate, while 2-5 HAAs were quantified in each of three base sub-fractions. Values obtained with the new procedure agree well with values reported in the literature and with results obtained from a commercial laboratory via a different analytical method. The potential contribution of each HAA to the overall mutagenic activity observed for CSC and its base fractions is discussed. When considered together, HAAs account for only a small portion (-7.8% of the observed mutagenicity of the CSC.
A molecular dynamics study of lithium-containing aprotic heterocyclic ionic liquid electrolytes

Science.gov (United States)

Lourenço, Tuanan C.; Zhang, Yong; Costa, Luciano T.; Maginn, Edward J.

2018-05-01

Classical molecular dynamics simulations were performed on twelve different ionic liquids containing aprotic heterocyclic anions doped with Li+. These ionic liquids have been shown to be promising electrolytes for lithium ion batteries. Self-diffusivities, lithium transference numbers, densities, and free volumes were computed as a function of lithium concentration. The dynamics and free volume decreased with increasing lithium concentration, and the trends were rationalized by examining the changes to the liquid structure. Of those examined in the present work, it was found that (methyloxymethyl)triethylphosphonium triazolide ionic liquids have the overall best performance.
Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Nitrogen Heterocycles (PANHs)

Science.gov (United States)

Mattioda, A. L.; Hudgins, D. M.; Bauschlicher, C. W.; Allamandola, L. J.; Biemesderfer, C. D.; Rosi, M.

2002-01-01

The mid-infrared spectra of the nitrogen-containing heterocyclic polycyclic aromatic compounds 1-azabenz[a]-anthracene; 2-azabenz[a]anthracene; 1-azachrysene; 2-azachrysene; 4-azachrysene; 2-azapyrene, and 7,8 benzoquinoline in their neutral and cation forms were investigated. The spectra of these species isolated in an argon matrix have been measured. Band frequencies and intensities were tabulated and these data compared with spectra computed using density functional theory at the B3LYP level. The overall agreement between experiment and theory is quite good, in keeping with earlier results on homonuclear polycyclic aromatic hydrocarbons. The differences between the spectral properties of nitrogen bearing aromatics and non-substituted, neutral polycyclic aromatic hydrocarbons will be discussed.
Determination of acid-base dissociation constants of very weak zwitterionic heterocyclic bases by capillary zone electrophoresis

Czech Academy of Sciences Publication Activity Database

Ehala, Sille; Grishina, Anastasia; Sheshenev, Andrey; Lyapkalo, Ilya; Kašička, Václav

2010-01-01

Roč. 1217, - (2010), s. 8048-8053 ISSN 0021-9673 R&D Projects: GA ČR(CZ) GA203/08/1428; GA ČR(CZ) GA203/09/0675 Institutional research plan: CEZ:AV0Z40550506 Keywords : acidity constant * capillary zone electrophoresis * zwitterionic heterocyclic bases Subject RIV: CC - Organic Chemistry Impact factor: 4.194, year: 2010
Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst

International Nuclear Information System (INIS)

Xiang Gao; Bo Yu; Qingqing Mei; Zhenzhen Yang; Yanfei Zhao; Hongye Zhang; Leiduan Hao, Zhimin Liu

2016-01-01

B(C 6 F 5 ) 3 combined with atmospheric CO 2 was found to be highly effective for the cyclization of ortho substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields. (authors)
Synthesis of quinolino[2 ,3 :8,7]cyclooct[ b]indole

Indian Academy of Sciences (India)

Among the nitrogen heterocycles, indole is an impor- tant structural components in alkaloids and many phar- maceutical agents. Indole exhibits a high degree of biological activities including antifungal, antibacterial, antitumour, anti-HIV and DNA interactions. Substi- tuted indoles have been referred to as 'privileged struc-.
Biologic activity of porphyromonas endodontalis complex lipids.

Science.gov (United States)

Mirucki, Christopher S; Abedi, Mehran; Jiang, Jin; Zhu, Qiang; Wang, Yu-Hsiung; Safavi, Kamran E; Clark, Robert B; Nichols, Frank C

2014-09-01

Periapical infections secondary to pulpal necrosis are associated with bacterial contamination of the pulp. Porphyromonas endodontalis, a gram-negative organism, is considered to be a pulpal pathogen. P. gingivalis is phylogenetically related to P. endodontalis and synthesizes several classes of novel complex lipids that possess biological activity, including the capacity to promote osteoclastogenesis and osteoclast activation. The purpose of this study was to extract and characterize constituent lipids of P. endodontalis and evaluate their capacity to promote proinflammatory secretory responses in the macrophage cell line, RAW 264.7, as well as their capacity to promote osteoclastogenesis and inhibit osteoblast activity. Constituent lipids of both organisms were fractionated by high-performance liquid chromatography and were structurally characterized using electrospray mass spectrometry or electrospray-mass spectrometry/mass spectrometry. The virulence potential of P. endodontalis lipids was then compared with known biologically active lipids isolated from P. gingivalis. P. endodontalis total lipids were shown to promote tumor necrosis factor alpha secretion from RAW 264.7 cells, and the serine lipid fraction appeared to account for the majority of this effect. P. endodontalis lipid preparations also increased osteoclast formation from RAW 264.7 cells, but osteoblast differentiation in culture was inhibited and appeared to be dependent on Toll-like receptor 2 expression. These effects underscore the importance of P. endodontalis lipids in promoting inflammatory and bone cell activation processes that could lead to periapical pathology. Copyright © 2014 American Association of Endodontists. Published by Elsevier Inc. All rights reserved.
Unexpected rearrangements in the synthesis of an unsymmetrical tridentate dianionic N-heterocyclic carbene

KAUST Repository

Despagnet-Ayoub, Emmanuelle; Miqueu, Karinne; Sotiropoulos, Jean-Marc; Henling, Lawrence M.; Day, Michael W.; Labinger, Jay A.; Bercaw, John E.

2013-01-01

Starting from the same ethylenediamine species, three valuable carbene precursors were synthesized under differing conditions: a tridentate dianionic N-heterocyclic carbene bearing an aniline, a phenol and a central dihydroimidazolium salt, its benzimidazolium isomer by intramolecular rearrangement and a dicationic benzimidazolium-benzoxazolium salt by changing the Brønsted acid from HCl to HBF4. A DFT study was performed to understand the rearrangement pathway. The structure of a bis[(NCO)carbene] zirconium complex was determined. © 2013 The Royal Society of Chemistry.
A Photolabile Linker for the Solid-Phase Synthesis of Peptide Hydrazides and Heterocycles

DEFF Research Database (Denmark)

Qvortrup, Katrine; Komnatnyy, Vitaly V.; Nielsen, Thomas Eiland

2014-01-01

A photolabile hydrazine linker for the solid-phase synthesis of peptide hydrazides and hydrazine-derived heterocycles is presented. The developed protocols enable the efficient synthesis of structurally diverse peptide hydrazides derived from the standard amino adds, including those with side......-chain protected residues at the C-terminal of the resulting peptide hydrazide, and are useful for the synthesis of dihydropyrano[2,3-c]pyrazoles. The linker is compatible with most commonly used coupling reagents and protecting groups for solid-phase peptide synthesis....
Bioactive Phytochemicals: Bioactivity, Sources, Preparations, and/or Modifications via Silver Tetrafluoroborate Mediation

Directory of Open Access Journals (Sweden)

Matthew C. Achilonu

2015-01-01

Full Text Available This review provides an overview of the biological activities, natural occurrences, and the silver tetrafluoroborate- (AgBF4- mediated synthesis of proanthocyanidins, glycosides, N-heterocyclic alkaloid analogues (of pyrrole, morphine, quinoline, isoquinoline, and indole, furan analogues, and halocompounds. AgBF4 has been reviewed as an effective reaction promoter, used extensively in the synthesis of relevant biologically active compounds via carbon-carbon and carbon-heteroatom bonds formation. The literatures from 1979 to April 2014 were reviewed.
Alkyne-Azide Cycloaddition Catalyzed by Silver Chloride and “Abnormal” Silver N-Heterocyclic Carbene Complex

Directory of Open Access Journals (Sweden)

Aldo I. Ortega-Arizmendi

2013-01-01

Full Text Available A library of 1,2,3-triazoles was synthesized from diverse alkynes and azides using catalytic amounts of silver chloride instead of copper compounds. In addition, a novel “abnormal” silver N-heterocyclic carbene complex was tested as catalyst in this process. The results suggest that the reaction requires only 0.5% of silver complex, affording 1,2,3-triazoles in good yields.
The Importance of Spatiotemporal Information in Biological Motion Perception: White Noise Presented with a Step-like Motion Activates the Biological Motion Area.

Science.gov (United States)

Callan, Akiko; Callan, Daniel; Ando, Hiroshi

2017-02-01

Humans can easily recognize the motion of living creatures using only a handful of point-lights that describe the motion of the main joints (biological motion perception). This special ability to perceive the motion of animate objects signifies the importance of the spatiotemporal information in perceiving biological motion. The posterior STS (pSTS) and posterior middle temporal gyrus (pMTG) region have been established by many functional neuroimaging studies as a locus for biological motion perception. Because listening to a walking human also activates the pSTS/pMTG region, the region has been proposed to be supramodal in nature. In this study, we investigated whether the spatiotemporal information from simple auditory stimuli is sufficient to activate this biological motion area. We compared spatially moving white noise, having a running-like tempo that was consistent with biological motion, with stationary white noise. The moving-minus-stationary contrast showed significant differences in activation of the pSTS/pMTG region. Our results suggest that the spatiotemporal information of the auditory stimuli is sufficient to activate the biological motion area.
Biological activity of Stevia rebaudiana Bertoni and their relationship to health.

Science.gov (United States)

Ruiz-Ruiz, Jorge Carlos; Moguel-Ordoñez, Yolanda Beatriz; Segura-Campos, Maira Rubi

2017-08-13

The leaves of Stevia rebaudiana Bertoni has nutrients and phytochemicals, which make it an adequate source for the extraction and production of functional food ingredients. Preclinical and clinical studies suggest therapeutic and pharmacological applications for stevia and their extracts because they are not toxic and exhibit several biological activities. This review presents the biological activity of Stevia rebaudiana Bertoni and their relationship to antidiabetic, anticariogenic, antioxidant, hypotensive, antihypertensive, antimicrobial, anti-inflammatory and antitumor activities. Consumption and adverse effects were also reviewed.
Heterocyclic anions of astrobiological interest

Energy Technology Data Exchange (ETDEWEB)

Cole, Callie A.; Demarais, Nicholas J.; Bierbaum, Veronica M. [Department of Chemistry and Biochemistry, 215 UCB, University of Colorado, Boulder, CO 80309 (United States); Yang, Zhibo [Department of Chemistry and Biochemistry, University of Oklahoma, Norman, OK 73019 (United States); Snow, Theodore P., E-mail: Callie.Cole@colorado.edu, E-mail: Nicholas.Demarais@colorado.edu, E-mail: Veronica.Bierbaum@colorado.edu, E-mail: Zhibo.Yang@ou.edu, E-mail: Theodore.Snow@colorado.edu [Department of Astrophysical and Planetary Sciences, 391 UCB, University of Colorado, Boulder, CO 80309 (United States)

2013-12-20

As more complex organic molecules are detected in the interstellar medium, the importance of heterocyclic molecules to astrobiology and the origin of life has become evident. 2-Aminothiazole and 2-aminooxazole have recently been suggested as important nucleotide precursors, highlighting azoles as potential prebiotic molecules. This study explores the gas-phase chemistry of three deprotonated azoles: oxazole, thiazole, and isothiazole. For the first time, their gas-phase acidities are experimentally determined with bracketing and H/D exchange techniques, and their reactivity is characterized with several detected interstellar neutral molecules (N{sub 2}O, O{sub 2}, CO, OCS, CO{sub 2}, and SO{sub 2}) and other reactive species (CS{sub 2}, CH{sub 3}Cl, (CH{sub 3}){sub 3}CCl, and (CH{sub 3}){sub 3}CBr). Rate constants and branching fractions for these reactions are experimentally measured using a modified commercial ion trap mass spectrometer whose kinetic data are in good accord with those of a flowing afterglow apparatus reported here. Last, we have examined the fragmentation patterns of these deprotonated azoles to elucidate their destruction mechanisms in high-energy environments. All experimental data are supported and complemented by electronic structure calculations at the B3LYP/6-311++G(d,p) and MP2(full)/aug-cc-pVDZ levels of theory.
The asymmetric hetero-Diels-Alder reaction in the syntheses of biologically relevant compounds.

Science.gov (United States)

Eschenbrenner-Lux, Vincent; Kumar, Kamal; Waldmann, Herbert

2014-10-13

The hetero-Diels-Alder reaction is one of the most powerful transformations in the chemistry toolbox for the synthesis of aza- and oxa-heterocycles embodying multiple stereogenic centers. However, as compared to other cycloadditions, in particular the dipolar cycloadditions and the Diels-Alder reaction, the hetero-Diels-Alder reaction has been much less explored and exploited in organic synthesis. Nevertheless, this powerful transformation has opened up efficient and creative routes to biologically relevant small molecules and different natural products which contain six-membered oxygen or nitrogen ring systems. Recent developments in this field, in particular in the establishment of enantioselectively catalyzed hetero-Diels-Alder cycloadditions steered by a plethora of different catalysts and the application of the resulting small molecules in chemical biology and medicinal chemistry research, are highlighted in this Minireview. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Some links on this page may take you to non-federal websites. Their policies may differ from this site.