Synthesis of Some Benzimidazole-substituted Benzotriazoles

African Journals Online (AJOL)

NJD

2-Alkylsubstituted benzimidazoles (3a–h) were prepared from the acid-catalyzed reaction of 4-methyl-1,2-phenylenediamine with corresponding carboxylic acids. Addition of these benzimidazoles to N-chloromethylbenzotriazole in the presence of sodium amide under reflux conditions gave the novel ...

Ball Milling Assisted Solvent and Catalyst Free Synthesis of Benzimidazoles and Their Derivatives.

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El-Sayed, Taghreed H; Aboelnaga, Asmaa; Hagar, Mohamed

2016-08-24

Benzoic acid and o-phenylenediamine efficiently reacted under the green solvent-free Ball Milling method. Several reaction parameters were investigated such as rotation frequency; milling balls weight and milling time. The optimum reaction condition was milling with 56.6 g weight of balls at 20 Hz frequency for one hour milling time. The study was extended for synthesis of a series of benzimidazol-2-one or benzimidazol-2-thione using different aldehydes; carboxylic acids; urea; thiourea or ammonium thiocyanate with o-phenylenediamine. Moreover; the alkylation of benzimidazolone or benzimidazolthione using ethyl chloroacetate was also studied.

Synthesis of Aminofuran-Linked Benzimidazoles and Cyanopyrrole-Fused Benzimidazoles by Condition-Based Skeletal Divergence.

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Hsu, Wei-Shun; Tsai, Min-Huan; Barve, Indrajeet J; Yellol, Gorakh S; Sun, Chung-Ming

2017-07-10

A condition-based skeletal divergent synthesis was explored to achieve skeletal diversity in two component condensation reaction. Cyanomethyl benzimidazole was reacted with α-bromoketone under thermal conditions to furnish 2-aminofuranyl-benzimidazoles, while the same reaction afforded 3-cyano-benzopyrrolo-imidazoles under microwave irradiation. Two nonequivalent nucleophilic centers on benzimidazole moiety were manipulated elegantly by different reaction conditions to achieve the skeletal diversity.

[Research of imidazo[1,2-a]benzimidazole derivatives. XXX. Synthesis and properties of (imidazo[1,2-a]benzimidazolyl-2)acetic acid derivatives].

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Anisimova, V A; Tolpygin, I E; Spasov, A A; Serdiuk, T S; Sukhov, A G

2011-01-01

Ethyl esters of (9-subtituted-imidazo[1,2-a]benzimidazolyl-2)acetic acids were synthesized. The chemical properties of these esters (hydrolysis, decarboxylation, hydrazinolysis) and biological activity (fungicidal, antimicrobial, antiarrhythmic activity, and also affects on the brain rhythmogenesis) of the prepared compounds were studied.

Benzimidazole condensed ring systems 10 (1). Synthesis and cytotoxic activity of some pyrido[1,2-a]benzimidazoles.

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Badawey, E S; Kappe, T

1995-01-01

As a part of research project on the synthesis of a number of pyrido[1,2-a]benzimidazole derivatives with possible antineoplastic activity and as a result of the interesting antineoplastic activity recorded for one such compounds (NSC 649900), some new pyrido[1,2-a]benzimidazoles were prepared and evaluated for such activity. Compound (11, NSC 660334) exhibited a moderate in vitro antineoplastic activity especially against most of the leukemia cell lines, while compound (10, VM30309) showed a good cytotoxic activity against Artina salina larvae (IC50 = 1.75 micrograms/ml).

Synthesis and photophysical characterizations of thermal-stable naphthalene benzimidazoles.

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Erten-Ela, Sule; Ozcelik, Serdar; Eren, Esin

2011-07-01

Microwave-assisted synthesis, photophysical and electrochemical properties of thermal-stable naphthalene benzimidazoles and naphthalimides are studied in this paper. Microwave-assisted synthesis of naphthalene benzimidazoles provide higher yields than the conventional thermal synthesis. Comparative photophysical properties of naphthalene benzimidazoles and naphthalimides are revealed that conjugation of electron-donating group onto naphthalimide moiety increases fluorescence quantum yields. Fluorophore-solvent interactions are also investigated using Lippert-Mataga equation for naphthalimides and naphthalene benzimidazoles. Thermal stabilities of naphthalene benzimidazoles are better than naphthalimides due to increased aromaticity. The experimental E(LUMO) levels of naphthalene benzimidazoles are found to be between 3.15 and 3.28 eV. Therefore, naphthalene benzimidazole derivatives consisting of anchoring groups are promising materials in organic dye sensitized solar cells. © Springer Science+Business Media, LLC 2011

Synthesis and Photophysical Characterizations of Thermal -Stable Naphthalene Benzimidazoles

OpenAIRE

Erten Ela, Şule; Özçelik, Serdar; Eren, Ersin

2011-01-01

Microwave-assisted synthesis, photophysical and electrochemical properties of thermal-stable naphthalene benzimidazoles and naphthalimides are studied in this paper. Microwave-assisted synthesis of naphthalene benzimidazoles provide higher yields than the conventional thermal synthesis. Comparative photophysical properties of naphthalene benzimidazoles and naphthalimides are revealed that conjugation of electron-donating group onto naphthalimide moiety increases fluorescence ...

Synthesis of benzimidazoles by PIDA-promoted direct C(sp2)-H imidation of N-arylamidines.

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Huang, Jinbo; He, Yimiao; Wang, Yong; Zhu, Qiang

2012-10-29

A metal-free synthesis of diversified benzimidazoles from N-arylamidines through a phenyliodine(III) diacetate (PIDA) promoted intramolecular direct C(sp(2))-H imidation has been developed. The reaction proceeds smoothly at 0 °C or ambient temperature to provide the desired products in good to excellent yields. The synthesis of 2-alkyl- or 2-alkyl-fused benzimidazoles, which are generally inaccessible by similar Pd- or Cu-catalyzed approaches, can also be achieved. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Microwave promoted simple, efficient and regioselective synthesis of trisubstituted imidazo[1,2-a]benzimidazoles on soluble support.

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Chen, Li-Hsun; Hsiao, Ya-Shan; Yellol, Gorakh S; Sun, Chung-Ming

2011-03-14

An efficient microwave-assisted and soluble polymer-supported synthesis of medicinally important imidazole-fused benzimidazoles has been developed. The protocol involves the rapid condensation of polymer-bound amino benzimidazoles with various α-bromoketones and subsequent in situ intramolecular cyclization under microwave irradiation resulting in a one pot synthesis of imidazole interlacing benzimidazole polymer conjugates. The condensed product was obtained with excellent regioselectivity. The biologically interesting imidazo[1,2-a]benzimidazoles was released from polymer support at ambient temperature. Diversity in the triheterocyclic nucleus was achieved by the different substitutions at its 2, 3, and 9 positions. The new protocol has the advantages of short reaction time, easy workup process, excellent yields, reduced environmental impact, wide substrate scope and convenient procedure.

Polystyrene-supported pyridinium chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for selective synthesis of benzimidazoles

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Parvanak Boroujeni Kaveh

2013-01-01

Full Text Available Polystyrene-supported pyridinium chloroaluminate ionic liquid was prepared from the reaction of Merrifield resin with pyridine followed by reaction with aluminium chloride. This catalyst was used as a new chemoselective Lewis acid catalyst for the exclusive synthesis of 2-substituted benzimidazoles from the reaction of aldehydes with o-phenylenediamines. The catalyst is stable (as a bench top catalyst and can be easily recovered and reused without appreciable change in its efficiency.

1-ethyl gallate-2-substituted phenoxymethyl benzimidazoles: synthesis, molecular structure, antimicrobial activities and complex with cr(iii)

International Nuclear Information System (INIS)

Zhao, L.; Wu, J.; Wu, J.; Wang, Z.; Gu, H.

2017-01-01

The design of gallate and benzimidazole containing derivatives is expected to produce new bioactive molecules with multiple applications. Here the synthesis of eight novel benzimidazole compounds containing ethyl gallate and substituted phenoxymethyl units are reported. Firstly, the ring closure reaction between o-phenylendiamine and substituted phenoxyacetic acids resulted in 2-substituted phenoxymethyl benzimidazoles that were then modified by the N-hydroxyethylation with 2-chloroethyl alcohol under a phase transfer catalysis condition. The obtained 1-hydroxyethyl-2-substituted phenoxymethyl benzimidazoles were finally translated into the target title compounds 8a-h by an indirect esterification method in which three O-H groups of gallic acid were first protected by acetyls and deprotected after the esterification reaction by adding hydrazine hydrate. The structures of the title products 8a-h were fully characterized and confirmed by elemental analysis, MS, IR, 1H-NMR, 13C-NMR and single crystal X-ray diffraction techniques. Antimicrobial tests by inhibition zones indicated that these compounds exhibited diverse inhibitory effects against the test bacteria and fungi, and the type and position of the substituent groups in the phenoxymethyl moieties had obvious influence on their antimicrobial activities. Furthermore, the Cr(III) complex of 8h was synthesized, and various spectral, elemental and thermal analysis results confirmed that the central Cr(III) atom coordinated with adjacent hydroxyl groups of two 8h ligands, nitrate and H2O, respectively. (author)

An improved synthesis of 1,3,5-triaryl-2-pyrazolines in acetic acid aqueous solution under ultrasound irradiation

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Lin Zhi-Ping

2007-03-01

Full Text Available Abstract Background Pyrazoline derivatives have been found to possess a broad spectrum of biological activities. Among various pyrazoline derivatives, 2-pyrazolines seem to be the most frequently studied. A variety of methods have been reported for the preparation of this class of compound. However, in spite of their potential utility, some of the reported methods suffer from drawbacks such as long reaction times, cumbersome product isolation procedures and environmental concerns. Organic reactions in aqueous media have attracted increasing interest recently because of environmental issues and the understanding of biochemical processes. Ultrasound has increasingly been used in organic synthesis in the last three decades. A large number of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions under ultrasound irradiation. Results Preparation of a series of 1,3,5-triaryl-2-pyrazolines through the reaction of chalcones and phenylhydrazine hydrochloride was carried out in 83–96% yield within 1.5–2 h in sodium acetate-acetic acid aqueous solution under ultrasound irradiation. Conclusion We have described a practical and convenient procedure for the synthesis of 1,3,5-triaryl-2-pyrazolines in sodium acetate-acetic acid aqueous solution at room temperature under ultrasound irradiation.

Synthesis and in-silico molecular docking simulation of 3-chloro-4-substituted-1-(2-(1H-benzimidazol-2-ylphenyl-azetidin-2-ones as novel analgesic anti-inflammatory agent

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Santosh S. Chhajed

2016-11-01

Full Text Available In the present investigation synthesis of some novel 1-(2-(1H-benzimidazol-2-ylphenyl-3-chloro-4-(Un/substitutedphenylazetidin-2-one (3a–3h is reported. All these compounds were characterized by IR, Mass, 1H NMR and elemental analysis. The newly synthesized compounds were screened for analgesic and anti-inflammatory activities on acetic acid induced writhing in mice and carrageenan induced paw edema in rats. Compound 3 g was found to have potent analgesic (46% at 20 mg/kg b.w and anti-inflammatory (66.5% at 20 mg/kg b.w activities as compared to standard drug nimesulide (20 mg/kg b.w. To check binding modes and binding affinity of synthesized compounds were docked into the active sites of enzyme COX-II. Compounds 3a, 3e and 3 h were found to have good affinity for COX-II. A good correlation is found between in silico docking analysis and in biological screening.

Synthesis of benzimidazoles by potassium tert-butoxide-promoted intermolecular cyclization reaction of 2-iodoanilines with nitriles.

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Xiang, Shi-Kai; Tan, Wen; Zhang, Dong-Xue; Tian, Xian-Li; Feng, Chun; Wang, Bi-Qin; Zhao, Ke-Qing; Hu, Ping; Yang, Hua

2013-11-14

The synthesis of benzimidazoles by intermolecular cyclization reaction of 2-iodoanilines with nitriles has been developed. These reactions proceeded without the aid of any transition metals or ligands and just using KOBu(t) as the base. A variety of substituted benzimidazole derivatives can be synthesized by the approach.

The Synthesis of Dicationic Extended Bis-Benzimidazoles

OpenAIRE

Kang, Zhijan; Dykstra, Christine C.; Boykin, David W.

2004-01-01

The synthesis of extended dicationic bis-benzimidazoles starting from trans-1,2-bis(4-cyanophenyl)ethene and trans-1,2-bis(4-cyanophenyl)cyclopropane is reported. The target diamidines show significant in vitro activity against B. subtilis.

Facile Synthesis of N -Substituted Benzimidazoles

NARCIS (Netherlands)

Kurhade, Santosh; Rossetti, Arianna; Dömling, Alexander

2016-01-01

A particularly mild and efficient one-pot synthesis of N-substituted benzimidazole derivatives was developed. 2-Fluoro-5-nitrophenylisocyanide reacts with a diverse set of primary amines to afford the respective products in moderate to very good yield (35-95%; 20 examples).

Structure of substituted 2-(phenoxy)benzimidazoles

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Pavlova, I. S.; Pervova, I. G.; Lipunova, G. N.; Novikova, R. K.; Slepukhin, P. A.; Lipunov, I. N.

2013-03-01

The synthesis and X-ray diffraction study of 1-benzyl-2-[2-(5-ethyltetrazole-2-yl)-phenoxy]-1H-benzimidazole and 1-benzyl-2-[2-(5-ethyltetrazole-2-yl)-4-nitrophenoxy]-1H-benzimidazole single crystals have been performed. The oxidative splitting of an azo-hydrazone group of 1-(2-hydroxy-(5-nitro)phenyl)-3-ethyl-5-(benzylbenzimidazolyl)formazans, a break in the C2-N1 bond, the interaction of o-hydroxyl group of aryl fragment with oxygen, and the formation of new 2-(phenoxy)benzimidazoles are found to occur in the presence of perchlorate iron(III).

1-Hydroxyethyl-2-Substituted Phenoxymethyl Benzimidazoles: Synthesis and Crystal Structures

International Nuclear Information System (INIS)

Wu, J.; Wang, Z.; Gu, H.; Chen, W.; Zhao, L.; Zhao, C.

2016-01-01

Five novel 1-hydroxyethyl-2-substituted phenoxymethyl benzimidazoles c1-c5 were successfully synthesized by a three-step route. Firstly, five substituted phenoxymethyl acids a1-a5 were prepared by the O-carboxymethylation reaction of the starting substituted phenols under microwave irradiation. Then, these compounds reacted with o-phenylendiamine to get the key intermediates 2-substituted phenoxymethyl benzimidazoles b1-b5. At last, the target compounds were synthesized by the N-hydroxyethylation reaction of b1-b5 with 2-chloroethyl alcohol through the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst. The structures of the target compounds were well characterized and verified by elemental analysis, MS, IR, 1H NMR, 13C NMR and single crystal X-ray diffraction analysis. (author)

Synthesis of acetic acid by catalytic oxidation of butenes-2. Synthesis of acetic acid from sec. -butyl alcohol and methyl ethyl ketone in vapor-phase catalytic oxidation

Energy Technology Data Exchange (ETDEWEB)

Yamashita, T.; Matsuzawa, Y.; Ninagawa, S.

1977-11-01

Eleven binary catalysts containing vanadium pentoxide (V/sub 2/O/sub 5/), 17 binary catalysts containing cobalt oxide (Co/sub 3/O/sub 4/), and 18 ternary catalysts containing both V/sub 2/O/sub 5/ and Co/sub 3/O/sub 4/ were screened for the stepwise conversion of sec.-butanol to methyl ethyl ketone (MEK) and acetic acid. Of the binary catalysts, 4:1 Rh/V and Co/V binary oxides gave the best acetic acid yields. With the Co/V catalyst, the selectivity for MEK increased rapidly as the cobalt content of the catalyst increased above 50%, reaching 81% at 226/sup 0/C and 90% conversion on 9:1 Co/V oxide. The 9:1 Co/V catalyst also yielded acetaldehyde from ethanol with 98% selectivity at 210/sup 0/C and acetone from isopropanol with 98% selectivity at 200/sup 0/C, but dehydrated tert.-butanol to isobutene. V/Cr and V/Sb binary oxides were the most effective catalysts for the oxidation of MEK to acetic acid, with 78-88% selectivities at 100% conversion at 260/sup 0/C. Of the ternary oxides tested for the one-step conversion of sec.-butanol to acetic acid, a 6:2:2 Co/V/Al catalyst gave best results, (i.e., 34% selectivity for acetic acid (45% for total acids) at 100% conversion and 68% selectivity (90% for total acids) at 50Vertical Bar3< conversion). Graphs, tables, and 21 references.

Benzimidazoles: A biologically active compounds

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Salahuddin

2017-02-01

Full Text Available Synthesis of commercially available benzimidazole involves condensation of o-phenylenediamine with formic acid. The most prominent benzimidazole compound in nature is N-riosyldimethylbenzimidazole, which serves as a axial ligand for cobalt in vitamin B12. The benzimidazole and its derivatives play a very important role as a therapeutic agent e.g. antiulcer and anthelmintic drugs. Apart from this the benzimidazole derivatives exhibit pharmacological activities such as antimicrobial, antiviral, anticancer, anti-inflammatory, analgesic, etc. The substituted benzimidazoles are summarized in this review to know about the chemistry as well as pharmacological activities.

Tautomerism and isomerism in some antitrichinellosis active benzimidazoles: Morphological study in polarized light, quantum chemical computations

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Anichina, Kameliya; Mavrova, Anelia; Yancheva, Denitsa; Tsenov, Jordan; Dimitrov, Rasho

2017-12-01

The morphology of the crystal structure of some antitrichinellosis active benzimidazole derivatives including (1H-benzimidazol-2-ylthio)acetic acids, [1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones, 1H-benzimidazol-2-ylthioacetylpiperazines and starting 2-mercapto benzimidazoles, was studied by the use of Polarized Light Microscopy (PLM). Characterization of the crystal phase was complimented by Differential scanning calorimetry analysis (DSC) and spectroscopic data. DFT computations were performed in order to investigate the prototropic tautomerism and the geometry of the molecule of the synthesized compounds. One distinct type of crystal structure for each one of 5 or 6-methyl-(1H-benzimidazol-2-ylthio)acetic acid 6 was observed by PLM - dendritic and needle-shaped formations. Compound 14, containing a methyl substituent in the benzimidazole ring crystallized also into two phases; while for the unsubstituted compound 13 a separation of phases does not take place. The influence of the both solvents - chloroform and ethanol on the phase separation and the formation of the crystalline structure of compound 14 was investigated. The morphological study showed that the cyclization of 6 in the presence of acetic anhydride in pyridine medium led to a mixture of 6-methyl-[1,3]tiazolo[3,2-a]benzimidazol-3(2H)-one (10a) and 7-methyl-[1,3]thiazolo[3,2-a]-benzimidazole-3(2H)-one (10b), which crystallized in the form of fibrils and spherulites respectively. It was found that a difference in the crystal structures of substituted and unsubstituted benzimidazol-2-thiones, respectively benzimidazol-2-thiol derivatives exists, which may be due not only to the thiol-thione tautomerism but to the prototropic properties of the hydrogen atom in first position of the ring. The calculation results indicated that the thione form is more stable than the thiol tautomer by 51-55 kJ mol-1. But at the same time ΔG for the two thiol tautomers is below 0.5 kJ mol-1. In solid phase the 5

An efficient one-pot two catalyst system in the construction of 2-substituted benzimidazoles: synthesis of benzimidazo[1,2-c]quinazolines.

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Cimarelli, Cristina; Di Nicola, Matteo; Diomedi, Simone; Giovannini, Riccardo; Hamprecht, Dieter; Properzi, Roberta; Sorana, Federico; Marcantoni, Enrico

2015-12-28

The benzimidazole core is a common moiety in a large number of natural products and pharmacologically active small molecules. The synthesis of novel benzimidazole derivatives remains a main focus in medicinal research. In continuation of the efforts towards Ce(III) catalysts for organic transformations, we observed for the first time the activity of the iodide ion and copper cation in activating CeCl3·7H2O in the selective formation of prototypical 2-substituted benzimidazoles. The one-pot CeCl3·7H2O-CuI catalytic system procedure includes the cyclo-dehydrogenation of aniline Schiff's bases, generated in situ from the condensation of 1,2-phenylenediamine and aldehydes, followed by the oxidation with iodine, which works as a hydrogen sponge. Mild reaction conditions, good to excellent yields, and clean reactions make the procedure a useful contribution to the synthesis of biologically active fused heterocycles containing benzimidazoquinazolines.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling.

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Sun, Xiang; Lv, Xiao-Hui; Ye, Lin-Miao; Hu, Yu; Chen, Yan-Yan; Zhang, Xue-Jing; Yan, Ming

2015-07-21

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Highly efficient water-mediated approach to access benzazoles: metal catalyst and base-free synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles.

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Bala, Manju; Verma, Praveen Kumar; Sharma, Deepika; Kumar, Neeraj; Singh, Bikram

2015-05-01

An efficient water-catalyzed method has been developed for the synthesis of 2-substituted benzimidazoles, benzoxazoles, and benzothiazoles in one step. The present method excludes the usage of toxic metal catalysts and bases to produce benzazoles in good to excellent yields. An efficient and versatile water-mediated method has been established for the synthesis of various 2-arylbenzazoles. The present protocol excludes the usage of any catalyst and additive provided excellent selectivities and yields with high functional group tolerance for the synthesis of 2-arylated benzimidazoles, benzoxazoles, and benzothiazoles. Benzazolones were also synthesized using similar reaction protocol.

Fatty acid synthesis by spinach chloroplasts, 2

International Nuclear Information System (INIS)

Yamada, Mitsuhiro; Nakamura, Yasunori

1975-01-01

By incorporation of 3 H 2 O into the fatty acid chain in the presence of unlabelled precursor, we showed that fatty acids are synthesized from PGA, PEP and pyruvate by intact spinach chloroplasts in the light. 13 C-tracer experiments confirmed that 1-C of pyruvate is decarboxylated and 2-C is incorporated into fatty acids by the chloroplasts. The patterns of fatty acids synthesized from PGA and pyruvate were the same as that from acetate. The highest rate of fatty acid synthesis was reached at the physiological concentration of PGA (3 mM) and pyruvate (1 mM). These results indicate the operation of the following path in the chloroplasts in light: PGA→PEP→pyruvate→acetylCoA→fatty acids. Since citrate and OAA were much less active and malate and glyoxylate were inert as precursors for fatty acid synthesis, PEP or pyruvate carboxylation, citrate lyase reaction and malate synthetase reaction are not involved in the formation of acetylCoA and fatty acids. Since pyruvate was much more effective as a substrate for fatty acid synthesis than lactate, acetaldehyde or acetate, direct decarboxylation path is considered to be the primary path from pyruvate to acetylCoA. The insignificant effect of chloroplast-washing on fatty acid synthesis from PGA and pyruvate indicates that the glycolytic path from PGA to pyruvate is associated with the chloroplasts. Since pyruvate was more effectively incorporated into fatty acids than acetylCoA, it is unlikely that pyruvate decarboxylation to acetylCoA is due to mitochondria contaminating the chloroplast preparation. On the basis of measurements of 3 H 2 O incorporation in the light and dark, the activity of fatty acid synthesis in spincah leaves appears to be shared by the activities in chloroplasts (87%) and other organelles (13%). (author)

The Synthesis and Biological Evaluation of N-Substituted 1H-Benzimidazol-2-yl-1H-pyrazole-3,5-diamines

Czech Academy of Sciences Publication Activity Database

Jedinák, L.; Kryštof, Vladimír; Cankař, P.

2016-01-01

Roč. 53, č. 2 (2016), s. 499-507 ISSN 0022-152X Institutional support: RVO:61389030 Keywords : ONE-POT SYNTHESIS * BENZIMIDAZOLE DERIVATIVES * EFFICIENT SYNTHESIS Subject RIV: CE - Biochemistry Impact factor: 0.893, year: 2016

Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

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Jilani JA

2013-07-01

Full Text Available Jamal A Jilani,1 Maha Shomaf,2 Karem H Alzoubi3 1Department of Medicinal Chemistry and Pharmacognosy, Jordan University of Science and Technology, Irbid, Jordan; 2Department of Pathology, Jordan University, Amman, Jordan; 3Department of Clinical Pharmacy, Jordan University of Science and Technology, Irbid, Jordan Abstract: In this study, the syntheses of 4-aminophenylbenzoxazol-2-yl-5-acetic acid, (an analogue of a known nonsteroidal anti-inflammatory drug [NSAID] and 5-[4-(benzoxazol-2-yl-5-acetic acidphenylazo]-2-hydroxybenzoic acid (a novel mutual azo prodrug of 5-aminosalicylic acid [5-ASA] are reported. The structures of the synthesized compounds were confirmed using infrared (IR, hydrogen-1 nuclear magnetic resonance (1H NMR, and mass spectrometry (MS spectroscopy. Incubation of the azo compound with rat cecal contents demonstrated the susceptibility of the prepared azo prodrug to bacterial azoreductase enzyme. The azo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were evaluated for inflammatory bowel diseases, in trinitrobenzenesulfonic acid (TNB-induced colitis in rats. The synthesized diazo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were found to be as effective as 5-aminosalicylic acid for ulcerative colitis. The results of this work suggest that the 4-aminophenylbenzoxazol-2-yl-5-acetic acid may represent a new lead for treatment of ulcerative colitis. Keywords: benzoxazole acetic acid, azo prodrug, colon drug delivery

Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides

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Chunxia Chen

2012-10-01

Full Text Available A straightforward method has been developed for the synthesis of the benzimidazole ring system through a carbon-nitrogen cross-coupling reaction. In the presence of 2.0 equiv. of K2CO3 in water at 100 °C for 30 h, the intramolecular cyclization of N-(2-iodoarylbenzamidine provides benzimidazole derivatives in moderate to high yields. Remarkably, the procedure occurs exclusively in water and doesn’t require the use of any additional reagent/catalyst, rendering the methodology highly valuable from both environmental and economical points of view.

Synthesis and molecular structures of 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles

International Nuclear Information System (INIS)

Wu, J.W.; Zhao, L.; Wang, Z.; Gu, H.; Chen, W.; Zhao, C.

2016-01-01

Five novel 1-hydroxyethyl-2-(p-substituted) phenoxymethyl benzimidazoles were synthesized by a three-step route. Under microwave irradiation, the p-substituted phenols were firstly O-carboxymethylated to prepare the corresponding p-substituted phenoxymethyl acids, which then reacted with o-phenylendiamine to get the key intermediates 2-(p-substituted) phenoxymethyl benzimidazole. Finally, the solid-liquid phase transfer catalysis method, where tetrabutyl ammonium bromide (TBAB) was used as the catalyst, was applied to synthesize the target compounds c/sub 1/-c/sub 5/ by the N-hydroxyethylation reaction with 2-chloroethyl alcohol. The structures of the obtained compounds were well characterized and confirmed by elemental analysis, MS, IR, /sup 1/H NMR, /sup 13/C NMR and single-crystal X-ray diffraction analysis. (author)

Rhenium(V) complexing with benzimidazole in acidic media

International Nuclear Information System (INIS)

Zakaeva, R.Sh.; Gagieva, S.Ch.; Kaloev, N.I.; Bukov, N.N.; Panyushkin, V.T.

2003-01-01

Coordination compounds of rhenium(V) with 1H-benzimidazole (L) separated from acid media: (HL) 2 [ReOX 5 ](H 2 O) n and [ReOL x X y (H 2 O) z ](H 2 O) n (HL and L - protonated and deprotonated forms of benzimidazole; X = Cl - , Br - ) were studied by the methods of IR spectroscopy, 1 H NMR spectroscopy and thermal gravimetric analysis. Methods of ligand coordination in the complexes are discussed on the basis of data obtained [ru

Synthesis, electronic properties, antioxidant and antibacterial activity of some new benzimidazoles.

Science.gov (United States)

Mavrova, Anelia Ts; Yancheva, Denitsa; Anastassova, Neda; Anichina, Kamelya; Zvezdanovic, Jelena; Djordjevic, Aleksandra; Markovic, Dejan; Smelcerovic, Andrija

2015-10-01

Two groups of benzimidazole derivatives were synthesized using as precursors 5(6)-substituted 2-mercapto-benzimidazol-thiols and their antioxidant activity was investigated using TBA-MDA test. In the group of 1,3-disubstituted-benzimidazol-2-imines the highest lipid peroxidation inhibition effect 74.04% (IC₅₀=141.89 μg/mL) revealed ethyl [3-(2-ethoxy-2-oxoethyl)-2-imino-5-benzoyl-2,3-dihydro-1H-benzimdazol-1-yl]acetate 12 while in the group of 2-substituted-1,3-thiazolo[3,2-a]benzimidazolones the highest inhibition effect showed 2-(4-fluorobenzylidene)-7-(phenylcarbonyl)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one 17 90.76% (IC₅₀=53.70 μg/mL). In order to estimate the capability of the studied benzimidazoles to act as radical scavengers the structure of the most active derivative within the both subseries was optimized at B3LYP/6-311++G(∗∗) level and the respective bond dissociation enthalpies were calculated. The appropriate models for the HAT and SET-mechanism of the antioxidant activity were proposed. The antibacterial activity of the compounds was evaluated against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and three Gram-negative bacteria (Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027 and Salmonella abony NCTC 6017). 1,3-Diphenylpropyl-5-methyl-1,3-dihydro-2H-benzimidazol-2-imine 14 exhibited significant activity against B. subtilis, S. aureus, S. abony and E. coli (with MIC values of 0.125, 0.016, 0.50 and 0.50mg/mL, respectively). The group of thiazolobenzimidazolones did not reveal antibacterial activity against the tested strains. Copyright © 2015. Published by Elsevier Ltd.

Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom

Science.gov (United States)

Begunov, Roman S.; Ryzvanovich, Galina A.

2013-01-01

Main methods for the synthesis of fused imidazole derivatives with a bridgehead nitrogen atom are systematically considered and summarized. The reaction mechanisms that underlie the methods for the synthesis of pyrido[1,2-a]benzimidazoles and related compounds are described. Biological properties and mechanisms of the biological activity of fused azaheterocycles are discussed. The bibliography includes 152 references.

Convenient synthesis of benzothiazoles and benzimidazoles through Brønsted acid catalyzed cyclization of 2-amino thiophenols/anilines with β-diketones.

Science.gov (United States)

Mayo, Muhammad Shareef; Yu, Xiaoqiang; Zhou, Xiaoyu; Feng, Xiujuan; Yamamoto, Yoshinori; Bao, Ming

2014-02-07

Brønsted acid catalyzed cyclization reactions of 2-amino thiophenols/anilines with β-diketones under oxidant-, metal-, and radiation-free conditions are described. Various 2-substituted benzothiazoles/benzimidazoles are obtained in satisfactory to excellent yields. Different groups such as methyl, chloro, nitro, and methoxy linked on benzene rings were tolerated under the optimized reaction conditions.

Polyethylene glycol (PEG-400: An efficient medium for the synthesis of 1,2-disubstituted benzimidazoles

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Raja Sekhar Mekala

2015-12-01

Full Text Available Polyethylene glycol (PEG-400 was found to be an inexpensive, non-toxic, and effective medium for the one-pot synthesis of 1,2-disubstituted benzimidazoles in excellent yields. Eco-friendliness, low cost, high yields, and recyclability of the PEG-400 are the important features of this protocol.

Synthesis and study of rhenium (5) complexes with benzimidazole and rubeanic acid

Energy Technology Data Exchange (ETDEWEB)

Basitova, S M; Yurina, R D; Kotegov, K V; Amindzhanov, A A

1986-01-01

Mixed rhenium (5) oxohalide complex compounds with benzimidazole and rubeanic acid are synthesized. Composition of the compounds obtained is established by IR spectroscpy thermal and chemical analyses. It is shown that rhenium (5) chloride compound stability to pyrolysis is rather lower than that of the corresponding bromide derivatives.

Synthesis and study of rhenium (5) complexes with benzimidazole and rubeanic acid

International Nuclear Information System (INIS)

Basitova, S.M.; Yurina, R.D.; Kotegov, K.V.; Amindzhanov, A.A.

1986-01-01

Mixed rhenium (5) oxohalide complex compounds with benzimidazole and rubeanic acid are synthesized. Composition of the compounds obtained is established by IR spectroscpy thermal and chemical analyses. It is shown that rhenium (5) chloride compound stability to pyrolysis is rather lower than that of the corresponding bromide derivatives

Techno-economic Analysis for the Thermochemical Conversion of Lignocellulosic Biomass to Ethanol via Acetic Acid Synthesis

Energy Technology Data Exchange (ETDEWEB)

Zhu, Yunhua; Jones, Susanne B.

2009-04-01

Biomass is a renewable energy resource that can be converted into liquid fuel suitable for transportation applications. As a widely available biomass form, lignocellulosic biomass can have a major impact on domestic transportation fuel supplies and thus help meet the Energy Independence and Security Act renewable energy goals (U.S. Congress 2007). This study performs a techno-economic analysis of the thermo chemical conversion of biomass to ethanol, through methanol and acetic acid, followed by hydrogenation of acetic acid to ethanol. The conversion of syngas to methanol and methanol to acetic acid are well-proven technologies with high conversions and yields. This study was undertaken to determine if this highly selective route to ethanol could provide an already established economically attractive route to ethanol. The feedstock was assumed to be wood chips at 2000 metric ton/day (dry basis). Two types of gasification technologies were evaluated: an indirectly-heated gasifier and a directly-heated oxygen-blown gasifier. Process models were developed and a cost analysis was performed. The carbon monoxide used for acetic acid synthesis from methanol and the hydrogen used for hydrogenation were assumed to be purchased and not derived from the gasifier. Analysis results show that ethanol selling prices are estimated to be $2.79/gallon and $2.81/gallon for the indirectly-heated gasifier and the directly-heated gasifier systems, respectively (1stQ 2008$, 10% ROI). These costs are above the ethanol market price for during the same time period ($1.50 - $2.50/gal). The co-production of acetic acid greatly improves the process economics as shown in the figure below. Here, 20% of the acetic acid is diverted from ethanol production and assumed to be sold as a co-product at the prevailing market prices ($0.40 - $0.60/lb acetic acid), resulting in competitive ethanol production costs.

Synthesis of ruthenium (III) complexes with benzimidazole derivatives

International Nuclear Information System (INIS)

Vyas, P.C.; Chahar, Yogesh K.; Garg, Yajula; Seth, Gita

2003-01-01

Complexes of ruthenium with biologically important benzimidazole derivatives, viz. 2-(2'-hydroxyphenyl) benzimidazole (HOPBI), 2-2'- mercaptophenyl) benzimidazole (HSPBI), 2- (2'-hydroxynaphthyl) benzimidazole (HONBI) have been synthesized and characterized. (author)

Multifunctional Poly(2,5-benzimidazole)/Carbon Nanotube Composite Films

Science.gov (United States)

2010-01-01

Multifunctional Poly(2,5- benzimidazole )/Carbon Nanotube Composite Films JI-YE KANG,1 SOO-MI EO,1 IN-YUP JEON,1 YEONG SUK CHOI,2 LOON-SENG TAN,3 JONG...molecular-weight poly(2,5- benzimidazole ) (ABPBI). ABPBI/carbon nanotube (CNT) compo- sites were prepared via in situ polymerization of the AB-monomer in the...polymerization; multiwalled carbon nanotube (MWCNT); nano- composites; poly(2,5- benzimidazole ); (ABPBI); polycondensa- tion; poly(phosphoric acid); single-walled

Synthesis and Analgesic Activity of Novel Derivatives of 1,2-Substituted Benzimidazoles

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Shobhit Srivastava

2013-01-01

Full Text Available A series of novel 2-phenylhydrazinomethyl and 2-(2-hydroxyphenyl-benzimidazole derivatives substituted at the N1-position of benzimidazole nucleus were synthesized as well as screened for analgesic activity. Some of these compounds showed promising analgesic activity when compared with the standard drug diclofenac sodium. The incorporation of a phenylhydrazinomethyl nucleus at 2-position of benzimidazole compound gave a biologically active pharmacophore.

L-shaped benzimidazole fluorophores: synthesis, characterization and optical response to bases, acids and anions.

Science.gov (United States)

Lirag, Rio Carlo; Le, Ha T M; Miljanić, Ognjen Š

2013-05-14

Nine L-shaped benzimidazole fluorophores have been synthesized, computationally evaluated and spectroscopically characterized. These "half-cruciform" fluorophores respond to bases, acids and anions through changes in fluorescence that vary from moderate to dramatic.

An Efficient Synthesis of 2-Substituted Benzimidazoles via Photocatalytic Condensation of o-Phenylenediamines and Aldehydes.

Science.gov (United States)

Kovvuri, Jeshma; Nagaraju, Burri; Kamal, Ahmed; Srivastava, Ajay K

2016-10-10

A photocatalytic method has been developed for the efficient synthesis of functionalized benzimidazoles. This protocol involves photocatalytic condensation of o-phenylenediamines with various aldehydes using the Rose Bengal as photocatalyst. The method was found to be general and was successfully employed for accessing pharmaceutically important benzimidazoles by the condensation of aromatic, heteroaromatic and aliphatic aldehydes with o-phenylenediamines, in good-to-excellent yields. Notably, the method was found to be effective for the condensation of less reactive heterocyclic aldehydes with o-phenylenediamines.

The selective generation of acetic acid directly from synthesis gas

International Nuclear Information System (INIS)

Knifton, J.F.

1986-01-01

The authors conclude that each of the ruthenium, cobalt and iodide-containing catalyst components have very specific roles to play in the ''melt'' catalyzed conversion of synthesis gas to acetic acid. C 1 -Oxygenate formation is only observed in the presence of ruthenium carbonyls - [Ru(CO) 3 I 3 ] - is here the dominant species - and there is a direct relationship between liquid yield, ΣOAc - productivity and [Ru(CO) 3 I 3 ] - content. Controlled quantities of iodide ensure that initially formed MeOH is rapidly converted to the more reactive methyl iodide. Subsequent cobalt-catalyzed carbonylation to acetic acid may be preparatively attractive (>80% selectivity, good yields) relative to competing syntheses, where the [Co(CO) 4 ] - concentration is maximized that is, where the Co/Ru ratio is >1, the syngas feedstock is rich in CO, and the initial iodide/cobalt ratios are ca. unity. Formation of cobalt-iodide species appears to be a competing, inhibitory step in this catalysis

Synthesis and biological evaluation of 2-substituted benzimidazole derivatives

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Gurusamy Mariappan

2015-09-01

Full Text Available A novel series of 2-substituted benzimidazole derivatives (3a–3j were synthesized by the reaction of 2-chloro methyl benzimidazole with substituted primary aromatic amines. All the compounds were characterized by UV, IR, 1H NMR, mass spectral data and CHN elemental analysis. The synthesized derivatives were screened for analgesic and anti-inflammatory activities. All the compounds showed significant effect at 100 mg/kg p.o. and the experimental data are statistically significant at p < 0.01 level.

Benzimidazoles as benzamide replacements within cyclohexane-based CC chemokine receptor 2 (CCR2) antagonists.

Science.gov (United States)

Cherney, Robert J; Mo, Ruowei; Meyer, Dayton T; Pechulis, Anthony D; Guaciaro, Michael A; Lo, Yvonne C; Yang, Gengjie; Miller, Persymphonie B; Scherle, Peggy A; Zhao, Qihong; Cvijic, Mary Ellen; Barrish, Joel C; Decicco, Carl P; Carter, Percy H

2012-10-01

We describe the design, synthesis, and evaluation of benzimidazoles as benzamide replacements within a series of trisubstituted cyclohexane CCR2 antagonists. 7-Trifluoromethylbenzimidazoles displayed potent binding and functional antagonism of CCR2 while being selective over CCR3. These benzimidazoles were also incorporated into lactam-containing antagonists, thus completely eliminating the customary bis-amide. Copyright © 2012 Elsevier Ltd. All rights reserved.

Kinetics of Ethyl Acetate Synthesis Catalyzed by Acidic Resins

Science.gov (United States)

Antunes, Bruno M.; Cardoso, Simao P.; Silva, Carlos M.; Portugal, Ines

2011-01-01

A low-cost experiment to carry out the second-order reversible reaction of acetic acid esterification with ethanol to produce ethyl acetate is presented to illustrate concepts of kinetics and reactor modeling. The reaction is performed in a batch reactor, and the acetic acid concentration is measured by acid-base titration versus time. The…

Fatty acid synthesis by spinach chloroplasts, 2. The path from PGA to fatty acids

Energy Technology Data Exchange (ETDEWEB)

Yamada, Mitsuhiro; Nakamura, Yasunori [Tokyo Univ. (Japan). Coll. of General Education

1975-02-01

By incorporation of /sup 3/H/sub 2/O into the fatty acid chain in the presence of unlabelled precursor, we showed that fatty acids are synthesized from PGA, PEP and pyruvate by intact spinach chloroplasts in the light. /sup 13/C-tracer experiments confirmed that 1-C of pyruvate is decarboxylated and 2-C is incorporated into fatty acids by the chloroplasts. The patterns of fatty acids synthesized from PGA and pyruvate were the same as that from acetate. The highest rate of fatty acid synthesis was reached at the physiological concentration of PGA (3 mM) and pyruvate (1 mM). These results indicate the operation of the following path in the chloroplasts in light: PGA..-->..PEP..-->..pyruvate..-->..acetylCoA..-->..fatty acids. Since citrate and OAA were much less active and malate and glyoxylate were inert as precursors for fatty acid synthesis, PEP or pyruvate carboxylation, citrate lyase reaction and malate synthetase reaction are not involved in the formation of acetylCoA and fatty acids. Since pyruvate was much more effective as a substrate for fatty acid synthesis than lactate, acetaldehyde or acetate, direct decarboxylation path is considered to be the primary path from pyruvate to acetylCoA. The insignificant effect of chloroplast-washing on fatty acid synthesis from PGA and pyruvate indicates that the glycolytic path from PGA to pyruvate is associated with the chloroplasts. Since pyruvate was more effectively incorporated into fatty acids than acetylCoA, it is unlikely that pyruvate decarboxylation to acetylCoA is due to mitochondria contaminating the chloroplast preparation. On the basis of measurements of /sup 3/H/sub 2/O incorporation in the light and dark, the activity of fatty acid synthesis in spincah leaves appears to be shared by the activities in chloroplasts (87%) and other organelles (13%).

Design, Synthesis and Biological Evaluation of 2-(2-Amino-5(6-nitro-1H-benzimidazol-1-yl-N-arylacetamides as Antiprotozoal Agents

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Emanuel Hernández-Núñez

2017-04-01

Full Text Available Parasitic diseases are a public health problem affecting millions of people worldwide. One of the scaffolds used in several drugs for the treatment of parasitic diseases is the benzimidazole moiety, a heterocyclic aromatic compound. This compound is a crucial pharmacophore group and is considered a privileged structure in medicinal chemistry. In this study, the benzimidazole core served as a model for the synthesis of a series of 2-(2-amino-5(6-nitro-1H-benzimidazol-1-yl-N-arylacetamides 1–8 as benznidazole analogues. The in silico pharmacological results calculated with PASS platform exhibited chemical structures highly similar to known antiprotozoal drugs. Compounds 1–8 when evaluated in silico for acute toxicity by oral dosing, were less toxic than benznidazole. The synthesis of compounds 1–8 were carried out through reaction of 5(6-nitro-1H-benzimidazol-2-amine (12 with 2-chlroactemides 10a–h, in the presence of K2CO3 and acetonitrile as solvent, showing an inseparable mixture of two regioisomers with the -NO2 group in position 5 or 6 with chemical yields of 60 to 94%. The prediction of the NMR spectra of molecule 1 coincided with the experimental chemical displacements of the regioisomers. Comparisons between the NMR prediction and the experimental data revealed that the regioisomer endo-1,6-NO2 predominated in the reaction. The in vitro antiparasitic activity of these compounds on intestinal unicellular parasites (Giardia intestinalis and Entamoeba histolytica and a urogenital tract parasite (Trichomonas vaginalis were tested. Compound 7 showed an IC50 of 3.95 μM and was 7 time more active against G. intestinalis than benznidazole. Compounds 7 and 8 showed 4 times more activity against T. vaginalis compared with benznidazole.

Development and Synthesis of DNA-Encoded Benzimidazole Library.

Science.gov (United States)

Ding, Yun; Chai, Jing; Centrella, Paolo A; Gondo, Chenaimwoyo; DeLorey, Jennifer L; Clark, Matthew A

2018-04-25

Encoded library technology (ELT) is an effective approach to the discovery of novel small-molecule ligands for biological targets. A key factor for the success of the technology is the chemical diversity of the libraries. Here we report the development of DNA-conjugated benzimidazoles. Using 4-fluoro-3-nitrobenzoic acid as a key synthon, we synthesized a 320 million-member DNA-encoded benzimidazole library using Fmoc-protected amino acids, amines and aldehydes as diversity elements. Affinity selection of the library led to the discovery of a novel, potent and specific antagonist of the NK3 receptor.

Synthesis and optical properties of novel pyrido[1,2-a]benzimidazole-containing 1,3,4-oxadiazole derivatives

International Nuclear Information System (INIS)

Yang He; Ge Yanqing; Jia Jiong; Wang Jianwu

2011-01-01

A series of novel substituted 1,3,4-oxadiazole derivatives containing pyrido[1,2-a]benzimidazole moiety were synthesized and characterized using FTIR, 1 H NMR, 13 C NMR, and HRMS. An efficient tandem reaction was employed as a key step in constructing the pyrido[1,2-a]benzimidazole moiety under very mild condition. The structure of compound 4a was established by X-ray crystallography. The UV-vis absorption and fluorescence spectral characteristics of these compounds were investigated in several solvents. Compounds 4a-i display similar absorptions, with absorption peaks ranging from 330 to 339 nm in acetonitrile, while the absorption maxima of compound 4j bearing a diphenylamino group on the benzene ring is red-shifted distinctly to 377 nm due to the strong electron-donating property of its substituent and extended π-conjugated system. All these target heterocyclic compounds present blue-green emissions (461-487 nm) in dilute solutions and show high quantum yields of fluorescence (φ PL =0.65-0.99) in dichloromethane. - Research Highlights: → The first report about the unique optical properties of pyrido[1,2-a]benzimidazole heteroaromatic compounds containing 1,3,4-oxadiazole unit. → Synthesis of pyrido[1,2-a]benzimidazole moiety via a novel efficient tandem reaction. → The target heterocyclic compounds showing high quantum yields of fluorescence, with great potential for use as fluorescent pigments and in optical/electro devices.

Synthesis and physical-chemical properties of functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid

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E. K. Mikhal’chenko

2017-08-01

Full Text Available Introduction. Synthetic research of new biologically active compounds occupies an important place in modern pharmaceutical science.Thus it is important to develop techniques for the biologically active substances functionalization. Esters and amides take special place among the variety of functional derivatives of organic acids,. These fragments are well-known pharmacophores and could be found in a wide range of drugs. Thus, the nootropic agent pyracetam is 2-oxo-1-pyrolidineacetamide, and is the selective antagonist of β-adrenoreceptores; atenolol is a derivative of benzeneacetamide. Substituted acetamide and ester fragments are also present in the structures of aprofen, spasmolitin, acetylidine and β-lactam cephalosporins and penicillins antibiotics.Aim of our research was the synthetic method development for functional derivatives of 3-benzyl-8-propylxanthinyl-7-acetic acid and the study of their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian» – USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Chemical shifts were reported in ppm (parts per million values. Infrared (IR spectra were measured on a Bruker Alpha instrument using a potassium bromide (KBr disk, scanning from 400 to 4000 cm-1. Results and discussion. We selected 3-benzyl-8-propylxanthinyl-7-acetic acid as initial compound for our study. For synthesis of hexyl, heptyl, octyl, nonyl, decyl and benzyl esters of 3-benzyl-8-propylxanthinyl-7-acetic acid we used alternative method, that included alkylation of sodium salts of acids with alkyl halogens. Reaction was made at DMF medium by reflux of reagents. Next stage of our research was the synthesis of amides of 3-beznyl-8-propylxanthinyl-7-acetic acid by the reaction of ethyl or propyl esters

One-pot, two-step synthesis of imidazo[1,2-a]benzimidazoles via a multicomponent [4 + 1] cycloaddition reaction.

Science.gov (United States)

Hsiao, Ya-Shan; Narhe, Bharat D; Chang, Ying-Sheng; Sun, Chung-Ming

2013-10-14

A one-pot, two-step synthesis of imidazo[1,2-a]benzimidazoles has been achieved by a three-component reaction of 2-aminobenzimidazoles with an aromatic aldehyde and an isocyanide. The reaction involving condensation of 2-aminobenzimidazole with an aldehyde is run under microwave activation to generate an imine intermediate under basic conditions which then undergoes [4 + 1] cycloaddition with an isocyanide.

Transition-metal-free synthesis of imidazo[2,1-b]thiazoles and thiazolo[3,2-a]benzimidazoles via an S-propargylation/5-exo-dig cyclization/isomerization sequence using propargyl tosylates as substrates.

Science.gov (United States)

Omar, Mohamed A; Frey, Wolfgang; Conrad, Jürgen; Beifuss, Uwe

2014-11-07

A transition-metal-free route for the synthesis of several N-fused heterocycles, including thiazolo[3,2-a]benzimidazoles and imidazo[2,1-b]thiazoles, is reported. The reaction between propargyl tosylates and 2-mercaptobenzimidazoles under basic conditions results in 3-substituted thiazolo[3,2-a]benzimidazoles, in yields up to 92% in a single synthesis step. With 2-mercaptoimidazoles as the substrate, the corresponding imidazo[2,1-b]thiazoles were exclusively obtained. The transformation is considered to proceed as an intermolecular S-propargylation that is followed by 5-exo-dig ring closure and double-bond isomerization.

Synthesis and characterisation of ruthenium(III) complexes with benzimidazole derivatives

International Nuclear Information System (INIS)

Vyas, P.C.; Kaur, N.; Goel, A.K.; Vyas, S.

1995-01-01

Complexes of ruthenium trichloride with biologically important benzimidazole derivatives, viz., 2-(hydroxy methyl) benzimidazole, 2-(l-hydroxy ethyl) benzimidazole, 2-(mercapto methyl) benzimidazole, 2-(l-mercapto ethyl) benzimidazole, and 2,2'-bis-benzimidazole have been synthesized by reacting the above metal chloride and ligands respectively in 1:3 molar ratio. These complexes are characterised on the basis of elemental analysis, molar conductance data, room temperature, magnetic moment values, electronic spectral and IR spectral studies. (author). 17 refs., 2 tabs

Synthesis of substituted 2-(β-D-glucopyranosyl)-benzimidazoles and their evaluation as inhibitors of glycogen phosphorylase.

Science.gov (United States)

Bokor, Éva; Szilágyi, Enikő; Docsa, Tibor; Gergely, Pál; Somsák, László

2013-11-15

Microwave assisted condensation of O-perbenzoylated C-(β-d-glucopyranosyl)formic acid with 1,2-diaminobenzenes in the presence of triphenylphosphite gave the corresponding O-protected 2-(β-d-glucopyranosyl)-benzimidazoles in moderate yields. O-Perbenzoylated C-(β-d-glucopyranosyl)formamide and -thioformamide were transformed into the corresponding ethyl C-(β-d-glucopyranosyl)formimidate and -thioformimidate, respectively, by Et3O·BF4. Treatment of the formimidate with 1,2-diaminobenzenes afforded O-protected 2-(β-d-glucopyranosyl)-benzimidazoles in good to excellent yields. Similar reaction of the thioformimidate gave these compounds in lower yields. The O-benzoyl protecting groups were removed by the Zemplén protocol. These test compounds were assayed against rabbit muscle glycogen phosphorylase (GP) b, the prototype of liver GP, the rate limiting enzyme of glycogen degradation. The best inhibitors were 2-(β-d-glucopyranosyl)-4-methyl-benzimidazole (Ki=2.8μM) and 2-(β-d-glucopyranosyl)-naphtho[2,3-d]imidazole (Ki=2.1μM) exhibiting a ∼3-4 times stronger binding than the unsubstituted parent compound. Copyright © 2013 Elsevier Ltd. All rights reserved.

Synthesis of methyl acetate from dimethyl ether using group VIII metal salts of phosphotungstic acid

Energy Technology Data Exchange (ETDEWEB)

Sardesai, A.; Lee, S.; Tartamella, T.

2002-04-01

Dimethyl ether (DME) can be produced much more efficiently in a single-stage, liquid-phase process from natural gas-based syngas as compared to the conventional process via dehydration of methanol. This process, based on dual catalysts slurried in inert oil, alleviates the chemical equilibrium limitation governing the methanol synthesis reaction and concurrently improves per-pass syngas conversion and reactor productivity. The potential, therefore, for production of methyl acetate via dimethyl ether carbonylation is of industrial importance. In the present study, conversion of dimethyl ether and carbon monoxide to methyl acetate is investigated over a variety of group VIII metal-substituted phosphotungstic acid salts. Experimental results of this catalytic reaction using rhodium, iridium, ruthenium, and palladium catalysts are evaluated and compared in terms of selectivity toward methyl acetate. The effects of active metal, support types, multiple metal loading, and feed conditions on carbonylation activity of DME are examined. Iridium metal substituted phosphotungstic acid supported on Davisil type 643 (pore size 150 A, surface area 279 m{sup 2}/g, mesh size 230-425) silica gel shows the highest activity for DME carbonylation. (author)

Rhodium(III)-catalyzed vinylic sp2 C-H bond functionalization: efficient synthesis of pyrido[1,2-α]benzimidazoles and imidazo[1,2-α]pyridines.

Science.gov (United States)

Dong, Lin; Huang, Ji-Rong; Qu, Chuan-Hua; Zhang, Qian-Ru; Zhang, Wei; Han, Bo; Peng, Cheng

2013-09-28

A simple approach for synthesis of novel aza-fused scaffolds such as pyrido[1,2-α]benzimidazoles and imidazo[1,2-α]pyridines was developed by Rh(III)-catalyzed direct oxidative coupling between alkenes and unactivated alkynes without an extra directing group. The method would allow a broad substrate scope, providing fused heterocycles with potential biological properties.

Preparation, characterization and catalytic application of CoFe2O4 nanoparticles in the synthesis of benzimidazoles

Science.gov (United States)

Borade, Ravikumar M.; Shinde, Pavan R.; Kale, Swati B.; Pawar, Rajendra P.

2018-05-01

A highly efficient magnetically recoverable cobalt ferrite nano-catalyst was prepared by sol-gel autocombustion method using glycine as green fuel. The prepared material has been characterized by X-ray powder diffraction and scanning. An investigation of its catalytic activity showed it to be a heterogeneous Lewis acid catalyst for the synthesis of substituted benzimidazoles. The aqueous ethanol used as green solvent for the reaction. The nm size range of these particles facilitates the catalysis process, as an increased surface area available for the reaction. The easy separation of the catalyst by an external magnet and their recovery and reuse in next cycle reaction are additional benefits.

Crystal structures of eight 3D molecular adducts derived from bis-imidazole, bis(benzimidazole), and organic acids

Science.gov (United States)

Ding, Aihua; Jin, Shouwen; Jin, Shide; Hu, KaiKai; Lin, Zhihao; Liu, Hui; Wang, Daqi

2018-01-01

Cocrystallization of the bis(imidazole)/bis(benzimidazole) with a series of organic acids gave a total of eight molecular adducts with the compositions: (3,6-bis(imidazole-1-yl)pyridazine): (trichloroacetic acid)2(1) [(H2L1)2+ · (tca-)2, L1 = 3,6-bis(imidazole-1-yl)pyridazine, tca- = trichloroacetate], (bis(N-imidazolyl)methane): (suberic acid) (2) [(L2) · (H2suba), L2 = bis(N-imidazolyl)methane, H2suba = suberic acid], bis(N-imidazolyl)methane: (3-nitrophthalic acid): 3H2O (3) [(H2L2)2+ · (3-Hnpa-)2 · 3H2O, 3-Hnpa- = 3-nitro hydrogenphthalate], (bis(N-imidazolyl)butane)0.5: (4-nitrophthalic acid): H2O (4) [(H2L3)0.5+ · (4-Hnpa-)- · H2O, L3 = bis(N-imidazolyl)butane, 4-Hnpa- = 4-nitro hydrogenphthalate], (1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole): (3,5-dinitrosalicylic acid) (5) [(HL4) · (3,5-dns-), L4 = 1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole, 3,5-dns- = 3,5-dinitrosalicylate], (1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole): (3-nitrophthalic acid) (6) [(H2L4) · (3-npa2-), L4 = 1-(3-(1H-benzimidazol-1-yl)propyl)-1H-benzimidazole, 3-npa2-=3-nitrogenphthalate], (bis(N-imidazolyl)butane): (pamoic acid) (7) [(H2L3) · (pam), pam = pamoate], and (3,6-bis(imidazole-1-yl)pyridazine): (1,5-naphthalenedisulfonic acid) [(H2L1)2+ · (npda)2- = 1,5-naphthalenedisulfonate] (8). The eight adducts have been characterized by X-ray diffraction technique, infrared spectrum, and elemental analysis, and the melting points of all adducts were also reported. And their structural and supramolecular aspects are fully analyzed. The result reveals that among the eight investigated crystals both the end ring N in the bis(imidazole) moieties are protonated when the organic acids are deprotonated except 2, and 5, and the crystal packing is interpreted in terms of the strong ionic Nsbnd H⋯O H-bond between the imidazolium and the deprotonated acidic groups. Except the Nsbnd H⋯O H-bond, the Osbnd H⋯O H-bonds were also found at the salts 3, 4

Synthesis and properties of mixed-ligand ruthenium(II) complexes containing 2-(2-pyridyl)-benzimidazole and related ligands

International Nuclear Information System (INIS)

Haga, Masaaki; Tanaka, Toshio.

1979-01-01

Mixed-ligand ruthenium(II) complexes of the [Ru(bpy) 2 L]sup(n+) (ClO 4 )sub(n) type, where bpy= 2,2'-bipyridine; L= 2-(2-pyridyl)-benzimidazole (PBImH) when n= 2, and L= 2-(2-pyridyl)-benzimidazolate (PBIm) and 2-(o-hydroxyphenyl)-benzimidazole (OBImH) when n= 1, were prepared. Anodic peak potentials and ruthenium-to-bipyridine charge transfer bands of these complexes are rationalized in terms of the donor ability of L. (author)

Synthesis and properties of mixed-ligand ruthenium(II) complexes containing 2-(2-pyridyl)-benzimidazole and related ligands

Energy Technology Data Exchange (ETDEWEB)

Haga, M [Mie Univ., Tsu (Japan); Tanaka, T

1979-07-01

Mixed-ligand ruthenium(II) complexes of the (Ru(bpy)/sub 2/L)sup(n+) (ClO/sub 4/)sub(n) type, where bpy= 2,2'-bipyridine; L= 2-(2-pyridyl)-benzimidazole (PBImH) when n= 2, and L= 2-(2-pyridyl)-benzimidazolate (PBIm) and 2-(o-hydroxyphenyl)-benzimidazole (OBImH) when n= 1, were prepared. Anodic peak potentials and ruthenium-to-bipyridine charge transfer bands of these complexes are rationalized in terms of the donor ability of L.

[Lipid synthesis by an acidic acid tolerant Rhodotorula glutinis].

Science.gov (United States)

Lin, Zhangnan; Liu, Hongjuan; Zhang, Jian'an; Wang, Gehua

2016-03-01

Acetic acid, as a main by-product generated in the pretreatment process of lignocellulose hydrolysis, significantly affects cell growth and lipid synthesis of oleaginous microorganisms. Therefore, we studied the tolerance of Rhodotorula glutinis to acetic acid and its lipid synthesis from substrate containing acetic acid. In the mixed sugar medium containing 6 g/L glucose and 44 g/L xylose, and supplemented with acetic acid, the cell growth was not:inhibited when the acetic acid concentration was below 10 g/L. Compared with the control, the biomass, lipid concentration and lipid content of R. glutinis increased 21.5%, 171% and 122% respectively when acetic acid concentration was 10 g/L. Furthermore, R. glutinis could accumulate lipid with acetate as the sole carbon source. Lipid concentration and lipid yield reached 3.20 g/L and 13% respectively with the initial acetic acid concentration of 25 g/L. The lipid composition was analyzed by gas chromatograph. The main composition of lipid produced with acetic acid was palmitic acid, stearic acid, oleic acid, linoleic acid and linolenic acid, including 40.9% saturated fatty acids and 59.1% unsaturated fatty acids. The lipid composition was similar to that of plant oil, indicating that lipid from oleaginous yeast R. glutinis had potential as the feedstock of biodiesel production. These results demonstrated that a certain concentration of acetic acid need not to be removed in the detoxification process when using lignocelluloses hydrolysate to produce microbial lipid by R. glutinis.

Interaction of Benzimidazoles and Benzotriazole: Its Corrosion Protection Properties on Mild Steel in Hydrochloric Acid

Science.gov (United States)

Ramya, K.; Mohan, Revathi; Joseph, Abraham

2014-11-01

Synergistic hydrogen-bonded interaction of alkyl benzimidazoles and 1,2,3-benzotrizole and its corrosion protection properties on mild steel in hydrochloric acid at different temperatures have been studied using polarization, EIS, adsorption, surface studies, and computational methods. The extent of synergistic interaction increases with temperature. Quantum chemical approach is used to calculate some electronic properties of the molecules and to ascertain the synergistic interaction, inhibitive effect, and molecular structures. The corrosion inhibition efficiencies and the global chemical reactivity relate to some parameters, such as total energy, E HOMO, E LUMO, and gap energy (Δ E). 1,2,3-Benzotrizole interacts with benzimidazoles derivatives up to a bond length of approximately 1.99 Å. This interaction represents the formation of a hydrogen bond between the 1,2,3-benzotrizole and benzimidazoles. This synergistic interaction of 1,2,3-benzotrizole and benzimidazole derivatives offers extended inhibition efficiency toward mild steel in hydrochloric acid.

The study of 2-acetylaminotoluene ozonolysis in acetic ACID

OpenAIRE

Галстян, Андрій Генрійович

2014-01-01

The kinetics and mechanism of ozone reaction with 2-aminotoluene and its acylated derivative in acetic acid were studied in order to determine the possibility of obtaining 2-aminobenzoic acid.It is shown that the 2-aminotoluene ozonolysis reaction in acetic acid solution runs at high speed, and preferably on the free electron pair of the amino group to form mainly resinous compounds; oxidation products by the methyl group of the substrate are not formed under these conditions. The ozone attac...

Alternative energy production pathways in Taenia crassiceps cysticerci in vitro exposed to a benzimidazole derivative (RCB20).

Science.gov (United States)

Fraga, Carolina Miguel; Da Costa, Tatiane Luiza; De Castro, Ana Maria; Reynoso-Ducoing, Olivia; Ambrosio, Javier; Hernández-Campos, Alicia; Castillo, Rafael; Vinaud, Marina Clare

2016-04-01

Biochemical studies of benzimidazole derivatives are important to determine their mode of action and activity against parasites. The lack of antihelminthic alternatives to treat parasitic infections and albendazole resistance cases make the search for new antiparasitary drugs of utmost importance. The 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20) is a benzimidazole derivative with promising effect. This study evaluated the effect of different concentrations of RCB20 in the alternative energetic pathway of in vitro Taenia crassiceps cysticerci. The parasites were in vitro exposed to 6.5 and 13 µM of RCB20 and albendazole sulfoxide (ABZSO). The quantification of acetate, acetoacetate, β-hydroxybutyrate, fumarate and propionate was performed by high-performance liquid chromatography. The quantification of urea, creatinine and total proteins was performed by spectrophotometry. The increase in β-hydroxybutyrate reflects the enhancement of the fatty acid oxidation in the treated groups. Volatile fatty acids secretion, acetate and propionate, was increased in the treated groups. The secretion mechanisms of the treated parasites were impaired due to organic acids increased concentrations in the cysticerci. It is possible to conclude that the metabolic effect on alternative energetic pathways is slightly increased in the parasites treated with RCB20 than the ones treated with ABZSO.

Synthesis and chemical characterization of the novel agronomically relevant pentadentate chelate 2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid (DCHA).

Science.gov (United States)

López-Rayo, Sandra; Hernández, Diana; Lucena, Juan J; Escudero, Rosa; Gómez-Gallego, Mar; Sierra, Miguel A

2010-07-14

Iron chelates analogous to o,o-EDDHA/Fe(3+) are the fertilizers chosen to treat iron chlorosis in plants growing on calcareous soil. The isomer o,p-EDDHA/Fe(3+) presents less stability but faster assimilation by the plant than o,o-EDDHA/Fe(3+), because only five coordinating groups are able to complex Fe(3+). The new chelating agent 2-(2-((2-hydroxybenzyl)amino)ethylamino)-2-(2-hydroxyphenyl)acetic acid (DCHA) has been synthesized to obtain an iron fertilizer with intermediate stability between o,o-EDDHA/Fe(3+) and o,p-EDDHA/Fe(3+) and with fast assimilation. Its synthesis has been done starting from phenol, N-acetylethylendiamine, glyoxylic acid, and NaOH in a three-step sequence. The purity of the DCHA chelating agent, its protonation, and Ca(2+), Mg(2+), Fe(3+), and Cu(2+) stability constants, together with its ability to maintain iron in solution in different agronomic conditions, have been determined. The results indicate that the chelate DCHA/Fe(3+) has intermediate stability between those of o,o-EDDHA/Fe(3+) and o,p-EDDHA/Fe(3+) complexes and that it is capable of maintaining the Fe(3+) in agronomic conditions. This new chelating agent may be effective in correcting iron chlorosis in plants.

2-(2-Pyridyl) Benzimidazole Analogs and their beta-Glucuronidase Inhibitory Activity

International Nuclear Information System (INIS)

Kamil, A.; Noureen, S.

2015-01-01

Synthesis of 2-(2-Pyridyl) benzimidazole analogs 1-11 have been carried out and evaluated for in vitro beta-glucuronidase inhibitory potential. The compounds 4 (IC/sub 50/ = 4.06 ± 0.34 meuM), 5 (IC/sub 50/ = 09.63 ± 0.81 meuM), 1 (IC/sub 50/ = 19.66 ± 0.44 meuM), 7 (IC/sub 50/ = 24.75 ± 0.25 meuM), 6 (IC/sub 50/ = 26.30 ± 1.37 meuM), and 3 (IC/sub 50/ = 32.11 ± 0.89 meuM), showed beta-glucuronidase inhibitory activity superior to the standard D-saccharic acid 1,4-lactone, with (IC/sub 50/ = 48.4 ± 1.25 meuM). Based on structure-activity relationship, we discover a new class of potent beta-glucuronidase inhibitors. (author)

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

A novel magnetic core-shell nanocomposite Fe3O4@chitosan@ZnO for the green synthesis of 2-benzimidazoles

Science.gov (United States)

Tian, Fei; Niu, Libo; Chen, Bo; Gao, Xuejia; Lan, Xingwang; Huo, Li; Bai, Guoyi

2017-10-01

A novel magnetic core-shell nanocomposite Fe3O4@Chitosan@ZnO was successfully prepared by in situ chemical precipitation method. It has a clear core-shell structure with magnetic Fe3O4 (about 160 nm in diameter) as core, chitosan as the inner shell, and ZnO as the outer shell, as demonstrated by the transmission electron microscopy and the related elemental mapping. Moreover, this nanocomposite has high magnetization (43.6 emu g-1) so that it can be easily separated from the reaction mixture within 4 s by an external magnetic field. The introduction of the natural chitosan shell, instead of the conventional SiO2 shell, and its combination with the active ZnO ensures this novel nanocomposite green character and good catalytic performance in the synthesis of 2-benzimidazoles with moderate to excellent isolated yields at room temperature. Notably, it can be recycled seven times without appreciable loss of its initial catalytic activity, demonstrating its good stability and making it an attractive candidate for the green synthesis of 2-benzimidazoles. [Figure not available: see fulltext.

Occurrence and metabolism of 7-hydroxy-2-indolinone-3-acetic acid in Zea mays

Science.gov (United States)

Lewer, P.; Bandurski, R. S.

1987-01-01

7-Hydroxy-2-indolinone-3-acetic acid was identified as a catabolite of indole-3-acetic acid in germinating kernels of Zea mays and found to be present in amounts of ca 3.1 nmol/kernel. 7-Hydroxy-2-indolinone-3-acetic acid was shown to be a biosynthetic intermediate between 2-indolinone-3-acetic acid and 7-hydroxy-2-indolinone-3-acetic acid-7'-O-glucoside in both kernels and roots of Zea mays. Further metabolism of 7-hydroxy-2-[5-3H]-indolinone-3-acetic acid-7'-O-glucoside occurred to yield tritiated water plus, as yet, uncharacterized products.

Anchoring of Cu(II) onto surface of porous metal-organic framework through post-synthesis modification for the synthesis of benzimidazoles and benzothiazoles

Science.gov (United States)

Kardanpour, Reihaneh; Tangestaninejad, Shahram; Mirkhani, Valiollah; Moghadam, Majid; Mohammadpoor-Baltork, Iraj; Zadehahmadi, Farnaz

2016-03-01

Efficient synthesis of various benzimidazoles and benzothiazoles under mild conditions catalyzed by Cu(II) anchored onto UiO-66-NH2 metal organic framework is reported. In this manner, first, the aminated UiO-66 was modified with thiophene-2-carbaldehyde and then the prepared Schiff base was reacted with CuCl2. The prepared catalyst was characterized by FT-IR, UV-vis, X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), N2 adsorption, inductively coupled plasma atomic emission spectroscopy (ICP-AES) and field emission scanning electron microscopy (FE-SEM). The UiO-66-NH2-TC-Cu was applied as a highly efficient catalyst for synthesis of benzimidazole and benzothiazole derivatives by the reaction of aldehydes with 1,2-diaminobenzene or 2-aminothiophenol. The Cu(II)-containing MOF was reused several times without any appreciable loss of its efficiency.

ACETIC ACID AND A BUFFER

DEFF Research Database (Denmark)

2009-01-01

The present invention relates to a composition comprising : a) 0.01-20% wt/wt acetic acid and b) a physiologically tolerable buffer capable of maintaining acetic acid at a pH in the range of 2-7; and use of such a composition as an antimicrobial agent.......The present invention relates to a composition comprising : a) 0.01-20% wt/wt acetic acid and b) a physiologically tolerable buffer capable of maintaining acetic acid at a pH in the range of 2-7; and use of such a composition as an antimicrobial agent....

Synthesis and evaluation of (S)-4-(3-(2'-[C-11]isopropylamino)-2-hydroxy-propoxy)-2H-benzimidazol-2-one ((S)-[C-11]CGP 12388) and (S)-4-(3-((1'-[F-18]-fluoroisopropyl)amino)-2-hydroxypropoxy)-2H-benzimidazol-2-one ((S)-[F-18]Fluoro-CGP 12388) for visualization of beta-adrenoceptors with positron emission tomography

NARCIS (Netherlands)

Elsinga, PH; vanWaarde, A; Jaeggi, KA; Schreiber, G; Heldoorn, M; Vaalburg, W

1997-01-01

The beta-adrenoceptor antagonist (S)-[C-11]CGP 12177 (4-(3-(tert-butylamino)-2-hydroxypropoxy)- 2H-benzimidazol-2[C-11]-one) is a generally accepted radioligand for cardiac and pulmonary PET studies. The synthesis of [C-11]CGP 12177 is a laborious and often troublesome procedure. Therefore, (S)-C GP

ANTIBACTERIAL ACTIVITY OF BENZIMIDAZOLES 2-THIO, 2-AMINODERIVATIVES AND COMPLEXES OF BENZIMIDAZOLES WITH TRANSITIONAL METALS

Directory of Open Access Journals (Sweden)

E. I. Mayboroda

2014-01-01

Full Text Available The literature data about antibacterial properties of benzimidazole 2-thio-, 2-aminoderivatives and benzimidazole complexes have been generalized and systematized in the review. Today prevention and treatment of diseases caused by microorganisms is an actual problem of modern therapy. Therefore, the search for active molecules, the based on them development of some new, more effective antimicrobial agents is an important task of modern pharmaceutical chemistry. Promising compounds for solving these problems are benzimidazole derivatives. They are available, functionally capable, stable and have a wide spectrum of biological activities (antiviral, anthelmintic, antibacterial, anticancer, antidiabetic.The purpose of this paper is to generalize and systematize information about the antimicrobial action of 2-thio-, 2-amino-substituted benzimidazoles and benzimidazole derivatives complexes with transition metals.These compounds and their complexes with transition metals are active against pathogenic strains Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhimurium, Proteus vulgaris, Bacillus cereus, Micrococcus luteus, Helicobacter рylori and others.

Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines.

Science.gov (United States)

Tran, Lam Quang; Li, Jihui; Neuville, Luc

2015-06-19

A copper-promoted three-component synthesis of 2-aminobenzimidazoles (1) or of 2-aminoquinazolines (2) involving cyanamides, arylboronic acids, and amines has been developed. The operationally simple oxidative process, performed in the presence of K2CO3, a catalytic amount of CuCl2·2H2O, 2,2'-bipyridine, and an O2 atmosphere (1 atm), allows the rapid assembly of either benzimidazoles or quinazolines starting from aryl- or benzyl-substituted cyanamides, respectively. In this process, the copper promotes the formation of three bonds, two C-N bonds, and an additional bond resulting from C-H functionalization event.

Novel synthesis of biologically active indolo [3,2-C] isoquinoline derivatives

Directory of Open Access Journals (Sweden)

Prabhuodeyara M. Veeresha Sharma

2017-07-01

Full Text Available Indole-2-carboxylates are refluxed with hydrazine hydrate to form 5-substituted-3-phenylindole-2-carboxyhydrazides. These are again converted to corresponding indole-2-carboxyazides. Azides are further converted into carbamates and finally these carbamates are cyclized to form the respective substituted 6H, 11H-indolo [3,2-C] isoquinolin-2-ones (1a–c. These (1a–c were reacted with phosphorus pentasulfide in refluxing pyridine to yield the respective thiones (2a–c. These thiones (2a–c on reaction with chloroacetic acid and sodium acetate in acetic acid under refluxing temperature for 5 h yielded isoquinoline-thioacetic acids (3a–c. Compounds (3a–c on reaction with orthopheneylene diamine dihydrochloride in ethylene glycol at refluxing temperature yielded substituted indolo [3,2-C] isoquinolin-2′-yl sulfanyl methylene benzimidazoles (4a–c.

Synthesis of Benzimidazole Derivatives: As Anti-hypertensive Agents

Directory of Open Access Journals (Sweden)

Jat Rakesh Kumar

2006-01-01

Full Text Available A new series of non peptide angiotensin(A-II receptor antagonist has been prepared. This N-(biphenyl methyl imidazoles e.g. 5-substituted (amino -2- phenyl-1-(2ʼcarboxy biphenyl-4-yl benzimidazoles differ from the previously reported and related compounds in that they produce a potent hypertensive effect upon oral administration. The earlier series were generally active only when administered intravenously. It has been found that 2’-position of biphenyl is essential. Only ortho substituted acid possess both high affinity for the AII receptor and oral anti-hypertensive potency.

Isolation of a high malic and low acetic acid-producing sake yeast Saccharomyces cerevisiae strain screened from respiratory inhibitor 2,4-dinitrophenol (DNP)-resistant strains.

Science.gov (United States)

Kosugi, Shingo; Kiyoshi, Keiji; Oba, Takahiro; Kusumoto, Kenichi; Kadokura, Toshimori; Nakazato, Atsumi; Nakayama, Shunichi

2014-01-01

We isolated 2,4-dinitrophenol (DNP)-resistant sake yeast strains by UV mutagenesis. Among the DNP-resistant mutants, we focused on strains exhibiting high malic acid and low acetic acid production. The improved organic acid composition is unlikely to be under the control of enzyme activities related to malic and acetic acid synthesis pathways. Instead, low mitochondrial activity was observed in DNP-resistant mutants, indicating that the excess pyruvic acid generated during glycolysis is not metabolized in the mitochondria but converted to malic acid in the cytosol. In addition, the NADH/NAD(+) ratio of the DNP-resistant strains was higher than that of the parental strain K901. These results suggest that the increased NADH/NAD(+) ratio together with the low mitochondrial activity alter the organic acid composition because malic acid synthesis requires NADH, while acetic acid uses NAD(+). Copyright © 2013 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Benzimidazole and imidazole hexachlorocerates

Energy Technology Data Exchange (ETDEWEB)

Bayanov, A P; Burylev, B P; Temerdashev, Z A; Gusev, V I [Kubanskij Gosudarstvennyj Univ., Krasnodar (USSR)

1983-02-01

The process of hexachlorocerium acid with benzimidazole and imidazole interaction and the reaction products are investigated. The values of thermodynamic characteristics of the hexachlorocerium acid reaction with benzimidazole are equal: ..delta..Gsub(298K)=-16.5+-0.2 kJ/mol, ..delta..Hsub(298K)=-63.6+-0.8 kJ/mol, ..delta..Ssub(298K)=-157+-5 J/mol degrees. By the IR spectroscopy and radiography method the individuality of separated compounds has been found. The thermal stability of compounds is determined. The temperature dependence of splitting off chlorine atom from benzimidazole hexachlorocerate on pressure is investigated. Thermodynamic characteristics and activation energies of the process are calculated.

Benzimidazole and imidazole hexachlorocerates

International Nuclear Information System (INIS)

Bayanov, A.P.; Burylev, B.P.; Temerdashev, Z.A.; Gusev, V.I.

1983-01-01

The process of hexachlorocerium acid with benzimidazole and imidazole interaction and the reaction products are investigated. The values of thermodynamic characteristics of the hexachlorocerium acid reaction with benzimidazole are equal: ΔGsub(298K)=-16.5+-0.2 kJ/mol, ΔHsub(298K)=-63.6+-0.8 kJ/mol, ΔSsub(298K)=-157+-5 J/mol degrees. By the IR spectroscopy and radiography method the individuality of separated compounds has been found. The thermal stability of compounds is determined. The temperature de-- pendence of splitting off chlorine atom from benzimidazole hexachlorocerate on pressure is investigated. Thermodynamic characteristics and activation energies of the process are calculated

Synthesis and Characterization of Nanostructured Nickel Diselenide NiSe2 from the Decomposition of Nickel Acetate, (CH3CO2)2Ni

OpenAIRE

Yin, Ming; O’Brien, Stephen

2014-01-01

Solution processed NiSe2 nanorods were synthesized by a modified colloidal synthesis technique, by chemical reaction of TOPSe and nickel acetate at 150°C. The rods exist as an oleic acid ligand stabilized solution, with oleic acid acting as a capping group. Structural characterization by X-ray diffraction and transmission electron microscopy indicates that the particles are rod-like shaped crystals with a high and relatively constant aspect ratio (30 : 1). TEM shows that the width and the len...

Synthesis and properties of poly(aryl sulfone benzimidazole) and its copolymers for high temperature membrane electrolytes for fuel cells

DEFF Research Database (Denmark)

Yang, Jingshuai; Li, Qingfeng; Cleemann, Lars Nilausen

2012-01-01

Poly(aryl sulfone benzimidazole) (SO2PBI) and its copolymers with poly[2,2′-p-(phenylene)-5,5′-bibenzimidazole] (pPBI), termed as Co-SO2PBI, were synthesized with varied feeding ratios of 4,4′-sulfonyldibenzoic acid (SDBA) to terephthalic acid (TPA). Incorporation of the stiff para-phenylene and ......Poly(aryl sulfone benzimidazole) (SO2PBI) and its copolymers with poly[2,2′-p-(phenylene)-5,5′-bibenzimidazole] (pPBI), termed as Co-SO2PBI, were synthesized with varied feeding ratios of 4,4′-sulfonyldibenzoic acid (SDBA) to terephthalic acid (TPA). Incorporation of the stiff para...

Synthesis of 2-(6-Acetamidobenzothiazolethioacetic Acid Esters as Photosynthesis Inhibitors

Directory of Open Access Journals (Sweden)

Dusan Loos

1998-04-01

Full Text Available The synthesis and photosynthesis-inhibiting activity of 13 new 2-(6-acetamidobenzothiazolethioacetic acid esters are reported. The new compounds were prepared by acetylation of 2-(alkoxycarbonylmethylthio-6-aminobenzothiazoles with acetic anhydride. The structure of the compounds was verified by 1H NMR spectra. The compounds inhibit photosynthetic electron transfer in spinach chloroplasts. The structure - activity relation was studied. Lipophilicity was found to influence substantially photosynthetic electron transfer.

21 CFR 184.1005 - Acetic acid.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Acetic acid. 184.1005 Section 184.1005 Food and... Substances Affirmed as GRAS § 184.1005 Acetic acid. (a) Acetic acid (C2H4O2, CAS Reg. No. 64-19-7) is known as ethanoic acid. It occurs naturally in plant and animal tissues. It is produced by fermentation of...

Preparation of mesoporous MnO2/C catalyst for n-hexyl acetate synthesis

International Nuclear Information System (INIS)

Yang Zeheng; Pan Yanmei; Mei Zhousheng; Zhang Weixin

2012-01-01

A mesoporous MnO 2 /C composite was prepared by impregnating self-made porous carbon spheres with manganese nitrate aqueous solution and subsequently reacting with KMnO 4 aqueous solution. It was characterized with X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), the Brunauer-Emmett-Teller (BET) surface area and the Barrett-Joyner-Halenda (BJH) pore size distribution. The as-prepared mesoporous MnO 2 /C composite was used as catalyst for the synthesis of n-hexyl acetate, and the effects of MnO 2 loading and esterification reaction parameters on the esterification rate were investigated. The results prove that MnO 2 loading has a significant effect on the catalytic activity and that the mesoporous MnO 2 /C composite exhibits high catalytic activity with an esterification rate of 96.42% under the conditions below: MnO 2 loading (73.09 wt%), catalyst dosage (0.1% in total weight), acetic acid/n-hexanol molar ratio (2:1), reaction temperature (130 °C) and reaction time (5 h).

Comparison of Conventional and Microwave-assisted Synthesis of Benzimidazole Derivative from Citronellal in Kaffir lime oil (Citrus hystrix DC.)

Science.gov (United States)

Warsito, W.; Noorhamdani, A. S.; Suratmo; Dwi Sapri, R.; Alkaroma, D.; Azhar, A. Z.

2018-04-01

Simple method has been used for the synthesis of benzimidazole derivative from citronellal in kaffir lime oil under microwave irradiation. These compounds were synthesized also by conventional heating for comparison. In addtion, microwave-assited synthesis was also compared between using to dichloromethane and methanol solvents with variation of reaction time for 30 to 70 minutes and 4 to 12 h for conventional heating. The 2-citronellyl benzimidazole compound synthesized were characterised by FT-IR, GC-MS, 1H and 13C NMR spectroscopy. Comparison between conventional and microwave-assisted synthesis was done by comparing between correlation of reaction time and percentage yield. The time optimum of microwave-assisted and conventional synthesis using dichloromethane solvent respectively at 60 minutes (yield 19.23%) and 8 hours (yield 11.54%). In addition, microwave-assited synthesis increasing 157.81 times compared by conventional heating. While using methanol solvent tends to increase linearly however the percentage of yield only 0.77 times of synthesis using dichloromethane solvent.

Polymer/organosilica nanocomposites based on polyimide with benzimidazole linkages and reactive organoclay containing isoleucine amino acid: Synthesis, characterization and morphology properties

International Nuclear Information System (INIS)

Mallakpour, Shadpour; Dinari, Mohammad

2012-01-01

Highlights: ► A reactive organoclay was formed using L-isoleucine amino acid as a swelling agent. ► Polyimide was synthesized from benzimidazole diamine and pyromellitic dianhydride. ► Imide and benzimidazole groups assured the thermal stability of the nanocomposites. ► Nanocomposite films were prepared by an in situ polymerization reaction. ► The TEM micrographs of nanocomposites revealed well-exfoliated structures. -- Abstract: Polyimide–silica nanocomposites are attractive hybrid architectures that possess excellent mechanical, thermal and chemical properties. But, the dispersion of inorganic domains in the polymer matrix and the compatibility between the organic and inorganic phases are critical factors in these hybrid systems. In this investigation, a reactive organoclay was prepared via ion exchange reaction between protonated form of difunctional L-isoleucine amino acid as a swelling agent and Cloisite Na + montmorillonite. Amine functional groups of this swelling agent formed an ionic bond with the negatively charged silicates, whereas the remaining acid functional groups were available for further interaction with polymer chains. Then organo-soluble polyimide (PI) have been successfully synthesized from the reaction of 2-(3,5-diaminophenyl)-benzimidazole and pyromellitic dianhydride in N,N-dimethylacetamide. Finally, PI/organoclay nanocomposite films enclosing 1%, 3%, 5%, 7% and 10% of synthesized organoclay were successfully prepared by an in situ polymerization reaction through thermal imidization. The synthesized hybrid materials were subsequently characterized by Fourier transform infrared spectroscopy, X-ray diffraction, electron microscopy, and thermogravimetric analysis techniques. The PI/organoclay nanocomposite films have good optical transparencies and the mechanical properties were substantially improved by the incorporation of the reactive organoclay.

The synthesis of benzimidazoles and quinoxalines from aromatic diamines and alcohols by iridium-catalyzed acceptorless dehydrogenative alkylation.

Science.gov (United States)

Hille, Toni; Irrgang, Torsten; Kempe, Rhett

2014-05-05

Benzimidazoles and quinoxalines are important N-heteroaromatics with many applications in pharmaceutical and chemical industry. Here, the synthesis of both classes of compounds starting from aromatic diamines and alcohols (benzimidazoles) or diols (quinoxalines) is reported. The reactions proceed through acceptorless dehydrogenative condensation steps. Water and two equivalents of hydrogen are liberated in the course of the reactions. An Ir complex stabilized by the tridentate P^N^P ligand N(2) ,N(6) -bis(di-isopropylphosphino)pyridine-2,6-diamine revealed the highest catalytic activity for both reactions. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Changes in isoprenoid lipid synthesis by gemfibrozil and clofibric acid in rat hepatocytes.

Science.gov (United States)

Hashimoto, F; Taira, S; Hayashi, H

2000-05-15

We studied whether gemfibrozil and clofibric acid alter isoprenoid lipid synthesis in rat hepatocytes. After incubation of the cells with the agent for 74 hr, [(14)C]acetate or [(3)H]mevalonate was added, and the cells were further incubated for 4 hr. Gemfibrozil and clofibric acid increased ubiquinone synthesis from [(14)C]acetate and [(3)H]mevalonate. The effect of gemfibrozil was greater than that of clofibric acid. Also, gemfibrozil decreased dolichol synthesis from [(14)C]acetate and [(3)H]mevalonate. However, clofibric acid increased dolichol synthesis from [(3)H]mevalonate. Gemfibrozil decreased cholesterol synthesis from [(14)C]acetate and [(3)H]mevalonate. Clofibric acid decreased cholesterol synthesis from [(14)C]acetate, but did not affect synthesis from [(3)H]mevalonate. These results suggest that both agents, at different rates, activate the synthetic pathway of ubiquinone, at least from mevalonate. Gemfibrozil may inhibit the synthetic pathway of dolichol, at least from mevalonate. Contrary to gemfibrozil, clofibric acid may activate the synthetic pathway of dolichol from mevalonate. Gemfibrozil may inhibit the synthetic pathway of cholesterol from mevalonate in addition to the pathway from acetate to mevalonate inhibited by both agents.

1-11C-acetate as a PET radiopharmaceutical for imaging fatty acid synthase expression in prostate cancer.

Science.gov (United States)

Vāvere, Amy L; Kridel, Steven J; Wheeler, Frances B; Lewis, Jason S

2008-02-01

Although it is accepted that the metabolic fate of 1-(11)C-acetate is different in tumors than in myocardial tissue because of different clearance patterns, the exact pathway has not been fully elucidated. For decades, fatty acid synthesis has been quantified in vitro by the incubation of cells with (14)C-acetate. Fatty acid synthase (FAS) has been found to be overexpressed in prostate carcinomas, as well as other cancers, and it is possible that imaging with 1-(11)C-acetate could be a marker for its expression. In vitro and in vivo uptake experiments in prostate tumor models with 1-(11)C-acetate were performed both with and without blocking of fatty acid synthesis with either C75, an inhibitor of FAS, or 5-(tetradecyloxy)-2-furoic acid (TOFA), an inhibitor of acetyl-CoA carboxylase (ACC). FAS levels were measured by Western blot and immunohistochemical techniques for comparison. In vitro studies in 3 different prostate tumor models (PC-3, LNCaP, and 22Rv1) demonstrated blocking of 1-(11)C-acetate accumulation after treatment with both C75 and TOFA. This was further shown in vivo in PC-3 and LNCaP tumor-bearing mice after a single treatment with C75. A positive correlation between 1-(11)C-acetate uptake into the solid tumors and FAS expression levels was found. Extensive involvement of the fatty acid synthesis pathway in 1-(11)C-acetate uptake in prostate tumors was confirmed, leading to a possible marker for FAS expression in vivo by noninvasive PET.

Cyclic Acetalization of Furfural on Porous Aluminosilicate Acid Catalysts

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Hartati Hartati

2016-12-01

Full Text Available Porous aluminosilicate materials included microporous and mesoporous ZSM-5, hierarchical aluminosilicates, and mesoporous aluminosilicate were tested for acetalization of furfural (furan-2-carbaldehyde with propylene glycol. The existing synthesis methods for aluminosilicate and ZSM-5 were modified to produce aluminosilicate material with hierarchical porous structure. Catalytic activity in acetalization of furfural by propylene glycol were conducted by refluxed of the mixture of furfural, propylene glycol and catalyst, using toluene as solvent and nitrobenzene as internal standard, at 106 °C for 4 h. The result showed that a combination of two structure directing agents, tetrapropylammonium hydroxide (TPAOH and cetyltrimethylammonium bromide (CTAB and modification of catalytic crystallization produced an active aluminosilicate framework that provides a wide access for a bulky reactants and strong acid sites to catalyze the reaction. The pore structure and the strength of the Brønsted acid sites were crucial for the high conversion of furfural to produce a cyclic acetal.

Copper-doped silica cuprous sulfate: A highly efficient heterogeneous nano-catalyst for one-pot three-component synthesis of 1-H-2-substituted benzimidazoles from 2-bromoanilines, aldehydes, and [bmim]N3

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Somayeh Behrouz

2018-03-01

Full Text Available A facile and highly efficient one-pot three-component synthesis of 1-H-2-substituted benzimidazole derivatives from readily available substrates catalyzed by copper-doped silica cuprous sulfate (CDSCS is described. In this method, treatment of diverse 2-bromoanilines, aldehydes, and [bmim]N3 in DMF at 110 °C in the presence of CDSCS as a highly efficient heterogeneous nano-catalyst affords the corresponding 1-H-2-substituted benzimidazoles in good to excellent yields. The CDSCS is an inexpensive and stable nano-catalyst that could be simply prepared, recovered and reused for many consecutive reaction runs without significant loss of its activity.

Overview on mechanisms of acetic acid resistance in acetic acid bacteria.

Science.gov (United States)

Wang, Bin; Shao, Yanchun; Chen, Fusheng

2015-02-01

Acetic acid bacteria (AAB) are a group of gram-negative or gram-variable bacteria which possess an obligate aerobic property with oxygen as the terminal electron acceptor, meanwhile transform ethanol and sugar to corresponding aldehydes, ketones and organic acids. Since the first genus Acetobacter of AAB was established in 1898, 16 AAB genera have been recorded so far. As the main producer of a world-wide condiment, vinegar, AAB have evolved an elegant adaptive system that enables them to survive and produce a high concentration of acetic acid. Some researches and reviews focused on mechanisms of acid resistance in enteric bacteria and made the mechanisms thoroughly understood, while a few investigations did in AAB. As the related technologies with proteome, transcriptome and genome were rapidly developed and applied to AAB research, some plausible mechanisms conferring acetic acid resistance in some AAB strains have been published. In this review, the related mechanisms of AAB against acetic acid with acetic acid assimilation, transportation systems, cell morphology and membrane compositions, adaptation response, and fermentation conditions will be described. Finally, a framework for future research for anti-acid AAB will be provided.

Features of fatty acid synthesis in higher plants

Energy Technology Data Exchange (ETDEWEB)

Yamada, M [Tokyo Univ. (Japan). Coll. of General Education; Nakamura, Y

1975-07-01

In the biosynthesis of fatty acid in the presence of /sup 3/H/sub 2/O, /sup 3/H is incorporated into the hydrocarbon chain of the fatty acid. The features in the fatty acid synthesis of higher plants were investigated by applying /sup 3/H/sub 2/O method to the measurement of the ability of spinach leaves synthesizing fatty acid. Sucrose, acetate, pyruvate, PGA, PEP, OAA, citrate, etc. were employed as the substrates of fatty acid synthesis to trace the process of synthesis of each fatty acid. The demand of various cofactors related to the ability of spinach chloroplast fatty acid synthesizing was also examined. Light dependence of the fatty acid synthesis of chloroplast as well as the influences of N,N'-dicyclohexyl carbodiimide, carbonylcyanide-4-trifluoromethoxy phenyl hydrazone and NH/sub 4/Cl were discussed. The results were compared with the reports on the fatty acid synthesis of avocado pear, castor bean, etc.

Solvent/oxidant-switchable synthesis of multisubstituted quinazolines and benzimidazoles via metal-free selective oxidative annulation of arylamidines.

Science.gov (United States)

Lin, Jian-Ping; Zhang, Feng-Hua; Long, Ya-Qiu

2014-06-06

A fast and simple divergent synthesis of multisubstituted quinazolines and benzimidazoles was developed from readily available amidines, via iodine(III)-promoted oxidative C(sp(3))-C(sp(2)) and C(sp(2))-N bond formation in nonpolar and polar solvents, respectively. Further selective synthesis of quinazolines in polar solvent was realized by TEMPO-catalyzed sp(3)C-H/sp(2)C-H direct coupling of the amidine with K2S2O8 as the oxidant. No metal, base, or other additives were needed.

Synthesis of amino ester-embedded benzimidazoles: a one-pot sequential protocol under metal-free neutral conditions.

Science.gov (United States)

Roy, Priyabrata; Bodhak, Chandan; Pramanik, Animesh

2017-02-01

A one-pot three-component protocol has been developed for the synthesis of amino ester-embedded benzimidazoles under metal-free neutral conditions. Sequentially, the methodology involves coupling of an amino ester with 1-fluoro-2-nitrobenzene, reduction of the coupled nitroarene by sodium dithionite, and cyclization of the corresponding diamine with an aldehyde.

Synthesis and investigation of the physicochemical properties of 2-(5-((theophylline-7'-ylmethyl-4-phenyl-4H-1,2,4-triazole-3-ylthio-acetic acid salts

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A. S. Gotsulya

2014-02-01

Full Text Available Introduction. In last decades considerable interest to the search of biologically active compounds in series of azole derivatives is indicated. This is mainly connected with the successful use of several drugs with heterocyclic system in the structure. Analysis of the pharmacological properties of heterocyclic nitrogen–containing compounds of the known groups let us to suggest, that the triazole substituent is an important pharmacophore fragment, responsible for the availability of diverse physiological activity. In addition, it causes a little toxicity. Considerable attention belongs to synthesis and research of the biological activity of 1,2,4-triazoles derivatives. The great importance also has research of the influence of heterocyclic fragments of different nature in combination in one molecule on the activity of the synthesized compounds. Like different synthons in the structure of 1,2,4-triazoles in various kinds of biological activity of the reaction products with an aim of new and highly efficient low-toxicity compounds reception. The aim of work was to study synthesis and properties of substances among salts of 2-(5-((theophylline-7'-ylmethyle-4-phenyle-4Н-1,2,4-triazole-3-ylthioacetate acid. Materials and methods of the research. In the process as a starting material for reception of new series of compounds theophylline has been chosen. It is important to note, that by the diversity and strength of pharmacological effects, which appears, this structure takes its rightful place among heterocyclic compounds. Through the series of the successive stages 4-phenyle-5-(1',3'-dimethylxantine-7'-ylmethyle-1,2,4-triazole-3-thiol was obtained from the theophylline. Research of the physico-chemical properties of the received compounds conducted according to methods, described in the State Pharmacopoeia of Ukraine. open capillary method, elemental analysis (Elementar Vario L cube (CHNS. 1H NMR spectra of compounds were recorded with a

Recyclization reactions leading to benzimidazoles

Science.gov (United States)

Mamedov, Vakhid A.; Murtazina, Anna M.

2011-05-01

The published data on the recyclization reactions that afford benzimidazoles are generalized and systematized. Both classical and new methods of benzimidazole synthesis are considered. Attention is focused on the publications over the recent 10-15 years; of the earlier publications, only those unknown to the wide circle of chemists are analyzed.

Recyclization reactions leading to benzimidazoles

International Nuclear Information System (INIS)

Mamedov, Vakhid A; Murtazina, Anna M

2011-01-01

The published data on the recyclization reactions that afford benzimidazoles are generalized and systematized. Both classical and new methods of benzimidazole synthesis are considered. Attention is focused on the publications over the recent 10-15 years; of the earlier publications, only those unknown to the wide circle of chemists are analyzed.

Synthesis of a novel series of 4-arylpiperazinyl derivatives linked to a 2-(pyridin-3-yl)-1H-benzimidazole as new Delavirdine analogues

International Nuclear Information System (INIS)

Pessoa-Mahana, David; Nunez, Andres; Espinosa, Christian; Mella-Raipn, Jaime; Pessoa-Mahana, Hernan

2010-01-01

The synthesis of a series of substituted arylpiperazines linked to a 2-(pyridin-3-yl)-1H-benzo[d]imidazole scaffold through an alkylic linker is reported. The novel 1-(2-(4-arylpiperazin-1-yl)alkyl)-2-(pyridin-3-yl)-1H-benzimidazole derivatives are structurally related to the anti-HIV-1 drug Delavirdine and belong to the bis(heteroaryl)piperazines family (BHAPs), a well known HIV-1 reverse transcriptase inhibitors group. (author)

Data on the effects of imidazo[1,2-a]benzimidazole and pyrimido[1,2-a]benzimidazole compounds on intraocular pressure of ocular normotensive rats

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Adrian Julian Marcus

2018-06-01

Full Text Available This data is to document the intraocular pressure (IOP lowering activity of imidazo[1,2-a]benzimidazole and pyrimido[1,2-a]benzimidazole compounds in ocular normotensive rats. Effects of single drop application of imidazo[1,2-a]benzimidazole and pyrimido[1,2-a]benzimidazole compounds on IOP in ocular normotensive rats are presented at 3 different concentrations (0.1%, 0.2% and 0.4%. Time course of changes in IOP is presented over 6 h period post-instillation. The IOP lowering activities of test compounds were determined by assessing maximum decrease in IOP from baseline and corresponding control, duration of IOP lowering and area under curve (AUC of time versus response curve. Data shown here may serve as benchmarks for other researchers studying IOP-lowering effect of imidazo[1,2-a]benzimidazole and pyrimido[1,2-a]benzimidazole compounds and would be useful in determining therapeutic potential of these test compounds as IOP lowering agents. Keywords: Drug screening, Intraocular pressure, Intraocular pressure lowering activity, Imidazo[1,2-a]benzimidazoles, Pyrimido[1,2-a]benzimidazoles, Ocular normotensive rats, Rebound tonometry

Chelating agents related to ethylenediamine bis(2-hydroxyphenyl)acetic acid (EDDHA): synthesis, characterization, and equilibrium studies of the free ligands and their Mg2+, Ca2+, Cu2+, and Fe3+ chelates.

Science.gov (United States)

Yunta, Felipe; García-Marco, Sonia; Lucena, Juan J; Gómez-Gallego, Mar; Alcázar, Roberto; Sierra, Miguel A

2003-08-25

Iron chelates such as ethylenediamine-N,N'-bis(2-hydroxyphenyl)acetic acid (EDDHA) and their analogues are the most efficient soil fertilizers to treat iron chlorosis in plants growing in calcareous soils. EDDHA, EDDH4MA (ethylenediamine-N,N'-bis(2-hydroxy-4-methylphenyl)acetic acid), and EDDCHA (ethylenediamine-N,N'-bis(2-hydroxy-5-carboxyphenyl)acetic acid) are allowed by the European directive, but also EDDHSA (ethylenediamine-N,N'-bis(2-hydroxy-5-sulfonylphenyl)acetic acid) and EDDH5MA (ethylenediamine-N,N'-bis(2-hydroxy-5-methylphenyl)acetic acid) are present in several commercial iron chelates. In this study, these chelating agents as well as p,p-EDDHA (ethylenediamine-N,N'-bis(4-hydroxyphenyl)acetic acid) and EDDMtxA (ethylenediamine-N,N'-bis(2-metoxyphenyl)acetic acid) have been obtained following a new synthetic pathway. Their chemical behavior has been studied to predict the effect of the substituents in the benzene ring on their efficacy as iron fertilizers for soils above pH 7. The purity of the chelating agents has been determined using a novel methodology through spectrophotometric titration at 480 nm with Fe(3+) as titrant to evaluate the inorganic impurities. The protonation constants were determined by both spectrophotometric and potentiometric methods, and Ca(2+) and Mg(2+) stability constants were determined from potentiometric titrations. To establish the Fe(3+) and Cu(2+) stability constants, a new spectrophotometric method has been developed, and the results were compared with those reported in the literature for EDDHA and EDDHMA and their meso- and rac-isomers. pM values have been also determined to provide a comparable basis to establish the relative chelating ability of these ligands. The purity obtained for the ligands is higher than 87% in all cases and is comparable with that obtained by (1)H NMR. No significant differences have been found among ligands when their protonation and stability constants were compared. As expected, no Fe(3

Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives

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E. K. Mikhalchenko

2017-04-01

Full Text Available Introduction. Heterocyclic compounds play an important role in the metabolic processes of human organism. Structures of vitamins, nucleotides, chromoproteins are based on Nitrogen-containing heterocycles (purine, pyrimidine, thiazole etc. Thus, it was obvious to use these organic substances as basic molecules for synthetic research of biologically active compounds which could be used for treatment of different pathological processes. In their research, some scientist pay special attention to xanthine derivatives that are well-known low toxic natural compounds with wide spectrum of pronounced pharmacological properties (antioxidant, diuretic, antibacterial, anti-inflammatory etc. Insertion of carboxyl group in the structure of xanthine molecule is a prospective ability of its synthetic potential increasing. Aim of our research was the development of method of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives synthesis and studying their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M. 1Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian», USA solvent – (DMSO-d6, internal standard – ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Results and discussion. We selected 3-benzyl-8-propyl xanthine as initial compound for our study. By its interaction with chloroacetic acid, chloroacetamide or propyl chloroacetate in DMF in the presence of calculated amount of NaHCO3 we synthesized 3-benzyl-8-propylxanthinyl-7-acetic acid its ester and amide. At the same time we found that obtaining of xanthinyl-7-acetic acid by hydrolysis of its ester produced with higher yield. On the next stage of our research we synthesized a number of water-soluble salts of 3-benzyl-8-propylxanthinyl-7-acetic acid by reaction of acid with different primary and secondary amines. The structures of all obtained compounds were

Efficient FeCl3/SiO2 as heterogeneous nanocatalysis for the synthesis of benzimidazoles under mild conditions

Science.gov (United States)

Taher, Mohammad Ali; Karami, Changiz; Arabi, Mehdi Sheikh; Ahmadian, Hossein; Karami, Yasaman

2016-11-01

Iron(III) supported on nano silica as a new catalyst has been synthesized. Structural properties of this complex have been studied by TEM, SEM and EDX. The average crystalline size of Iron(III) supported on nano silica is 30-50 nm. Catalytic activity of this catalyst has been investigated by synthesis of benzimidazoles from 1, 2-diaminobenzene and aromatic aldehydes, and also the other variables investigated such as the amount of catalyst, reaction temperature and the effect of various solvents are also studied. The present procedure offers several advantages such as short reaction time, simple workup, recovery and reusability of the catalyst.

Effect of Whole-Body X-Irradiation of the Synthesis of Individual Fatty Acids in Liver Slices from Normal and Fasted Rats

DEFF Research Database (Denmark)

Hansen, Heinz Johs. Max; Hansen, Lisbeth Grænge; Faber, M.

1965-01-01

(1) Using (2-14C) acetate and (1-14C) butyrate as precursors, rat-liver fatty acids were synthesized in vitro and assayed by paper chromatography. (2) Whole-body x-irradiation induced a change in the synthetic pattern of hepatic fatty acids towards a relatively enhanced synthesis of palmitic acid....... (3) X-irradiation and fasting seem to have opposite effects on fatty-acid synthesis. X-irradiation counteracts the drop in total synthesis and the relatively enhanced synthesis of palmitoleic acid induced by fasting. The relative enhancement of palmitic-acid synthesis mentioned under (2) stands...... in contrast to the effect of fasting, which specifically decreases the hepatic synthesis of palmitic acid. (4) There is a general similarity between corresponding fatty-acid patterns based on synthesis from (2-14C) acetate and (1-14C) butyrate, respectively....

Microwave-assisted Synthesis of Benzimidazole Derivatives from Citronellal in Kaffir Lime (Citrus hystrix DC.) Oil

Science.gov (United States)

Sapri Ramadhan, Dwi; Warsito; Dhiaul Iftitah, Elvina

2018-01-01

Benzimidazoles are an important group of heterocyclic aromatic organic compound in the field of medicinal chemistry. It plays a very important role in pharmacological activity such as, analgesic, antiinflammatory, antibacterial, anti ungal, anti iral, antithelmenthic, anti convulsant, antihypertensive, and antiulcer. The synthesis of benzimidazole derivative under microwave irradiation of citronellal as raw material which is extracted from Citrus hystrix DC. (kaffir lime) leaves. The reaction using methanol and dichloromethane as solvent with variation of reaction time at 30, 40, 50, 60, and 70 minutes and mole ratio of citronellal to 1,2-phenylenediamine, 1:1, 1:1.5, and 1:2, respectively. Synthesis products was characterized by FT-IR and GC-MS. The optimum reaction time was obtained at 60 minutes in the present of dichloromethane and 1:2 mole ratio of citronellal to 1,2-phenylenediamine. The yield of the product is 42.19%. Structure of the synthesized compound were assigned on spectrum bands for C=N str at 1661 cm-1, C-N str at 1271 cm-1, C=C str of benzene ring at 1622 and 1456 cm-1 and C=C str of alkene at 1379 cm-1. GC-MS analysis showed single peak with retention time of 15.339 minute and m/z 242.

Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines.

Science.gov (United States)

Xu, Zhigang; Shaw, Arthur Y; Dietrich, Justin; Cappelli, Alexandra P; Nichol, Gary; Hulme, Christopher

2012-02-01

Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

Facile, novel two-step syntheses of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines

OpenAIRE

Xu, Zhigang; Shaw, Arthur Y.; Dietrich, Justin; Cappelli, Alexandra P.; Nichol, Gary; Hulme, Christopher

2012-01-01

Three scaffolds of benzimidazoles, bis-benzimidazoles, and bis-benzimidazole-dihydroquinoxalines were synthesized via Ugi/de-protection/cyclization methodology. Benzimidazole forming ring closure was enabled under microwave irradiation in the presence of 10% TFA/DCE. The methodology demonstrates the utility of 2-(N-Boc-amino)-phenyl-isocyanide for the generation of new molecular diversity.

Development of an automated modular system for the synthesis of [11C]acetate.

Science.gov (United States)

Felicini, Chiara; Någren, Kjell; Berton, Andrea; Pascali, Giancarlo; Salvadori, Piero Alberto

2010-12-01

Carboxylation reactions offer a straightforward method for the synthesis of carbon-11 labelled carboxylic acids. Among these, the preparation of carbon-11 (C)-acetate is receiving increasing attention because of diagnostic applications in oncology in addition to its well-established use as a probe for myocardial oxidative metabolism. Although a number of dedicated modules are commercially available, the development of the synthesis on flexible platforms would be beneficial to widen the number of tracers, in particular for preclinical assessment and testing. In this study, the carboxylation reaction was implemented for the synthesis of sodium 1-[C]acetate after the classic route of carboxylation of methylmagnesium chloride by [C]carbon dioxide, followed by the acidic hydrolysis, purification and sterile filtration. This was performed using a commercially available kit of preassembled hardware units and fully compatible components of radiochemistry automation (VarioSystem). The system proved be to highly versatile and inexpensive and allowed a quick translation of the radiochemistry project into a working system even by less experienced personnel, because of predefined interfaces between electronic parts and operating software (preloaded on a laptop and included in the kit). The automatic module proved to be a simple and reliable system for the production of 1-[C]acetate that was prepared in 24 min (total synthesis time) with stable radiochemical yields (20% nondecay corrected) and high radiochemical purity (>97%). The module is used routinely to produce 1-[C]acetate for preclinical studies and is being implemented for the production of the labelled fatty acids.

Chemistry and electrochemistry in trifluoroacetic acid. Comparison with acetic acid

International Nuclear Information System (INIS)

Petit, Gerard

1972-01-01

As the trifluoroacetic acid is, with the acetic acid, one of most often used carboxylic acids as solvent, notably in organic chemistry, this research thesis addresses some relatively simple complexing and redox reactions to highlight the peculiar feature of this acid, and to explain its very much different behaviour with respect to acetic acid. The author develops the notion of acidity level in solvents of low dielectric constant. The second part addresses a specific solvent: BF 3 (CH 3 COOH) 2 . The boron trifluoride strengthens the acidity of acetic acid and modifies its chemical and physical-chemical properties. In the third part, the author compares solvent properties of CF 3 COOH and CH 3 COOH. Noticed differences explain why the trifluoroacetic acid is a more interesting reaction environment than acetic acid for reactions such as electrophilic substitutions or protein solubilisation [fr

Ionic conducting poly-benzimidazoles

International Nuclear Information System (INIS)

Jouanneau, J.

2006-11-01

Over the last years, many research works have been focused on new clean energy systems. Hydrogen fuel cell seems to be the most promising one. However, the large scale development of this technology is still limited by some key elements. One of them is the polymer electrolyte membrane 'Nafion' currently used, for which the ratio performance/cost is too low. The investigations we carried out during this thesis work are related to a new class of ionic conducting polymer, the sulfonated poly-benzimidazoles (sPBI). Poly-benzimidazoles (PBI) are aromatic heterocyclic polymers well-known for their excellent thermal and chemical stability. Ionic conduction properties are obtained by having strong acid groups (sulfonic acid SO 3 H) on the macromolecular structure. For that purpose, we first synthesized sulfonated monomers. Their poly-condensation with an appropriate non-sulfonated co-monomer yields to sPBI with sulfonation range from 0 to 100 per cent. Three different sPBI structures were obtained, and verified by appropriate analytical techniques. We also showed that the protocol used for the synthesis resulted in high molecular weights polymers. We prepared ionic conducting membrane by casting sPBI solutions on glass plates. Their properties of stability, water swelling and ionic conductivity were investigated. Surprisingly, the behaviour of sPBI was quite different from the other sulfonated aromatic polymers with same amount of SO 3 H, their stability was much higher, but their water swelling and ionic conductivity were quite low. We attributed these differences to strong ionic interactions between the sulfonic acid groups and the basic benzimidazole groups of our polymers. However, we managed to solve this problem synthesizing very highly sulfonated PBI, obtaining membranes with a good balance between all the properties necessary. (author)

Synthesis, antimicrobial and cytotoxic activity of novel azetidine-2-one derivatives of 1H-benzimidazole

Directory of Open Access Journals (Sweden)

Malleshappa Noolvi

2014-04-01

Full Text Available A series of 1-methyl-N-[(substituted-phenylmethylidene-1H-benzimidazol-2-amines (4a–4g were prepared via the formation of 1-methyl-1H-benzimidazol-2-amine (3, which was prepared by the cycloaddition of o-phenylenediamine (1 with cyanogen bromide in the presence of aqueous base followed by N-methylation with methyl iodide in the presence of anhydrous potassium carbonate in dry acetonitrile. Moreover, the four-membered β-lactam ring was introduced by the cycloaddition of 4a–4g and chloroacetyl chloride in the presence of triethylamine catalyst to give 3-chloro-1-(1-methyl-1H-benzimidazol-2-yl-(4′-substituted-phenylazetidin-2-one 5a–5g. A total of 14 compounds were synthesized and characterized by IR, 1H NMR, 13C NMR and Mass spectral technique, in addition they were evaluated for anti-bacterial and cytotoxic properties. Among the chemicals tested 4a, 4b, 5a, 5b, 5g exhibited good antibacterial activity and 5f, 5g shown good cytotoxic activity in vitro.

Structure of eight molecular salts assembled from noncovalent bonding between carboxylic acids, imidazole, and benzimidazole

Science.gov (United States)

Jin, Shouwen; Zhang, Huan; Liu, Hui; Wen, Xianhong; Li, Minghui; Wang, Daqi

2015-09-01

Eight organic salts of imidazole/benzimidazole have been prepared with carboxylic acids as 2-methyl-2-phenoxypropanoic acid, α-ketoglutaric acid, 5-nitrosalicylic acid, isophthalic acid, 4-nitro-phthalic acid, and 3,5-dinitrosalicylic acid. The eight crystalline forms reported are proton-transfer compounds of which the crystals and compounds were characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. These structures adopted hetero supramolecular synthons, with the most common R22(7) motif observed at salts 2, 3, 5, 6 and 8. Analysis of the crystal packing of 1-8 suggests that there are extensive strong Nsbnd H⋯O, and Osbnd H⋯O hydrogen bonds (charge assisted or neutral) between acid and imidazolyl components in all of the salts. Except the classical hydrogen bonding interactions, the secondary propagating interactions also play important roles in structure extension. This variety, coupled with the varying geometries and number of acidic groups of the acids utilized, has led to the creation of eight supramolecular arrays with 1D-3D structure. The role of weak and strong noncovalent interactions in the crystal packing is analyzed. The results presented herein indicate that the strength and directionality of the Nsbnd H⋯O, and Osbnd H⋯O hydrogen bonds between acids and imidazole/benzimidazole are sufficient to bring about the formation of organic salts.

One-pot green synthesis of zinc oxide nano rice and its application as sonocatalyst for degradation of organic dye and synthesis of 2-benzimidazole derivatives

Science.gov (United States)

Paul, Bappi; Vadivel, Sethumathavan; Dhar, Siddhartha Sankar; Debbarma, Shyama; Kumaravel, M.

2017-05-01

In this paper, we report novel and green approach for one-pot biosynthesis of zinc oxide (ZnO) nanoparticles (NPs). Highly stable and hexagonal phase ZnO nanoparticles were synthesized using seeds extract from the tender pods of Parkia roxburghii and characterized by XRD, FT-IR, EDX, TEM, and N2 adsorption-desorption (BET) studies. The present method of synthesis of ZnO NPs is very efficient and cost effective. The powder XRD pattern furnished evidence for the formation of hexagonal close packing structure of ZnO NPs having average crystallite size 25.6 nm. The TEM image reveals rice shapes ZnO NPs are with an average diameter of 40-60 nm. The as-synthesized ZnO NPs has proved to be an excellent sonocatalysts for degradation of organic dye and synthesis of 2-benzimidazole derivatives.

Tannic acid Catalyzed an Efficient Synthesis of 2,4,5-Triaryl-1H-Imidazole

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Shitole Nana Vikram

2013-05-01

Full Text Available Tannic acid (C76H52O46 has been found to be an efficient catalyst for one-pot synthesis of 2,4,5-triaryl substituted imidazoles by the reaction of an arylaldehyde, benzyl/benzoin and an ammonium acetate. The short reaction time and excellent yields making this protocol practical and economically attractive.

Photodissociation spectroscopy of the Mg+-acetic acid complex

Science.gov (United States)

Abate, Yohannes; Kleiber, P. D.

2006-11-01

We have studied the structure and photodissociation of Mg+-acetic acid clusters. Ab initio calculations suggest four relatively strongly bound ground state isomers for the [MgC2H4O2]+ complex. These isomers include the cis and trans forms of the Mg+-acetic acid association complex with Mg+ bonded to the carbonyl O atom of acetic acid, the Mg+-acetic acid association complex with Mg+ bonded to the hydroxyl O atom of acetic acid, or to a Mg+-ethenediol association complex. Photodissociation through the Mg+-based 3p←3s absorption bands in the near UV leads to direct (nonreactive) and reactive dissociation products: Mg+, MgOH+, Mg(H2O )+, CH3CO+, and MgCH3+. At low energies the dominant reactive quenching pathway is through dehydration to Mg(H2O)+, but additional reaction channels involving C-H and C-C bond activation are also open at higher energies.

A Practical Green Synthesis and Biological Evaluation of Benzimidazoles Against Two Neglected Tropical Diseases: Chagas and Leishmaniasis.

Science.gov (United States)

Bandyopadhyay, Debashis; Samano, Selina; Villalobos-Rocha, Juan Carlos; Sanchez-Torres, Luvia Enid; Nogueda-Torres, Benjamin; Rivera, Gildardo; Banik, Bimal K

2017-01-01

Antimicrobial resistance is an ever-increasing problem throughout the world and has already reached severe proportions. Two very common neglected tropical diseases are Chagas' disease and leishmaniasis. Chagas' disease is a severe health problem, mainly in Latin America, causing approximately 50000 deaths a year and millions of people are infected. About 25-30% of the patients infected with Trypanosoma cruzi develop the chronic form of the disease. On the other hand, Leishmaniasis represents complex diseases with an important clinical and epidemiological diversity. It is endemic in 88 countries 72 of which are developing countries and it has been estimated that are 12 million people infected and 350 million are in areas with infection risk. On this basis, research on organic compounds that can be used against these two diseases is an important target. A very simple, green, and efficient protocol is developed in which bismuth nitrate pentahydrate is employed as a Lewis acid catalyst in aqueous media under microwave irradiation for the synthesis of various 2-aryl substituted benzimidazoles from aldehydes and o-phenylenediamine. Other salient features of this protocol include milder conditions, atom-economy, easy extraction, and no wastes. Nine 1H-benzimidazole derivatives (1-9) with substituents at positions 2 and 5 were synthesized and the structure of the compounds was elucidated by spectroscopic methods. The compounds were screened to identify whether they posses pharmacological activity against Chagas' disease and leishmaniasis. Compound 8 showed better activity than the control Nifurtimox against INC-5 Trypanosoma cruzi strain whereas compounds 3 and 9 have demonstrated potent leshmanicidal activity. A systematic green synthetic procedure and in vitro biological evaluation of nine 1H-benzimidazoles are described. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

Design, synthesis, α-glucosidase inhibitory activity, molecular docking and QSAR studies of benzimidazole derivatives

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Dinparast, Leila; Valizadeh, Hassan; Bahadori, Mir Babak; Soltani, Somaieh; Asghari, Behvar; Rashidi, Mohammad-Reza

2016-06-01

In this study the green, one-pot, solvent-free and selective synthesis of benzimidazole derivatives is reported. The reactions were catalyzed by ZnO/MgO containing ZnO nanoparticles as a highly effective, non-toxic and environmentally friendly catalyst. The structure of synthesized benzimidazoles was characterized using spectroscopic technics (FT-IR, 1HNMR, 13CNMR). Synthesized compounds were evaluated for their α-glucosidase inhibitory potential. Compounds 3c, 3e, 3l and 4n were potent inhibitors with IC50 values ranging from 60.7 to 168.4 μM. In silico studies were performed to explore the binding modes and interactions between enzyme and synthesized benzimidazoles. Developed linear QSAR model based on density and molecular weight could predict bioactivity of newly synthesized compounds well. Molecular docking studies revealed the availability of some hydrophobic interactions. In addition, the bioactivity of most potent compounds had good correlation with estimated free energy of binding (ΔGbinding) which was calculated according to docked best conformations.

Involvement of yeast HSP90 isoforms in response to stress and cell death induced by acetic acid.

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Alexandra Silva

Full Text Available Acetic acid-induced apoptosis in yeast is accompanied by an impairment of the general protein synthesis machinery, yet paradoxically also by the up-regulation of the two isoforms of the heat shock protein 90 (HSP90 chaperone family, Hsc82p and Hsp82p. Herein, we show that impairment of cap-dependent translation initiation induced by acetic acid is caused by the phosphorylation and inactivation of eIF2α by Gcn2p kinase. A microarray analysis of polysome-associated mRNAs engaged in translation in acetic acid challenged cells further revealed that HSP90 mRNAs are over-represented in this polysome fraction suggesting preferential translation of HSP90 upon acetic acid treatment. The relevance of HSP90 isoform translation during programmed cell death (PCD was unveiled using genetic and pharmacological abrogation of HSP90, which suggests opposing roles for HSP90 isoforms in cell survival and death. Hsc82p appears to promote survival and its deletion leads to necrotic cell death, while Hsp82p is a pro-death molecule involved in acetic acid-induced apoptosis. Therefore, HSP90 isoforms have distinct roles in the control of cell fate during PCD and their selective translation regulates cellular response to acetic acid stress.

Alternate fuels and chemicals from synthesis gas: Vinyl acetate monomer. Final report

Energy Technology Data Exchange (ETDEWEB)

Richard D. Colberg; Nick A. Collins; Edwin F. Holcombe; Gerald C. Tustin; Joseph R. Zoeller

1999-01-01

There has been a long-standing desire on the part of industry and the U.S. Department of Energy to replace the existing ethylene-based vinyl acetate monomer (VAM) process with an entirely synthesis gas-based process. Although there are a large number of process options for the conversion of synthesis gas to VAM, Eastman Chemical Company undertook an analytical approach, based on known chemical and economic principles, to reduce the potential candidate processes to a select group of eight processes. The critical technologies that would be required for these routes were: (1) the esterification of acetaldehyde (AcH) with ketene to generate VAM, (2) the hydrogenation of ketene to acetaldehyde, (3) the hydrogenation of acetic acid to acetaldehyde, and (4) the reductive carbonylation of methanol to acetaldehyde. This report describes the selection process for the candidate processes, the successful development of the key technologies, and the economic assessments for the preferred routes. In addition, improvements in the conversion of acetic anhydride and acetaldehyde to VAM are discussed. The conclusion from this study is that, with the technology developed in this study, VAM may be produced from synthesis gas, but the cost of production is about 15% higher than the conventional oxidative acetoxylation of ethylene, primarily due to higher capital associated with the synthesis gas-based processes.

Efficient Synthesis of Functionalized 1-oxo-1-phenyl-2-acetic Acids through Ru(II)-catalyzed Transfer Hydrogenation

Energy Technology Data Exchange (ETDEWEB)

Wang, Xiaowei; Gong, Binwei; Meng, Yanqiu [Shenyang Univ. of Chemical Technology, Shenyang (Korea, Republic of); Yan, Yunnan [Gannan Medical Univ., Ganzhou (Korea, Republic of); Tang, Xiaobo; Eric Xu, H.; Yi, Wei [Chinese Academy of Sciences, Shanghai (China); Li, Qiu [Univ. of Science and Technology of China, Suzhou (China)

2013-10-15

A new and alternative method for the efficient synthesis of indanylacetic acid 2 has been developed. The methodology used RuCl(p-cymene)[(R,R)-TsDPEN] as the catalyst and formic acid-triethylamine as the hydrogen source at room temperature under solvent-free conditions, and the reactions have excellent chemoselectivity and good compatibility of substrates. Used our developed method as the starting step, gram scale synthesis of GR24 was achieved smoothly with an overall yield of 72%. All the results suggested that further development of such methodology may be of interest. Further work to establish the mechanistic reasons for selectivity and to further explore the synthetic scope of this mode of transfer hydrogenation is in progress. The synthetic SL analog, GR24 is a very potent germination stimulant, which is widely used in parasitic weed research to stimulate germination and as a standard for comparison of new germinating agents. Owing to the prevalence of GR24, its total synthesis constitutes a hot area of research. So far all known synthetic routes of GR24 used indanylacetic acid 2 as a key intermediate, for which very few methods of building compound 2 have been reported.

Sol-gel process for preparation of YBa2Cu4O8 from acidic acetates/ammonia/ascorbic acid systems

International Nuclear Information System (INIS)

Deptula, A.; Lada, W.; Olczak, T.; Goretta, K.C.

1997-01-01

YBa 2 Cu 4 O x sols were prepared by addition of ammonia to acidic acetate solutions of Y 3+ , Ba 2+ , and Cu 2+ . Ascorbic acid was added to part of the sol. The resultant sols were gelled to a shard or a coating by evaporation at 60 C. Addition of ethanol to the sols facilitated formation of gel coatings, fabricated by a dipping technique, on Ag or glass or substrates. At 100 C, gels formed in the presence of ascorbic acid were perfectly amorphous, in contrast to crystalline acetate gels. The quality of coatings prepared from ascorbate gels was superior to that of acetate gel coatings

Sequential injection redox or acid-base titration for determination of ascorbic acid or acetic acid.

Science.gov (United States)

Lenghor, Narong; Jakmunee, Jaroon; Vilen, Michael; Sara, Rolf; Christian, Gary D; Grudpan, Kate

2002-12-06

Two sequential injection titration systems with spectrophotometric detection have been developed. The first system for determination of ascorbic acid was based on redox reaction between ascorbic acid and permanganate in an acidic medium and lead to a decrease in color intensity of permanganate, monitored at 525 nm. A linear dependence of peak area obtained with ascorbic acid concentration up to 1200 mg l(-1) was achieved. The relative standard deviation for 11 replicate determinations of 400 mg l(-1) ascorbic acid was 2.9%. The second system, for acetic acid determination, was based on acid-base titration of acetic acid with sodium hydroxide using phenolphthalein as an indicator. The decrease in color intensity of the indicator was proportional to the acid content. A linear calibration graph in the range of 2-8% w v(-1) of acetic acid with a relative standard deviation of 4.8% (5.0% w v(-1) acetic acid, n=11) was obtained. Sample throughputs of 60 h(-1) were achieved for both systems. The systems were successfully applied for the assays of ascorbic acid in vitamin C tablets and acetic acid content in vinegars, respectively.

Phosphorylated benzimedazoles. 8. Synthesis of phosphorylated with /sup 32/P benzimidazoles

Energy Technology Data Exchange (ETDEWEB)

Makarov, A M; Matevosyan, G L; Zavlin, P M [Leningradskij Sel' skokhozyajstvennyj Inst. (USSR)

1983-03-01

Accessible methods of synthesis and identification of phosphorylated benzimidazoles with specific activity close to the maximum permissible with labelled /sup 32/P are developed. These methods permit to determine the permissible residual amounts of the above preparations in nutrition products and the maximum permissible amounts of growth regulators in different objects of the environment, because it is impossible to detect, for example, tri(1-benzimidazolido)phosphate with other physico-chemical methods with the existing concentration of 10/sup -9/%.

[Effect of acetic acid, furfural and 5-hydroxymethylfurfural on production of 2,3-butanediol by Klebsiella oxytoca].

Science.gov (United States)

Wu, Jing; Cheng, Keke; Li, Wenying; Feng, Jie; Zhang, Jian'an

2013-03-01

To get the tolerability and consumption of Klebsiella oxytoca on major inhibitors in lignocelluloses hydrolysate, we studied the effect of acetic acid, furfural and 5-hydroxymethylfurfural on production of 2,3-butanediol by Klebsiella oxytoca. The metabolites of furfural and 5-hydroxymethylfurfural were measured. The results show that when acetic acid, furfural and 5-hydroxymethylfurfural was individually added, tolerance threshold for Klebsiella oxytoca was 30 g/L, 4 g/L and 5 g/L, respectively. Acetic acid was likely used as substrate to produce 2,3-butanediol. The yield of 2,3-butanediol increased when acetic acid concentration was lower than 30 g/L. In the fermentation, more than 70% 5-hydroxymethylfurfural was converted to 2,5-furandimethanol. All furfural and the rest of 5-hydroxymethylfurfural were metabolized by Klebsiella oxytoca. It showed that in the detoxification process of 2,3-butanediol production using lignocelluloses hydrolysate, furfural should be given priority to remove and a certain concentration of acetic acid is not need to removal.

Facile and Selective Synthesis of 2-Substituted Benzimidazoles Catalyzed by FeCl3/ Al2O3

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Guo-Feng Chen

2012-01-01

Full Text Available 2-Substituted benzimidazoles were synthesized in a single pot from aromatic aldehydes and o-phenylenediamine catalyzed by FeCl3/ Al2O3 in DMF at ambient temperature attained good yields and high selectivity.

Antituberculosis: Synthesis and Antimycobacterial Activity of Novel Benzimidazole Derivatives

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Yeong Keng Yoon

2013-01-01

Full Text Available A total of seven novel benzimidazoles were synthesized by a 4-step reaction starting from 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The synthesized compounds were screened for their antimycobacterial activity against M. tuberculosis H37Rv (MTB-H37Rv and INH-resistant M. tuberculosis (INHR-MTB strains using agar dilution method. Three of them displayed good activity with MIC of less than 0.2 μM. Compound ethyl 1-(2-(4-(4-(ethoxycarbonyl-2-aminophenylpiperazin-1-ylethyl-2-(4-(5-(4-fluorophenylpyridin-3-ylphenyl-1H-benzo[d]imidazole-5-carboxylate (5g was found to be the most active with MIC of 0.112 μM against MTB-H37Rv and 6.12 μM against INHR-MTB, respectively.

Research on the differences between 2-(2-Chlorophenyl)benzimidazole and 2-(4-Chlorophenyl)benzimidazole based on terahertz time domain spectroscopy

Science.gov (United States)

Song, Maojiang; Yang, Fei; Liu, Liping; Shen, Li; Hu, Pengfei; Zhang, Li; Su, Caixia

2018-05-01

Due to wide variety of biological and pharmacological activities of benzimidazole derivatives, the differences between 2-(2-Chlorophenyl)benzimidazole and 2-(4-Chlorophenyl) benzimidazole were researched by employing terahertz time-domain spectroscopy and density functional theory systematically. Although the only difference between their molecular configurations is the arrangement of chlorine atom on chlorophenyl ring, there are distinctive differences in their fingerprint spectra in the range of 0.2-2.5 THz, such as amount, amplitude, and frequency position of absorption peaks. The validity of these results was confirmed by the theoretical results simulated by using density functional theory. The possible reasons of these differences originate from the different van der Waals forces and the different dihedral angles of the molecules within crystal cell. These results indicate the importance of this spectral range as a conformational fingerprint region where even minor changes in the molecular configuration lead to major differences in its THz absorption.

Prebiotic Amino Acid Thioester Synthesis: Thiol-Dependent Amino Acid Synthesis from Formose substrates (Formaldehyde and Glycolaldehyde) and Ammonia

Science.gov (United States)

Weber, Arthur L.

1998-01-01

Formaldehyde and glycolaldehyde (substrates of the formose autocatalytic cycle) were shown to react with ammonia yielding alanine and homoserine under mild aqueous conditions in the presence of thiol catalysts. Since similar reactions carried out without ammonia yielded alpha-hydroxy acid thioesters, the thiol-dependent synthesis of alanine and homoserine is presumed to occur via amino acid thioesters-intermediates capable of forming peptides. A pH 5.2 solution of 20 mM formaldehyde, 20 mM glycolaldehyde, 20 mM ammonium chloride, 23 mM 3-mercaptopropionic acid, and 23 mM acetic acid that reacted for 35 days at 40 C yielded (based on initial formaldehyde) 1.8% alanine and 0.08% homoserine. In the absence of thiol catalyst, the synthesis of alanine and homoserine was negligible. Alanine synthesis required both formaldehyde and glycolaldehyde, but homoserine synthesis required only glycolaldehyde. At 25 days the efficiency of alanine synthesis calculated from the ratio of alanine synthesized to formaldehyde reacted was 2.1%, and the yield (based on initial formaldehyde) of triose and tetrose intermediates involved in alanine and homoserine synthesis was 0.3 and 2.1%, respectively. Alanine synthesis was also seen in similar reactions containing only 10 mM each of aldehyde substrates, ammonia, and thiol. The prebiotic significance of these reactions that use the formose reaction to generate sugar intermediates that are converted to reactive amino acid thioesters is discussed.

Sequential one-pot synthesis of imidazoles and 2H-imidazolones from β-ketoamines, acylating agents and ammonium acetate

Energy Technology Data Exchange (ETDEWEB)

Jalani, Hitesh B.; Venkateswararao, Edda; Manickam, Manoj; Jung, Sang Hun [College of Pharmacy and Institute of Drug Research and Development, Chungnam National University, Daejeon (Korea, Republic of)

2016-12-15

An efficient, practical, straight forward, and transition metal-free three-component synthesis of diversely substituted imidazoles and 2H-imidazolones from β-ketoamines, acylating agents, and ammonium acetate has been described herein. This approach involves [3+1+1] cyclization through consecutive formation of three C–N bonds as a sequence of initial amidation of β-ketoamines with acylating agent, β-iminoketoamide formation with ammonia, and acid catalyzed concomitant cyclodehydration to afford the imidazoles and 2H-imidazolones. This methodology has advantages such as single flask operation, readily available starting materials, mild conditions, broad functional groups tolerance, and simple work-up procedure.

Methyl 2-Benzamido-2-(1H-benzimidazol-1-ylmethoxyacetate

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Alami Anouar

2012-09-01

Full Text Available The heterocyclic carboxylic α-aminoester methyl 2-benzamido-2-(1H-benzimidazol-1-ylmethoxyacetate is obtained by O-alkylation of methyl α-azido glycinate N-benzoylated with 1H-benzimidazol-1-ylmethanol.

Acetic acid extraction from aqueous solutions using fatty acids

NARCIS (Netherlands)

IJmker, H.M.; Gramblicka, M.; Kersten, Sascha R.A.; van der Ham, Aloysius G.J.; Schuur, Boelo

2014-01-01

A major challenge for production of acetic acid via bio-based routes is cost-effective concentration and purification of the acetic acid from the aqueous solutions, for which liquid–liquid extraction is a possible method. A main challenge in extraction of acetic acid from dilute aqueous solutions is

DNA-Compatible Nitro Reduction and Synthesis of Benzimidazoles.

Science.gov (United States)

Du, Huang-Chi; Huang, Hongbing

2017-10-18

DNA-encoded chemical libraries have emerged as a cost-effective alternative to high-throughput screening (HTS) for hit identification in drug discovery. A key factor for productive DNA-encoded libraries is the chemical diversity of the small molecule moiety attached to an encoding DNA oligomer. The library structure diversity is often limited to DNA-compatible chemical reactions in aqueous media. Herein, we describe a facile process for reducing aryl nitro groups to aryl amines. The new protocol offers simple operation and circumvents the pyrophoric potential of the conventional method (Raney nickel). The reaction is performed in aqueous solution and does not compromise DNA structural integrity. The utility of this method is demonstrated by the versatile synthesis of benzimidazoles on DNA.

Eight supramolecular assemblies constructed from bis(benzimidazole) and organic acids through strong classical hydrogen bonding and weak noncovalent interactions

Science.gov (United States)

Jin, Shouwen; Wang, Daqi

2014-05-01

Eight crystalline organic acid-base adducts derived from alkane bridged bis(N-benzimidazole) and organic acids (2,4,6-trinitrophenol, p-nitrobenzoic acid, m-nitrobenzoic acid, 3,5-dinitrobenzoic acid, 5-sulfosalicylic acid and oxalic acid) were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis. Of the eight compounds five are organic salts (1, 4, 6, 7 and 8) and the other three (2, 3, and 5) are cocrystals. In all of the adducts except 1 and 8, the ratio of the acid and the base is 2:1. All eight supramolecular assemblies involve extensive intermolecular classical hydrogen bonds as well as other noncovalent interactions. The role of weak and strong noncovalent interactions in the crystal packing is ascertained. These weak interactions combined, all the complexes displayed 3D framework structure. The results presented herein indicate that the strength and directionality of the classical N+-H⋯O-, O-H⋯O, and O-H⋯N hydrogen bonds (ionic or neutral) and other nonbonding associations between acids and ditopic benzimidazoles are sufficient to bring about the formation of cocrystals or organic salts.

Properties and synthesis of D2EHPA and of alkylphosphoric acid

International Nuclear Information System (INIS)

Elias, Abdelhamid

1996-07-01

A great interest has been devoted to alkylphosphates which are used in various field of chemical industry as: agents for extracting metals (uranium, actinides and lanthanides), flame-retardant solid plasticizers for cellulose acetate,cellulose ethers and vinyls,ignition control agents for gasoline, lubricant additive,antifoam agents for water-based paints and in inks and paper manufacture. In this context, the present work is achieved in order to supply a selected bibliography and the main theoretical aspects concerning physical and chemical properties, analysis techniques, synthesis and purification processes and some applications of D2EHPA (di(2-ethylhexyl)phosphoric acid or di(2-ethylhexyl)phosphate) and of alkylphosphates in general

21 CFR 582.1005 - Acetic acid.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Acetic acid. 582.1005 Section 582.1005 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS....1005 Acetic acid. (a) Product. Acetic acid. (b) Conditions of use. This substance is generally...

Gold nanoparticles supported on titanium dioxide: an efficient catalyst for highly selective synthesis of benzoxazoles and benzimidazoles.

Science.gov (United States)

Tang, Lin; Guo, Xuefeng; Yang, Yu; Zha, Zhenggen; Wang, Zhiyong

2014-06-11

A highly efficient and selective reaction for the synthesis of 2-substituted benzoxazoles and benzimidazoles catalyzed by Au/TiO2 has been developed via two hydrogen-transfer processes. This reaction has a good tolerance to air and water, a wide substrate scope, and represents a new avenue for practical C-N and C-O bond formation. More importantly, no additional additives, oxidants and reductants are required for the reaction and the catalyst can be recovered and reused readily.

The fate of acetic acid during glucose co-metabolism by the spoilage yeast Zygosaccharomyces bailii.

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Fernando Rodrigues

Full Text Available Zygosaccharomyces bailii is one of the most widely represented spoilage yeast species, being able to metabolise acetic acid in the presence of glucose. To clarify whether simultaneous utilisation of the two substrates affects growth efficiency, we examined growth in single- and mixed-substrate cultures with glucose and acetic acid. Our findings indicate that the biomass yield in the first phase of growth is the result of the weighted sum of the respective biomass yields on single-substrate medium, supporting the conclusion that biomass yield on each substrate is not affected by the presence of the other at pH 3.0 and 5.0, at least for the substrate concentrations examined. In vivo(13C-NMR spectroscopy studies showed that the gluconeogenic pathway is not operational and that [2-(13C]acetate is metabolised via the Krebs cycle leading to the production of glutamate labelled on C(2, C(3 and C(4. The incorporation of [U-(14C]acetate in the cellular constituents resulted mainly in the labelling of the protein and lipid pools 51.5% and 31.5%, respectively. Overall, our data establish that glucose is metabolised primarily through the glycolytic pathway, and acetic acid is used as an additional source of acetyl-CoA both for lipid synthesis and the Krebs cycle. This study provides useful clues for the design of new strategies aimed at overcoming yeast spoilage in acidic, sugar-containing food environments. Moreover, the elucidation of the molecular basis underlying the resistance phenotype of Z. bailii to acetic acid will have a potential impact on the improvement of the performance of S. cerevisiae industrial strains often exposed to acetic acid stress conditions, such as in wine and bioethanol production.

Spectral characteristics of 2-(4'-amino-3-pyridyl)benzimidazole: Effects of solvent and acid or base concentration

International Nuclear Information System (INIS)

Dogra, Sneh K.

2006-01-01

Spectral characteristics of 2-(4'-amino-3-pyridyl)benzimidazole (4-A3PyBI) have been studied in different solvents, as well as at different acid or base concentrations using absorption, fluorescence excitation and fluorescence spectroscopy. Excited singlet state (S 1 ) lifetimes for each species were measured using nanosecond time-dependent spectrofluorimeter. AM1 semi-empirical and density functional theoretical (DFT) calculations were performed on each species for the spectral assignment. From the above results it is concluded that 4-A3PyBI exists only in the amine form. First protonation occurs at pyridine=N- atom and second protonation at the benzimidazole (BI)=N- atom. When dication (DC) species is excited, two emission bands are observed, having the same fluorescence excitation spectra, suggesting the same ground state (S ) precursor. Short wavelength (SW) emission band is assigned to the π-π* transition and long wavelength (LW) emission to the charge transfer transition. First deprotonation in S state occurs from >N-H moiety, whereas in S 1 state it is from -NH 2 group. Monoanion (MA) so formed in S 1 state is non-fluorescent. Dianion (DA) is formed by further deprotonating >N-H moiety in S 1 state and it is fluorescent. pK a values were determined and discussed

Synthesis of 4-(3-t-butylamino-2-hydroxypropoxy)- benzimidazol -2 (/sup 11/C)-one (CGP 12177)

Energy Technology Data Exchange (ETDEWEB)

Boullais, C; Crouzel, C; Syrota, A

1986-05-01

4-(3-t-butylamino-2-hydroxypropoxy)-benzimidazol-2 (/sup 11/C)-one (CGP 12177) was synthesized in a short time (30 min) and with a specific activity of 130 mCi/..mu..Mo1 for ..beta.. receptor studies by the positron emission tomography. The radioactive reagent was /sup 11/C-phosgene and the starting material 1-(3-t-butylamino-2-hydroxypropoxy)-2,3-diamino benzene.

Synthesis, crystal structure determination and antiproliferative activity of novel 2-amino-4-aryl-4,10-dihydro[1,3,5]triazino[1,2- a]benzimidazoles

Science.gov (United States)

Hranjec, Marijana; Pavlović, Gordana; Karminski-Zamola, Grace

2012-01-01

This manuscript describes the synthesis of novel 2-amino-4-aryl-4,10-dihydro-[1,3,5]triazino[1,2- a]benzimidazoles as hydrochloride salts 4a-n and 5b which were prepared in the reaction of cyclocondensation between 2-guanidinobenzimidazole and versatile heteroaromatic aldehydes. Structures of all prepared compounds have been studied by using 1H and 13C NMR, IR and UV/Vis spectroscopy. The crystal and molecular structure of 4f was determined by X-ray diffraction on single crystals. The molecule of 2-amino-4-(4'-methylphenyl)-4,10-dihydro[1,3,5]triazino[1,2- a]benzimidazole hydrochloride 4f (C 16H 16N 5+·Cl -) exists in the solid state in one of the possible tautomeric forms, being protonated at the one of the nitrogen atoms of the 1,4-dihydrotriazine ring. The molecule is highly delocalized within the 4,10-dihydro[1,3,5]triazino[1,2- a]benzimidazole moiety with the highest deviation from the plane for the methine carbon atom and the protonated nitrogen atom of the 1,4-dihydrotriazine ring. The cations are joined via N-H⋯N hydrogen bonds into R22(8) centrosymmetric dimers. Cation dimers are further connected with Cl - ions via N-H⋯Cl and C-H⋯Cl hydrogen bonds into 2D chains spreading along the b axis. The obtained single-crystal X-ray structure determination unequivocally confirms tautomeric form of the compound present in the solid-state and can represent tantative pattern for other prepared compounds. All prepared compounds were tested on their antiproliferative activity in vitro on several human cancer cell lines. Compound 4m was the most active one (IC 50 ≈ 20 μM), while compounds 4d, 4f, 4k, 4l4m showed moderate, but non-selective, antiproliferative activity with IC 50 25-60 μM.

Effect of substituents on polarizability and hyperpolarizability values of benzimidazole metal complexes

Energy Technology Data Exchange (ETDEWEB)

Praveen, P. A.; Babu, R. Ramesh, E-mail: rampap2k@yahoo.co.in [Crystal Growth and Thin films Laboratory, Department of Physics, Bharathidasan University, Tiruchirappalli - 620 024, Tamilnadu (India)

2016-05-23

In this report, the polarizability and first and second order hyperpolarizability values of bis benzimidazole Zn(II)-2R and bis benzimidazole Cd(II)-2R complexes, with different electron donating moieties R (R= Cl, Br, I, Acetate) were calculated using time dependent Hartree-Fock (TDHF) formalism embedded in MOPAC2012 package. Further the role of substituents on polarizability and hyperpolarizability values is investigated for the first time by analyzing the frontier molecular orbitals of the complexes with respect to the electronegativity of the substituents. It is found that the increase in electronegativity of the substituents correspondingly increases the energy gap of the molecules, which in turn reduces the polarizability values of both Zn and Cd benzimidazole complexes. Similarly, increase in electronegativity reduces the electric quadrupole moments of both the metal complexes, which in turn reduces the hyperpolarizability values.

Low-temperature synthesis and characterization of anatase TiO2 nanoparticles by an acid assisted sol–gel method

International Nuclear Information System (INIS)

Leyva-Porras, C.; Toxqui-Teran, A.; Vega-Becerra, O.; Miki-Yoshida, M.; Rojas-Villalobos, M.; García-Guaderrama, M.

2015-01-01

The synthesis of anatase TiO 2 nanoparticles by an acid-assisted sol–gel method at 25 and 80 °C is described. Specifically, acetic acid (AA) was used and the evolution of the anatase phase with the amount of AA was observed. The results of X-ray diffraction (XRD) and transmission electron microscopy (TEM) both showed that a pure anatase phase was obtained with particle size smaller than 5 nm. Structural refinements and quantitative determination of phase composition was achieved by using the Rietveld method. The particle size distribution became slightly narrower as the amount of AA was increased. Raman spectroscopy showed that when the amount of AA was increased a small amount of brookite was present at the contamination level. The anatase phase was studied by differential thermal analysis (DTA), providing phase stability up to 600 °C. These and other results were discussed in terms of particle size and structure. Likewise, the formation of the anatase phase under these synthesis conditions was explained. - Highlights: • Synthesis of anatase TiO 2 nanoparticles by an acid assisted sol–gel method at mild conditions. • Microstructure characterization by XRD, TEM and Raman spectroscopy. • Observation of the formation and evolution of the anatase phase as acetic acid was increased. • Anatase thermal stability up to 600 °C and band gap range between 3.2 and 3.5 eV. • A simplified method which can be considered as a green chemistry process

α-Amino Acid Derived Benzimidazole-Linked Rhodamines: A Case of Substitution Effect at the Amino Acid Site toward Spiro Ring Opening for Selective Sensing of Al3+ Ions.

Science.gov (United States)

Majumdar, Anupam; Mondal, Subhendu; Daniliuc, Constantin G; Sahu, Debashis; Ganguly, Bishwajit; Ghosh, Sourav; Ghosh, Utpal; Ghosh, Kumaresh

2017-08-07

α-Amino acid derived benzimidazole-linked rhodamines have been synthesized, and their metal ion sensing properties have been evaluated. Experimentally, l-valine- and l-phenylglycine-derived benzimidazole-based rhodamines 1 and 2 selectively recognize Al 3+ ion in aqueous CH 3 CN (CH 3 CN/H 2 O 4/1 v/v, 10 mM tris HCl buffer, pH 7.0) over the other cations by exhibiting color and "turn-on" emission changes. In contrast, glycine-derived benzimidazole 3 remains silent in the recognition event and emphasizes the role of α-substitution of amino acid undertaken in the design. The fact has been addressed on the basis of the single-crystal X-ray structures and theoretical calculations. Moreover, pink 1·Al 3+ and 2·Al 3+ ensembles selectively sensed F - ions over other halides through a discharge of color. Importantly, compounds 1 and 2 are cell permeable and have been used as imaging reagents for the detection of Al 3+ uptake in human lung carcinoma cell line A549.

Synthesis of (benzimidazol-2-yl)aniline derivatives as glycogen phosphorylase inhibitors.

Science.gov (United States)

Galal, Shadia A; Khattab, Muhammad; Andreadaki, Fotini; Chrysina, Evangelia D; Praly, Jean-Pierre; Ragab, Fatma A F; El Diwani, Hoda I

2016-11-01

A series of (benzimidazol-2-yl)-aniline (1) derivatives has been synthesized and evaluated as glycogen phosphorylase (GP) inhibitors. Kinetics studies revealed that compounds displaying a lateral heterocyclic residue with several heteroatoms (series 3 and 5) exhibited modest inhibitory properties with IC 50 values in the 400-600μM range. Arylsulfonyl derivatives 7 (Ar: phenyl) and 9 (Ar: o-nitrophenyl) of 1 exhibited the highest activity (series 2) among the studied compounds (IC 50 324μM and 357μM, respectively) with stronger effect than the p-tolyl analogue 8. Copyright © 2016 Elsevier Ltd. All rights reserved.

The Genealogical Tree of Ethanol: Gas-phase Formation of Glycolaldehyde, Acetic Acid, and Formic Acid

Science.gov (United States)

Skouteris, Dimitrios; Balucani, Nadia; Ceccarelli, Cecilia; Vazart, Fanny; Puzzarini, Cristina; Barone, Vincenzo; Codella, Claudio; Lefloch, Bertrand

2018-02-01

Despite the harsh conditions of the interstellar medium, chemistry thrives in it, especially in star-forming regions where several interstellar complex organic molecules (iCOMs) have been detected. Yet, how these species are synthesized is a mystery. The majority of current models claim that this happens on interstellar grain surfaces. Nevertheless, evidence is mounting that neutral gas-phase chemistry plays an important role. In this paper, we propose a new scheme for the gas-phase synthesis of glycolaldehyde, a species with a prebiotic potential and for which no gas-phase formation route was previously known. In the proposed scheme, the ancestor is ethanol and the glycolaldehyde sister species are acetic acid (another iCOM with unknown gas-phase formation routes) and formic acid. For the reactions of the new scheme with no available data, we have performed electronic structure and kinetics calculations deriving rate coefficients and branching ratios. Furthermore, after a careful review of the chemistry literature, we revised the available chemical networks, adding and correcting several reactions related to glycolaldehyde, acetic acid, and formic acid. The new chemical network has been used in an astrochemical model to predict the abundance of glycolaldehyde, acetic acid, and formic acid. The predicted abundance of glycolaldehyde depends on the ethanol abundance in the gas phase and is in excellent agreement with the measured one in hot corinos and shock sites. Our new model overpredicts the abundance of acetic acid and formic acid by about a factor of 10, which might imply a yet incomplete reaction network.

Voltammetric Determination of a Benzimidazole Anthelmintic Mixture ...

African Journals Online (AJOL)

2002-10-17

Oct 17, 2002 ... Electrochemistry, square-wave voltammetry, benzimidazole anthelmintics, ... potential application, cathodic reduction/anodic oxidation, the type of the electrode ... benzimidazole anthelmintic in 10 cm3 of methanol-formic acid.

Potentiometric titrations in anhydrous acetic acid

International Nuclear Information System (INIS)

Le Port, L.

1966-03-01

The method used for studying anhydrous acetic acid is potentiometry with a glass electrode. We have in this way studied the titration of common inorganic acids (HClO 4 - HBr - H 2 SO 4 - HCl - HNO 3 - H 3 PO 4 ) and of some metallic salts. Furthermore we have shown that complex acids are formed between HCl and some metallic chlorides. An analysis of the titration curves for the inorganic acids against pyridinium chloride has made it possible to calculate a certain number of values for the dissociation pK of these acids and of the corresponding pyridinium salts. The titration of metallic perchlorates constitutes a method of studying the stability of acetates; we have thus been able to draw up a classification for some of these acetates. The metallic chlorides studied fall into two groups according to their behaviour in weak or strong acids. The differences have been explained on the basis of the role played by solvolysis. In the third part we have studied the acidic properties of mixtures of HCl with certain metallic chlorides. This work has demonstrated the existence, in certain cases, of acid complexes of the type (HCl) m MCl n . (author) [fr

Effect of acetic acid on citric acid fermentation in an integrated citric acid-methane fermentation process.

Science.gov (United States)

Xu, Jian; Chen, Yang-Qiu; Zhang, Hong-Jian; Tang, Lei; Wang, Ke; Zhang, Jian-Hua; Chen, Xu-Sheng; Mao, Zhong-Gui

2014-09-01

An integrated citric acid-methane fermentation process was proposed to solve the problem of extraction wastewater in citric acid fermentation process. Extraction wastewater was treated by anaerobic digestion and then recycled for the next batch of citric acid fermentation to eliminate wastewater discharge and reduce water resource consumption. Acetic acid as an intermediate product of methane fermentation was present in anaerobic digestion effluent. In this study, the effect of acetic acid on citric acid fermentation was investigated and results showed that lower concentration of acetic acid could promote Aspergillus niger growth and citric acid production. 5-Cyano-2,3-ditolyl tetrazolium chloride (CTC) staining was used to quantify the activity of A. niger cells, and the results suggested that when acetic acid concentration was above 8 mM at initial pH 4.5, the morphology of A. niger became uneven and the part of the cells' activity was significantly reduced, thereby resulting in deceasing of citric acid production. Effects of acetic acid on citric acid fermentation, as influenced by initial pH and cell number in inocula, were also examined. The result indicated that inhibition by acetic acid increased as initial pH declined and was rarely influenced by cell number in inocula.

Potential radiosensitizing agents. 5. 2-Substituted benzimidazole derivatives

International Nuclear Information System (INIS)

Gupta, R.P.; Larroquette, C.A.; Agrawal, K.C.

1982-01-01

A series of 2-substituted benzimidazoles and their derivatives have been synthesized and tested for their ability to selectively sensitize hypoxic Chinese hamster cells (V-79) toward the lethal effect of ionizing radiation. These compounds were prepared by reacting the 2-substituted benzimidazoles with 1,2-epoxy-3-methoxypropane in the presence of potassium carbonate. Reaction of the 2-nitro and 2-methylfonyl analogue with the epoxide also yielded a cyclized material, which was confirmed to be a benzimidazo[2,1-b]oxazole. In an attempt to increase the electron affinity, 5- or 6-nitro-2-substituted-benzimidazoles were also synthesized and then reacted with the epoxide to yield the corresponding 1-substituted derivatives. The results of the biological tests for the radiosensitizing activity of these agents against Chinese hamster cells (V-79) in culture indicated that the 2-nitro-substituted analogues were the most effective sensitizers in this series

Effect of acetic acid on lipid accumulation by glucose-fed activated sludge cultures

Energy Technology Data Exchange (ETDEWEB)

Mondala, Andro; Hernandez, Rafael; French, Todd; McFarland, Linda; Sparks, Darrell; Holmes, William; Haque, Monica

2012-01-01

The effect of acetic acid, a lignocellulose hydrolysis by-product, on lipid accumulation by activated sludge cultures grown on glucose was investigated. This was done to assess the possible application of lignocellulose as low-cost and renewable fermentation substrates for biofuel feedstock production. Results: Biomass yield was reduced by around 54% at a 2 g L -1 acetic acid dosage but was increased by around 18% at 10 g L -1 acetic acid dosage relative to the control run. The final gravimetric lipid contents at 2 and 10 g L -1 acetic acid levels were 12.5 + 0.7% and 8.8 + 3.2% w/w, respectively, which were lower than the control (17.8 + 2.8% w/w). However, biodiesel yields from activated sludge grown with acetic acid (5.6 + 0.6% w/w for 2 g L -1 acetic acid and 4.2 + 3.0% w/w for 10 g L -1 acetic acid) were higher than in raw activated sludge (1-2% w/w). The fatty acid profiles of the accumulated lipids were similar with conventional plant oil biodiesel feedstocks. Conclusions: Acetic acid enhanced biomass production by activated sludge at high levels but reduced lipid production. Further studies are needed to enhance acetic acid utilization by activated sludge microorganisms for lipid biosynthesis.

Measurement of the rates of oxindole-3-acetic acid turnover, and indole-3-acetic acid oxidation in Zea mays seedlings

Science.gov (United States)

Nonhebel, H. M.; Bandurski, R. S. (Principal Investigator)

1986-01-01

Oxindole-3-acetic acid is the principal catabolite of indole-3-acetic acid in Zea mays seedlings. In this paper measurements of the turnover of oxindole-3-acetic acid are presented and used to calculate the rate of indole-3-acetic acid oxidation. [3H]Oxindole-3-acetic acid was applied to the endosperm of Zea mays seedlings and allowed to equilibrate for 24 h before the start of the experiment. The subsequent decrease in its specific activity was used to calculate the turnover rate. The average half-life of oxindole-3-acetic acid in the shoots was found to be 30 h while that in the kernels had an average half-life of 35h. Using previously published values of the pool sizes of oxindole-3-acetic acid in shoots and kernels from seedlings of the same age and variety, and grown under the same conditions, the rate of indole-3-acetic acid oxidation was calculated to be 1.1 pmol plant-1 h-1 in the shoots and 7.1 pmol plant-1 h-1 in the kernels.

Potassium hydroxide/dimethyl sulfoxide promoted intramolecular cyclization for the synthesis of benzimidazol-2-ones.

Science.gov (United States)

Beyer, Astrid; Reucher, Christine M M; Bolm, Carsten

2011-06-03

A new protocol for intramolecular N-arylations of ureas to form benzimidazol-2-ones has been developed. The cyclization reaction occurs in the presence of KOH and DMSO at close to ambient temperature. Under these conditions the yields are high and a wide range of functional groups are tolerated.

Low-temperature synthesis and characterization of anatase TiO{sub 2} nanoparticles by an acid assisted sol–gel method

Energy Technology Data Exchange (ETDEWEB)

Leyva-Porras, C. [Centro de Investigación en Materiales DIP-CUCEI, Universidad de Guadalajara, Av. Revolución # 1500, Col. Olímpica, C.P. 44430, Guadalajara (Mexico); Centro de Investigación en Materiales Avanzados, S.C. (CIMAV), Alianza Norte No. 202, Parque de Investigación e Innovación Tecnológica (PIIT), Carretera Aeropuerto km. 10, C.P. 66600, Apodaca, N.L. (Mexico); Toxqui-Teran, A.; Vega-Becerra, O. [Centro de Investigación en Materiales Avanzados, S.C. (CIMAV), Alianza Norte No. 202, Parque de Investigación e Innovación Tecnológica (PIIT), Carretera Aeropuerto km. 10, C.P. 66600, Apodaca, N.L. (Mexico); Miki-Yoshida, M. [Centro de Investigación en Materiales Avanzados, S.C. (CIMAV), Miguel de Cervantes No. 120, Parque Industrial Chihuahua, C.P. 31109, Chihuahua (Mexico); Rojas-Villalobos, M.; García-Guaderrama, M. [Centro de Investigación en Materiales DIP-CUCEI, Universidad de Guadalajara, Av. Revolución # 1500, Col. Olímpica, C.P. 44430, Guadalajara (Mexico); and others

2015-10-25

The synthesis of anatase TiO{sub 2} nanoparticles by an acid-assisted sol–gel method at 25 and 80 °C is described. Specifically, acetic acid (AA) was used and the evolution of the anatase phase with the amount of AA was observed. The results of X-ray diffraction (XRD) and transmission electron microscopy (TEM) both showed that a pure anatase phase was obtained with particle size smaller than 5 nm. Structural refinements and quantitative determination of phase composition was achieved by using the Rietveld method. The particle size distribution became slightly narrower as the amount of AA was increased. Raman spectroscopy showed that when the amount of AA was increased a small amount of brookite was present at the contamination level. The anatase phase was studied by differential thermal analysis (DTA), providing phase stability up to 600 °C. These and other results were discussed in terms of particle size and structure. Likewise, the formation of the anatase phase under these synthesis conditions was explained. - Highlights: • Synthesis of anatase TiO{sub 2} nanoparticles by an acid assisted sol–gel method at mild conditions. • Microstructure characterization by XRD, TEM and Raman spectroscopy. • Observation of the formation and evolution of the anatase phase as acetic acid was increased. • Anatase thermal stability up to 600 °C and band gap range between 3.2 and 3.5 eV. • A simplified method which can be considered as a green chemistry process.

Biotechnological applications of acetic acid bacteria.

Science.gov (United States)

Raspor, Peter; Goranovic, Dusan

2008-01-01

products of biotransformations by AAB or their enzymes include 2-keto-L-gulonic acid, which is used for the production of vitamin C; D-tagatose, which is used as a bulking agent in food and a noncalorific sweetener; and shikimate, which is a key intermediate for a large number of antibiotics. Recently, for the first time, a pathogenic acetic acid bacterium was described, representing the newest and tenth genus of AAB.

Acetic acid treatment in S. cerevisiae creates significant energy deficiency and nutrient starvation that is dependent on the activity of the mitochondrial transcriptional complex Hap2-3-4-5

International Nuclear Information System (INIS)

Kitanovic, Ana; Bonowski, Felix; Heigwer, Florian; Ruoff, Peter; Kitanovic, Igor; Ungewiss, Christin; Wölfl, Stefan

2012-01-01

Metabolic pathways play an indispensable role in supplying cellular systems with energy and molecular building blocks for growth, maintenance and repair and are tightly linked with lifespan and systems stability of cells. For optimal growth and survival cells rapidly adopt to environmental changes. Accumulation of acetic acid in stationary phase budding yeast cultures is considered to be a primary mechanism of chronological aging and induction of apoptosis in yeast, which has prompted us to investigate the dependence of acetic acid toxicity on extracellular conditions in a systematic manner. Using an automated computer controlled assay system, we investigated and model the dynamic interconnection of biomass yield- and growth rate-dependence on extracellular glucose concentration, pH conditions and acetic acid concentration. Our results show that toxic concentrations of acetic acid inhibit glucose consumption and reduce ethanol production. In absence of carbohydrates uptake, cells initiate synthesis of storage carbohydrates, trehalose and glycogen, and upregulate gluconeogenesis. Accumulation of trehalose and glycogen, and induction of gluconeogenesis depends on mitochondrial activity, investigated by depletion of the Hap2-3-4-5 complex. Analyzing the activity of glycolytic enzymes, glyceraldehyde-3-phosphate dehydrogenase (GAPDH), pyruvate kinase (PYK), and glucose-6-phosphate dehydrogenase (G6PDH) we found that while high acetic acid concentration increased their activity, lower acetic acids concentrations significantly inhibited these enzymes. With this study we determined growth and functional adjustment of metabolism to acetic acid accumulation in a complex range of extracellular conditions. Our results show that substantial acidification of the intracellular environment, resulting from accumulation of dissociated acetic acid in the cytosol, is required for acetic acid toxicity, which creates a state of energy deficiency and nutrient starvation.

Acetic acid treatment in S. cerevisiae creates significant energy deficiency and nutrient starvation that is dependent on the activity of the mitochondrial transcriptional complex Hap2-3-4-5

Energy Technology Data Exchange (ETDEWEB)

Kitanovic, Ana; Bonowski, Felix; Heigwer, Florian [Institute for Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg (Germany); Ruoff, Peter [Faculty of Science and Technology, Centre for Organelle Research, University of Stavanger, Stavanger (Norway); Kitanovic, Igor; Ungewiss, Christin; Wölfl, Stefan, E-mail: wolfl@uni-hd.de [Institute for Pharmacy and Molecular Biotechnology, Heidelberg University, Heidelberg (Germany)

2012-09-21

Metabolic pathways play an indispensable role in supplying cellular systems with energy and molecular building blocks for growth, maintenance and repair and are tightly linked with lifespan and systems stability of cells. For optimal growth and survival cells rapidly adopt to environmental changes. Accumulation of acetic acid in stationary phase budding yeast cultures is considered to be a primary mechanism of chronological aging and induction of apoptosis in yeast, which has prompted us to investigate the dependence of acetic acid toxicity on extracellular conditions in a systematic manner. Using an automated computer controlled assay system, we investigated and model the dynamic interconnection of biomass yield- and growth rate-dependence on extracellular glucose concentration, pH conditions and acetic acid concentration. Our results show that toxic concentrations of acetic acid inhibit glucose consumption and reduce ethanol production. In absence of carbohydrates uptake, cells initiate synthesis of storage carbohydrates, trehalose and glycogen, and upregulate gluconeogenesis. Accumulation of trehalose and glycogen, and induction of gluconeogenesis depends on mitochondrial activity, investigated by depletion of the Hap2-3-4-5 complex. Analyzing the activity of glycolytic enzymes, glyceraldehyde-3-phosphate dehydrogenase (GAPDH), pyruvate kinase (PYK), and glucose-6-phosphate dehydrogenase (G6PDH) we found that while high acetic acid concentration increased their activity, lower acetic acids concentrations significantly inhibited these enzymes. With this study we determined growth and functional adjustment of metabolism to acetic acid accumulation in a complex range of extracellular conditions. Our results show that substantial acidification of the intracellular environment, resulting from accumulation of dissociated acetic acid in the cytosol, is required for acetic acid toxicity, which creates a state of energy deficiency and nutrient starvation.

The effective reaction of 2-chloro-3-formylquinoline and acetic acid ...

African Journals Online (AJOL)

formylquinolines in a single step by treating with sodium acetate and acetic acid under microwave irradiation. The structures of the compounds have been established by IR, NMR and mass spectral data. Unexpectedly ...

The method of quantitative determination of iodine in acetic acid

International Nuclear Information System (INIS)

Sukhomlinov, A.B.; Kalinchenko, N.B.

1988-01-01

Method for separate determination of J 2 and J - concentrations in acetic acid is suggested. Iodine concentration in acetic acid is determined by measuring potential of iodine-selective electrode first in the initial solution of acetic acid, where molecular iodine dissociation equals 0.5, and then in acetic acid, with alkali (NaOH) addition up to pH > 3, where molecular iodine dissociation equals 1. Determination is conducted in 5x10 -7 -5x10 -6 mol/l concentration range with relative standard deviation not more than 0.1. 1 fig

Biological Activity and Molecular Structures of Bis(benzimidazole and Trithiocyanurate Complexes

Directory of Open Access Journals (Sweden)

Pavel Kopel

2015-06-01

Full Text Available 1-(1H-Benzimidazol-2-yl-N-(1H-benzimidazol-2-ylmethylmethanamine (abb and 2-(1H-benzimidazol-2-ylmethylsulfanylmethyl-1H-benzimidazole (tbb have been prepared and characterized by elemental analysis. These bis(benzimidazoles have been further used in combination with trithiocyanuric acid for the preparation of complexes. The crystal and molecular structures of two of them have been solved. Each nickel atom in the structure of trinuclear complex [Ni3(abb3(H2O3(μ-ttc](ClO43·3H2O·EtOH (1, where ttcH3 = trithiocyanuric acid, is coordinated with three N atoms of abb, the N,S donor set of ttc anion and an oxygen of a water molecule. The crystal of [(tbbH2(ttcH22(ttcH3(H2O] (2 is composed of a protonated bis(benzimidazole, two ttcH2 anions, ttcH3 and water. The structure is stabilized by a network of hydrogen bonds. These compounds were primarily synthesized for their potential antimicrobial activity and hence their possible use in the treatment of infections caused by bacteria or yeasts (fungi. The antimicrobial and antifungal activity of the prepared compounds have been evaluated on a wide spectrum of bacterial and yeast strains and clinical specimens isolated from patients with infectious wounds and the best antimicrobial properties were observed in strains after the use of ligand abb and complex 1, when at least 80% growth inhibition was achieved.

Ionic conducting poly-benzimidazoles; Polybenzimidazoles conducteurs ioniques

Energy Technology Data Exchange (ETDEWEB)

Jouanneau, J

2006-11-15

Over the last years, many research works have been focused on new clean energy systems. Hydrogen fuel cell seems to be the most promising one. However, the large scale development of this technology is still limited by some key elements. One of them is the polymer electrolyte membrane 'Nafion' currently used, for which the ratio performance/cost is too low. The investigations we carried out during this thesis work are related to a new class of ionic conducting polymer, the sulfonated poly-benzimidazoles (sPBI). Poly-benzimidazoles (PBI) are aromatic heterocyclic polymers well-known for their excellent thermal and chemical stability. Ionic conduction properties are obtained by having strong acid groups (sulfonic acid SO{sub 3}H) on the macromolecular structure. For that purpose, we first synthesized sulfonated monomers. Their poly-condensation with an appropriate non-sulfonated co-monomer yields to sPBI with sulfonation range from 0 to 100 per cent. Three different sPBI structures were obtained, and verified by appropriate analytical techniques. We also showed that the protocol used for the synthesis resulted in high molecular weights polymers. We prepared ionic conducting membrane by casting sPBI solutions on glass plates. Their properties of stability, water swelling and ionic conductivity were investigated. Surprisingly, the behaviour of sPBI was quite different from the other sulfonated aromatic polymers with same amount of SO{sub 3}H, their stability was much higher, but their water swelling and ionic conductivity were quite low. We attributed these differences to strong ionic interactions between the sulfonic acid groups and the basic benzimidazole groups of our polymers. However, we managed to solve this problem synthesizing very highly sulfonated PBI, obtaining membranes with a good balance between all the properties necessary. (author)

Fully automated synthesis of 11C-acetate as tumor PET tracer by simple modified solid-phase extraction purification

International Nuclear Information System (INIS)

Tang, Xiaolan; Tang, Ganghua; Nie, Dahong

2013-01-01

Introduction: Automated synthesis of 11 C-acetate ( 11 C-AC) as the most commonly used radioactive fatty acid tracer is performed by a simple, rapid, and modified solid-phase extraction (SPE) purification. Methods: Automated synthesis of 11 C-AC was implemented by carboxylation reaction of MeMgBr on a polyethylene Teflon loop ring with 11 C-CO 2 , followed by acidic hydrolysis with acid and SCX cartridge, and purification on SCX, AG11A8 and C18 SPE cartridges using a commercially available 11 C-tracer synthesizer. Quality control test and animals positron emission tomography (PET) imaging were also carried out. Results: A high and reproducible decay-uncorrected radiochemical yield of (41.0±4.6)% (n=10) was obtained from 11 C-CO 2 within the whole synthesis time about 8 min. The radiochemical purity of 11 C-AC was over 95% by high-performance liquid chromatography (HPLC) analysis. Quality control test and PET imaging showed that 11 C-AC injection produced by the simple SPE procedure was safe and efficient, and was in agreement with the current Chinese radiopharmaceutical quality control guidelines. Conclusion: The novel, simple, and rapid method is readily adapted to the fully automated synthesis of 11 C-AC on several existing commercial synthesis module. The method can be used routinely to produce 11 C-AC for preclinical and clinical studies with PET imaging. - Highlights: • A fully automated synthesis of 11 C-acetate by simple modified solid-phase extraction purification has been developed. • Typical non-decay-corrected yields were (41.0±4.6)% (n=10) • Radiochemical purity was determined by radio-HPLC analysis on a C18 column using the gradient program, instead of expensive organic acid column or anion column. • QC testing (RCP>99%)

Oxidation of indole-3-acetic acid to oxindole-3-acetic acid by an enzyme preparation from Zea mays

Science.gov (United States)

Reinecke, D. M.; Bandurski, R. S.

1988-01-01

Indole-3-acetic acid is oxidized to oxindole-3-acetic acid by Zea mays tissue extracts. Shoot, root, and endosperm tissues have enzyme activities of 1 to 10 picomoles per hour per milligram protein. The enzyme is heat labile, is soluble, and requires oxygen for activity. Cofactors of mixed function oxygenase, peroxidase, and intermolecular dioxygenase are not stimulatory to enzymic activity. A heat-stable, detergent-extractable component from corn enhances enzyme activity 6- to 10-fold. This is the first demonstration of the in vitro enzymic oxidation of indole-3-acetic acid to oxindole-3-acetic acid in higher plants.

SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE

Directory of Open Access Journals (Sweden)

Muhammad Idham Darussalam Mardjan

2012-02-01

Full Text Available Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.

Polarographic study of Cd(2), Pb(2), Hg(1) in anhydrous acetic acid; Etude polarographique de Cd(2), Pb(2), Hg(1) dans l'acide acetique anhydre

Energy Technology Data Exchange (ETDEWEB)

Conesa-Botta, M C [Commissariat a l' Energie Atomique, Fontenay-aux-Roses (France). Centre d' Etudes Nucleaires

1966-07-01

Anhydrous acetic acid is a solvent which can be compared to water as far as its behaviour towards acid-base reactions is concerned. It is in fact, like water both a proton acceptor (basic) - and as such it can provoke the dissociation of acids - and a proton donor (acid). This amphoteric behaviour is characterized by the equilibrium: 2 H O Ac {r_reversible} Ac OH{sub 2}{sup +} + Ac O{sup -} with K{sub i} = |Ac O H{sub 2}|{sup +} |Ac O{sup -}| = 10{sup -14.5} analogue to 2 H{sub 2}O {r_reversible} H{sub 3}O{sup +} + HO{sup -} with K{sub i} = |H{sub 3}O{sup +}| |HO{sup -}| = 10{sup -14} The acid-base reactions can in principle be characterized by a pH scale based on a definition similar to that for the pH scale in aqueous solutions. The essential difference however between aqueous and acetic acid solutions is due to the fact that acetic acid has a low dielectric constant. {epsilon} = 6.1 (at 25 deg. C) The ions therefore remain associated, almost completely, in the form of ion-pairs produced as a result of the strong electrostatic interactions. This phenomenon requires us to modify the reasoning usually applied to aqueous solutions. The new general methods of reasoning have been established and discussed by G. CHARLOT and B. TREMILLON. We will make use of them for the particular case under consideration. In the first part, we have employed the polarographic method for the study of the acetic complexes of two elements: cadmium(II) and lead (II). In the second part we have tried to show that mercurous halides are formed in acetic acid; we have attempted to determine their stability. (author) [French] L'acide acetique anhydre est un solvant qui peut etre rapproche de l'eau par son comportement envers les reactions acides-bases. Il est en effet, comme l'eau, a la fois accepteur de protons (basique) - et comme tel agit sur la dissociation des acides - et donneur de protons (acide). Ce pouvoir amphotere est caracterise par l'equilibre: 2 H O Ac {r_reversible} Ac OH{sub 2

Synthesis of Enantiomerically Pure 6-Substituted-Piperazine-2-Acetic Acid Esters as Intermediates for Library Production.

Science.gov (United States)

Chamakuri, Srinivas; Jain, Prashi; Guduru, Shiva Krishna Reddy; Arney, Joseph Winston; MacKenzie, Kevin; Santini, Conrad; Young, Damian W

2018-05-11

Amino acids from the chiral pool have been used to produce a 24-member branch of 2,6-disubstituted piperazine scaffolds suitable for use in compound library production. Each scaffold was obtained as a single absolute stereoisomer in multi-gram quantities. Stereochemistry was confirmed by 2D NMR protocols and enantiomeric purity was determined by chiral HPLC. The scaffolds are intended for use as intermediates in parallel synthesis of small-molecule libraries.

Aminosilanes derived from 1H-benzimidazole-2(3H)-thione

International Nuclear Information System (INIS)

Palomo-Molina, Juliana; García-Báez, Efrén V.; Contreras, Rosalinda; Pineda-Urbina, Kayim; Ramos-Organillo, Angel

2015-01-01

In two trimethylsilyl-substituted 1H-benzimidazole-2(3H)-thiones, noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe 3 groups form helicoidal arrangements in one, and dimerization results in the formation of R s 2 (8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings, in the second compound. Two new molecular structures, namely 1,3-bis(trimethylsilyl)-1H-benzimidazole-2(3H)-thione, C 13 H 22 N 2 SSi 2 , (2), and 1-trimethylsilyl-1H-benzimidazole-2(3H)-thione, C 10 H 14 N 2 SSi, (3), are reported. Both systems were derived from 1H-benzimidazole-2(3H)-thione. Noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe 3 groups form helicoidal arrangements in (2). Dimerization of (3) results in the formation of R 2 2 (8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings

Lipases and whole cell biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid and its ester.

Science.gov (United States)

Majewska, Paulina; Serafin, Monika; Klimek-Ochab, Magdalena; Brzezińska-Rodak, Małgorzata; Żymańczyk-Duda, Ewa

2016-06-01

A wide spectrum of commercially available lipases and microbial whole cells catalysts were tested for biotransformations of 2-hydroxy-2-(ethoxyphenylphosphinyl)acetic acid 1 and its butyryl ester. The best results were achieved for biocatalytic hydrolysis of ester: 2-butyryloxy-2-(ethoxyphenylphosphinyl)acetic acid 2 performed by lipase from Candida cylindracea, what gave optically active products with 85% enantiomeric excess, 50% conversion degree and enantioselectivity 32.9 for one pair of enantiomers. Also enzymatic systems of Penicillium minioluteum and Fusarium oxysporum were able to hydrolyze tested compound with high enantiomeric excess (68-93% ee), enantioselectivity (44 for one pair of enantiomers) and conversion degree about 50-55%. Enzymatic acylation of hydroxyphosphinate was successful in case when porcine pancreas lipase was used. After 4days of biotransformation the conversion reaches 45% but the enantiomeric enrichment of the isomers mixture do not exceed 43%. Obtained chiral compounds are valuable derivatizing agents for spectroscopic (NMR) evaluation of enantiomeric excess for particular compounds (e.g. amino acids). Copyright © 2016 The Authors. Published by Elsevier Inc. All rights reserved.

Antibiofilm Properties of Acetic Acid

DEFF Research Database (Denmark)

Bjarnsholt, Thomas; Alhede, Morten; Jensen, Peter Østrup

2014-01-01

Bacterial biofilms are known to be extremely tolerant toward antibiotics and other antimicrobial agents. These biofilms cause the persistence of chronic infections. Since antibiotics rarely resolve these infections, the only effective treatment of chronic infections is surgical removal of the inf......Bacterial biofilms are known to be extremely tolerant toward antibiotics and other antimicrobial agents. These biofilms cause the persistence of chronic infections. Since antibiotics rarely resolve these infections, the only effective treatment of chronic infections is surgical removal...... of the infected implant, tissue, or organ and thereby the biofilm. Acetic acid is known for its antimicrobial effect on bacteria in general, but has never been thoroughly tested for its efficacy against bacterial biofilms. In this article, we describe complete eradication of both Gram-positive and Gram......-negative biofilms using acetic acid both as a liquid and as a dry salt. In addition, we present our clinical experience of acetic acid treatment of chronic wounds. In conclusion, we here present the first comprehensive in vitro and in vivo testing of acetic acid against bacterial biofilms....

An Efficient and Versatile Synthesis of Isoflavones from 2-Methoxybenzoic Acids

Energy Technology Data Exchange (ETDEWEB)

Lee, Jae In [Duksung Women' s University, Seoul (Korea, Republic of)

2016-07-15

Isoflavones (3-aryl-4H-1-benzopyran-4-ones) are found naturally in soybeans and many plants of the Leguminosae family. They have attracted much attention due to their biological activities, such as their anti-cancer, anti-inflammatory, and antifungal properties. Isoflavones intake through foods is important to human health, because they potentially regulate fatty acid metabolism and methoxy-substituted isoflavones in particular increase cell permeability. Isoflavones have also been synthesized by the coupling of 3-iodochromones with arylboronic acids. The condensation of 2'-hydroxyacetophenones with DMF dimethyl acetal formed 3-(dimethylamino)-2'-hydroxyphenylpropenones, which were cyclized using iodine to form 3-iodochromones. This process was followed by Suzuki coupling with arylboronic acids or aryl boronates to obtain isoflavones. The synthesis of isoflavones (6) from 5 was based on the formylation of the methylene group of 5 using DMF-POCl{sub 3}. Previously, the reaction of the DMF-POCl{sub 3} complex on benzyl 2-hydroxyphenyl ketones led to isoflavones, for which DMF was used as the reagent and solvent for 18 h at gentle reflux.

Synthesis and Antiradical/Antioxidant Activities of Caffeic Acid Phenethyl Ester and Its Related Propionic, Acetic, and Benzoic Acid Analoguesc

Directory of Open Access Journals (Sweden)

Mohamed Touaibia

2012-12-01

Full Text Available Caffeic acid phenethyl ester (CAPE is a bioactive component isolated from propolis. A series of CAPE analogues was synthesized and their antiradical/antioxidant effects analyzed. The effect of the presence of the double bond and of the conjugated system on the antioxidant effect is evaluated with the analogues obtained from 3-(3,4-dihydroxyphenyl propanoic acid. Those obtained from 2-(3,4-dihydroxyphenyl acetic acid and 3,4-dihydroxybenzoic acid allow the evaluation of the effect of the presence of two carbons between the carbonyl and aromatic system.

Biosynthetic origin of acetic acid using SNIF-NMR

International Nuclear Information System (INIS)

Boffo, Elisangela Fabiana; Ferreira, Antonio Gilberto

2006-01-01

The main purpose of this work is to describe the use of the technique Site-Specific Natural Isotopic Fractionation of hydrogen (SNIF-NMR), using 2 H and 1 H NMR spectroscopy, to investigate the biosynthetic origin of acetic acid in commercial samples of Brazilian vinegar. This method is based on the deuterium to hydrogen ratio at a specific position (methyl group) of acetic acid obtained by fermentation, through different biosynthetic mechanisms, which result in different isotopic ratios. We measured the isotopic ratio of vinegars obtained through C 3 , C 4 , and CAM biosynthetic mechanisms, blends of C 3 and C 4 (agrins) and synthetic acetic acid. (author)

Lead optimization of 2-(piperidin-3-yl)-1H-benzimidazoles: identification of 2-morpholin- and 2-thiomorpholin-2-yl-1H-benzimidazoles as selective and CNS penetrating H₁-antihistamines for insomnia.

Science.gov (United States)

Ravula, Satheesh Babu; Yu, Jinghua; Tran, Joe A; Arellano, Melissa; Tucci, Fabio C; Moree, Wilna J; Li, Bin-Feng; Petroski, Robert E; Wen, Jianyun; Malany, Siobhan; Hoare, Samuel R J; Madan, Ajay; Crowe, Paul D; Beaton, Graham

2012-01-01

The structure-activity relationships of 2-(piperidin-3-yl)-1H-benzimidazoles, 2-morpholine and 2-thiomorpholin-2-yl-1H-benzimidazoles are described. In the lead optimization process, the pK(a) and/or logP of benzimidazole analogs were reduced either by attachment of polar substituents to the piperidine nitrogen or incorporation of heteroatoms into the piperidine heterocycle. Compounds 9a and 9b in the morpholine series and 10g in the thiomorpholine series demonstrated improved selectivity and CNS profiles compared to lead compound 2 and these are potential candidates for evaluation as sedative hypnotics. Copyright © 2011 Elsevier Ltd. All rights reserved.

Fluorescence tuning of 2-(1H-Benzimidazol-2-yl)phenol-ESIPT process

International Nuclear Information System (INIS)

Prakash, S.M.; Jayamoorthy, K.; Srinivasan, N.; Dhanalekshmi, K.I.

2016-01-01

Catalytic synthesis of potential chemosensor 2-(1H-Benzimidazol-2-yl)phenol (HBYP) has been prepared by three components cyclization reaction. It can behaves as a selective fluorescent sensor for the detection of Fe 3+ metal ion. HBYP has been characterized by 1 H NMR, 13 C NMR, mass spectral studies and elemental analysis. Single crystal XRD analysis has been carried out to confirm the structure of HBYP and it shows the imidazole ring is essentially planar and monoclinic crystal. Addition and increasing concentration of Fe 3+ ions into HBYP results dramatic fluorescence quenching. Other cations, including Ca 2+ , Co 2+ , Ni 2+ , Cd 2+ , Pb 2+ , Zn 2+ and Mg 2+ had little influence in the fluorescence intensity. Surprisingly reversible fluorescence enhancement has been observed with the addition of H 3 PO 4 due to the deactivation of iron complex.

Acetic acid sclerotheraphy of renal cysts

International Nuclear Information System (INIS)

Hong, Hoon Pyo; Oh, Joo Hyeong; Yoon, Yup; Kong, Keun Young; Kim, Eui Jong; Goo, Jang Sung

1998-01-01

Sclerotherapy for renal cysts was performed, using 50% acetic acid as new sclerosing agent. We report the methods and results of this procedure. Fifteen patients underwent sclerotherapy for renal cyst, using 50% acetic acid. Because four patients were lost to follow-up, only 11 of the 15 were included in this study. The renal cysts, including one infected case, were diagnosed by ultrasonograpy (n=3D10) ormagnetic resonance imaging (n=3D1). The patient group consisted of four men and seven women(mean age, 59 years; range, 23-77). At first, the cyst was completely aspirated, and 25 volume% of aspirated volume was replaced with 50% sterile acetic acid through the drainage catheter. During the follwing 20 minutes, the patient changed position, and the acetic acid was then removed from the cyst. Finally, the drainage catheter was removed, after cleaning the cyst with saline. After treatment of infection by antibiotics and catheter drainage for 7 days, sclerotherapy in the infected case followed the same procedure. In order to observe changes in the size of renal cysts and recurrence, all patients were followed up by ultrasound between 2 and 8 months. We defined response to therapy as follows:complete regression as under 5 volume%, partial regression as 5-50 volume% and no response as more than 50 volume% of initial cyst volume. No clinically significant complication occured during the procedures or follow-up periods. All cysts regressed completely during follow-up of 8 months. Complete regression occurred as follows: two cysts at 2 months, seven cysts at 4 months, two cysts at 6 months. Two cysts showed residues at the last follow-up, at 4 and 6 months, respectively. The volume of residual cysts decreased to under 5 volume% of initial volume, however. Completely regressed cysts did not recurr during follow-up. Acetic acid sclerotherapy for renal cysts showed good results, regardless of the dilution of sclerosing agent with residual cyst fluid, and no significant

The influence of surface oxygen and hydroxyl groups on the dehydrogenation of ethylene, acetic acid and hydrogenated vinyl acetate on pure Pd(1 0 0): A DFT study

Energy Technology Data Exchange (ETDEWEB)

Huang, Yanping [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072 (China); Dong, Xiuqin [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Yu, Yingzhe, E-mail: yzhyu@tju.edu.cn [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China); Zhang, Minhua, E-mail: mhzhangtj@163.com [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin (China)

2016-12-01

Highlights: • All dehydrogenation reactions in vinyl acetate synthesis on Pd(1 0 0) were studied. • The energy barriers of the transition state of the three reactions were calculated. • The influence of surface Os and OHs on all dehydrogenation actions was discussed. - Abstract: On the basis of a Langmuir–Hinshelwood-type mechanism, the dehydrogenation of ethylene, acetic acid and hydrogenated vinyl acetate (VAH) on pure Pd(1 0 0) with surface oxygen atoms (Os) and hydroxyl groups (OHs) was studied with density functional theory (DFT) method. Our calculation results show that both Os and OHs can consistently reduce the activation energies of dehydrogenation of ethylene, acetic acid and VAH to some degree with only one exception that OHs somehow increase the activation energy of VAH. Based on Langmuir–Hinshelwood mechanism, the three dehydrogenation reactions in presence of surface Os and OHs are almost consistently favored, compared with the corresponding processes on clean Pd(1 0 0) surfaces, and thus a Langmuir–Hinshelwood-type mechanism may not be excluded beforehand when investigating the microscopic performance of the oxygen-assisted vinyl acetate synthesis on Pd(1 0 0) catalysts.

2-Aryl benzimidazoles: Synthesis, In vitro α-amylase inhibitory activity, and molecular docking study.

Science.gov (United States)

Adegboye, Akande Akinsola; Khan, Khalid Mohammed; Salar, Uzma; Aboaba, Sherifat Adeyinka; Kanwal; Chigurupati, Sridevi; Fatima, Itrat; Taha, Mohammad; Wadood, Abdul; Mohammad, Jahidul Isalm; Khan, Huma; Perveen, Shahnaz

2018-04-25

Despite of many diverse biological activities exhibited by benzimidazole scaffold, it is rarely explored for the α-amylase inhibitory activity. For that purpose, 2-aryl benzimidazole derivatives 1-45 were synthesized and screened for in vitro α-amylase inhibitory activity. Structures of all synthetic compounds were deduced by various spectroscopic techniques. All compounds revealed inhibition potential with IC 50 values of 1.48 ± 0.38-2.99 ± 0.14 μM, when compared to the standard acarbose (IC 50  = 1.46 ± 0.26 μM). Limited SAR suggested that the variation in the inhibitory activities of the compounds are the result of different substitutions on aryl ring. In order to rationalize the binding interactions of most active compounds with the active site of α-amylase enzyme, in silico study was conducted. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

rac-Dichlorido[3-ethoxy-3-(1-ethyl-1H-benzimidazol-2-yl-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole]copper(II

Directory of Open Access Journals (Sweden)

Robert T. Stibrany

2013-02-01

Full Text Available The title complex, [CuCl2(C21H22N4O], contains a bis(benzimidazole unit with a chiral bridgehead C atom that forms part of a tetrahydropyrrole ring fused to one of the benzimidazoles. The chelate angle is 90.45 (9° and the dihedral angle between the essentially planar benzimidazole fragments is 26.68 (9°. The CuII coordination geometry lies approximately midway between tetrahedral and square planar. Overall, each chiral molecule contains six fused rings, and a racemic mixture is formed with symmetry-related enantiomers. In the crystal, C—H...π and C—H...Cl interactions link molecules into a supramolecular chain along the a-axis direction.

Regioselective Synthesis of Some Pyrazole Scaffolds Attached to Benzothiazole and Benzimidazole Moieties

Directory of Open Access Journals (Sweden)

Nabila A. Kheder

2014-01-01

Full Text Available Condensation of 2-(benzothiazol-2-ylacetonitrile (1 or 2-(1-methyl-1H-benzimidazol-2-ylacetonitrile (2 with thiophene-2-carbaldehyde afforded the corresponding acrylonitrile derivatives 3 or 4, respectively. The 1,3-dipolar cycloaddition reaction of the acrylonitrile 3 or 4 with nitrile-imine 6 gave novel pyrazole derivatives pendant to benzothiazole and benzimidazole. The pyrazoline derivative 7 was converted into the corresponding pyrazole derivative 11 via thermal elimination of hydrogen cyanide upon heating in sodium ethoxide solution. The structures of the synthesized products were confirmed by IR, 1H NMR, and mass spectral techniques.

Aminosilanes derived from 1H-benzimidazole-2(3H)-thione

Energy Technology Data Exchange (ETDEWEB)

Palomo-Molina, Juliana [Facultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán-Colima, Coquimatlán Colima 28400 (Mexico); García-Báez, Efrén V. [Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Avenida Acueducto s/n, Barrio La Laguna Ticomán, México DF 07340 (Mexico); Contreras, Rosalinda [Departamento de Química, Centro de Investigación y de Estudios Avanzados del IPN, Apartado Postal 14-740, México DF 07000 (Mexico); Barrio La Laguna Ticomán, México DF 07340 (Mexico); Pineda-Urbina, Kayim; Ramos-Organillo, Angel, E-mail: aaramos@ucol.mx [Facultad de Ciencias Químicas, Universidad de Colima, Carretera Coquimatlán-Colima, Coquimatlán Colima 28400 (Mexico)

2015-08-12

In two trimethylsilyl-substituted 1H-benzimidazole-2(3H)-thiones, noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe{sub 3} groups form helicoidal arrangements in one, and dimerization results in the formation of R{sub s} {sup 2}(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings, in the second compound. Two new molecular structures, namely 1,3-bis(trimethylsilyl)-1H-benzimidazole-2(3H)-thione, C{sub 13}H{sub 22}N{sub 2}SSi{sub 2}, (2), and 1-trimethylsilyl-1H-benzimidazole-2(3H)-thione, C{sub 10}H{sub 14}N{sub 2}SSi, (3), are reported. Both systems were derived from 1H-benzimidazole-2(3H)-thione. Noncovalent C—H⋯π interactions between the centroid of the benzmidazole system and the SiMe{sub 3} groups form helicoidal arrangements in (2). Dimerization of (3) results in the formation of R{sub 2}{sup 2}(8) rings via N—H⋯S interactions, along with parallel π–π interactions between imidazole and benzene rings.

Sol-gel process for preparing YBa2Cu4O8 precursors from Y, Ba, and Cu acidic acetates/ammonia/ascorbic acid systems

International Nuclear Information System (INIS)

Deptula, A.; Lada, W.; Olczak, T.; Goretta, K.C.

1995-08-01

Sols were prepared by addition of ammonia to acidic acetate solutions of Y 3+ , Ba 2+ , and Cu 2+ . Ascorbic acid was added to a part of the sol. The resultant sols were gelled to a shard, a film, or microspheres by evaporation at 60 C or by extraction of water from drops of emulsion suspended in 2-ethylhexanol-1. Addition of ethanol to the sols facilitated the formation of gel films, fabricated by a dipping technique, on glass or silver substrates. At 100 C, gels that were formed in the presence of ascorbic acid were perfectly amorphous, in contrast to the crystalline acetate gels. Conversion of the amorphous ascorbate gels to final products was easier than for the acetate gels. The quality of coatings prepared from ascorbate gels was superior to that of acetate gel coatings

Insights into the mechanism of acetic acid hydrogenation to ethanol on Cu(111) surface

International Nuclear Information System (INIS)

Zhang, Minhua; Yao, Rui; Jiang, Haoxi; Li, Guiming; Chen, Yifei

2017-01-01

Highlights: • The scission of C–OH bond of acetic acid is the rate-determined step in acetic acid hydrogenation to ethanol on Cu(111). • Acetic acid adsorption and reaction barrier of C–OH scission of acetic acid are factors related to acetic acid conversion. • Acetaldehyde adsorption and reaction barriers of O–H formation of C_2–oxygenates are factors related to ethanol selectivity. - Abstract: Density functional theory (DFT) calculations were employed to theoretically explain the reaction mechanism of acetic acid hydrogenation to ethanol on Cu catalyst. The activation barriers of key elementary steps and the adsorption configurations of key intermediates involved in acetic acid hydrogenation on Cu(111) surface were investigated. The results indicated that the direct dissociation of acetic acid to acetyl (CH_3COOH → CH_3CO + OH) is the rate-determined step. The activation barrier of acetic acid scission to acetyl and the adsorption energy of acetic acid are two descriptors which could determine the conversion of acetic acid. The descriptors might have effects on the ethanol selectivity including: the adsorption energy of acetaldehyde and the activation barriers for O−H bond formation of C_2-oxygenates (CH_3CO + H → CH_3COH, CH_3CHO + H → CH_3CHOH and CH_3CH_2O + H → CH_3CH_2OH). These proposed descriptors could be used as references to design new Cu-based catalysts that have excellent catalytic performance.

Omics analysis of acetic acid tolerance in Saccharomyces cerevisiae.

Science.gov (United States)

Geng, Peng; Zhang, Liang; Shi, Gui Yang

2017-05-01

Acetic acid is an inhibitor in industrial processes such as wine making and bioethanol production from cellulosic hydrolysate. It causes energy depletion, inhibition of metabolic enzyme activity, growth arrest and ethanol productivity losses in Saccharomyces cerevisiae. Therefore, understanding the mechanisms of the yeast responses to acetic acid stress is essential for improving acetic acid tolerance and ethanol production. Although 329 genes associated with acetic acid tolerance have been identified in the Saccharomyces genome and included in the database ( http://www.yeastgenome.org/observable/resistance_to_acetic_acid/overview ), the cellular mechanistic responses to acetic acid remain unclear in this organism. Post-genomic approaches such as transcriptomics, proteomics, metabolomics and chemogenomics are being applied to yeast and are providing insight into the mechanisms and interactions of genes, proteins and other components that together determine complex quantitative phenotypic traits such as acetic acid tolerance. This review focuses on these omics approaches in the response to acetic acid in S. cerevisiae. Additionally, several novel strains with improved acetic acid tolerance have been engineered by modifying key genes, and the application of these strains and recently acquired knowledge to industrial processes is also discussed.

Cataluminescence sensor for gaseous acetic acid using a thin film of In2O3

International Nuclear Information System (INIS)

Tao, Y.; Cao, X.; Peng, Y.; Liu, Y.; Zhang, R.

2012-01-01

We report on a cataluminescence sensor for the determination of gaseous acetic acid. It is based on a 60-nm thick sol-gel film of In 2 O 3 on a ceramic support. SEM, XPS and surface profiling were applied for its characterization. It is found that aluminum ions of the ceramic substrate penetrate into the film and produce a synergetic catalytic effect. The sensor displays high sensitivity and specificity for acetic acid, a low detection limit, a wide linear range and a fast response. No (or only very low) interference was observed by formic acid, ammonia, acrolein, benzene, formaldehyde, ethanol, and acetaldehyde. The sensor was successfully applied to the determination of acetic acid in spiked air samples. We also discuss a conceivable mechanism (based on the reaction products) for the cataluminescence resulting from the oxidation reaction on the surface of the sensor film. (author)

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated ...

African Journals Online (AJOL)

GREGORY

2010-09-20

Sep 20, 2010 ... Betulinic acid acetate (BAAC) was most effective than other betulinic acid derivatives. It had most ... blastoma (Schmidt et al., 1997), malignant brain tumor .... 96 well plate and incubated in 37oC, 5% CO2 and 90% humidity.

Degradation of acetic acid with sulfate radical generated by persulfate ions photolysis.

Science.gov (United States)

Criquet, Justine; Leitner, Nathalie Karpel Vel

2009-09-01

The photolysis of S(2)O(8)(2-) was studied for the removal of acetic acid in aqueous solution and compared with the H(2)O(2)/UV system. The SO(4)(-) radicals generated from the UV irradiation of S(2)O(8)(2-) ions yield a greater mineralization of acetic acid than the ()OH radicals. Acetic acid is oxidized by SO(4)(-) radicals without significant formation of intermediate by-products. Increasing system pH results in the formation of ()OH radicals from SO(4)(-) radicals. Maximum acetic acid degradation occurred at pH 5. The results suggest that above this pH, competitive reactions with the carbon mineralized inhibit the reaction of the solute with SO(4)(-) and also ()OH radicals. Scavenging effects of two naturally occurring ions were tested; in contrast to HCO(3)(-) ions, the presence of Cl(-) ions enhances the efficiency of the S(2)O(8)(2-)/UV process towards the acetate removal. It is attributed to the formation of the Cl() radical and its great reactivity towards acetate.

Modification of wheat starch with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures I. Thermophysical and pasting properties.

Science.gov (United States)

Subarić, Drago; Ačkar, Durđica; Babić, Jurislav; Sakač, Nikola; Jozinović, Antun

2014-10-01

The aim of this research was to investigate the influence of modification with succinic acid/acetic anhydride and azelaic acid/acetic anhydride mixtures on thermophysical and pasting properties of wheat starch. Starch was isolated from two wheat varieties and modified with mixtures of succinic acid and acetic anhydride, and azelaic acid and acetic anhydride in 4, 6 and 8 % (w/w). Thermophysical, pasting properties, swelling power, solubility and amylose content of modified starches were determined. The results showed that modifications with mixtures of afore mentioned dicarboxylic acids with acetic anhydride decreased gelatinisation and pasting temperatures. Gelatinisation enthalpy of Golubica starch increased, while of Srpanjka starch decreased by modifications. Retrogradation after 7 and 14 day-storage at 4 °C decreased after modifications of both starches. Maximum, hot and cold paste viscosity of both starches increased, while stability during shearing at high temperatures decreased. % setback of starches modified with azelaic acid/acetic anhydride mixture decreased. Swelling power and solubility of both starches increased by both modifications.

Trapping social wasps (Hymenoptera: Vespidae) with acetic acid and saturated short chain alcohols.

Science.gov (United States)

Landolt, P J; Smithhisler, C S; Reed, H C; McDonough, L M

2000-12-01

Nineteen compounds were evaluated in combination with a solution of acetic acid as baits for trapping the German yellowjacket, Vespula germanica (F.), the western yellowjacket Vespula pensylvanica (Sausssure), and the golden paper wasp Polistes aurifer Saussure. Compounds with three to six carbon chains or branched chains and with a hydroxy functional group were selected for testing based on their similarity to isobutanol. They were compared with isobutanol with acetic acid, which is a known wasp attractant. None of the compounds tested were superior to isobutanol when presented with acetic acid as a lure for these species of wasps. However, traps baited with either the S-(-)- or the racemic mixture of 2-methyl-1-butanol in combination with acetic acid captured similar numbers of both species of yellowjackets, compared with isobutanol with acetic acid. Polistes aurifer responded strongly to the S-(-)-enantiomer and to the racemic mixture of 2-methyl-1-butanol with acetic acid and not to the R-(+)-enantiomer with acetic acid.

Insights into the mechanism of acetic acid hydrogenation to ethanol on Cu(111) surface

Energy Technology Data Exchange (ETDEWEB)

Zhang, Minhua; Yao, Rui; Jiang, Haoxi; Li, Guiming [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin 300072 (China); Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072 (China); Chen, Yifei, E-mail: yfchen@tju.edu.cn [Key Laboratory for Green Chemical Technology of Ministry of Education, R& D Center for Petrochemical Technology, Tianjin University, Tianjin 300072 (China); Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072 (China)

2017-08-01

Highlights: • The scission of C–OH bond of acetic acid is the rate-determined step in acetic acid hydrogenation to ethanol on Cu(111). • Acetic acid adsorption and reaction barrier of C–OH scission of acetic acid are factors related to acetic acid conversion. • Acetaldehyde adsorption and reaction barriers of O–H formation of C{sub 2}–oxygenates are factors related to ethanol selectivity. - Abstract: Density functional theory (DFT) calculations were employed to theoretically explain the reaction mechanism of acetic acid hydrogenation to ethanol on Cu catalyst. The activation barriers of key elementary steps and the adsorption configurations of key intermediates involved in acetic acid hydrogenation on Cu(111) surface were investigated. The results indicated that the direct dissociation of acetic acid to acetyl (CH{sub 3}COOH → CH{sub 3}CO + OH) is the rate-determined step. The activation barrier of acetic acid scission to acetyl and the adsorption energy of acetic acid are two descriptors which could determine the conversion of acetic acid. The descriptors might have effects on the ethanol selectivity including: the adsorption energy of acetaldehyde and the activation barriers for O−H bond formation of C{sub 2}-oxygenates (CH{sub 3}CO + H → CH{sub 3}COH, CH{sub 3}CHO + H → CH{sub 3}CHOH and CH{sub 3}CH{sub 2}O + H → CH{sub 3}CH{sub 2}OH). These proposed descriptors could be used as references to design new Cu-based catalysts that have excellent catalytic performance.

Triphenylamine based benzimidazole and benzothiazole: Synthesis and applications in fluorescent chemosensors and laser dyes

Energy Technology Data Exchange (ETDEWEB)

Yang, Yang [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); University of Chinese Academy of Sciences, Beijing 100039 (China); Li, Bin, E-mail: libinteacher@163.com [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China); Zhang, Liming; Guan, Yunlong [State Key Laboratory of Luminescence and Applications, Changchun Institute of Optics Fine Mechanics and Physics, Chinese Academy of Sciences, Changchun 130033 (China)

2014-01-15

Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. The TPA-benzimidazole chemosensor was tested for a number of metal ions and found to exhibit binding affinity for Fe{sup 3+} and Hg{sup 2+} in acetonitrile, and the fluorescence quenching was achieved through a PET process. The appearance of an isosbestic point in absorption titrations and Job's plot analysis supported 1:1 stoichiometries for Fe{sup 3+} and Hg{sup 2+} ions. Laser experiments showed that under transversal pumping with a Q-switched Nd:YAG (355 nm) laser in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) at 436 nm. -- Highlights: • Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. • The TPA-benzimidazole exhibits binding affinity for Fe{sup 3+} and Hg{sup 2+} in acetonitrile and the fluorescence quenching was achieved through a PET process. • Under transversal pumping at 355 nm in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) in 436 nm.

Triphenylamine based benzimidazole and benzothiazole: Synthesis and applications in fluorescent chemosensors and laser dyes

International Nuclear Information System (INIS)

Yang, Yang; Li, Bin; Zhang, Liming; Guan, Yunlong

2014-01-01

Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. The TPA-benzimidazole chemosensor was tested for a number of metal ions and found to exhibit binding affinity for Fe 3+ and Hg 2+ in acetonitrile, and the fluorescence quenching was achieved through a PET process. The appearance of an isosbestic point in absorption titrations and Job's plot analysis supported 1:1 stoichiometries for Fe 3+ and Hg 2+ ions. Laser experiments showed that under transversal pumping with a Q-switched Nd:YAG (355 nm) laser in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) at 436 nm. -- Highlights: • Triphenylamine based fluorescent dyes TPA-benzimidazole and TPA-benzothiazole have been designed and synthesized. • The TPA-benzimidazole exhibits binding affinity for Fe 3+ and Hg 2+ in acetonitrile and the fluorescence quenching was achieved through a PET process. • Under transversal pumping at 355 nm in toluene, TPA-benzothiazole exhibits efficient and stable amplified spontaneous emissions (ASE) in 436 nm

Receptor-mediated uptake of low density lipoprotein stimulates bile acid synthesis by cultured rat hepatocytes

International Nuclear Information System (INIS)

Junker, L.H.; Davis, R.A.

1989-01-01

The cellular mechanisms responsible for the lipoprotein-mediated stimulation of bile acid synthesis in cultured rat hepatocytes were investigated. Adding 280 micrograms/ml of cholesterol in the form of human or rat low density lipoprotein (LDL) to the culture medium increased bile acid synthesis by 1.8- and 1.6-fold, respectively. As a result of the uptake of LDL, the synthesis of [14C]cholesterol from [2-14C]acetate was decreased and cellular cholesteryl ester mass was increased. Further studies demonstrated that rat apoE-free LDL and apoE-rich high density lipoprotein (HDL) both stimulated bile acid synthesis 1.5-fold, as well as inhibited the formation of [14C]cholesterol from [2-14C]acetate. Reductive methylation of LDL blocked the inhibition of cholesterol synthesis, as well as the stimulation of bile acid synthesis, suggesting that these processes require receptor-mediated uptake. To identify the receptors responsible, competitive binding studies using 125I-labeled apoE-free LDL and 125I-labeled apoE-rich HDL were performed. Both apoE-free LDL and apoE-rich HDL displayed an equal ability to compete for binding of the other, suggesting that a receptor or a group of receptors that recognizes both apolipoproteins is involved. Additional studies show that hepatocytes from cholestyramine-treated rats displayed 2.2- and 3.4-fold increases in the binding of apoE-free LDL and apoE-rich HDL, respectively. These data show for the first time that receptor-mediated uptake of LDL by the liver is intimately linked to processes activating bile acid synthesis

Synthesis and potential cytotoxic activity of some new benzoxazoles, imidazoles, benzimidazoles and tetrazoles.

Science.gov (United States)

Arulmurugan, Subramaniyan; Kavitha, Helen P

2013-06-01

2 The present work deals with the synthesis of some novel heterocyclic compounds such as benzoxazoles , 7, 13 and 19, imidazoles 3, 8, 14 and 20, benzimidazoles 4, 9, 15 and 21, and tetrazoles 10, 16, and 22. The synthesized compounds were characterized by IR, 1H NMR, mass spectrometry and elemental analysis. The compounds were evaluated for cytotoxicity against human cancer cell lines such as MCF-7 (breast cancer) and HT-29 (colon cancer) by the MTT assay method. Among the tested compounds, 4,4'-sulfonylbis(N-(2-(1H-benzo[d]imidazol- -2-yl)ethyl)aniline (9), N-bis(2-(benzo[d]oxazol-2-yl)-ethyl)- 6-phenyl-1,3,5-triazine-2,4-diamine (13), N-bis(2-(1H-benzo[ d]imidazol-2-yl)ethyl)-6-phenyl-1,3,5-triazine-2,4-diamine (15) and N-tris(2-1H-benzo[d]imidazol-2-yl)ethyl)- 1,3,5-triazine-2,4,6-triamine (21) showed potent cytotoxicity.

Complexes of Zn(2) and Cd(2) with 2-methyl-benzimidazole

Energy Technology Data Exchange (ETDEWEB)

Slyusarenko, K F; Artemenko, M V; Pokhodnya, G A; Kononenko, O.M. (Kievskij Tekhnologicheskij Inst. Pishchevoj Promyshlennosti (Ukrainian SSR))

1978-07-01

Coordination compounds of Zn(2) and Cd(2) salts with 2-methyl-benzimidazole (MBI) of 2MBIxMeX/sub 2/ composition, where Me is Zn (2), Cd (2); X is NO/sub 3//sup -/, CH/sub 3/COO/sup -/, CL/sup -/, Br/sup -/, I/sup -/, 1/2SO/sub 4//sup -2/, as well as acid compounds of (MBIH)/sub 2/(CdX/sub 4/) composition, where X is Cl/sup -/, Br/sup -/, I/sup -/, have been obtained and investigated. The synthetized compounds are of white colour, they are stable in air, soluble in alcohols, decomposed by water. Decomposition temperatures for most of the Cd(2) compounds lie above 250 deg C. Infrared spectra and diffractograms of these compounds have been studied. From the curves of radial distribution of atomic density, the ionic nature of the bonding of halide groups in the complexes has been established.

Co-production of furfural and acetic acid from corncob using ZnCl2 through fast pyrolysis in a fluidized bed reactor.

Science.gov (United States)

Oh, Seung-Jin; Jung, Su-Hwa; Kim, Joo-Sik

2013-09-01

Corncob was pyrolyzed using ZnCl2 in a pyrolysis plant equipped with a fluidized bed reactor to co-produce furfural and acetic acid. The effects of reaction conditions, the ZnCl2 content and contacting method of ZnCl2 with corncob on the yields of furfural and acetic acid were investigated. The pyrolysis was performed within the temperature range between 310 and 410°C, and the bio-oil yield were 30-60 wt% of the product. The furfural yield increased up to 8.2 wt%. The acetic acid yield was maximized with a value of 13.1 wt%. A lower feed rate in the presence of ZnCl2 was advantageous for the production of acetic acid. The fast pyrolysis of a smaller corncob sample mechanically mixed with 20 wt% of ZnCl2 gave rise to a distinct increase in furfural. A high selectivity for furfural and acetic acid in bio-oil would make the pyrolysis of corncob with ZnCl2 very economically attractive. Copyright © 2013 Elsevier Ltd. All rights reserved.

Synthesis and characterisation of dioxouranium(VI) and thorium(IV) complexes with 2(2'-pyridyl) 1-methyl benzimidazole

International Nuclear Information System (INIS)

Mohanty, R.R.; Rout, K.C.; Jena, S.; Dash, K.C.

1995-01-01

The ligand 2(2'-pyridyl) 1-methyl benzimidazole (MePB) forms a number of mononuclear complex of the type UO 2 (MePB)X 2 (X = Cl,I,NO 3 ,CH 3 COO,0.5 SO 4 ); UO 2 (MePB) 2 -(NCS) 2 and Th(MEPB) 2 X 4 (X = NO 3 ,NCS,I) and the biheteronuclear complex UO 2 (MePB)HgCl 4 . All these complexes were characterised by elemental analysis, conductivity measurements, thermogravimetric studies and IR, electronic, mass and NMR ( 1 H and 13 C) spectral studies. (author). 5 refs

Study of alkaline-earth element complexes in anhydrous acetic acid

International Nuclear Information System (INIS)

Petit, N.

1968-10-01

We have studied the complexes of alkaline-earth elements in anhydrous acetic acid. Using glass-electrode potentiometry we have studied the titration of alkaline earth acetates with perchloric acid which is the strongest acid in anhydrous acetic acid. These titrations have shown that the basic strength of these acetates increases as follows: Mg 4 ); the mixed acetate-acid sulfate complex of barium: Ba (OAc)(HSO 4 ); the mixed acetate-chloride of barium: Ba (OAc)(Cl). (author) [fr

Effect of substituted benzimidazoles on acid secretion in isolated and enriched guinea pig parietal cells.

Science.gov (United States)

Sewing, K F; Harms, P; Schulz, G; Hannemann, H

1983-01-01

The inhibitory effect of the three benzimidazole derivatives timoprazole, picoprazole, and omeprazole on histamine and dbcAMP stimulated 14C-aminopyrine accumulation (= H+ secretion) has been studied in isolated and enriched guinea-pig parietal cells. All compounds tested inhibited H+ secretion in a concentration dependent manner with IC50 values of 8.5 +/- 1.9 mumol/l for timoprazole, 3.9 +/- 0.7 mumol/l for picoprazole, and 0.13 +/- 0.03 mumol/l for omeprazole. The IC50 of timoprazole, when dbcAMP was used as a stimulus, did not differ significantly from that of histamine stimulation. The type of inhibition was of a non-competitive nature. The full acid response to histamine after temporary exposure of the cells to the benzimidazoles could be restored by washing the cells twice; this suggests that the inhibition is reversible. The data - among others - indicate that the properties of the benzimidazoles described here would allow these compounds to be used as effective antisecretagogues. PMID:6303916

Synthesis and characterization of related substances of Azilsartan Kamedoxomil

Directory of Open Access Journals (Sweden)

Maddi N. V. D. Harikiran

2017-03-01

Full Text Available Azilsartan Kamedoxomil is an AT1-subtype angiotensin II receptor blocker (ARB. During the laboratory synthesis of Azilsartan Kamedoxomil, four related substances of Azilsartan Kamedoxomil were observed and identified. These were 2-Ethoxy-3-[[4-[2- [4-[(5-methyl-2-oxo-1,3-dioxol-4-ylmethyl]-5-oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylic acid (azilsartan N-medoxomil, 9, (5-methyl-2-oxo- 1,3-dioxol-4-ylmethyl 2-ethoxy-3-[[4-[2-[4-[(5-methyl-2-oxo-1,3-dioxol-4-ylmethyl]-5- oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylate (azilsartan dimedoxomil, 10, (5-methyl-2-oxo-1,3-dioxo-4-ylmethyl 1-[2’-(4,5-dihydro-5-oxo-4H- 1,2,4-oxadiazol-3-ylbiphenyl-4-yl]methyl]-2-methoxy-1H-benzimidazole-7-carboxylate (methoxy analogue of azilsartan medoxomil, 11, Methyl 1-((2’-amidobiphenyl-4-yl methyl-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (amide methyl ester, 12. The present work describes the origin, synthesis and characterization of these related substances.

Effect of acetic acid on wet patterning of copper/molybdenum thin films in phosphoric acid solution

International Nuclear Information System (INIS)

Seo, Bo.-Hyun; Lee, Sang-Hyuk; Park, In-Sun; Seo, Jong Hyun; Choe, HeeHwan; Jeon, Jae-Hong; Hong, Munpyo; Lee, Yong Uk; Winkler, Joerg

2011-01-01

Copper metallization is a key issue for high performance thin film transistor (TFT) technology. A phosphoric acid based copper etchant is a potentially attractive alternative to the conventional hydrogen peroxide based etchant due to its longer-life expectancy time and higher stability in use. In this paper, it is shown that amount of the acetic acid in the phosphoric based copper etchant plays an important role in controlling the galvanic reaction between the copper and the molybdenum. As the concentration of acetic acid in the phosphoric mixture solution increased from 0 M to 0.4 M, the measured galvanic current density dropped from 32 mA/cm 2 to 26 mA/cm 2 , indicating that the acetic acid induces the lower galvanic reaction between the copper and the molybdenum in the solution. From the XPS analysis, with the addition of the acetic acid, the thickness of the protective MoO 2 passive film covering the molybdenum surface grew and the dissolution rate of the molybdenum thin film decreased. However, the dissolution rate of the copper thin film increased as the concentration of acetic acid in the mixture solution increased.

Effect of acetic acid on wet patterning of copper/molybdenum thin films in phosphoric acid solution

Energy Technology Data Exchange (ETDEWEB)

Seo, Bo.-Hyun; Lee, Sang-Hyuk; Park, In-Sun [Department of Materials Engineering, Korea Aerospace University, Hwajeon, Goyang, Gyonggi-do 412-791 (Korea, Republic of); Seo, Jong Hyun, E-mail: jhseo@kau.ac.kr [Department of Materials Engineering, Korea Aerospace University, Hwajeon, Goyang, Gyonggi-do 412-791 (Korea, Republic of); Choe, HeeHwan; Jeon, Jae-Hong [School of Electronics, Telecommunications and Computer Engineering, Korea Aerospace University, Hwajeon, Goyang, Gyonggi-do 412-791 (Korea, Republic of); Hong, Munpyo [Display and Semiconductor Physics, Korea University (Korea, Republic of); Lee, Yong Uk [PETEC (The Printable Electronics Technology Centre) (United Kingdom); Winkler, Joerg [PLANSEE Metal GmbH, Metallwerk-Plansee-Str. 71A-6600, Reutte (Austria)

2011-08-01

Copper metallization is a key issue for high performance thin film transistor (TFT) technology. A phosphoric acid based copper etchant is a potentially attractive alternative to the conventional hydrogen peroxide based etchant due to its longer-life expectancy time and higher stability in use. In this paper, it is shown that amount of the acetic acid in the phosphoric based copper etchant plays an important role in controlling the galvanic reaction between the copper and the molybdenum. As the concentration of acetic acid in the phosphoric mixture solution increased from 0 M to 0.4 M, the measured galvanic current density dropped from 32 mA/cm{sup 2} to 26 mA/cm{sup 2}, indicating that the acetic acid induces the lower galvanic reaction between the copper and the molybdenum in the solution. From the XPS analysis, with the addition of the acetic acid, the thickness of the protective MoO{sub 2} passive film covering the molybdenum surface grew and the dissolution rate of the molybdenum thin film decreased. However, the dissolution rate of the copper thin film increased as the concentration of acetic acid in the mixture solution increased.

Enantioselective conjugate addition of silylketene acetals to beta-enamidomalonates. Synthesis of beta-amino acid derivatives.

Science.gov (United States)

Sibi, Mukund P; Chen, Jianxie

2002-08-22

[reaction: see text] Conjugate addition of silylketene acetals or enolsilanes to enamidomalonates proceeds with excellent chemical efficiency and good selectivity using Cu(OTf)2 and a chiral bisoxazoline. The effect of the Lewis acid, ligand, the N-acyl substituent, and the nucleophile on yield and selectivity for the addition product have been evaluated.

Depressing effect of phenoxyl acetic acids on flotation of minerals containing Ca2+/Mg2+ gangues

Institute of Scientific and Technical Information of China (English)

无

2007-01-01

Phenoxyl acetic acids were applied to determine their depressing effect on minerals containing Ca2+/Mg2+ gangues. Calcite,mixture of calcite and fluorite, and nickel ore were used in the flotation. And the depression mechanism was studied by the determination of contact angle, zeta potential, adsorptive capacity of collector, and IR analysis as well. It is found that 0.1 mmol/L of phenoxyl acetic acid derived from pyrogallol or gallic acid exhibits strong depressing ability on calcite in almost zero yields at pH value of 9.8, and calcite can be depressed in the flotation of calcite/fluorite mixture for approximate 87% yield of fluorite. The flotation result of practical nickel ore containing serpentine indicates that these two depressants may also show better depression performance to serpentine than traditional depressants such as sodium fluosilicate and carboxylmethyl cellulose. Analysis for the depression mechanism reveals that there exists strong chemical interaction between the depressants and minerals.

Proteome analysis of Acetobacter pasteurianus during acetic acid fermentation.

Science.gov (United States)

Andrés-Barrao, Cristina; Saad, Maged M; Chappuis, Marie-Louise; Boffa, Mauro; Perret, Xavier; Ortega Pérez, Ruben; Barja, François

2012-03-16

Acetic acid bacteria (AAB) are Gram-negative, strictly aerobic microorganisms that show a unique resistance to ethanol (EtOH) and acetic acid (AcH). Members of the Acetobacter and Gluconacetobacter genera are capable of transforming EtOH into AcH via the alcohol dehydrogenase (ADH) and aldehyde dehydrogenase (ALDH) enzymes and are used for the industrial production of vinegar. Several mechanisms have been proposed to explain how AAB resist high concentrations of AcH, such as the assimilation of acetate through the tricarboxylic acid (TCA) cycle, the export of acetate by various transporters and modifications of the outer membrane. However, except for a few acetate-specific proteins, little is known about the global proteome responses to AcH. In this study, we used 2D-DIGE to compare the proteome of Acetobacter pasteurianus LMG 1262(T) when growing in glucose or ethanol and in the presence of acetic acid. Interesting protein spots were selected using the ANOVA p-value of 0.05 as threshold and 1.5-fold as the minimal level of differential expression, and a total of 53 proteins were successfully identified. Additionally, the size of AAB was reduced by approximately 30% in length as a consequence of the acidity. A modification in the membrane polysaccharides was also revealed by PATAg specific staining. Copyright © 2011 Elsevier B.V. All rights reserved.

Obestatin Accelerates the Healing of Acetic Acid-Induced Colitis in Rats

Directory of Open Access Journals (Sweden)

Aleksandra Matuszyk

2016-01-01

Full Text Available Obestatin, a 23-amino acid peptide derived from the proghrelin, has been shown to exhibit some protective and therapeutic effects in the gut. The aim of present study was to determine the effect of obestatin administration on the course of acetic acid-induced colitis in rats. Materials and Methods. Studies have been performed on male Wistar rats. Colitis was induced by a rectal enema with 3.5% acetic acid solution. Obestatin was administered intraperitoneally twice a day at a dose of 8 nmol/kg, starting 24 h after the induction of colitis. Seven or 14 days after the induction of colitis, the healing rate of the colon was evaluated. Results. Treatment with obestatin after induction of colitis accelerated the healing of colonic wall damage and this effect was associated with a decrease in the colitis-evoked increase in mucosal activity of myeloperoxidase and content of interleukin-1β. Moreover, obestatin administration significantly reversed the colitis-evoked decrease in mucosal blood flow and DNA synthesis. Conclusion. Administration of exogenous obestatin exhibits therapeutic effects in the course of acetic acid-induced colitis and this effect is related, at least in part, to the obestatin-evoked anti-inflammatory effect, an improvement of local blood flow, and an increase in cell proliferation in colonic mucosa.

Acetic acid activates the AMP-activated protein kinase signaling pathway to regulate lipid metabolism in bovine hepatocytes.

Directory of Open Access Journals (Sweden)

Xinwei Li

Full Text Available The effect of acetic acid on hepatic lipid metabolism in ruminants differs significantly from that in monogastric animals. Therefore, the aim of this study was to investigate the regulation mechanism of acetic acid on the hepatic lipid metabolism in dairy cows. The AMP-activated protein kinase (AMPK signaling pathway plays a key role in regulating hepatic lipid metabolism. In vitro, bovine hepatocytes were cultured and treated with different concentrations of sodium acetate (neutralized acetic acid and BML-275 (an AMPKα inhibitor. Acetic acid consumed a large amount of ATP, resulting in an increase in AMPKα phosphorylation. The increase in AMPKα phosphorylation increased the expression and transcriptional activity of peroxisome proliferator-activated receptor α, which upregulated the expression of lipid oxidation genes, thereby increasing lipid oxidation in bovine hepatocytes. Furthermore, elevated AMPKα phosphorylation reduced the expression and transcriptional activity of the sterol regulatory element-binding protein 1c and the carbohydrate responsive element-binding protein, which reduced the expression of lipogenic genes, thereby decreasing lipid biosynthesis in bovine hepatocytes. In addition, activated AMPKα inhibited the activity of acetyl-CoA carboxylase. Consequently, the triglyceride content in the acetate-treated hepatocytes was significantly decreased. These results indicate that acetic acid activates the AMPKα signaling pathway to increase lipid oxidation and decrease lipid synthesis in bovine hepatocytes, thereby reducing liver fat accumulation in dairy cows.

Halide/pseudohalide complexes of cadmium(II) with benzimidazole: Synthesis, crystal structures and fluorescence properties

Science.gov (United States)

Zhao, Hai-Yan; Yang, Fu-Li; Li, Na; Wang, Xiao-Jing

2017-11-01

Two new dinuclear Cd(II) complexes, [CdL1Cl2]2·H2O (1) and [CdL1(N3)2]2·CH3OH (2) and one dicyanamide bridged one-dimensional polynuclear network [CdL1(μ1,5-dca)dca]n (3) of the potentially tridentate NNN-donor Schiff base 2-((1H-benzimidazol-2-yl-ethylimino)-methyl)pyridine (L1) and another dinucler Cd(II) complex [CdL2Cl(dca)]2 (4) of a similar NNN-donor Schiff base ligand 2-((1H-benzimidazol-2-yl-propylimino)-methyl)pyridine (L2), have been synthesized and characterized by elemental analyses, IR and single crystal X-ray crystallography. The ligands L1 and L2 are [1 + 1] condensation products of pyridine-2-carbaldehyde with 2-aminoethyl-1H-benzimidazole and 2-aminopropyl-1H-benzimidazole, respectively. In the complexes 1 and 4 the two Cd(II) centers are held together by the bridged chloride ligands, while in 2 the two Cd(II) centers are bridged by μ1,1-azide ions. Complex 3 has a one-dimensional infinite chain structure in which Cd(II) ions are bridged by single dicyanamide groups in end-to-end fashion. All the metal centers have a distorted octahedral geometry and H-bonding or π⋯π interactions are operative to bind the complex units in the solid state. Furthermore, these complexes have been investigated by thermogravimetric analyses and fluorescence spectra.

GAS-PHASE SYNTHESIS OF PRECURSORS OF INTERSTELLAR GLYCINE: A COMPUTATIONAL STUDY OF THE REACTIONS OF ACETIC ACID WITH HYDROXYLAMINE AND ITS IONIZED AND PROTONATED DERIVATIVES

Energy Technology Data Exchange (ETDEWEB)

Barrientos, Carmen; Redondo, Pilar; Largo, Laura; Rayon, Victor M.; Largo, Antonio, E-mail: alargo@qf.uva.es [Departamento de Quimica Fisica y Quimica Inorganica, Facultad de Ciencias, Universidad de Valladolid, 47005 Valladolid (Spain)

2012-04-01

A computational study of the reactions of hydroxylamine and its ionized and protonated derivatives with acetic acid is provided. The reaction of neutral hydroxylamine with acetic acid, despite being clearly exothermic, involves a very large energy barrier. The reaction of ionized hydroxylamine with acetic acid is also clearly exothermic, but again a significant energy barrier is found (around 24 kcal mol{sup -1} at the CCSD(T) level). The reaction of the most stable protonated isomer of hydroxylamine, NH{sub 3}OH{sup +}, with acetic acid also involves a high barrier (more than 27 kcal mol{sup -1} at the CCSD(T) level). Only the higher energy isomer, NH{sub 2}OH{sup +}{sub 2}, leads to a sensibly lower energy barrier (about 2.3 kcal mol{sup -1} at the CCSD(T) level). Nevertheless, an estimate of the reaction coefficient at low temperatures such as those reigning in the interstellar medium gives very low values. Therefore, it seems that precursors of interstellar glycine could not be efficiently produced from the reactions of hydroxylamine-derived ions with acetic acid.

GAS-PHASE SYNTHESIS OF PRECURSORS OF INTERSTELLAR GLYCINE: A COMPUTATIONAL STUDY OF THE REACTIONS OF ACETIC ACID WITH HYDROXYLAMINE AND ITS IONIZED AND PROTONATED DERIVATIVES

International Nuclear Information System (INIS)

Barrientos, Carmen; Redondo, Pilar; Largo, Laura; Rayón, Víctor M.; Largo, Antonio

2012-01-01

A computational study of the reactions of hydroxylamine and its ionized and protonated derivatives with acetic acid is provided. The reaction of neutral hydroxylamine with acetic acid, despite being clearly exothermic, involves a very large energy barrier. The reaction of ionized hydroxylamine with acetic acid is also clearly exothermic, but again a significant energy barrier is found (around 24 kcal mol –1 at the CCSD(T) level). The reaction of the most stable protonated isomer of hydroxylamine, NH 3 OH + , with acetic acid also involves a high barrier (more than 27 kcal mol –1 at the CCSD(T) level). Only the higher energy isomer, NH 2 OH + 2 , leads to a sensibly lower energy barrier (about 2.3 kcal mol –1 at the CCSD(T) level). Nevertheless, an estimate of the reaction coefficient at low temperatures such as those reigning in the interstellar medium gives very low values. Therefore, it seems that precursors of interstellar glycine could not be efficiently produced from the reactions of hydroxylamine-derived ions with acetic acid.

Aluminium, extractable from soil samples by the acid ammonium acetate soil-testing method

Directory of Open Access Journals (Sweden)

Osmo Mäkitie

1968-05-01

Full Text Available The extractant, 0.5 M acetic acid –0.5 M ammonium acetate at pH 4.65, which is used in soil-testing, extracts relatively high amounts of aluminium from acid soils. The mean values of acetate-extractable aluminium at pH 4.65, 1.75 meq Al/100 g of soil, and of exchangeable aluminium (M KCI extraction, 0.41 meq Al were obtained from a material of 30 samples of acid soils (Table 2. Several other acetic acid ammonium acetate extractants, from M acetic acid to M ammonium acetate solution were also used for studying the extractability of soil aluminium. The soil-testing extractant can be used for the estimation of the soluble amounts of aluminium in acid soils, however, further studies are needed for a better interpretation of the ammonium acetate extractable (at pH 4.65 aluminium in our soils.

Proton-conducting membranes based on benzimidazole-containing sulfonated poly(ether ether ketone) compared with their carboxyl acid form

Energy Technology Data Exchange (ETDEWEB)

Li, Hongtao; Wu, Jing; Zhao, Chengji; Zhang, Gang; Zhang, Yang; Shao, Ke; Xu, Dan; Lin, Haidan; Han, Miaomiao; Na, Hui [Alan G MacDiarmid Institute, College of Chemistry, Jilin University, Changchun 130012 (China)

2009-10-15

A series of sulfonated poly(ether ether ketone) containing pendant carboxyl (C-SPEEKs) have been synthesized using a nucleophilic polycondesation reaction. A condensation reaction between 1,2-diaminobenzene and carboxyl resulted in a new series of copolymers containing benzimidazole groups (SPEEK-BIms). The expected structures of the sulfonated copolymers are confirmed by {sup 1}H NMR. The dependence of ion exchange capacity, water uptake, proton conductivity and methanol diffusion coefficient of SPEEK-BIm membranes has been studied and compared with their carboxyl acid form. The results suggest that the introduction of benzimidazole groups may be responsible for many excellent properties of the membranes for fuel cell. It is noticeable that the markedly improved oxidative stability is benefit for the application of membrane. (author)

Efficient fluorescent deep-blue and hybrid white emitting devices based on carbazole/benzimidazole compound

KAUST Repository

Yang, Xiaohui; Zheng, Shijun; Bottger, Rebecca; Chae, HyunSik; Tanaka, Takeshi; Li, Sheng; Mochizuki, Amane; Jabbour, Ghassan E.

2011-01-01

We report the synthesis, photophysics, and electrochemical characterization of carbazole/benzimidazole-based compound (Cz-2pbb) and efficient fluorescent deep-blue light emitting devices based on Cz-2pbb with the peak external quantum efficiency

Co-administration of α-lipoic acid and cyclosporine aggravates colon ulceration of acetic acid-induced ulcerative colitis via facilitation of NO/COX-2/miR-210 cascade

Energy Technology Data Exchange (ETDEWEB)

El-Gowelli, Hanan M., E-mail: dr_Hanan_el_gowali@hotmail.com; Saad, Evan I.; Abdel-Galil, Abdel-Galil A.; Ibrahim, Einas R.

2015-11-01

In this work, α-lipoic acid and cyclosporine demonstrated significant protection against acetic acid-induced ulcerative colitis in rats. We proposed that α-lipoic acid and cyclosporine co-administration might modulate their individual effects. Induction of ulcerative colitis in rats was performed by intra-rectal acetic acid (5% v/v) administration for 3 consecutive days. Effects of individual or combined used of α-lipoic acid (35 mg/kg ip) or cyclosporine (5 mg/kg sc) for 6 days starting 2 days prior to acetic acid were assessed. Acetic acid caused colon ulceration, bloody diarrhea and weight loss. Histologically, there was mucosal atrophy and inflammatory cells infiltration in submucosa, associated with depletion of colon reduced glutathione, superoxide dismutase and catalase activities and elevated colon malondialdehyde, serum C-reactive protein (C-RP) and tumor necrosis factor-α (TNF-α). Colon gene expression of cyclooxygenase-2 and miR-210 was also elevated. These devastating effects of acetic acid were abolished upon concurrent administration of α-lipoic acid. Alternatively, cyclosporine caused partial protection against acetic acid-induced ulcerative colitis. Cyclosporine did not restore colon reduced glutathione, catalase activity, serum C-RP or TNF-α. Unexpectedly, co-administration of α-lipoic acid and cyclosporine aggravated colon ulceration. Concomitant use of α-lipoic acid and cyclosporine significantly increased nitric oxide production, cyclooxygenase-2 and miR-210 gene expression compared to all other studied groups. The current findings suggest that facilitation of nitric oxide/cyclooxygenase-2/miR-210 cascade constitutes, at least partially, the cellular mechanism by which concurrent use of α-lipoic acid and cyclosporine aggravates colon damage. Collectively, the present work highlights the probable risk of using α-lipoic acid/cyclosporine combination in ulcerative colitis patients. - Highlights: • Lipoic acid is more effective than

The obtaining of iron acetate from processed iron comprising catalyst of ammonia synthesis

International Nuclear Information System (INIS)

Mansurov, M.M.; Lugovenko, A.N.; Mirzoeva, M.M.

1993-01-01

Present article is devoted to obtaining of iron acetate from processed iron comprising catalyst of ammonia synthesis. The method of synthesis of iron acetate from processed iron comprising catalyst of ammonia synthesis was elaborated. The structure of complex was determined.

Recovery of arabinan in acetic acid-catalyzed hydrothermal pretreatment on corn stover

DEFF Research Database (Denmark)

Xu, Jian; Hedegaard, Mette Christina; Thomsen, Anne Belinda

2009-01-01

Acetic acid-catalyzed hydrothermal pretreatment was done on corn stover under 195 °C, 15 min with the acetic acid ranging from 5 × 10−3 to 0.2 g g−1 corn stover. After pretreatment, the water-insoluble solids (WISs) and liquors were collected respectively. Arabinan recoveries from both WIS...... and liquors were investigated. The results indicate that there was no detectable arabinan left in the WIS when the acetic acid of 0.1 and 0.2 g g−1 corn stover were used in the pretreatment. The arabinan contents in the other WISs were not more than 10%. However, the arabinan found in the liquors...... was not covering the amount of arabinan released from the raw corn stover. For the arabinan recovery from liquor fractions, the highest of 43.57% was obtained by the pretreatment of acetic acid of 0.01 g g−1 of corn stover and the lowest was only 26.77% when the acetic acid of 0.2 g g−1 corn stover was used...

Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl] acetic acids, 2-[3-(1-adamantyl)-4-substituted-5-thioxo-1,2,4-triazolin-1-yl]propionic acids and related derivatives.

Science.gov (United States)

Al-Deeb, Omar A; Al-Omar, Mohamed A; El-Brollosy, Nasser R; Habib, Elsayed E; Ibrahim, Tarek M; El-Emam, Ali A

2006-01-01

The reaction of 3-(1-adamantyl)-4-substituted-1,2,4-triazoline-5-thiones 3a-g with sodium chloroacetate, in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivatives 4a-g. The interaction of 3a-g with ethyl 2-bromopropionate in acetone, in the presence of potassium carbonate, yielded the corresponding N1-ethyl propionate derivatives 5a-g, which upon hydrolysis with aqueous sodium hydroxide afforded the corresponding propionic acid derivatives 6a-g. Similarly, the reaction of 3-(1-adamantyl)-4-amino-1,2,4-triazoline-5-thione 7 with sodium chloroacetate in ethanolic sodium hydroxide yielded the corresponding N1-acetic acid derivative 8. On the other hand, the reaction of 2-(1-adamantyl)-1,3,4-oxadiazoline-5-thione 9 with sodium chloroacetate yielded the corresponding S-acetic acid derivative 10. Compounds 4a-g, 5b, 5c, 5g, 6a-g, 8 and 10 were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Several derivatives produced good or moderate activities particularly against Bacillus subtilis. In addition, the in vivo anti-inflammatory activities of these compounds were determined using the carrageenin-induced paw oedema method in rats. Compounds 4a, 4b, 4e, 4f, 6f, 6g and 10 produced good dose-dependent anti-inflammatory activities.

Benzimidazole grafted polybenzimidazoles for proton exchange membrane fuel cells

DEFF Research Database (Denmark)

Yang, Jingshuai; Aili, David; Li, Qingfeng

2013-01-01

High molecular weight polybenzimidazole (PBI) was synthesized and grafted with benzimidazole pendant groups. The high molecular weight of PBI resulted in good film-forming properties and superior tensile strength. With a phosphoric acid doping level (ADL) of 13.1, a tensile strength of 16 MPa...... was achieved at room temperature. Grafting of benzimidazole moieties onto the PBI macromolecular chain introduced additional basic sites which allowed the membrane to achieve higher phosphoric acid uptakes. A molar acid conductivity, defined as the specific conductivity of each mole of doping acid...

Acetic acid removal from corn stover hydrolysate using ethyl acetate and the impact on Saccharomyces cerevisiae bioethanol fermentation.

Science.gov (United States)

Aghazadeh, Mahdieh; Ladisch, Michael R; Engelberth, Abigail S

2016-07-08

Acetic acid is introduced into cellulose conversion processes as a consequence of composition of lignocellulose feedstocks, causing significant inhibition of adapted, genetically modified and wild-type S. cerevisiae in bioethanol fermentation. While adaptation or modification of yeast may reduce inhibition, the most effective approach is to remove the acetic acid prior to fermentation. This work addresses liquid-liquid extraction of acetic acid from biomass hydrolysate through a pathway that mitigates acetic acid inhibition while avoiding the negative effects of the extractant, which itself may exhibit inhibition. Candidate solvents were selected using simulation results from Aspen Plus™, based on their ability to extract acetic acid which was confirmed by experimentation. All solvents showed varying degrees of toxicity toward yeast, but the relative volatility of ethyl acetate enabled its use as simple vacuum evaporation could reduce small concentrations of aqueous ethyl acetate to minimally inhibitory levels. The toxicity threshold of ethyl acetate, in the presence of acetic acid, was found to be 10 g L(-1) . The fermentation was enhanced by extracting 90% of the acetic acid using ethyl acetate, followed by vacuum evaporation to remove 88% removal of residual ethyl acetate along with 10% of the broth. NRRL Y-1546 yeast was used to demonstrate a 13% increase in concentration, 14% in ethanol specific production rate, and 11% ethanol yield. This study demonstrated that extraction of acetic acid with ethyl acetate followed by evaporative removal of ethyl acetate from the raffinate phase has potential to significantly enhance ethanol fermentation in a corn stover bioethanol facility. © 2016 American Institute of Chemical Engineers Biotechnol. Prog., 32:929-937, 2016. © 2016 American Institute of Chemical Engineers.

Synthesis, crystal structure and properties of [Co(L2](ClO42 (L=1,3-bis(1H-benzimidazol-2-yl-2-oxapropane

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Tavman Aydin

2015-01-01

Full Text Available The reaction of 1,3-bis(1H-benzimidazol-2-yl-2-oxapropane (L with Co(ClO42•6H2O in absolute ethanol produces di[1,3-bis(1H-benzimidazol-2-yl-2-oxapropane-k2N,N’]cobalt(IIdiperchlorate chelate complex ([Co(L2](ClO42, 1. The complex 1 was characterized by elemental analysis, magnetic moment, molar conductivity, thermogravimetric analysis, FT-IR, UV-visible, mass spectrometry, and its solid state structure was determined by single crystal X-ray diffraction. According to the thermogravimetric analysis data, there is no any water coordinated or uncoordinated in 1 as well as elemental analysis. The complex 1 has 1:2 M:L ionic characteristic according to the molar conductivity. In the complex, the distances between the cobalt and the ethereal oxygen atoms (Co1-O2: 2.805(3; Co2-O1: 2.752(2 Å show the semi-coordination bonding and the Co(II ion is six-coordinated with a N4O2 ligand set, resulting in a distorted octahedron.

A convergent approach to the total synthesis of telmisartan via a Suzuki cross-coupling reaction between two functionalized benzimidazoles.

Science.gov (United States)

Martin, Alex D; Siamaki, Ali R; Belecki, Katherine; Gupton, B Frank

2015-02-06

A direct and efficient total synthesis has been developed for telmisartan, a widely prescribed treatment for hypertension. This approach brings together two functionalized benzimidazoles using a high-yielding Suzuki reaction that can be catalyzed by either a homogeneous palladium source or graphene-supported palladium nanoparticles. The ability to perform the cross-coupling reaction was facilitated by the regio-controlled preparation of the 2-bromo-1-methylbenzimidazole precursor. This convergent approach provides telmisartan in an overall yield of 72% while circumventing many issues associated with previously reported processes.

Synthesis of 2-Diethyl- and 2-Diisopropylaminoethanesulfonic Acids

National Research Council Canada - National Science Library

Hsu, Fu-Lian

1997-01-01

Methods for the synthesis of 2-diethyl- and diisopropylaminoethanesulfonic acids have been developed by the reaction of the corresponding 2-aminoethyl chloride hydrochloride and sodium sulfite in water at 110 deg C...

Synthesis and NMR spectral studies if some nucleosides and their analoges

International Nuclear Information System (INIS)

Ansari, F.L.; Awan, H.S.; Kazmi, N.A.

1995-01-01

Massive efforts have been extended towards the analysis of nucleosides due mainly to their applications in the field of medicine. Present work describes two methods for the synthesis of nucleosides and their analogues. The first method involves the use of phase transfer catalysis for the glycosidation of benzimidazoles. The reaction of 2,3,5-tri-o-benzoyl-beta -d-arabinofuranosyl chloride with benzimidazole and 2 (alpha-hydroxyethyl) benzimidazole in the presence of tetrabutylammoniumhydroensulfide led to the synthesis of nucleosides respectively. Likewise the coupling of 1,2:4, 6-di-O-isopropylidene-3-chloro-alpha-D-fructofurano side with benzimidazole led to the desired product. The second method involves a triflate mediated coupling of benzyl-2,3-anhydro-4-O-triflyl-beta-L-ribopyranoside with benzimidazole which led to the facile displacement of the triflyl group with benzimidazole resulting in the synthesis of nucleoside. However, an attempt towards the coupling of 1,2:5,6-di-O-isopropylidene-3-O-triflyl-alpha-D-glucofuranoside with benzimidazole does not led to the desired coupling, instead an unusual conversion of the triflate ester to mesitylate ester of the sugar appears to have been taken place. (author)

The behaviour of tungsten electrodes in a mixture of acetic acid and acetic anhydride

International Nuclear Information System (INIS)

Pastor, T.J.; Vajgand, V.H.

1976-01-01

Tungsten electrodes have advantageously been used for potentiometric end-point detection in perchloric acid titration of bases in a mixture of acetic acid and acetic anhydride. They have also given good results in biamperometric detection of the equivalence point in continuous coulometric titration of small quantities of bases and acids in the same solvent. Tungsten electrodes in the presence of quinhydrone behave like platinum electrodes, but in biamperometric end-point determination in the absence of quinhydrone it is better to remove the oxide layer from their surface. Some other factors affecting their behaviour have also been studied. Errors in determination do not exceed +-2% even in titration of very small quantities of substances. (author)

Polybenzimidazole Membranes Containing Benzimidazole Side Groups for High Temprature Polymer Electrolyte Membrane Fuel Cells

DEFF Research Database (Denmark)

Yang, Jingshuai; Li, Xueyuan; Xu, Yizin

2013-01-01

Polybenzimidazole (PBI) with a high molecular weight of 69,000 was first synthesized. It was afterwards grafted with benzimidazole pendant groups on the backbones. The acid doped benzimidaozle grafted PBI membranes were investigated and characterized including fuel cell tests at elevated temperat......Polybenzimidazole (PBI) with a high molecular weight of 69,000 was first synthesized. It was afterwards grafted with benzimidazole pendant groups on the backbones. The acid doped benzimidaozle grafted PBI membranes were investigated and characterized including fuel cell tests at elevated...... temperatures without humidification. At an acid doping level of 13.1 mol H3PO4 per average molar repeat unit, the PBI membranes with a benzimidazole grafting degree of 10.6% demonstrated a conductivity of 0.15 S cm-1 and a H2-air fuel cell peak power density of 378 mW cm-2 at 180 oC at ambient pressure without...

[Physiological response to acetic acid stress of Acetobacter pasteuranus during vinegar fermentation].

Science.gov (United States)

Qi, Zhengliang; Yang, Hailin; Xia, Xiaole; Wang, Wu; Leng, Yunwei; Yu, Xiaobin; Quan, Wu

2014-03-04

The aim of the study is to propose a dynamic acetic acid resistance mechanism through analysis on response of cellular morphology, physiology and metabolism of A. pasteurianus CICIM B7003 during vinegar fermentation. Vinegar fermentation was carried out in a Frings 9 L acetator by strain B7003 and cultures were sampled at different cellular growth phases. Simultaneously, percentage of capsular polysaccharide versus dry cells weight, ratio of unsaturated fatty acids to saturated fatty acids, transcription of acetic acid resistance genes, activity of alcohol respiratory chain enzymes and ATPase were detected for these samples to assay the responses of bacterial morphology, physiology and metabolism. When acetic acid was existed, no obvious capsular polysaccharide was secreted by cells. As vinegar fermentation proceeding, percentage of capsular polysaccharide versus dry cells weight was reduced from 2.5% to 0.89%. Ratio of unsaturated fatty acids to saturated fatty acids was increased obviously which can improve membrane fluidity. Also transcription level of acetic acid resistance genes was promoted. Interestingly, activity of alcohol respiratory chain and ATPase was not inhibited but promoted obviously with acetic acid accumulation which could provide enough energy for acetic acid resistance mechanism. On the basis of the results obtained from the experiment, A. pasteurianus CICIM B7003 relies mainly on the cooperation of changes of extracellular capsular polysaccharide and membrane fatty acids, activation of acid resistance genes transcription, enhancement of activity of alcohol respiratory chain and rapid energy production to tolerate acidic environment.

Synthesis and Structural Characterization of 1- and 2-Substituted Indazoles: Ester and Carboxylic Acid Derivatives

Directory of Open Access Journals (Sweden)

Isabel Bento

2006-11-01

Full Text Available A series of indazoles substituted at the N-1 and N-2 positions with ester-containing side chains -(CH2nCO2R of different lengths (n = 0-6, 9, 10 are described.Nucleophilic substitution reactions on halo esters (X(CH2nCO2R by 1H-indazole inalkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomerpredominates. Basic hydrolysis of the ester derivatives allowed the synthesis of thecorresponding indazole carboxylic acids. All compounds were fully characterised bymultinuclear NMR and IR spectroscopies, MS spectrometry and elemental analysis; theNMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers.The molecular structure of indazol-2-yl-acetic acid (5b was determined by X-raydiffraction, which shows a supramolecular architecture involving O2-H...N1intermolecular hydrogen bonds.

Oxidation of indole-3-acetic acid to oxindole-3-acetic acid by etiolated and green corn tissues

International Nuclear Information System (INIS)

Reinecke, D.

1989-01-01

Etiolated corn tissues oxidase indole-3-acetic acid (IAA) to oxindole-3-acetic acid (OxIAA). This oxidation results in loss of auxin activity and may plant a role in regulating IAA-stimulated growth. The enzyme has been partially purified and characterized and shown to require O 2 , and a heat-stable lipid-soluble corn factor which can be replaced by linolenic or linoleic acids in the oxidation of IAA. Corn oil was tested as a cofactor in the IAA oxidation reaction. Corn oil stimulated enzyme activity by 30% while trilinolein was inactive. The capacity of green tissue to oxidize IAA was examined by incubating leaf sections from 2 week old light-grown corn seedlings with 14 C-IAA. OxIAA and IAA were separated from other IAA metabolites on a 3 ml anion exchange column. Of the IAA taken up by the sections, 13% was oxidized to OxIAA. This is the first evidence that green tissue of corn may also regulate IAA levels by oxidizing IAA to OxIAA

Orthorhombic polymorph of 4-[(1H-benzimidazol-1-ylmethyl]benzoic acid

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Hai-Wei Kuai

2011-11-01

Full Text Available We reported recently the first polymorph of the title compound [Kuai & Cheng (2011a. Acta Cryst., E67, o2787]. A second polymorph of the title compound, C15H12N2O2, was unexpectedly obtained by the hydrothermal reaction of the title compound with manganese chloride in the presence of potassium hydroxide at 413 K. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.015 (2 Å. The benzimidazole and benzene rings are inclined at a dihedral angle of 79.00 (1°. In the crystal, adjacent molecules are connected through O—H...N hydrogen bonds into a one-dimensional chain along the [001] direction.

First total synthesis of (-)-ichthyothereol and its acetate.

Science.gov (United States)

Mukai, C; Miyakoshi, N; Hanaoka, M

2001-08-24

The first and stereoselective total syntheses of (-)-ichthyothereol (1) and its acetate ((+)-2) were achieved by incorporation of the two chiral centers of diethyl L-tartrate. The starting diethyl L-tartrate was converted into trans-2-ethynyl-3-hydroxytetrahydropyran 14 in a stereoselective manner via the endo mode cyclization of the epoxy-alkyne derivative 12. The alcohol 12 was then transformed into (E)-iodoolefin derivative 15, which was exposed to a coupling reaction with 1-tributylstannyl-1,3,5-heptyne (19), derived from the corresponding 1-trimethylsilyl-1,3,5-heptyne (18), under Stille conditions to produce the all-carbon framework of the target natural products. Chemical modification of the coupled product 20 under conventional conditions completed the first total synthesis of (-)-ichthyothereol (1) and its acetate ((+)-2).

Stereodivergent Mannich reaction of bis(trimethylsilyl)ketene acetals with N-tert-butanesulfinyl imines by Lewis acid or Lewis base activation, a one-pot protocol to obtain chiral β-amino acids.

Science.gov (United States)

Cantú-Reyes, Margarita; Alvarado-Beltrán, Isabel; Ballinas-Indilí, Ricardo; Álvarez-Toledano, Cecilio; Hernández-Rodríguez, Marcos

2017-09-20

We report a one-pot synthesis of chiral β 2,2,3 -amino acids by the Mannich addition of bistrimethylsilyl ketene acetals to N-tert-butanesulfinyl imines followed by the removal of the chiral auxiliary. The synthesis and isolation of pure β-amino acid hydrochlorides were conducted under mild conditions, without strong bases and this method is operationally simple. The stereoselective reaction was promoted by two different activation methods that lead to different stereoisomers: (1) Lewis Acid (LA) catalysis with boron trifluoride diethyl etherate and (2) Lewis Base (LB) catalysis with tetrabutylammonium difluorotriphenylsilicate. The reaction presented good diastereoselectivity with LB activation and moderate to good dr with LA catalysis. The exceptions in both protocols were imines with electron donating groups in the aromatic ring.

Ultrasound promoted and SiO2/CCl3COOH mediated synthesis of 2 ...

Indian Academy of Sciences (India)

First one-pot synthesis of 2-aryl-1-arylmethyl-1H- benzimidazole derivatives from ... to promote chemical reactions is called sonochemistry .... −1): 1615, 2845, 2980, 3036, 3067; 1H NMR (500MHz,. CDCl3):δ 5.38 (s, 2H, CH2), 6.65 (d, J = 8.0 ...

Acetic acid production from marine algae. Progress report No. 2, September 30 to December 31, 1977

Energy Technology Data Exchange (ETDEWEB)

Sanderson, J E; Wise, D L

1978-03-10

Preliminary results on the production of acetic acid from marine algae by anaerobic fermentation indicates that the rate is quite fast. First order rate constants of 0.77 day/sup -1/ have been observed. This rate constant gives a half-life of less than one day. In other words, with a properly designed product removal system a five day retention time would yield 98% of theoretical conversion. Determination of the theoretical conversion of marine algae to acetic acid is the subject of much experimentation. The production of one acetic acid molecule (or equivalent in higher organic acids) for each three carbon atoms in the substrate has been achieved; but it is possible that with a mixed culture more than one acetic acid molecule may be produced for each three carbons in the substrate.

A novel stereospecific synthesis of 14C labeled 1-glutamic acid

International Nuclear Information System (INIS)

Wurz, R.E.; Kepner, R.E.; Webb, A.D.

1989-01-01

A stereospecific synthesis of 4- 14 C-1-glutamic acid was completed in five steps from sodium 2- 14 C-acetate. The morpholine derived enamine of ethyl pyruvate was reacted with ethyl 2- 14 C-bromoacetate to give after hydrolysis diethyl 4- 14 C-2-oxoglutarate. The 2-oxoglutarate was reacted with hydroxylamine hydrochloride to give diethyl 4-14C-2-hydroxyiminoglutarate which was then reduced with a LiAlH4, (-)-N-methylephedrine and 3,5-dimethylphenol mixture to give 4- 14 C-1-glutamic acid. The 4- 14 C-1-glutamic acid was used in investigations into the biosynthesis of gamma-lactones in sherries

Insights into the mechanism of acetic acid hydrogenation to ethanol on Cu(111) surface

Science.gov (United States)

Zhang, Minhua; Yao, Rui; Jiang, Haoxi; Li, Guiming; Chen, Yifei

2017-08-01

Density functional theory (DFT) calculations were employed to theoretically explain the reaction mechanism of acetic acid hydrogenation to ethanol on Cu catalyst. The activation barriers of key elementary steps and the adsorption configurations of key intermediates involved in acetic acid hydrogenation on Cu(111) surface were investigated. The results indicated that the direct dissociation of acetic acid to acetyl (CH3COOH → CH3CO + OH) is the rate-determined step. The activation barrier of acetic acid scission to acetyl and the adsorption energy of acetic acid are two descriptors which could determine the conversion of acetic acid. The descriptors might have effects on the ethanol selectivity including: the adsorption energy of acetaldehyde and the activation barriers for Osbnd H bond formation of C2-oxygenates (CH3CO + H → CH3COH, CH3CHO + H → CH3CHOH and CH3CH2O + H → CH3CH2OH). These proposed descriptors could be used as references to design new Cu-based catalysts that have excellent catalytic performance.

Highly Concentrated Acetic Acid Poisoning: 400 Cases Reviewed

Directory of Open Access Journals (Sweden)

Konstantin Brusin

2012-12-01

Full Text Available Background: Caustic substance ingestion is known for causing a wide array of gastrointestinal and systemic complications. In Russia, ingestion of acetic acid is a major problem which annually affects 11.2 per 100,000 individuals. The objective of this study was to report and analyze main complications and outcomes of patients with 70% concentrated acetic acid poisoning. Methods: This was a retrospective study of patients with acetic acid ingestion who were treated at Sverdlovsk Regional Poisoning Treatment Center during 2006 to 2012. GI mucosal injury of each patient was assessed with endoscopy according to Zargar’s scale. Data analysis was performed to analyze the predictors of stricture formation and mortality. Results: A total of 400 patients with median age of 47 yr were included. GI injury grade I was found in 66 cases (16.5%, IIa in 117 (29.3%, IIb in 120 (30%, IIIa in 27 (16.7% and IIIb in 70 (17.5%. 11% of patients developed strictures and overall mortality rate was 21%. Main complications were hemolysis (55%, renal injury (35%, pneumonia (27% and bleeding during the first 3 days (27%. Predictors of mortality were age 60 to 79 years, grade IIIa and IIIb of GI injury, pneumonia, stages “I”, “F” and “L” of kidney damage according to the RIFLE scale and administration of prednisolone. Predictors of stricture formation were ingestion of over 100 mL of acetic acid and grade IIb and IIIa of GI injury. Conclusion: Highly concentrated acetic acid is still frequently ingested in Russia with a high mortality rate. Patients with higher grades of GI injury, pneumonia, renal injury and higher amount of acid ingested should be more carefully monitored as they are more susceptible to develop fatal consequences.          

Aerobic oxidation of aqueous ethanol using heterogeneous gold catalysts: Efficient routes to acetic acid and ethyl acetate

DEFF Research Database (Denmark)

Jørgensen, Betina; Christiansen, Sofie Egholm; Thomsen, M.L.D.

2007-01-01

The aerobic oxidation of aqueous ethanol to produce acetic acid and ethyl acetate was studied using heterogeneous gold catalysts. Comparing the performance of Au/MgAl2O4 and Au/TiO2 showed that these two catalysts exhibited similar performance in the reaction. By proper selection of the reaction...

SYNTHESIS OF ACETIC ACID FROM ETHANOL BY ELECTROOXIDATION TECHNIQUE USING Ni-Cu-PVC ELECTRODE

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Riyanto Riyanto

2017-11-01

Full Text Available A usage of Ni-Cu-PVC electrode for the oxidation of ethanol by electrochemical technique will be reported in this paper. In this work, the effect of electrodes on the yields of acetic acid was determined. Electrode used was made of the mixtures of Ni powder, Cu powder and of polyvinyl chloride (PVC with various percentages. Electrooxidation of 0.20 M ethanol in 0.16 M KOH  (24 mL were carried out using chrono coulometry (CC at a potential of 1050 mV for 6 hours with continious stirring. Electrooxdation result obtained was analyzed using High Performance Liquid Chromatography (HPLC. The test result shows that the composition of  Ni:Cu:PVC  at 75:20:5 have higher efficiency in the electrooxidation of ethanol to acetic acid.

Simultaneous production of acetic and gluconic acids by a thermotolerant Acetobacter strain during acetous fermentation in a bioreactor.

Science.gov (United States)

Mounir, Majid; Shafiei, Rasoul; Zarmehrkhorshid, Raziyeh; Hamouda, Allal; Ismaili Alaoui, Mustapha; Thonart, Philippe

2016-02-01

The activity of bacterial strains significantly influences the quality and the taste of vinegar. Previous studies of acetic acid bacteria have primarily focused on the ability of bacterial strains to produce high amounts of acetic acid. However, few studies have examined the production of gluconic acid during acetous fermentation at high temperatures. The production of vinegar at high temperatures by two strains of acetic acid bacteria isolated from apple and cactus fruits, namely AF01 and CV01, respectively, was evaluated in this study. The simultaneous production of gluconic and acetic acids was also examined in this study. Biochemical and molecular identification based on a 16s rDNA sequence analysis confirmed that these strains can be classified as Acetobacter pasteurianus. To assess the ability of the isolated strains to grow and produce acetic acid and gluconic acid at high temperatures, a semi-continuous fermentation was performed in a 20-L bioreactor. The two strains abundantly grew at a high temperature (41°C). At the end of the fermentation, the AF01 and CV01 strains yielded acetic acid concentrations of 7.64% (w/v) and 10.08% (w/v), respectively. Interestingly, CV01 was able to simultaneously produce acetic and gluconic acids during acetic fermentation, whereas AF01 mainly produced acetic acid. In addition, CV01 was less sensitive to ethanol depletion during semi-continuous fermentation. Finally, the enzymatic study showed that the two strains exhibited high ADH and ALDH enzyme activity at 38°C compared with the mesophilic reference strain LMG 1632, which was significantly susceptible to thermal inactivation. Copyright © 2015 The Society for Biotechnology, Japan. Published by Elsevier B.V. All rights reserved.

Concurrent coordination of ligand in metal chloride complexes with 1-vinyl-2-(2-pyridyl)benzimidazole

International Nuclear Information System (INIS)

Bajkalov, L.V.; Domnina, E.S.

1996-01-01

The properties and structure of bivalent cadmium and 1-vinyl-2-(2-pyridyl)benzimidazole chloride complexes, which have been prepared for the first time, have been studied by the methods of potentiometric titration and PMR, 35 Cl NQR, UV and IR spectroscopy. For the complexes above di- and polymeric structures in crystal phase are suggested, where ligand plays the role of a bridge. N,N-bidentate ligand. In solution the complexes dissociate with formation of monomeric coordination compounds, their metal being bound by different ways, stemming from participation of N benzimidazole or pyridine fragment of the ligand. Adducts of ionic type with second sphere 1-vinyl-2-(2-pyridyl)benzimidazole cation have been obtained in the course of hydrochlorination of the complexes prepared

Endogenous lycopene improves ethanol production under acetic acid stress in Saccharomyces cerevisiae.

Science.gov (United States)

Pan, Shuo; Jia, Bin; Liu, Hong; Wang, Zhen; Chai, Meng-Zhe; Ding, Ming-Zhu; Zhou, Xiao; Li, Xia; Li, Chun; Li, Bing-Zhi; Yuan, Ying-Jin

2018-01-01

Acetic acid, generated from the pretreatment of lignocellulosic biomass, is a significant obstacle for lignocellulosic ethanol production. Reactive oxidative species (ROS)-mediated cell damage is one of important issues caused by acetic acid. It has been reported that decreasing ROS level can improve the acetic acid tolerance of Saccharomyces cerevisiae . Lycopene is known as an antioxidant. In the study, we investigated effects of endogenous lycopene on cell growth and ethanol production of S. cerevisiae in acetic acid media. By accumulating endogenous lycopene during the aerobic fermentation of the seed stage, the intracellular ROS level of strain decreased to 1.4% of that of the control strain during ethanol fermentation. In the ethanol fermentation system containing 100 g/L glucose and 5.5 g/L acetic acid, the lag phase of strain was 24 h shorter than that of control strain. Glucose consumption rate and ethanol titer of yPS002 got to 2.08 g/L/h and 44.25 g/L, respectively, which were 2.6- and 1.3-fold of the control strain. Transcriptional changes of INO1 gene and CTT1 gene confirmed that endogenous lycopene can decrease oxidative stress and improve intracellular environment. Biosynthesis of endogenous lycopene is first associated with enhancing tolerance to acetic acid in S. cerevisiae . We demonstrate that endogenous lycopene can decrease intracellular ROS level caused by acetic acid, thus increasing cell growth and ethanol production. This work innovatively   puts forward a new strategy for second generation bioethanol production during lignocellulosic fermentation.

The Influence of Substituents on the Tautomerism of Symmetrically Substituted 2,2'-Bis-benzimidazoles

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Dall'Oglio Evandro

2002-01-01

Full Text Available The tautomerism of five symmetrically substituted 2,2'-bis-benzimidazoles [5(6,5'(6'-tetramethyl- (1; 5(6,5'(6'-dimethyl-(2; 5(6,5'(6'-dichloro- (3; 5(6,5'(6'-dimethoxy- (4 and 4(7,4'(7'-dimethyl-2,2'-bis-benzimidazole (5], was studied by means of ¹H NMR spectroscopy at variable temperatures, and the influence of the substituents on the energy barriers for tautomeric interconversion was interpreted with the aid of theoretical calculations.

2-(4-Hydroxyphenyl-1H-benzimidazol-3-ium chloride monohydrate

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Jazmin E. González-Padilla

2013-09-01

Full Text Available The title molecular salt, C13H11N2O+·Cl−·H2O, crystallizes as a monohydrate. In the cation, the phenol and benzimidazole rings are almost coplanar, making a dihedral angle of 3.18 (4°. The chloride anion and benzimidazole cation are linked by two N+—H...Cl− hydrogen bonds, forming chains propagating along [010]. These chains are linked through O—H...Cl hydrogen bonds involving the water molecule and the chloride anion, which form a diamond core, giving rise to the formation of two-dimensional networks lying parallel to (10-2. Two π–π interactions involving the imidazolium ring with the benzene and phenol rings [centroid–centroid distances = 3.859 (3 and 3.602 (3 Å, respectively], contribute to this second dimension. A strong O—H...O hydrogen bond involving the water molecule and the phenol substituent on the benzimidazole unit links the networks, forming a three-dimensional structure.

21 CFR 862.1390 - 5-Hydroxyindole acetic acid/serotonin test system.

Science.gov (United States)

2010-04-01

... 21 Food and Drugs 8 2010-04-01 2010-04-01 false 5-Hydroxyindole acetic acid/serotonin test system... Test Systems § 862.1390 5-Hydroxyindole acetic acid/serotonin test system. (a) Identification. A 5-hydroxyindole acetic acid/serotonin test system is a device intended to measure 5-hydroxyindole acetic acid...

Development of Acetic Acid Removal Technology for the UREX+Process

International Nuclear Information System (INIS)

Counce, Robert M.; Watson, Jack S.

2009-01-01

It is imperative that acetic acid is removed from a waste stream in the UREX+process so that nitric acid can be recycled and possible interference with downstream steps can be avoided. Acetic acid arises from acetohydrozamic acid (AHA), and is used to suppress plutonium in the first step of the UREX+process. Later, it is hydrolyzed into hydroxyl amine nitrate and acetic acid. Many common separation technologies were examined, and solvent extraction was determined to be the best choice under process conditions. Solvents already used in the UREX+ process were then tested to determine if they would be sufficient for the removal of acetic acid. The tributyl phosphage (TBP)-dodecane diluent, used in both UREX and NPEX, was determined to be a solvent system that gave sufficient distribution coefficients for acetic acid in addition to a high separation factor from nitric acid

Development of Acetic Acid Removal Technology for the UREX+Process

Energy Technology Data Exchange (ETDEWEB)

Robert M. Counce; Jack S. Watson

2009-06-30

It is imperative that acetic acid is removed from a waste stream in the UREX+process so that nitric acid can be recycled and possible interference with downstreatm steps can be avoidec. Acetic acid arises from acetohydrozamic acid (AHA), and is used to suppress plutonium in the first step of the UREX+process. Later, it is hydrolyzed into hydroxyl amine nitrate and acetic acid. Many common separation technologies were examined, and solvent extraction was determined to be the best choice under process conditions. Solvents already used in the UREX+ process were then tested to determine if they would be sufficient for the removal of acetic acid. The tributyl phosphage (TBP)-dodecane diluent, used in both UREX and NPEX, was determined to be a solvent system that gave sufficient distribution coefficients for acetic acid in addition to a high separation factor from nitric acid.

Anhydrous formic acid and acetic anhydride as solvent or additive in nonaqueous titrations.

Science.gov (United States)

Buvári-Barcza, A; Tóth, I; Barcza, L

2005-09-01

The use and importance of formic acid and acetic anhydride (Ac2O) is increasing in nonaqueous acid-base titrations, but their interaction with the solutes is poorly understood. This paper attempts to clarify the effect of the solvents; NMR and spectrophotometric investigations were done to reveal the interactions between some bases and the mentioned solvents. Anhydrous formic acid is a typical protogenic solvent but both the relative permittivity and acidity are higher than those of acetic acid (mostly used in assays of bases). These differences originate from the different chemical structures: liquid acetic acid contains basically cyclic dimers while formic acid forms linear associates. Ac2O is obviously not an acidic but an aprotic (very slightly protophilic) solvent, which supposedly dissociates slightly into acetyl (CH3CO+) and acetate (AcO-) ions. In fact, some bases react with Ac2O forming an associate: the Ac+ group is bound to the delta- charged atom of the reactant while AcO- is associated with the delta+ group at appropriate distance.

Antimalarial pyrido[1,2-a]benzimidazoles.

Science.gov (United States)

Ndakala, Albert J; Gessner, Richard K; Gitari, Patricia W; October, Natasha; White, Karen L; Hudson, Alan; Fakorede, Foluke; Shackleford, David M; Kaiser, Marcel; Yeates, Clive; Charman, Susan A; Chibale, Kelly

2011-07-14

A novel class of antimalarial pyrido[1,2-a]benzimidazoles were synthesized and evaluated for antiplasmodial activity and cytotoxicity following hits identified from screening commercially available compound collections. The most active of these, TDR86919 (4c), showed improved in vitro activity vs the drug-resistant K1 strain of Plasmodium falciparum relative to chloroquine (IC(50) = 0.047 μM v 0.17 μM); potency was retained against a range of drug-sensitive and drug-resistant strains, with negligible cytotoxicity against the mammalian (L-6) cell line (selectivity index of >600). 4c and several close analogues (as HCl or mesylate salts) showed significant efficacy in P. berghei infected mice following both intraperitoneal (ip) and oral (po) administration, with >90% inhibition of parasitemia, accompanied by an increase in the mean survival time (MSD). The pyrido[1,2-a]benzimidazoles appeared to be relatively slow acting in vivo compared to chloroquine, and metabolic stability of the alkylamino side chain was identified as a key issue in influencing in vivo activity.

Aqueous-Phase Acetic Acid Ketonization over Monoclinic Zirconia

Energy Technology Data Exchange (ETDEWEB)

Cai, Qiuxia [Institute for Integrated Catalysis, Pacific Northwest; College; Lopez-Ruiz, Juan A. [Institute for Integrated Catalysis, Pacific Northwest; Cooper, Alan R. [Institute for Integrated Catalysis, Pacific Northwest; Wang, Jian-guo [College; Albrecht, Karl O. [Institute for Integrated Catalysis, Pacific Northwest; Mei, Donghai [Institute for Integrated Catalysis, Pacific Northwest

2017-12-13

The effect of aqueous phase on the acetic acid ketonization over monoclinic zirconia has been investigated using first-principles based density functional theory (DFT) calculations. To capture the aqueous phase chemistry over the solid zirconia catalyst surface, the aqueous phase is represented by 111 explicit water molecules with a liquid water density of 0.93 g/cm3 and the monoclinic zirconia is modeled by the most stable surface structure . The dynamic nature of aqueous phase/ interface was studied using ab initio molecular dynamics simulation, indicating that nearly half of the surface Zr sites are occupied by either adsorbed water molecules or hydroxyl groups at 550 K. DFT calculations show that the adsorption process of acetic acid from the liquid water phase to the surface is nearly thermodynamically neutral with a Gibbs free energy of -2.3 kJ/mol although the adsorption strength of acetic acid on the surface in aqueous phase is much stronger than in vapor phase. Therefore it is expected that the adsorption of acetic acid will dramatically affects aqueous phase ketonization reactivity over the monoclinic zirconia catalyst. Using the same ketonization mechanism via the β-keto acid intermediate, we have compared acetic acid ketonization to acetone in both vapor and aqueous phases. Our DFT calculation results show although the rate-determining step of the β-keto acid formation via the C-C coupling is not pronouncedly affected, the presence of liquid water molecules will dramatically affect dehydrogenation and hydrogenation steps via proton transfer mechanism. This work was financially supported by the United States Department of Energy (DOE)’s Bioenergy Technologies Office (BETO) and performed at the Pacific Northwest National Laboratory (PNNL). PNNL is a multi-program national laboratory operated for DOE by Battelle Memorial Institute. Computing time and advanced catalyst characterization use was granted by a user proposal at the William R. Wiley

Acetic acid production from marine algae. Progress report No. 2, September 30--December 31, 1977

Energy Technology Data Exchange (ETDEWEB)

1977-01-01

Preliminary results on the production of acetic acid from marine algae by anaerobic fermentation indicate that the rate is quite fast. First order rate constants of 0.77 day/sup -1/ were observed. This rate constant gives a half-life of less than one day. In other words, with a properly designed product removal system a five day retention time would yield 98% of theoretical conversion. Determination of the theoretical conversion of marine algae to acetic acid is the subject of much experimentation. The production of one acetic acid molecule (or equivalent in higher organic acids) for each three carbon atoms in the substrate has been achieved; but it is possible that with a mixed culture more than one acetic acid molecule may be produced for each three carbons in the substrate. Work is continuing to improve the yield of acetic acid from marine algae. Marine algae have been found to be rather low in carbon, but the carbon appears to be readily available for fermentation. It, therefore, lends itself to the production of higher value chemicals in relatively expensive equipment, where the rapid conversion rate is particularly cost effective. Fixed packed bed fermenters appear to be desirable for the production of liquid products which are inhibitory to the fermentation from coarse substrates. The inhibitory products may be removed from the fermentation by extraction during recirculation. This technique lends itself to either conventional processing or low capital processing of substrates which require long retention times.

Effect of acetic acid on rice seeds coated with rice husk ash

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Lizandro Ciciliano Tavares

2013-06-01

Full Text Available Flooded rice cultivation promotes anaerobic conditions, favoring the formation of short chain organic acids such as acetic acid, which may be toxic to the crop. The objective of this study was to evaluate the effect of acetic acid on rice seeds coated with rice husk ash. The experiment was arranged in a 2 x 5 x 5 factorial randomized design, with two cultivars (IRGA 424 and BRS Querência, five doses of coating material (0, 2, 3,4 e 5 g kg-1 seed and five concentrations of acetic acid (0, 3, 6, 9 and 12 mM, with 4 replications, totaling 50 treatments. The variables first count of germination, germination, shoot and root length, dry weight of shoots and roots were recorded. The results showed that coating rice seeds with rice husk ash up to 5 g kg-1 seed does not influence the performance of rice seeds of cultivars IRGA 424 and BRS Querência when exposed to concentrations of 12 mM acetic acid. The presence of acetic acid in the substrates used for seed germination reduced the vigor and viability of seeds of cultivars IRGA 424 and BRS Querência, as well as seedling development, affecting mainly the roots of BRS Querência.

Recovery of acetic acid from waste streams by extractive distillation.

Science.gov (United States)

Demiral, H; Yildirim, M Ercengiz

2003-01-01

Wastes have been considered to be a serious worldwide environmental problem in recent years. Because of increasing pollution, these wastes should be treated. However, industrial wastes can contain a number of valuable organic components. Recovery of these components is important economically. Using conventional distillation techniques, the separation of acetic acid and water is both impractical and uneconomical, because it often requires large number of trays and a high reflux ratio. In practice special techniques are used depending on the concentration of acetic acid. Between 30 and 70% (w/w) acetic acid contents, extractive distillation was suggested. Extractive distillation is a multicomponent-rectification method similar in purpose to azeotropic distillation. In extractive distillation, to a binary mixture which is difficult or impossible to separate by ordinary means, a third component termed an entrainer is added which alters the relative volatility of the original constituents, thus permitting the separation. In our department acetic acid is used as a solvent during the obtaining of cobalt(III) acetate from cobalt(II) acetate by an electrochemical method. After the operation, the remaining waste contains acetic acid. In thiswork, acetic acid which has been found in this waste was recovered by extractive distillation. Adiponitrile and sulfolane were used as high boiling solvents and the effects of solvent feed rate/solution feed rate ratio and type were investigated. According to the experimental results, it was seem that the recovery of acetic acid from waste streams is possible by extractive distillation.

Complexes of molybdenum(III) with 2-(2'-pyridyl)benzimidazole

International Nuclear Information System (INIS)

Ghosh, S.P.; Prasad, K.M.

1979-01-01

Molybdenum(III) forms with 2-(2'-pyridyl) benzimidazole(LH) the trischelated complexes, [Mo(LH) 3 ]X 3 as well as the cationic-anionic complexes, [Mo(LH) 3 X 2 ] + [Mo(LH)X 4 ] - (X=Cl - ,Br - or NCS - ), depending on pH. These complexes have been synthesised and characterised from elemental analyses, i.r. and electronic spectra, magnetic moments and molar conductance. (auth.)

Measurement of formic acid, acetic acid and hydroxyacetaldehyde, hydrogen peroxide, and methyl peroxide in air by chemical ionization mass spectrometry: airborne method development

Science.gov (United States)

Treadaway, Victoria; Heikes, Brian G.; McNeill, Ashley S.; Silwal, Indira K. C.; O'Sullivan, Daniel W.

2018-04-01

A chemical ionization mass spectrometry (CIMS) method utilizing a reagent gas mixture of O2, CO2, and CH3I in N2 is described and optimized for quantitative gas-phase measurements of hydrogen peroxide (H2O2), methyl peroxide (CH3OOH), formic acid (HCOOH), and the sum of acetic acid (CH3COOH) and hydroxyacetaldehyde (HOCH2CHO; also known as glycolaldehyde). The instrumentation and methodology were designed for airborne in situ field measurements. The CIMS quantification of formic acid, acetic acid, and hydroxyacetaldehyde used I- cluster formation to produce and detect the ion clusters I-(HCOOH), I-(CH3COOH), and I-(HOCH2CHO), respectively. The CIMS also produced and detected I- clusters with hydrogen peroxide and methyl peroxide, I-(H2O2) and I-(CH3OOH), though the sensitivity was lower than with the O2- (CO2) and O2- ion clusters, respectively. For that reason, while the I- peroxide clusters are presented, the focus is on the organic acids. Acetic acid and hydroxyacetaldehyde were found to yield equivalent CIMS responses. They are exact isobaric compounds and indistinguishable in the CIMS used. Consequently, their combined signal is referred to as the acetic acid equivalent sum. Within the resolution of the quadrupole used in the CIMS (1 m/z), ethanol and 1- and 2-propanol were potential isobaric interferences to the measurement of formic acid and the acetic acid equivalent sum, respectively. The CIMS response to ethanol was 3.3 % that of formic acid and the response to either 1- or 2-propanol was 1 % of the acetic acid response; therefore, the alcohols were not considered to be significant interferences to formic acid or the acetic acid equivalent sum. The multi-reagent ion system was successfully deployed during the Front Range Air Pollution and Photochemistry Éxperiment (FRAPPÉ) in 2014. The combination of FRAPPÉ and laboratory calibrations allowed for the post-mission quantification of formic acid and the acetic acid equivalent sum observed during the Deep

THE INCORPORATION OF ACETATE-1-C14 INTO CHOLESTEROL AND FATTY ACIDS BY SURVIVING TISSUES OF NORMAL AND SCORBUTIC GUINEA PIGS

Science.gov (United States)

Bolker, H. I.; Fishman, S.; Heard, R. D. H.; O'Donnell, V. J.; Webb, J. L.; Willis, G. C.

1956-01-01

The synthesis of cholesterol and fatty acids from acetate-l-C14 by the isolated liver, adrenal, and aorta of scorbutic and pair-fed control guinea pigs has been studied. It was found that ascorbic acid deficiency does not affect the rate of incorporation of C14-acetate into cholesterol and fatty acids by the tissues investigated, under our experimental conditions. The relatively high metabolic activity of the artery with regard to cholesterogenesis and lipogenesis was noted. The elevation of serum cholesterol and hexosamine in scurvy has been confirmed. PMID:13286427

Effect of penicillin on fatty acid synthesis and excretion in Streptococcus mutans BHT

International Nuclear Information System (INIS)

Brissette, J.L.; Pieringer, R.A.

1985-01-01

Treatment of exponentially growing cultures of Streptococcus mutans BHT with growth-inhibitory concentrations (0.2 microgram/ml) of benzylpenicillin stimulates the incorporation of [2- 14 C] acetate into lipids excreted by the cells by as much as 69-fold, but does not change the amount of 14 C incorporated into intracellular lipids. At this concentration of penicillin cellular lysis does not occur. The radioactive label is incorporated exclusively into the fatty acid moieties of the glycerolipids. During a 4-hr incubation in the presence of penicillin, the extracellular fatty acid ester concentration increases 1.5 fold, even though there is no growth or cellular lysis. An indication of the relative rate of fatty acid synthesis was most readily obtained by placing S. mutans BHT in a buffer containing 14 C-acetate. Under these nongrowing conditions free fatty acids are the only lipids labeled, a factor which simplifies the assay. The addition of glycerol to the buffer causes all of the nonesterified fatty acids to be incorporated into glycerolipid. The cells excrete much of the lipid whether glycerol is present or not. Addition of penicillin to the nongrowth supporting buffer system does not stimulate the incorporation of [ 14 C]-acetate into fatty acids

Acetic Acid Causes Endoplasmic Reticulum Stress and Induces the Unfolded Protein Response in Saccharomyces cerevisiae

Directory of Open Access Journals (Sweden)

Nozomi Kawazoe

2017-06-01

Full Text Available Since acetic acid inhibits the growth and fermentation ability of Saccharomyces cerevisiae, it is one of the practical hindrances to the efficient production of bioethanol from a lignocellulosic biomass. Although extensive information is available on yeast response to acetic acid stress, the involvement of endoplasmic reticulum (ER and unfolded protein response (UPR has not been addressed. We herein demonstrated that acetic acid causes ER stress and induces the UPR. The accumulation of misfolded proteins in the ER and activation of Ire1p and Hac1p, an ER-stress sensor and ER stress-responsive transcription factor, respectively, were induced by a treatment with acetic acid stress (>0.2% v/v. Other monocarboxylic acids such as propionic acid and sorbic acid, but not lactic acid, also induced the UPR. Additionally, ire1Δ and hac1Δ cells were more sensitive to acetic acid than wild-type cells, indicating that activation of the Ire1p-Hac1p pathway is required for maximum tolerance to acetic acid. Furthermore, the combination of mild acetic acid stress (0.1% acetic acid and mild ethanol stress (5% ethanol induced the UPR, whereas neither mild ethanol stress nor mild acetic acid stress individually activated Ire1p, suggesting that ER stress is easily induced in yeast cells during the fermentation process of lignocellulosic hydrolysates. It was possible to avoid the induction of ER stress caused by acetic acid and the combined stress by adjusting extracellular pH.

Steam Reforming of Acetic Acid over Co-Supported Catalysts: Coupling Ketonization for Greater Stability

Energy Technology Data Exchange (ETDEWEB)

Davidson, Stephen D. [Energy and Environmental; Spies, Kurt A. [Energy and Environmental; Mei, Donghai [Energy and Environmental; Kovarik, Libor [Energy and Environmental; Kutnyakov, Igor [Energy and Environmental; Li, Xiaohong S. [Energy and Environmental; Lebarbier Dagle, Vanessa [Energy and Environmental; Albrecht, Karl O. [Energy and Environmental; Dagle, Robert A. [Energy and Environmental

2017-09-11

We report on the markedly improved stability of a novel 2-bed catalytic system, as compared to a conventional 1-bed steam reforming catalyst, for the production of H2 from acetic acid. The 2-bed catalytic system comprises of i) a basic oxide ketonization catalyst for the conversion of acetic acid to acetone, and a ii) Co-based steam reforming catalyst, both catalytic beds placed in sequence within the same unit operation. Steam reforming catalysts are particularly prone to catalytic deactivation when steam reforming acetic acid, used here as a model compound for the aqueous fraction of bio-oil. Catalysts comprising MgAl2O4, ZnO, CeO2, and activated carbon (AC) both with and without Co-addition were evaluated for conversion of acetic acid and acetone, its ketonization product, in the presence of steam. It was found that over the bare oxide support only ketonization activity was observed and coke deposition was minimal. With addition of Co to the oxide support steam reforming activity was facilitated and coke deposition was significantly increased. Acetone steam reforming over the same Co-supported catalysts demonstrated more stable performance and with less coke deposition than with acetic acid feedstock. DFT analysis suggests that over Co surface CHxCOO species are more favorably formed from acetic acid versus acetone. These CHxCOO species are strongly bound to the Co catalyst surface and could explain the higher propensity for coke formation from acetic acid. Based on these findings, in order to enhance stability of the steam reforming catalyst a dual-bed (2-bed) catalyst system was implemented. Comparing the 2-bed and 1-bed (Co-supported catalyst only) systems under otherwise identical reaction conditions the 2-bed demonstrated significantly improved stability and coke deposition was decreased by a factor of 4.

Mild oxidation of methane to methanol or acetic acid on supported isolated rhodium catalysts

Science.gov (United States)

Shan, Junjun; Li, Mengwei; Allard, Lawrence F.; Lee, Sungsik; Flytzani-Stephanopoulos, Maria

2017-11-01

An efficient and direct method of catalytic conversion of methane to liquid methanol and other oxygenates would be of considerable practical value. However, it remains an unsolved problem in catalysis, as typically it involves expensive or corrosive oxidants or reaction media that are not amenable to commercialization. Although methane can be directly converted to methanol using molecular oxygen under mild conditions in the gas phase, the process is either stoichiometric (and therefore requires a water extraction step) or is too slow and low-yielding to be practical. Methane could, in principle, also be transformed through direct oxidative carbonylation to acetic acid, which is commercially obtained through methane steam reforming, methanol synthesis, and subsequent methanol carbonylation on homogeneous catalysts. However, an effective catalyst for the direct carbonylation of methane to acetic acid, which might enable the economical small-scale utilization of natural gas that is currently flared or stranded, has not yet been reported. Here we show that mononuclear rhodium species, anchored on a zeolite or titanium dioxide support suspended in aqueous solution, catalyse the direct conversion of methane to methanol and acetic acid, using oxygen and carbon monoxide under mild conditions. We find that the two products form through independent pathways, which allows us to tune the conversion: three-hour-long batch-reactor tests conducted at 150 degrees Celsius, using either the zeolite-supported or the titanium-dioxide-supported catalyst, yield around 22,000 micromoles of acetic acid per gram of catalyst, or around 230 micromoles of methanol per gram of catalyst, respectively, with selectivities of 60-100 per cent. We anticipate that these unusually high activities, despite still being too low for commercial application, may guide the development of optimized catalysts and practical processes for the direct conversion of methane to methanol, acetic acid and other useful

Validation of a multi-analyte HPLC-DAD method for determination of uric acid, creatinine, homovanillic acid, niacinamide, hippuric acid, indole-3-acetic acid and 2-methylhippuric acid in human urine.

Science.gov (United States)

Remane, Daniela; Grunwald, Soeren; Hoeke, Henrike; Mueller, Andrea; Roeder, Stefan; von Bergen, Martin; Wissenbach, Dirk K

2015-08-15

During the last decades exposure sciences and epidemiological studies attracts more attention to unravel the mechanisms for the development of chronic diseases. According to this an existing HPLC-DAD method for determination of creatinine in urine samples was expended for seven analytes and validated. Creatinine, uric acid, homovanillic acid, niacinamide, hippuric acid, indole-3-acetic acid, and 2-methylhippuric acid were separated by gradient elution (formate buffer/methanol) using an Eclipse Plus C18 Rapid Resolution column (4.6mm×100mm). No interfering signals were detected in mobile phase. After injection of blank urine samples signals for the endogenous compounds but no interferences were detected. All analytes were linear in the selected calibration range and a non weighted calibration model was chosen. Bias, intra-day and inter-day precision for all analytes were below 20% for quality control (QC) low and below 10% for QC medium and high. The limits of quantification in mobile phase were in line with reported reference values but had to be adjusted in urine for homovanillic acid (45mg/L), niacinamide 58.5(mg/L), and indole-3-acetic acid (63mg/L). Comparison of creatinine data obtained by the existing method with those of the developed method showing differences from -120mg/L to +110mg/L with a mean of differences of 29.0mg/L for 50 authentic urine samples. Analyzing 50 authentic urine samples, uric acid, creatinine, hippuric acid, and 2-methylhippuric acid were detected in (nearly) all samples. However, homovanillic acid was detected in 40%, niacinamide in 4% and indole-3-acetic acid was never detected within the selected samples. Copyright © 2015 Elsevier B.V. All rights reserved.

Corn stover lignin is modified differently by acetic acid compared to sulfuric acid

NARCIS (Netherlands)

Mouthier, Thibaut; Appeldoorn, Maaike M.; Pel, Herman; Schols, Henk A.; Gruppen, Harry; Kabel, Mirjam A.

2018-01-01

In this study, two acid catalysts, acetic acid (HAc) and sulfuric acid (H2SO4), were compared in thermal pretreatments of corn stover, in particular to assess the less understood fate of lignin. HAc-insoluble lignin, analyzed by pyrolysis GC–MS, showed decreasing levels (%) of Cα-oxidized (from 3.7

Design, synthesis and evaluation of novel 2,5,6-trisubstituted benzimidazoles targeting FtsZ as antitubercular agents.

Science.gov (United States)

Park, Bora; Awasthi, Divya; Chowdhury, Soumya R; Melief, Eduard H; Kumar, Kunal; Knudson, Susan E; Slayden, Richard A; Ojima, Iwao

2014-05-01

Filamenting temperature-sensitive protein Z (FtsZ), an essential cell division protein, is a promising target for the drug discovery of new-generation antibacterial agents against various bacterial pathogens. As a part of SAR studies on benzimidazoles, we have synthesized a library of 376 novel 2,5,6-trisubstituted benzimidazoles, bearing ether or thioether linkage at the 6-position. In a preliminary HTP screening against Mtb H37Rv, 108 compounds were identified as hits at a cut off concentration of 5 μg/mL. Among those hits, 10 compounds exhibited MIC values in the range of 0.63-12.5 μg/mL. Light scattering assay and TEM analysis with the most potent compound 5a clearly indicate that its molecular target is Mtb-FtsZ. Also, the Kd of 5a with Mtb-FtsZ was determined to be 1.32 μM. Copyright © 2014 Elsevier Ltd. All rights reserved.

Recovery of Acetic Acid from An Ethanol Fermentation Broth by Liquid-Liquid Extraction (LLE) Using Various Solvents

International Nuclear Information System (INIS)

Pham, Thi Thu Huong; Kim, Tae Hyun; Um, Byung Hwan

2015-01-01

Liquid-liquid extraction (LLE) using various solvents was studied for recovery of acetic acid from a synthetic ethanol fermentation broth. The microbial fermentation of sugars presented in hydrolyzate gives rise to acetic acid as a byproduct. In order to obtain pure ethanol for use as a biofuel, fermentation broth should be subjected to acetic acid removal step and the recovered acetic acid can be put to industrial use. Herein, batch LLE experiments were carried out at 25°C using a synthetic fermentation broth comprising 20.0 g l -1 acetic acid and 5.0 g l -1 ethanol. Ethyl acetate (EtOAc), tri-n-octylphosphine oxide (TOPO), tri-n-octylamine (TOA), and tri-n-alkylphosphine oxide (TAPO) were utilized as solvents, and the extraction potential of each solvent was evaluated by varying the organic phase-to-aqueous phase ratios as 0.2, 0.5, 1.0, 2.0, and 4.0. The highest acetic acid extraction yield was achieved with TAPO; however, the lowest ethanol-to-acetic acid extraction ratio was obtained using TOPO. In a single-stage batch extraction, 97.0 % and 92.4 % of acetic acid could be extracted using TAPO and TOPO when the ratio of organic-to-aqueous phases is 4:1 respectively. A higher solvent-to-feed ratio resulted in an increase in the ethanol-to-acetic acid ratio, which decreased both acetic acid purity and acetic acid extraction yield.

Effects of culture conditions on acetic acid production by bacteria ...

African Journals Online (AJOL)

SARAH

2015-11-30

Nov 30, 2015 ... acid under certain culture conditions similar to cocoa fermentation stress. However ... Keywords: Acetic acid bacteria, acetic acid production, Cocoa fermentation, culture conditions ..... American Society Microbiology Press, pp.

Fatty Acid Biosynthesis IX

DEFF Research Database (Denmark)

Carey, E. M.; Hansen, Heinz Johs. Max; Dils, R.

1972-01-01

# 1. I. [I-14C]Acetate was covalently bound to rabbit mammary gland fatty acid synthetase by enzymic transacylation from [I-14C]acetyl-CoA. Per mole of enzyme 2 moles of acetate were bound to thiol groups and up to I mole of acetate was bound to non-thiol groups. # 2. 2. The acetyl-fatty acid...... synthetase complex was isolated free from acetyl-CoA. It was rapidly hydrolysed at 30°C, but hydrolysis was greatly diminished at o°C and triacetic lactone synthesis occurred. In the presence of malonyl-CoA and NADPH, all the acetate bound to fatty acid synthetase was incorporated into long-chain fatty acids....... Hydrolysis of bound acetate and incorporation of bound acetate into fatty acids were inhibited to the same extent by guanidine hydrochloride. # 3. 3. Acetate was also covalently bound to fatty acid synthetase by chemical acetylation with [I-14C]acetic anhydride in the absence of CoASH. A total of 60 moles...

Effect of acetic acid in recycling water on ethanol production for cassava in an integrated ethanol-methane fermentation process.

Science.gov (United States)

Yang, Xinchao; Wang, Ke; Zhang, Jianhua; Tang, Lei; Mao, Zhonggui

2016-11-01

Recently, the integrated ethanol-methane fermentation process has been studied to prevent wastewater pollution. However, when the anaerobic digestion reaction runs poorly, acetic acid will accumulate in the recycling water. In this paper, we studied the effect of low concentration of acetic acid (≤25 mM) on ethanol fermentation at different initial pH values (4.2, 5.2 or 6.2). At an initial pH of 4.2, ethanol yields increased by 3.0% and glycerol yields decreased by 33.6% as the acetic acid concentration was increased from 0 to 25 mM. Raising the concentration of acetic acid to 25 mM increased the buffering capacity of the medium without obvious effects on biomass production in the cassava medium. Acetic acid was metabolized by Saccharomyces cerevisiae for the reason that the final concentration of acetic acid was 38.17% lower than initial concentration at pH 5.2 when 25 mM acetic acid was added. These results confirmed that a low concentration of acetic acid in the process stimulated ethanol fermentation. Thus, reducing the acetic acid concentration to a controlled low level is more advantageous than completely removing it.

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

International Nuclear Information System (INIS)

Koc, Ziya Erdem; Bingol, Haluk; Saf, Ahmet O.; Torlak, Emrah; Coskun, Ahmet

2010-01-01

Four new tripodal-benzimidazole derivatives were synthesized by Schiff base reaction between 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) and different diamine derivatives. The structures of the obtained compounds were identified by FT-IR, 1 H NMR, 13 C NMR and UV-vis spectral data, thermal analysis and elemental analysis. Electrochemical behaviors of the compounds were studied by cyclic voltammetry in DMF including 0.1 M [NBu 4 ] [PF 6 ]. The voltammograms showed peaks having similar characteristics except tripodal-benzimidazole including -NO 2 derivative. In addition, their antimicrobial activities were evaluated by using the standard disk diffusion method in dimethylformamide media. The activities were determined against 4 bacteria cultures by comparing to those of gentamycin.

Production of itaconic acid from acetate by engineering acid-tolerant Escherichia coli W.

Science.gov (United States)

Noh, Myung Hyun; Lim, Hyun Gyu; Woo, Sung Hwa; Song, Jinyi; Jung, Gyoo Yeol

2018-03-01

Utilization of abundant and cheap carbon sources can effectively reduce the production cost and enhance the economic feasibility. Acetate is a promising carbon source to achieve cost-effective microbial processes. In this study, we engineered an Escherichia coli strain to produce itaconic acid from acetate. As acetate is known to inhibit cell growth, we initially screened for a strain with a high tolerance to 10 g/L of acetate in the medium, and the W strain was selected as the host. Subsequently, the WC strain was obtained by overexpression of cad (encoding cis-aconitate decarboxylase) using a synthetic promoter and 5' UTR. However, the WC strain produced only 0.13 g/L itaconic acid because of low acetate uptake. To improve the production, the acetate assimilating pathway and glyoxylate shunt pathway were amplified by overexpression of pathway genes as well as its deregulation. The resulting strain, WCIAG4 produced 3.57 g/L itaconic acid (16.1% of theoretical maximum yield) after 88 hr of fermentation with rapid acetate assimilation. These efforts support that acetate can be a potential feedstock for biochemical production with engineered E. coli. © 2017 Wiley Periodicals, Inc.

Transcriptome Analysis in Haematococcus pluvialis: Astaxanthin Induction by High Light with Acetate and Fe2.

Science.gov (United States)

He, Bangxiang; Hou, Lulu; Dong, Manman; Shi, Jiawei; Huang, Xiaoyun; Ding, Yating; Cong, Xiaomei; Zhang, Feng; Zhang, Xuecheng; Zang, Xiaonan

2018-01-07

Haematococcus pluvialis is a commercial microalga, that produces abundant levels of astaxanthin under stress conditions. Acetate and Fe 2+ are reported to be important for astaxanthin accumulation in H. pluvialis . In order to study the synergistic effects of high light stress and these two factors, we obtained transcriptomes for four groups: high light irradiation (HL), addition of 25 mM acetate under high light (HA), addition of 20 μM Fe 2+ under high light (HF) and normal green growing cells (HG). Among the total clean reads of the four groups, 156,992 unigenes were found, of which 48.88% were annotated in at least one database (Nr, Nt, Pfam, KOG/COG, SwissProt, KEGG, GO). The statistics for DEGs (differentially expressed genes) showed that there were more than 10 thousand DEGs caused by high light and 1800-1900 DEGs caused by acetate or Fe 2+ . The results of DEG analysis by GO and KEGG enrichments showed that, under the high light condition, the expression of genes related to many pathways had changed, such as the pathway for carotenoid biosynthesis, fatty acid elongation, photosynthesis-antenna proteins, carbon fixation in photosynthetic organisms and so on. Addition of acetate under high light significantly promoted the expression of key genes related to the pathways for carotenoid biosynthesis and fatty acid elongation. Furthermore, acetate could obviously inhibit the expression of genes related to the pathway for photosynthesis-antenna proteins. For addition of Fe 2+ , the genes related to photosynthesis-antenna proteins were promoted significantly and there was no obvious change in the gene expressions related to carotenoid and fatty acid synthesis.

Transcriptome Analysis in Haematococcus pluvialis: Astaxanthin Induction by High Light with Acetate and Fe2+

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Bangxiang He

2018-01-01

Full Text Available Haematococcus pluvialis is a commercial microalga, that produces abundant levels of astaxanthin under stress conditions. Acetate and Fe2+ are reported to be important for astaxanthin accumulation in H. pluvialis. In order to study the synergistic effects of high light stress and these two factors, we obtained transcriptomes for four groups: high light irradiation (HL, addition of 25 mM acetate under high light (HA, addition of 20 μM Fe2+ under high light (HF and normal green growing cells (HG. Among the total clean reads of the four groups, 156,992 unigenes were found, of which 48.88% were annotated in at least one database (Nr, Nt, Pfam, KOG/COG, SwissProt, KEGG, GO. The statistics for DEGs (differentially expressed genes showed that there were more than 10 thousand DEGs caused by high light and 1800–1900 DEGs caused by acetate or Fe2+. The results of DEG analysis by GO and KEGG enrichments showed that, under the high light condition, the expression of genes related to many pathways had changed, such as the pathway for carotenoid biosynthesis, fatty acid elongation, photosynthesis-antenna proteins, carbon fixation in photosynthetic organisms and so on. Addition of acetate under high light significantly promoted the expression of key genes related to the pathways for carotenoid biosynthesis and fatty acid elongation. Furthermore, acetate could obviously inhibit the expression of genes related to the pathway for photosynthesis-antenna proteins. For addition of Fe2+, the genes related to photosynthesis-antenna proteins were promoted significantly and there was no obvious change in the gene expressions related to carotenoid and fatty acid synthesis.

Synthesis and in Vitro Antiproliferative Evaluation of Some B-norcholesteryl Benzimidazole and Benzothiazole Derivatives

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Jianguo Cui

2015-04-01

Full Text Available Taking orostanal (a compound from a Japanese marine sponge, Stelletta hiwasaensis as a lead compound, some novel B-norcholesteryl benzimidazole and benzothiazole derivatives were synthesized. The antiproliferative activity of the compounds against human cervical carcinoma (HeLa, human lung carcinoma (A549, human liver carcinoma cells (HEPG2 and normal kidney epithelial cells (HEK293T was assayed. The results revealed that the benzimidazole group was a better substituent than benzothiazole group for increasing the antiproliferative activity of compounds. 2-(3β′-Acetoxy-5β′-hydroxy-6′-B-norcholesterylbenzimidazole (9b with the structure of 6-benzimidazole displays the best antiproliferative activity to the cancer cells in all compounds, but is almost inactive to normal kidney epithelial cells (HEK293T. The assay of compound 9b to cancer cell apoptosis by flow cytometry showed that the compound was able to effectively induce cancer cell apoptosis. The research provided a theoretical reference for the exploration of new anti-cancer agents and may be useful for the design of novel chemotherapeutic drugs.

Journal of Chemical Sciences | Indian Academy of Sciences

Indian Academy of Sciences (India)

BIG was formed by the reaction of Cu(ClO₄)₂ ·6H₂O and tridentate benzimidazole-glycine conjugate ligand, 2-((1H-benzimidazol- 2-yl)methylamino) acetic acid, BIGH and its structure has been determined by IR, UV, powder XRD, VSM, CV, ...

SYNTHESIS, SPECTRAL AND THEORETICAL CHARACTERIZATION OF 5,6-DICHLORO/DIMETHYL-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-DIMETHOXYPHENYL-1H-BENZIMIDAZOLES

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Demet Gürbüz

2016-12-01

Full Text Available 5,6-Dichloro/dimethyl-2-(2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl-1H-benzimidazoles were synthesized and characterized by using analytical data, FT-IR, FT-Raman, NMR, ESI-MS and fl uorescence spectroscopy. The optimized molecular geometry, zero point energy, dipole moment, ESE, band gap and charge distributions were calculated by Gaussian 09 using Density Functional Theory (DFT, RB3LYP with 6-31++G(d,p basis set. According to the calculations, the molecules have structures with various torsion angles between the benzimidazole and benzene rings from 9.7º to 47.8º. The calculated energy values with ZPE correction and DFT show that the methyl derivatives are more stable than the chloro forms. 3´,4´-Dimethoxy derivatives have higher decomposition points in comparison with the other compounds in series. The chlorine atoms of 5,6-dichloro-2- (2´,3´/2´,4´/2´,5´/3´,4´/3´,5´-dimethoxyphenyl-1H-benzimidazoles are positively charged whereas the C5 and C6 carbon atoms are negatively charged due to the attached chlorine atoms, in virtue of the electron withdrawing characteristic of the imidazole part of the benzimidazole ring. Also, some calculated prominent bond lengths and bond angles were discussed.

Diastereoselective and one-pot synthesis of trans-isoquinolonic acids via three-component condensation of homophthalic anhydride, aldehydes, and ammonium acetate catalyzed by aspartic acid

Czech Academy of Sciences Publication Activity Database

Ghorbani-Choghamarani, A.; Hajjami, M.; Norouzi, M.; Abbasityula, Y.; Eigner, Václav; Dušek, Michal

2013-01-01

Roč. 69, č. 32 (2013), s. 6541-6544 ISSN 0040-4020 Grant - others:AVČR(CZ) Praemium Academiae Institutional support: RVO:68378271 Keywords : isoquinolonic acid * diastereoselective * aldehyde * homophthalic anhydride * ammonium acetate Subject RIV: CC - Organic Chemistry Impact factor: 2.817, year: 2013

Employing natural reagents from turmeric and lime for acetic acid determination in vinegar sample

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Sam-ang Supharoek

2018-04-01

Full Text Available A simple, rapid and environmentally friendly sequential injection analysis system employing natural extract reagents was developed for the determination of acetic acid following an acid–base reaction in the presence of an indicator. Powdered lime and turmeric were utilized as the natural base and indicator, respectively. Mixing lime and turmeric produced an orange to reddish-brown color solution which absorbed the maximum wavelength at 455 nm, with absorbance decreasing with increasing acetic acid concentration. Influential parameters including lime and turmeric concentrations, reagent and sample aspirated volumes, mixing coil length and dispensing flow rate were investigated and optimized. A standard calibration graph was plotted for 0–5.0 mmol/L acetic acid with r2 = 0.9925. Relative standard deviations (RSD at 2.0 and 4.0 mmol/L acetic acid were less than 3% (n = 7, with limit of detection (LOD and limit of quantification (LOQ at 0.12 and 0.24 mmol/L, respectively. The method was successfully applied to assay acetic acid concentration in cooking vinegar samples. Results achieved were not significantly different from those obtained following a batchwise standard AOAC titration method. Keywords: Acetic acid assay, Natural reagent, Turmeric, Lime, Sequential injection analysis

Granisetron ameliorates acetic acid-induced colitis in rats.

Science.gov (United States)

Fakhfouri, Gohar; Rahimian, Reza; Daneshmand, Ali; Bahremand, Arash; Rasouli, Mohammad Reza; Dehpour, Ahmad Reza; Mehr, Shahram Ejtemaei; Mousavizadeh, Kazem

2010-04-01

Inflammatory bowel disease (IBD) is a chronically relapsing inflammation of the gastrointestinal tract, of which the definite etiology remains ambiguous. Considering the adverse effects and incomplete efficacy of currently administered drugs, it is indispensable to explore new candidates with more desirable therapeutic profiles. 5-HT( 3) receptor antagonists have shown analgesic and anti-inflammatory properties in vitro and in vivo. This study aims to investigate granisetron, a 5-HT( 3) receptor antagonist, in acetic acid-induced rat colitis and probable involvement of 5-HT(3) receptors. Colitis was rendered by instillation of 1 mL of 4% acetic acid (vol/vol) and after 1 hour, granisetron (2 mg/kg), dexamethasone (1 mg/kg), meta-chlorophenylbiguanide (mCPBG, 5 mg/kg), a 5-HT( 3) receptor agonist, or granisetron + mCPBG was given intraperitoneally. Twenty-four hours following colitis induction, animals were sacrificed and distal colons were assessed macroscopically, histologically and biochemically (malondialdehyde, myeloperoxidase, tumor necrosis factor-alpha, interleukin-1 beta and interleukin-6). Granisetron or dexamethasone significantly (p granisetron were reversed by concurrent administration of mCPBG. Our data suggests that the salutary effects of granisetron in acetic acid colitis could be mediated by 5-HT(3) receptors.

Design, synthesis and biological evaluation of novel hydroxy-phenyl-1H-benzimidazoles as radical scavengers and UV-protective agents.

Science.gov (United States)

Bino, Alessia; Baldisserotto, Anna; Scalambra, Emanuela; Dissette, Valeria; Vedaldi, Daniela Ester; Salvador, Alessia; Durini, Elisa; Manfredini, Stefano; Vertuani, Silvia

2017-12-01

An ever-increasing incidence of skin neoplastic diseases is registered. Therefore, it is important to protect the skin from the UV radiation that reaches the epidermis and dermis but also to block ROS generated by them. Our attention was attracted in developing new compounds provided with both UV filtering and antioxidant capacities. To this end, 2-phenyl-1H-benzimidazole-5-sulfonic acid (PBSA), a known UV filter, was selected as lead compound for its lack of antioxidant activity, high water solubility and good safety profile. PBSA was sequentially modified introducing hydroxyls on the phenyl ring and also substituting the functional group in position 5 of the benzimidazole ring. At the end of the synthetic study, a new, very potent class of antioxidants has been obtained. Surprisingly some of the developed molecules, while devoid of significant UV-filtering activity was endowed with potent UV-filtering booster capability if associated with known commercial UVB and UVA filters.

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

Energy Technology Data Exchange (ETDEWEB)

Koc, Ziya Erdem, E-mail: zerdemkoc@gmail.com [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey); Bingol, Haluk; Saf, Ahmet O. [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey); Torlak, Emrah [Provincial Control Laboratory, Konya (Turkey); Coskun, Ahmet [Department of Chemistry, Faculty of Science, Selcuk University, 42031 Konya (Turkey)

2010-11-15

Four new tripodal-benzimidazole derivatives were synthesized by Schiff base reaction between 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine (TRIPOD) and different diamine derivatives. The structures of the obtained compounds were identified by FT-IR, {sup 1}H NMR, {sup 13}C NMR and UV-vis spectral data, thermal analysis and elemental analysis. Electrochemical behaviors of the compounds were studied by cyclic voltammetry in DMF including 0.1 M [NBu{sub 4}] [PF{sub 6}]. The voltammograms showed peaks having similar characteristics except tripodal-benzimidazole including -NO{sub 2} derivative. In addition, their antimicrobial activities were evaluated by using the standard disk diffusion method in dimethylformamide media. The activities were determined against 4 bacteria cultures by comparing to those of gentamycin.

Aerobic Oxidation of 5-(Hydroxymethyl)furfural Cyclic Acetal Enables Selective Furan-2,5-dicarboxylic Acid Formation with CeO2 -Supported Gold Catalyst.

Science.gov (United States)

Kim, Minjune; Su, Yaqiong; Fukuoka, Atsushi; Hensen, Emiel J M; Nakajima, Kiyotaka

2018-05-14

The utilization of 5-(hydroxymethyl)furfural (HMF) for the large-scale production of essential chemicals has been largely limited by the formation of solid humin as a byproduct, which prevents the operation of stepwise batch-type and continuous flow-type processes. The reaction of HMF with 1,3-propanediol produces an HMF acetal derivative that exhibits excellent thermal stability. Aerobic oxidation of the HMF acetal with a CeO 2 -supported Au catalyst and Na 2 CO 3 in water gives a 90-95 % yield of furan 2,5-dicarboxylic acid, an increasingly important commodity chemical for the biorenewables industry, from concentrated solutions (10-20 wt %) without humin formation. The six-membered acetal ring suppresses thermal decomposition and self-polymerization of HMF in concentrated solutions. Kinetic studies supported by DFT calculations identify two crucial steps in the reaction mechanism, that is, the partial hydrolysis of the acetal into 5-formyl-2-furan carboxylic acid involving OH - and Lewis acid sites on CeO 2 , and subsequent oxidative dehydrogenation of the in situ generated hemiacetal involving Au nanoparticles. These results represent a significant advance over the current state of the art, overcoming an inherent limitation of the oxidation of HMF to an important monomer for biopolymer production. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Complexes of molybdenum(III) with 2-(2'-pyridyl)benzimidazole

Energy Technology Data Exchange (ETDEWEB)

Ghosh, S P [Patna Univ. (India). Dept. of Chemistry; Prasad, K M [H.D. Jain Coll., Arrah (India). Dept. of Chemistry

1979-07-01

Molybdenum(III) forms with 2-(2'-pyridyl) benzimidazole(LH) the trischelated complexes, (Mo(LH)/sub 3/)X/sub 3/ as well as the cationic-anionic complexes, (Mo(LH)/sub 3/X/sub 2/)/sup +/ (Mo(LH)X/sub 4/)/sup -/(X=Cl/sup -/,Br/sup -/ or NCS/sup -/), depending on pH. These complexes have been synthesised and characterised from elemental analyses, i.r. and electronic spectra, magnetic moments and molar conductance.

Fully automated synthesis of ¹¹C-acetate as tumor PET tracer by simple modified solid-phase extraction purification.

Science.gov (United States)

Tang, Xiaolan; Tang, Ganghua; Nie, Dahong

2013-12-01

Automated synthesis of (11)C-acetate ((11)C-AC) as the most commonly used radioactive fatty acid tracer is performed by a simple, rapid, and modified solid-phase extraction (SPE) purification. Automated synthesis of (11)C-AC was implemented by carboxylation reaction of MeMgBr on a polyethylene Teflon loop ring with (11)C-CO2, followed by acidic hydrolysis with acid and SCX cartridge, and purification on SCX, AG11A8 and C18 SPE cartridges using a commercially available (11)C-tracer synthesizer. Quality control test and animals positron emission tomography (PET) imaging were also carried out. A high and reproducible decay-uncorrected radiochemical yield of (41.0 ± 4.6)% (n=10) was obtained from (11)C-CO2 within the whole synthesis time about 8 min. The radiochemical purity of (11)C-AC was over 95% by high-performance liquid chromatography (HPLC) analysis. Quality control test and PET imaging showed that (11)C-AC injection produced by the simple SPE procedure was safe and efficient, and was in agreement with the current Chinese radiopharmaceutical quality control guidelines. The novel, simple, and rapid method is readily adapted to the fully automated synthesis of (11)C-AC on several existing commercial synthesis module. The method can be used routinely to produce (11)C-AC for preclinical and clinical studies with PET imaging. Copyright © 2013 Elsevier Ltd. All rights reserved.

An OmpA family protein, a target of the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius, controls acetic acid fermentation.

Science.gov (United States)

Iida, Aya; Ohnishi, Yasuo; Horinouchi, Sueharu

2008-07-01

Via N-acylhomoserine lactones, the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius NCI1051, a gram-negative acetic acid bacterium, represses acetic acid and gluconic acid fermentation. Two-dimensional polyacrylamide gel electrophoretic analysis of protein profiles of strain NCI1051 and ginI and ginR mutants identified a protein that was produced in response to the GinI/GinR regulatory system. Cloning and nucleotide sequencing of the gene encoding this protein revealed that it encoded an OmpA family protein, named GmpA. gmpA was a member of the gene cluster containing three adjacent homologous genes, gmpA to gmpC, the organization of which appeared to be unique to vinegar producers, including "Gluconacetobacter polyoxogenes." In addition, GmpA was unique among the OmpA family proteins in that its N-terminal membrane domain forming eight antiparallel transmembrane beta-strands contained an extra sequence in one of the surface-exposed loops. Transcriptional analysis showed that only gmpA of the three adjacent gmp genes was activated by the GinI/GinR quorum-sensing system. However, gmpA was not controlled directly by GinR but was controlled by an 89-amino-acid protein, GinA, a target of this quorum-sensing system. A gmpA mutant grew more rapidly in the presence of 2% (vol/vol) ethanol and accumulated acetic acid and gluconic acid in greater final yields than strain NCI1051. Thus, GmpA plays a role in repressing oxidative fermentation, including acetic acid fermentation, which is unique to acetic acid bacteria and allows ATP synthesis via ethanol oxidation. Consistent with the involvement of gmpA in oxidative fermentation, its transcription was also enhanced by ethanol and acetic acid.

Crystal structure of a complex of human chymase with its benzimidazole derived inhibitor

International Nuclear Information System (INIS)

Matsumoto, Yoshiyuki; Kakuda, Shinji; Koizumi, Masahiro; Mizuno, Tsuyoshi; Muroga, Yumiko; Kawamura, Takashi; Takimoto-Kamimura, Midori

2013-01-01

The crystal structure of human chymase complexed with a novel benzimidazole inhibitor, TJK002, was determined at 2.8 Å resolution. The present study shows that the benzimidazole ring of the inhibitor takes the stable stacking interaction with the protonated His57 in the catalytic domain of human chymase. The crystal structure of human chymase complexed with a novel benzimidazole inhibitor, TJK002, was determined at 2.8 Å resolution. The X-ray crystallographic study shows that the benzimidazole inhibitor forms a non-covalent interaction with the catalytic domain of human chymase. The hydrophobic fragment of the inhibitor occupies the S1 pocket. The carboxylic acid group of the inhibitor forms hydrogen bonds with the imidazole N(∊) atom of His57 and/or the O(γ) atom of Ser195 which are members of the catalytic triad. This imidazole ring of His57 induces π–π stacking to the benzene ring of the benzimidazole scaffold as P2 moiety. Fragment molecular orbital calculation of the atomic coordinates by X-ray crystallography shows that this imidazole ring of His57 could be protonated with the carboxyl group of Asp102 or hydroxyl group of Ser195 and the stacking interaction is stabilized. A new drug design strategy is proposed where the stacking to the protonated imidazole of the drug target protein with the benzimidazole scaffold inhibitor causes unpredicted potent inhibitory activity for some enzymes

Soil washing of chromium- and cadmium-contaminated sludge using acids and ethylenediaminetetra acetic acid chelating agent.

Science.gov (United States)

Gitipour, Saeid; Ahmadi, Soheil; Madadian, Edris; Ardestani, Mojtaba

2016-01-01

In this research, the effect of soil washing in the removal of chromium- and cadmium-contaminated sludge samples collected from Pond 2 of the Tehran Oil Refinery was investigated. These metals are considered as hazardous substances for human health and the environment. The carcinogenicity of chromate dust has been established for a long time. Cadmium is also a potential environmental toxicant. This study was carried out by collecting sludge samples from different locations in Pond 2. Soil washing was conducted to treat the samples. Chemical agents, such as acetic acid, ethylenediaminetetra acetic acid (EDTA) and hydrochloric acid, were used as washing solutions to remove chromium and cadmium from sludge samples. The results of this study indicated that the highest removal efficiencies from the sludge samples were achieved using a 0.3 M HCl solution with 82.69% and 74.47% for chromium and cadmium, respectively. EDTA (0.1 M) in the best condition extracted 66.81% of cadmium and 72.52% of chromium from the sludges. The lowest efficiency values for the samples, however, were achieved using 3 M acetic acid with 41.7% and 46.96% removals for cadmium and chromium, respectively. The analysis of washed sludge indicated that the heavy metals removal decreased in the order of 3 M acetic acid < 0.1 M EDTA<0.3 M HCl, thus hydrochloric acid appears to offer a greater potential as a washing agent in remediating the sludge samples.

On the formation of C2H5O2+ ions having the structure of hydroxy-protonated acetic acid

NARCIS (Netherlands)

Terlouw, J.K.; Koster, C.G. de; Levsen, K.

1984-01-01

Experiments are reported which are best explained in terms of the formation of the long-sought hydroxy-protonated acetic acid, CH3C(O)OH2- This C2 H5O2+ species, generated upon dissociative ionization of 2,4-dihydroxy-2-methylpentane (consecutive losses of CH3. and C3H6), is characterized by a

Acetic acid dressings: Finding the Holy Grail for infected wound management

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Kapil S Agrawal

2017-01-01

Full Text Available Background: Wounds have since long, contributed majorly to the health-care burden. Infected long-standing non-healing wounds place many demands on the treating surgeon and are devastating for the patients physically, nutritionally, vocationally, financially, psychologically and socially. Acetic acid has long been included among agents used in the treatment of infected wounds. In this study, we have evaluated the use of acetic acid for topical application in the treatment of infected wounds. Materials and Methods: A total of 100 patients with infected wounds were treated with topical application of 1% acetic acid as dressing material after appropriate cleaning. A specimen of wound swab was collected before first application and further on days 3, 7, 10 and 14. Daily dressings of wounds were done similarly. Minimum inhibitory concentration (MIC of acetic acid against various organisms isolated was determined. Results: The patients treated ranged between 9 and 60 years, with the mean age 33 years. Nearly 70% of patients were male. Aetiologies of wounds: infective 35, diabetic 25, trauma 20, burns 10, venous ulcers 5 and infected graft donor site 5. Various microorganisms isolated include Pseudomonas aeruginosa (40%, Staphylococcus aureus (2%, Acinetobacter (12%, Escherichia Coli (5%, Proteus mirabilis (3%, Klebsiella (18%, methicillin-resistant S. aureus (10%, Streptococcus (2% and Enterococcus (1%, Citrobacter (1%. Few wounds (6% also isolated fungi. About 28%, 64% and 8% of patients isolated no growth on culture after 7, 14 and 21 days, respectively. MIC of all isolated organisms was ≤0.5%. Conclusion: pH of the wound environment plays a pivotal role in wound healing. Acetic acid with concentration of 1% has shown to be efficacious against wide range of bacteria as well as fungi, simultaneously accelerating wound healing. Acetic acid is non-toxic, inexpensive, easily available and efficient topical agent for effective elimination of wound

Microwave-assisted one-step synthesis of acetate-capped NaYF4

DEFF Research Database (Denmark)

Reddy, Kumbam Lingeshwar; Prabhakar, Neeraj; Arppe, Riikka

2017-01-01

Acetate-capped hydrophilic cubic phase NaYF4:Yb/Er upconversion nanophosphors were effectively synthesized in a single step employing a facile microwave-assisted synthesis route by applying relatively low temperatures in a short span of time compared to the conventional synthetic methods. The nan......Acetate-capped hydrophilic cubic phase NaYF4:Yb/Er upconversion nanophosphors were effectively synthesized in a single step employing a facile microwave-assisted synthesis route by applying relatively low temperatures in a short span of time compared to the conventional synthetic methods...

1-[2,2-Bis(1,3-benzimidazol-1-ylmethyl-3-bromopropyl]-1,3-benzimidazole

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Tai-Bao Wei

2011-07-01

Full Text Available The title compound, C26H23BrN6, has been synthesized as a potential ligand for the construction of metal–organic frameworks. The three benzimidazolyl groups present three potential coordination nodes. The dihedral angles between the benzimidazole ring systems are 74.03 (10, 66.49 (9 and 74.09 (9°. The structure contains large voids, which contain highly disordered solvent molecules that may be CH3CH2OH. Since the solvent molecules could not be located, the PLATON/SQUEEZE procedure [Spek (2009. Acta Cryst. D65, 148–155] was used.

Process design of high-concentration benzimidazole wastewater treatment based on the molecular structure of contaminants.

Science.gov (United States)

Li, Chenru; Qian, Kun; Liu, Qinyao; Zhang, Qianyi; Yao, Chen; Song, Wei; Wang, Yihong

2018-04-01

Benzimidazole is an important intermediate in industry and it is usually difficult to be degraded by many treatment technologies. Looking for a highly effective, environment-friendly degradation process for benzimidazole wastewater is of great significance to reduce pollution. Based on the structure of contaminants, the micro-electrolysis (ME) coupled with the Fenton technique was chosen to degrade the industrial benzimidazole wastewater. Special feeding was applied to maintain the suitable hydrogen peroxide (H 2 O 2 ) concentration to produce the hydroxyl radicals (•OH) as much as possible and protect •OH from being quenched by excess H 2 O 2 according to the reaction mechanism. The results showed that this combined technique was highly efficient to decompose benzimidazole compounds. More chemical oxygen demand (COD) could be reduced when flow control was used, compared to the flow not being controlled. The COD removal rate could reach 85.2% at optimal parameters. Then the effluent of this process was combined with the existing biochemical system for further degradation. The studies of Ultraviolet Spectrophotometry, Fourier Transform Infrared Spectroscopy and Liquid Chromatography Mass Spectrometry showed that both 2-(a-Hydroxyethyl) benzimidazole and 2-Acetylbenzimidazole were decomposed to the isopropanolamine and aniline after the ME treatment; then the intermediates were oxidized into oxalic acid after the Fenton reaction.

2-[(1R*,4R*-1,4-Dihydroxycyclohexyl]acetic acid

Directory of Open Access Journals (Sweden)

Mohammad Arfan

2011-04-01

Full Text Available The title compound, C8H14O4, is an isolation product of the aerial parts of Senecio desfontanei. The acetic acid group is oriented at a dihedral angle of 48.03 (9° with respect to the basal plane of the cyclohexane-1,4-diol chair. An intramolecular O—H...O hydrogen bond generates an S(6 ring with an envelope conformation. In the crystal, molecules are linked by O—H...O hydrogen bonds, resulting in R33(20 ring motifs and C(2 O—H...O—H...O—H... chains. Overall, a three-dimensional polymeric network arises. A C—H...O contact is also present.

Employing natural reagents from turmeric and lime for acetic acid determination in vinegar sample.

Science.gov (United States)

Supharoek, Sam-Ang; Ponhong, Kraingkrai; Siriangkhawut, Watsaka; Grudpan, Kate

2018-04-01

A simple, rapid and environmentally friendly sequential injection analysis system employing natural extract reagents was developed for the determination of acetic acid following an acid-base reaction in the presence of an indicator. Powdered lime and turmeric were utilized as the natural base and indicator, respectively. Mixing lime and turmeric produced an orange to reddish-brown color solution which absorbed the maximum wavelength at 455 nm, with absorbance decreasing with increasing acetic acid concentration. Influential parameters including lime and turmeric concentrations, reagent and sample aspirated volumes, mixing coil length and dispensing flow rate were investigated and optimized. A standard calibration graph was plotted for 0-5.0 mmol/L acetic acid with r 2  = 0.9925. Relative standard deviations (RSD) at 2.0 and 4.0 mmol/L acetic acid were less than 3% (n = 7), with limit of detection (LOD) and limit of quantification (LOQ) at 0.12 and 0.24 mmol/L, respectively. The method was successfully applied to assay acetic acid concentration in cooking vinegar samples. Results achieved were not significantly different from those obtained following a batchwise standard AOAC titration method. Copyright © 2017. Published by Elsevier B.V.

Synthesis and characterization of 2-substituted benzimidazoles and their evaluation as anticancer agent

Science.gov (United States)

Azam, Mohammad; Khan, Azmat Ali; Al-Resayes, Saud I.; Islam, Mohammad Shahidul; Saxena, Ajit Kumar; Dwivedi, Sourabh; Musarrat, Javed; Trzesowska-Kruszynska, Agata; Kruszynski, Rafal

2015-05-01

In this work, we report a series of benzimidazole derivatives synthesized from benzene-1,2-diamine and aryl-aldehydes at room temperature. The synthesized compounds have been characterized on the basis of elemental analysis and various spectroscopic studies viz., IR, 1H- and 13C-NMR, ESI-MS as well by X-ray single X-ray crystallographic study. Interaction of these compounds with CT-DNA has been examined with fluorescence experiments and showed significant binding ability. All the synthesized compounds have been screened for their antitumor activities against various human cancer cell lines viz., Human breast adenocarcinoma cell line (MCF-7), Human leukemia cell line (THP-1), Human prostate cancer cell lines (PC-3) and adenocarcinomic human alveolar basal epithelial cell lines (A-549). Interestingly, all the compounds showed significant anticancer activity.

Fermentative utilization of glycerol residue for the production of acetic acid

Science.gov (United States)

Irvan; Trisakti, B.; Hasibuan, R.; Joli, M.

2018-02-01

Glycerol residue, frequently known as pitch, is a waste produced from the downstream product of crude glycerine distillation. With the increasing need of pure glycerine in the world, the glycerol residue produced is also increasing. Glycerol residue is a solid waste at room temperature, highly alkaline (pH > 13), corrosive, and categorized as hazardous and poisonous waste. In this research, acetic acid was produced from glycerol residue through the anaerobic fermentation process by using purple non-sulphur photosynthetic bacteria. The purpose of this study was to find out the influence of concentration change of glycerol residue on time and to find out the possibility of glycerol residue to be utilized as acetic acid. In this research, at first 400 g of glycerol residue was diluted with 200 ml of distilled water to change the glycerine phase, from solid to liquid at room temperature, acidified by using hydrochloric acid until pH 2. The top layer formed was fatty acid and triglycerides that should be removed. Meanwhile, the bottom layer was diluted glycerol residue which was then neutralized with caustic soda. To produce acetic acid, glycerol residue with various concentrations, salt, and purple non-sulphur photosynthetic bacteria were put together into a 100 ml bottle which had been previously sterilized, then incubated for four weeks under the light of 40-watt bulb. The result showed that on the 28th day of fermentation, the produced acetic acid were 0.28, 1.85, and 0.2% (w/w) by using glycerine with the concentration of 0.5, 1.0, and 1.5% (w/w), respectively.

An OmpA Family Protein, a Target of the GinI/GinR Quorum-Sensing System in Gluconacetobacter intermedius, Controls Acetic Acid Fermentation▿ †

Science.gov (United States)

Iida, Aya; Ohnishi, Yasuo; Horinouchi, Sueharu

2008-01-01

Via N-acylhomoserine lactones, the GinI/GinR quorum-sensing system in Gluconacetobacter intermedius NCI1051, a gram-negative acetic acid bacterium, represses acetic acid and gluconic acid fermentation. Two-dimensional polyacrylamide gel electrophoretic analysis of protein profiles of strain NCI1051 and ginI and ginR mutants identified a protein that was produced in response to the GinI/GinR regulatory system. Cloning and nucleotide sequencing of the gene encoding this protein revealed that it encoded an OmpA family protein, named GmpA. gmpA was a member of the gene cluster containing three adjacent homologous genes, gmpA to gmpC, the organization of which appeared to be unique to vinegar producers, including “Gluconacetobacter polyoxogenes.” In addition, GmpA was unique among the OmpA family proteins in that its N-terminal membrane domain forming eight antiparallel transmembrane β-strands contained an extra sequence in one of the surface-exposed loops. Transcriptional analysis showed that only gmpA of the three adjacent gmp genes was activated by the GinI/GinR quorum-sensing system. However, gmpA was not controlled directly by GinR but was controlled by an 89-amino-acid protein, GinA, a target of this quorum-sensing system. A gmpA mutant grew more rapidly in the presence of 2% (vol/vol) ethanol and accumulated acetic acid and gluconic acid in greater final yields than strain NCI1051. Thus, GmpA plays a role in repressing oxidative fermentation, including acetic acid fermentation, which is unique to acetic acid bacteria and allows ATP synthesis via ethanol oxidation. Consistent with the involvement of gmpA in oxidative fermentation, its transcription was also enhanced by ethanol and acetic acid. PMID:18487322

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

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Iliyan Ivanov

2013-02-01

Full Text Available We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylation of the obtained amines with different acid chlorides or sulfochlorides. We compared the cyclisation step using conventional (milieu of acetic-trifluoracetic acid = 4:1 and solid supported reagents (SiO2/PPA, as recovered, regenerated and reused without loss of its activity catalyst. We found that in comparison to conventional methods, the yields of the reaction are greater and the reaction time is shorter.

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated ...

African Journals Online (AJOL)

Cytotoxic effect of betulinic acid and betulinic acid acetate isolated from Melaleuca cajuput on human myeloid leukemia (HL-60) cell line. ... The cytotoxic effect of betulinic acid (BA), isolated from Melaleuca cajuput a Malaysian plant and its four synthetic derivatives were tested for their cytotoxicity in various cell line or ...

Intravenous supplementation of acetate, glucose or essential amino acids to an energy and protein deficient diet in lactating dairy goats

DEFF Research Database (Denmark)

Safayi, S.; Nielsen, M. O.

2013-01-01

amino acid supply is suboptimal. Goats were fed a basal diet deficient in energy (90% of requirements) and protein (80% of requirements), and were randomly allocated to 4 treatments in a balanced 4 x 4 Latin square design. The treatments consisted of 4-d continuous intravenous infusions of isoosmotic...... and close to significantly by ACE, but not by GLU treatment. GLU reduced milk protein percentage compared to all other treatments. High milk protein yields on EM and ACE treatments were associated with higher arterial AVD for acetate and oxygen (not significant for ACE), and higher AVD also for beta......In the present experiment we aimed to study, if milk synthesis is more sensitive toward deficiency in supply of amino acids in early (EL) versus late lactation (LL), and if energy yielding substrates in the form of acetate (but not glucose) can contribute to sustain milk (protein) synthesis, when...

Catabolism of indole-3-acetic acid and 4- and 5-chloroindole-3-acetic acid in Bradyrhizobium japonicum

DEFF Research Database (Denmark)

Jensen, J B; Egsgaard, H; Van Onckelen, H

1995-01-01

Some strains of Bradyrhizobium japonicum have the ability to catabolize indole-3-acetic acid. Indoleacetic acid (IAA), 4-chloro-IAA (4-Cl-IAA), and 5-Cl-IAA were metabolized to different extents by strains 61A24 and 110. Metabolites were isolated and analyzed by high-performance liquid chromatogr...

Genome-wide identification of Saccharomyces cerevisiae genes required for tolerance to acetic acid

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Sá-Correia Isabel

2010-10-01

Full Text Available Abstract Background Acetic acid is a byproduct of Saccharomyces cerevisiae alcoholic fermentation. Together with high concentrations of ethanol and other toxic metabolites, acetic acid may contribute to fermentation arrest and reduced ethanol productivity. This weak acid is also a present in lignocellulosic hydrolysates, a highly interesting non-feedstock substrate in industrial biotechnology. Therefore, the better understanding of the molecular mechanisms underlying S. cerevisiae tolerance to acetic acid is essential for the rational selection of optimal fermentation conditions and the engineering of more robust industrial strains to be used in processes in which yeast is explored as cell factory. Results The yeast genes conferring protection against acetic acid were identified in this study at a genome-wide scale, based on the screening of the EUROSCARF haploid mutant collection for susceptibility phenotypes to this weak acid (concentrations in the range 70-110 mM, at pH 4.5. Approximately 650 determinants of tolerance to acetic acid were identified. Clustering of these acetic acid-resistance genes based on their biological function indicated an enrichment of genes involved in transcription, internal pH homeostasis, carbohydrate metabolism, cell wall assembly, biogenesis of mitochondria, ribosome and vacuole, and in the sensing, signalling and uptake of various nutrients in particular iron, potassium, glucose and amino acids. A correlation between increased resistance to acetic acid and the level of potassium in the growth medium was found. The activation of the Snf1p signalling pathway, involved in yeast response to glucose starvation, is demonstrated to occur in response to acetic acid stress but no evidence was obtained supporting the acetic acid-induced inhibition of glucose uptake. Conclusions Approximately 490 of the 650 determinants of tolerance to acetic acid identified in this work are implicated, for the first time, in tolerance to

Anion exchange membrane based on alkali doped poly(2,5-benzimidazole) for alkaline membrane fuel cell

CSIR Research Space (South Africa)

Luo, H

2010-03-01

Full Text Available was prepared. The alkali doped poly(2,5-benzimidazole) membrane is a promising candidate as anion exchange membrane for fuel cell application. The alkali doped poly(2,5-benzimidazole) membrane reached an anion conductivity of 2.3×10-2 S cm-1 at room temperature...

Dibromido[1,1′-dibutyl-2,2′-(pentane-1,1-diyldi-1H-benzimidazole]copper(II

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Robert T. Stibrany

2010-07-01

Full Text Available In the title compound, [CuBr2(C27H36N4], the CuII ion exhibits a distorted tetrahedral coordination geometry provided by two bromide ions and by chelation of two imine N-atom donors from a bis(benzimidazole ligand. Chelation results in a six-membered boat-shaped ring which links the benzimidazole groups. Each bis(benzimidazole fragment contains three n-butyl substituents, two of which have the expected trans conformation; the third exhibits the higher-energy cis conformation, an orientation consistent with several short intramolecular C—H...Br interactions. Essentially planar (r.m.s. deviations of 0.0101 and 0.0183 Å benzimidazole groups are oriented so as to give the bis(benzimidazole fragment a V-shaped appearance in profile with the cis and trans n-butyl groups directed to opposite sides of the planes. In the crystal, columns of molecules along the b-axis direction form layers parallel to the (202 planes. Within a given column, the molecules are linked by C—H...Br hydrogen bonds. The molecules in adjacent columns are also linked by intermolecular C—H...π interactions, forming a three-dimensional network.

Additive effects of acetic acid upon hydrothermal reaction of amylopectin

International Nuclear Information System (INIS)

Sugano, Motoyuki; Katoh, Harumi; Komatsu, Akihiro; Kobayashi, Hiroshi; Okado, Kohta; Kakuta, Yusuke; Hirano, Katsumi

2012-01-01

It is well known that over 0.8 kg kg −1 of starch is consisted of amylopectin (AP). In this study, production of glucose for raw material of ethanol by hydrothermal reaction of AP as one of the model compound of food is discussed. Further, additive effects of acetic acid upon hydrothermal reactions of AP are also investigated. During hydrothermal reaction of AP, production of glucose occurred above 453 K, and the glucose yield increased to 0.48 kg kg −1 at 473 K. Upon hydrothermal reaction of AP at 473 K, prolongation of the holding time was not effective for the increase of the glucose yield. Upon hydrothermal reaction of AP at 473 K for 0 s, the glucose yield increased significantly by addition between 0.26 mol L −1 and 0.52 mol L −1 of acetic acid. However, the glucose yield decreased and the yield of the other constituents increased with the increases of concentration of acetic acid from 0.65 mol L −1 to 3.33 mol L −1 . It was considered that hydrolysis of AP to yield glucose was enhanced due to the increase of the amount of proton derived from acetic acid during hydrothermal reaction with 0.52 mol L −1 of acetic acid. -- Highlights: ► Glucose production by hydrothermal reaction of amylopectin (AP) at 473 K. ► Glucose yield increased to 0.48 kg kg -1 at 473 K. ► Prolongation of holding time was not effective for glucose yield. ► Glucose yield increased significantly by acetic acid (0.26–0.52 mol L-1) addition. ► Hydrolysis of AP to glucose was enhanced due to increase of proton from acetic acid.

Poly(imide benzimidazole)s for high temperature polymer electrolyte membrane fuel cells

DEFF Research Database (Denmark)

Yuan, Sen; Guo, Xiaoxia; Aili, David

2014-01-01

A series of poly(imide benzimidazole) random copolymers (PIBIs) was synthesized by condensation polymerization of biphenyl-4,4'-diyldi(oxo)-4,4'-bis(1,8-naphthalenedicarboxylic anhydride) (BPNDA), 2-(4-aminophenyl)-5-aminobenzimidazole (APABI) and 4,4'diaminodiphenyl ether (ODA) in m-cresol in th......A series of poly(imide benzimidazole) random copolymers (PIBIs) was synthesized by condensation polymerization of biphenyl-4,4'-diyldi(oxo)-4,4'-bis(1,8-naphthalenedicarboxylic anhydride) (BPNDA), 2-(4-aminophenyl)-5-aminobenzimidazole (APABI) and 4,4'diaminodiphenyl ether (ODA) in m...

10-Undecenoic Acid, an Inexpensive Source for the Synthesis of the Pheromones of Cotton Pests, Peach Tree Borer and Cherry Tree Borer

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Subrata Chattopadhyay

1997-06-01

Full Text Available The aldehyde 7, derived from 10-undecenoic acid (5 on cis-selective Wittig reaction with pentylidenetriphenylphosphorane, subsequent deprotection and oxidation gave the pheromone (11Z-hexadecenal (1. Wittig-Horner olefination of 1 with the phosphonate 9 furnished the conjugated ester 10 which on base catalyzed isomerization to the (3Z-ester 11 followed by LAH reduction and acetylation gave (3Z,13Z-octadeadien-1-yl acetate (2. Compound 10 on the other hand was chemoselectively reduced and acetylated to furnish the pheromone (2E,13Z-octadeadien-1-yl acetate (4. For the synthesis of (3E,13Z-octadeadien-1-yl acetate (3, 1 was condensed with malonic acid under modified condition to afford the acid 13 which was converted to 3 by standard reaction protocol.

CT-guided percutaneous acetic acid injection therapy for liver metastasis

International Nuclear Information System (INIS)

Yu Tongfu; Wang Dehang; Zhuang Zhenwu; Li Linxun; Shi Haibin

2002-01-01

Objective: To evaluate the efficacy of CT-guided percutaneous acetic acid injection (PAI) for liver metastasis. Methods: Thirty-five cases (40 lesions) with liver metastasis were treated with PAI. 4-10 ml of 30% acetic acid with 1 ml contrast media was injected into every lesion. PAI was performed twice a week, and repeated for 2 to 3 weeks. Results: The tumors shrunk in 23 lesions, and remained unchanged in 12 lesions. The efficiency was 87.5%. All cases were followed up for 3 months to 3 years. One year survival rates was 62.9% (22 cases), 2 years 40.0% (14 cases), and 3 years 22.9% (8 cases). Conclusion: PAI was an effective therapy for liver metastasis

Novel benzimidazole derivatives as corrosion inhibitors of mild steel in the acidic media. Part II: Theoretical studies

International Nuclear Information System (INIS)

Cao, Ziyi; Tang, Yongming; Cang, Hui; Xu, Jinqiu; Lu, Gang; Jing, Wenheng

2014-01-01

Highlights: • Quantum chemical and MD studies of benzimidazole derivatives inhibitors. • Inhibition effectiveness depends on the ability to accept electrons. • Active sites of adsorption are mainly centralized on imidazole rings. • Steric effect results in the non-planar adsorption of BBIA and TBIA. - Abstract: In this paper, the adsorption behavior and inhibition mechanism of 2-aminomethyl benzimidazole (ABI), bis(2-benzimidazolylmethyl) amine (BBIA) and tri-(2-benzimidazolylmethyl) amine (TBIA) on the surface of mild steel were studied by quantum chemical calculations and molecular dynamics (MD) simulations. It was found that the three molecules show the similar ability to donate electrons while the difference in inhibition performance should mainly be attributed to the difference in accepting electrons. MD simulations show that steric effect between the benzimidazole segments significantly affects the adsorptive configurations of the molecules on Fe (1 0 0) surface

Acetic acid bacteria: A group of bacteria with versatile biotechnological applications.

Science.gov (United States)

Saichana, Natsaran; Matsushita, Kazunobu; Adachi, Osao; Frébort, Ivo; Frebortova, Jitka

2015-11-01

Acetic acid bacteria are gram-negative obligate aerobic bacteria assigned to the family Acetobacteraceae of Alphaproteobacteria. They are members of the genera Acetobacter, Gluconobacter, Gluconacetobacter, Acidomonas, Asaia, Kozakia, Swaminathania, Saccharibacter, Neoasaia, Granulibacter, Tanticharoenia, Ameyamaea, Neokomagataea, and Komagataeibacter. Many strains of Acetobacter and Komagataeibacter have been known to possess high acetic acid fermentation ability as well as the acetic acid and ethanol resistance, which are considered to be useful features for industrial production of acetic acid and vinegar, the commercial product. On the other hand, Gluconobacter strains have the ability to perform oxidative fermentation of various sugars, sugar alcohols, and sugar acids leading to the formation of several valuable products. Thermotolerant strains of acetic acid bacteria were isolated in order to serve as the new strains of choice for industrial fermentations, in which the cooling costs for maintaining optimum growth and production temperature in the fermentation vessels could be significantly reduced. Genetic modifications by adaptation and genetic engineering were also applied to improve their properties, such as productivity and heat resistance. Copyright © 2014 Elsevier Inc. All rights reserved.

Supported Ionic Liquid Phase (SILP) Catalysis for the Production of Acetic acid by Methanol Carbonylation

DEFF Research Database (Denmark)

Hanning, Christopher William

at the beginning with the construction of a suitable test reactor, then followed by the synthesis and testing of all the catalysts reported. A variety of nitrogen based ionic liquids were initially tested, giving good results and stability in the system. Later a number of phosphonium based salts were tested (these......The work presented here is focused on the development of a new reaction process. It applies Supported Ionic Liquid Phase (SILP) catalysis to a specific reaction. By reacting methanol and carbon monoxide over a rhodium catalyst, acetic acid can be formed. This reaction is important on a large scale...... were no longer classified as ionic liquids due to melting points above 100◦C). The phosphonium salts showed even better activity in the system compared to the ionic liquids. Overall the work has shown that this process for the manufacture of acetic acid is viable industrially. This is backed up...

Gas chromatography/isotope ratio mass spectrometry: analysis of methanol, ethanol and acetic acid by direct injection of aqueous alcoholic and acetic acid samples.

Science.gov (United States)

Ai, Guomin; Sun, Tong; Dong, Xiuzhu

2014-08-15

Methanol, ethanol, and acetic acid are not easily extracted from aqueous samples and are susceptible to isotope fractionation in gas chromatography/isotope ratio mass spectrometry (GC/IRMS) analysis. Developing a direct dilution GC/IRMS method for aqueous samples, by adjusting the sample concentrations in common solvents to be similar to each other and using a fixed GC split ratio, is very convenient and important because any linearity effects caused by amount-dependent isotope fractionation can be avoided. The suitability of acetonitrile and acetone solvents for the GC/IRMS analysis of pure methanol, ethanol and acetic acid, and commercial liquor and vinegar samples was evaluated using n-hexane and water as control solvents. All the solvents including water were separated from the analyte on a HP-INNOWAX column and were diverted away from the combustion interface. The influence of liquor matrix on the ethanol GC/IRMS analyses was evaluated by adding pure ethanol to liquor samples. Acetonitrile and acetone gave similar δ(13) C values for pure ethanol and pure acetic acid to those obtained in water and n-hexane, and also gave similar δ(13) C values of ethanol in liquor and acetic acid in white vinegar to that obtained in water. For methanol analysis, acetonitrile and refined acetone gave similar δ(13) C values to that obtained in water, but n-hexane was not a suitable solvent. In addition, isotopic fractionation caused by solvent and solute interactions was observed. We recommend using acetonitrile for the GC/IRMS analysis of aqueous alcoholic samples, and acetone for the analysis of aqueous acetic acid samples. This direct dilution method can provide high accurate and precise GC/IRMS analysis of the relative changes in δ(13) C values of methanol, ethanol, and acetic acid. Copyright © 2014 John Wiley & Sons, Ltd.

Effects of benzylaminopurine and naphthalene acetic acid on ...

African Journals Online (AJOL)

This study was conducted to evaluate the pineapple regeneration and shoot growth as affected by 6- benzylaminopurine (BAP) at 2.0 mg/l and naphthalene acetic acid (NAA) at 0.2 mg/l in vitro. BAP and NAA at the concentration of 2.0 and 0.2 mg/l were used in this study. BAP at 2.0 mg/l significantly affected the production ...

A study of butyl acetate synthesis. 4-reaction kinetics

OpenAIRE

Álvaro Orjuela Londoño; Fernando Leiva Lenis; Luis Alejandro Boyacá Mendivelso; Gerardo Rodríguez Niño; Luis María Carballo Suárez

2006-01-01

This work was aimed at studying liquid-phase acetic acid and butyl alcohol esterification reaction (P atm =0.76 Bar),using an ion exchange resin (Lewatit K-2431) as catalyst. The effect of the absence of internal and external mass transport on catalyst particles was established in the research conditions used here. A set of assays to determine the effect of catalyst load (0.5%, 1%, 2% w/w) temperature (73°C, 80°C, 87°C) and molar ratio (1:2, 1:1, 2:1 acid/alcohol) on reaction rate was carrie...

Microwave-assisted synthesis of some nitro-benzimidazoles and their salicyl and isatin Schiff bases

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F. Yılmaz

2017-11-01

Full Text Available A series of 5-nitrosubstituted benzimidazole and 6-nitro substituted benzimidazole derivatives were synthesized starting from iminoester hydrochloride and 4-nitro-o-phenylenediamine under microwave irradiation. The structure of newly synthesized compounds was confirmed by IR, 1H-NMR, 13C-NMR, LC-MS spectroscopy and elemental analysis.

Sustainable hydrogen from bio-oil - Catalytic steam reforming of acetic acid as a model oxygenate

NARCIS (Netherlands)

Takanabe, Kazuhiro; Seshan, K.; Lefferts, Leon; Aika, Ken-ichi

2004-01-01

Steam reforming of acetic acid as a model oxygenate present in bio-oil over Pt/ZrO2 catalysts has been studied. Pt/ZrO2 catalysts are very active, completely converting acetic acid and give hydrogen yield close to thermodynamic equilibrium. The catalyst deactivated by formation of oligomers, which

An experimental study for efficacy of acetic acid as a sclerosing agent

International Nuclear Information System (INIS)

Kim, Young Chan; Oh, Ju Hyung; Yoon, Yup; Ko, Young Tae; Choi, Woo Suk; Kim, Eui Jong; Lim, Joo Won

1997-01-01

To evaluate the efficacy of acetic acid as a sclerosing agent by observation of histologic change in urinary bladder epithelium after the instillation of acetic acid. Urinary bladder of the rabbit was catheterized with a Foley catheter, and acetic acid of 10%, 20%, 30%, 40% and 50% concentration was instilled for 5 minutes. After evacuation of the acid, the bladder was irrigated three times with normal saline. After two days, gross and histologic examinations of the bladder were performed. A bladder into which 10% acetic acid had been instilled revealed a nearly normal epithelium without denudation. In two cases, 20% acetic acid was instilled;one revealed partial denudation of the epithelium and the other revealed complete denudation. Mild to moderate interstitial edema and vascular congestion of the bladder wall were evident in all cases in which acid at a concentration of 30% or more had been instilled. In all cases in which the concentration of acid was greater than 30%, the epithelium was completely denuded. An acetic acid concentration of 40% or more is sufficient to completely destroy the epithelium of rabbit urinary bladder, and may be effective as a new sclerosing agent in cases of renal or hepatic cyst

Mild and Efficient One Pot Synthesis of Imidazolinesand Benzimidazoles from Aldehydes

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Rajesh Kumar

2007-01-01

Full Text Available A series of some imidazolines and benzimidazoles were synthesizedfrom various aldehydes and 1,2-diamines in the presence of ceric(IVammonium nitrate (CAN. The title compounds were prepared via one stepsynthesis method. The simplicity of the reaction conditions with shorterreaction time and with out use of column chromatography to get the pureproducts in high yields makes this method more attractive for organic chemists.

Synthesis, DNA binding ability and anticancer activity of 2-heteroaryl substituted benzimidazoles linked pyrrolo[2,1-c][1,4]benzodiazepine conjugates.

Science.gov (United States)

Kamal, Ahmed; Pogula, Praveen Kumar; Khan, Mohammed Naseer Ahmed; Seshadri, Bobburi Naga; Sreekanth, Kokkonda

2013-08-01

As a continuation of our efforts to develop the benzimidazole-PBD conjugates as potential anticancer agents, a series of heteroaryl substituted benzimidazole linked PBD conjugates has been synthesized and evaluated for their anticancer potential in 60 human cancer cell lines. Most of the compounds exhibited promising anticancer activity and interestingly, compounds 4c and 4d displayed significant activity in most of the cell lines tested. Whereas, compound 4e showed selectivity in renal cancer cells with GI50 values of <10 and 70 nM against RXF 393 and UO-31 cell lines, respectively. Further, these compounds also showed significant DNA-binding affinity by thermal denaturation study using duplex form of calf thymus (CT) DNA.

Methanogenesis from acetate by Methanosarcina barkeri: Catalysis of acetate formation from methyl iodide, CO/sub 2/, and H/sub 2/ by the enzyme system involved

Energy Technology Data Exchange (ETDEWEB)

Laufer, K; Eikmanns, B; Frimmer, U; Thauer, R K

1987-04-01

Cell suspensions of Methanosarcina barkeri grown on acetate catalyze the formation of methane and CO/sub 2/ from acetate as well as an isotopic exchange between the carboxyl group of acetate and CO/sub 2/. Here we report that these cells also mediate the synthesis of acetate from methyl iodide, CO/sub 2/, and reducing equivalents (H/sub 2/ or CO), the methyl group of acetate being derived from methyl iodide and the carboxyl group from CO/sub 2/. Methyl chloride and methyltosylate but not methanol can substitute for methyl iodide in this reaction. Acetate formation from methyl iodide, CO/sub 2/, and reducing equivalents is coupled with the phosphorylation of ADP. Evidence is presented that methyl iodide is incorporated into the methyl group of acetate via a methyl corrinoid intermediate (deduced from inhibition experiments with propyl iodide) and that CO/sub 2/ is assimilated into the carboxyl group via a C/sub 1/ intermediate which does not exchange with free formate or free CO. The effects of protonophores, of the proton-translocating ATPase inhibitor N,N'-dicyclohexylcarbodiimide, and of arsenate on acetate formation are interpreted to indicate that the reduction of CO/sub 2/ to the oxidation level of the carboxyl group of acetate requires the presence of an electrochemical proton potential and that acetyl-CoA or acetyl-phosphate rather than free acetate is the immediate product of the condensation reaction. These results are dicsussed with respect to the mechanism of methanogenesis from acetate.

Density functional theory study of acetic acid steam reforming on Ni(111)

Science.gov (United States)

Ran, Yan-Xiong; Du, Zhen-Yi; Guo, Yun-Peng; Feng, Jie; Li, Wen-Ying

2017-04-01

Catalytic steam reforming of bio-oil is a promising process to convert biomass into hydrogen. To shed light on this process, acetic acid is selected as the model compound of the oxygenates in bio-oil, and density functional theory is applied to investigate the mechanism of acetic acid steam reforming on the Ni(111) surface. The most favorable pathway of this process on the Ni(111) surface is suggested as CH3COOH* → CH3COO* → CH3CO* → CH2CO* → CH2* + CO* → CH* → CHOH* → CHO* → CO*, followed by the water gas shift reaction to produce CO2 and H2. CH* species are identified as the major carbon deposition precursor, and the water gas shift reaction is the rate-determining step during the whole acetic acid steam reforming process, as CO* + OH* → cis-COOH* is kinetically restricted with the highest barrier of 1.85 eV. Furthermore, the formation pathways and initial dissociation of important intermediates acetone and acetaldehyde are also investigated.

Early effects of dietary orotic acid upon liver lipid synthesis and bile cholesterol secretion in rats

International Nuclear Information System (INIS)

Tokmakjian, S.D.; Haines, D.S.

1985-01-01

Dietary orotic acid is known to cause impaired fatty acid synthesis and increased cholesterol synthesis in rats. The authors found that the impaired fatty acid synthesis occurs during the first day of orotic acid feeding and, in studies with albumin-bound [1- 14 C]palmitic acid, an associated decrease in the rate of esterification of this fatty acid into triacylglycerol, phospholipid, and cholesteryl ester was observed. These changes may result from the known decreases in liver levels of adenine nucleotides or, as reported here, from decreased liver CoASH levels in orotic acid-fed rats. The increase in hepatic cholesterol synthesis occurred during the second day of orotic acid feeding. It was detected by increased incorporation of [1,2- 14 C]acetate into cholesterol by liver slices and by a 7-fold increase in HMG-CoA reductase activity. At the same time the biliary output of cholesterol was increased 2-fold and studies using 3 H 2 O revealed that the output of newly synthesized cholesterol in bile was increased 5-fold. The content of cholesteryl ester in hepatic microsomes decreased during orotic acid feeding but free cholesterol was unchanged. The findings are interpreted to suggest that the increased bile cholesterol secretion caused by orotic acid is a result of impaired hepatic cholesterol esterification and that the increase in HMG-CoA reductase activity is a result of diminished negative feedback due to the depleted content of cholesteryl ester in the hepatic microsomes

Synthesis and Characterization of Nanostructured Nickel Diselenide NiSe2 from the Decomposition of Nickel Acetate, (CH3CO22Ni

Directory of Open Access Journals (Sweden)

Ming Yin

2014-01-01

Full Text Available Solution processed NiSe2 nanorods were synthesized by a modified colloidal synthesis technique, by chemical reaction of TOPSe and nickel acetate at 150°C. The rods exist as an oleic acid ligand stabilized solution, with oleic acid acting as a capping group. Structural characterization by X-ray diffraction and transmission electron microscopy indicates that the particles are rod-like shaped crystals with a high and relatively constant aspect ratio (30 : 1. TEM shows that the width and the length of the nanorods are in the range 10–20 nm and 300–350 nm, respectively. XRD indicates that the nanorods are pure and well crystallized. The size of nanorods based on the Debye-Scherrer effect, was 150 nm, the average value of length and width. They display thermal stability over prolonged heating times (<100 hours at 150°C, for which the average particle size is roughly constant. After about 100 hours of heating time there is an onset and growth of micron sized cubes and concurrent decomposition of NiSe2 to Ni and NiSe at 150°C.

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.