摘要 :
Novel benzimidazole and fused benzimidazole derivatives such as triazinobenzimidazoles 3a-f, oxadia-zolylthio-methyl-1H-benzimidazoles 5a-c, triazolylthiomethyl-1H-benzirnidazoles 7a,b, thiazolidinyl-methyl-1H-benzimidazoles 9a-e ...
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Novel benzimidazole and fused benzimidazole derivatives such as triazinobenzimidazoles 3a-f, oxadia-zolylthio-methyl-1H-benzimidazoles 5a-c, triazolylthiomethyl-1H-benzirnidazoles 7a,b, thiazolidinyl-methyl-1H-benzimidazoles 9a-e and pyrimidopyrrolobenzimidazoles 12a,b have been synthesized via several reactions of the key intermediate 2-chloromcthyl-1H-benzimidazole with various reagents. Moreover, triazinobenzimidazoles 15a-c have been prepared starting with 2-cyanomethyl-1H-benzimidazole. Finally, another series of oxadiazoles 21a,b and triazoles 23a,b linked to benzimidazole moiety at one position have been synthesized starting with 2-mercapto-1H-benzimidazole. The structures of the newly synthesized compounds have been confirmed on the basis of elemental analysis and spectral studies. Some of the newly synthesized compounds exhibit significant antimicrobial activity, the most active compound is 21a.
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Following foliar application of [C-14]thiabendazole to growing wheat, soybean, and sugar beet plants, samples were taken 2 h post-treatment, at immature stages, and at normal harvest. Significant levels of [C-14]thiabendazole resi...
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Following foliar application of [C-14]thiabendazole to growing wheat, soybean, and sugar beet plants, samples were taken 2 h post-treatment, at immature stages, and at normal harvest. Significant levels of [C-14]thiabendazole residues were found in straw and immature leaves (similar to 10-22 ppm), but residues were far lower in wheat grain, soybean seeds, and sugar beet roots (similar to 0.12-0.88 ppm), demonstrating very limited translocation of thiabendazole-derived residues. Thiabendazole was the major component (greater than or equal to 91%) of the total residues in early foliage. Samples harvested at later growth stages contained increased levels of polar (aqueous-soluble) and nonextractable residues and diminished levels of organic-extractable residues. Most of the extractable radioactivity consisted of thiabendazole. The major transformation product of thiabendazole found was benzimidazole, present mainly in conjugated form. Fractionation of nonextractable residues in wheat straw demonstrated some incorporation into tissue components.
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2-(1-Chloroethyl)-1H-benzimidazole on condensation with 2-mercaptobenzimidazole in methanol using triethylamine as a base under reflux for 3 h yielded 2-((1-(1H-benzimidazol-2-yl)ethyl)thio)-1H-benzimidazole which on alkylation us...
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2-(1-Chloroethyl)-1H-benzimidazole on condensation with 2-mercaptobenzimidazole in methanol using triethylamine as a base under reflux for 3 h yielded 2-((1-(1H-benzimidazol-2-yl)ethyl)thio)-1H-benzimidazole which on alkylation using two equivalent of alkylating agent under phase transfer catalyst conditions give N,N'-dialkylbisbenzimidazole sulphides. Upon oxidation with H2O2 in acetic acid under reflux for 2 h gave N,N'-dialkylbisbenzimidazole sulphones which are analogues of prazoles.
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摘要 :
2-(1-Chloroethyl)-1H-benzimidazole on condensation with 2-mercaptobenzimidazole in methanol using triethylamine as a base under reflux for 3 h yielded 2-((1-(1H-benzimidazol-2-yl)ethyl)thio)-1H-benzimidazole which on alkylation us...
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2-(1-Chloroethyl)-1H-benzimidazole on condensation with 2-mercaptobenzimidazole in methanol using triethylamine as a base under reflux for 3 h yielded 2-((1-(1H-benzimidazol-2-yl)ethyl)thio)-1H-benzimidazole which on alkylation using two equivalent of alkylating agent under phase transfer catalyst conditions give N,N'-dialkylbisbenzimidazole sulphides. Upon oxidation with H2O2 in acetic acid under reflux for 2 h gave N,N'-dialkylbisbenzimidazole sulphones which are analogues of prazoles.
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The title compound 1 was prepared by condensation of 3,5-dibromo-o-phenylenediamine 10 with cyclohexanone and oxidation of the resulting 4,6-dibromo-1,3 -dihydro-2H-benzimidazole-2-spiro-cyclohexane 5 with manganese dioxide. With ...
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The title compound 1 was prepared by condensation of 3,5-dibromo-o-phenylenediamine 10 with cyclohexanone and oxidation of the resulting 4,6-dibromo-1,3 -dihydro-2H-benzimidazole-2-spiro-cyclohexane 5 with manganese dioxide. With sodium 2,3-dichlorophenoxide, sodium benzenesulfinate, or piperidine it reacts by loss of bromine, to give the 6-substituted derivatives 2, 3, and 4, respectively. Morpholine, however, gives 5,7-dibromo-4-morpholino-2H-benzimidazol-2-spirocyclohexane 15 whilst pyrid-2(1H)-thione and pyrimidin-2(1H)-thione give 4-bromo-1,3-dihydro-6-(pyridin-2-ylthio)-2H-benzimidazole-2-spirocyclohexa ne 6 and 5,7-dibromo-1,3-dihydro-4-(pyrimidin-2-ylthio)-2H- benzimidazole-2-spirocyclohexane 14, respectively. In the presence of 1 or 2 mol equiv. of sodium methoxide an aryne mechanism appears to operate, leading to the formation of either a mixture of 5-bromo-6-methoxy- 11 and 6-bromo-4-methoxy-2H-benzimidazole-2-spirocyclohexane 12 or 5,6-dimethoxy-2H-benzimidazole-2-spirocyclohexane 13, respectively. Oxidation of the title compound 1 with m-chloroperoxybenzoic acid yields the 1-oxide 7 exclusively, which reacts with piperidine and morpholine by loss of the 4-bromine atom, to give compounds 16 and 17, respectively, in the latter case with concomitant loss of oxygen. [References: 16]
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Treatment of alpha-acetamido-cinnamhydrazides with aromatic aldehydes produces N-(1-aza-2-arylvinyl)-2-(acetylamino)-3-aryl prop-2-enamides. These on treatment with methyl isothiocyanate yielded the novel unknown title compounds.
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The crystal structure of the title compound, C14H9Cl3N2, is stabilized by C-H ... Cl hydrogen bonds. All of the Cl atoms are involved in hydrogen bonding as accepters. [References: 13]
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The present study is the synthesis of new heterocyclic moieties like pyrazole, isoxazole and thiazole containing benzimidazole nucleus. The title compounds were synthesized from 4-(1H-benzo[d]imidazol-2-yl) oxazol-2-amine. The new...
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The present study is the synthesis of new heterocyclic moieties like pyrazole, isoxazole and thiazole containing benzimidazole nucleus. The title compounds were synthesized from 4-(1H-benzo[d]imidazol-2-yl) oxazol-2-amine. The newly synthesised compounds were screened for their in vitro anti-inflammatory activity and demonstrated excellent to moderate activity and molecular docking study reports are supporting anti-inflammatory activity showed high inhibition constant and binding energy. The structures of synthesised compounds were characterized by IR, (HNMR)-H-1, Mass spectroscopic methods.
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A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivativ...
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A facile, general, and economical synthesis of diversely functionalized benzimidazoles and 2-substituted benzimidazoles has been realized via the imidazolium chloride-catalyzed cyclization of o-phenylenediamines with DMF derivatives. This protocol shows a broad substrate scope for aliphatic, aromatic, and heteroaromatic amides. A series of benzimidazoles and 2-substituted benzimidazoles have been obtained in moderate to excellent yields. (C) 2018 Elsevier Ltd. All rights reserved.
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In this work, the in vitro tests of biological activity of benzimidazoles were conducted. This group of benzimidazole derivatives was evaluated as potential bioreductive agents and their characteristic pro-apoptosis activity and c...
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In this work, the in vitro tests of biological activity of benzimidazoles were conducted. This group of benzimidazole derivatives was evaluated as potential bioreductive agents and their characteristic pro-apoptosis activity and cell cycle interruption on the human lung adenocarcinoma A549 cells were discussed. Their toxicity on the healthy human erythrocytes and their influence on the healthy human erythrocytes acetylcholinesterase enzyme (AChE) were established. Their apoptosis activity on A549 cells line was determined by Annexin V-APC test, and it was visualized by Hoechst test. In the next stage, their influence on the cell cycle interruption was determined by using the ribonuclease reagent. The AChE inhibition test was defined by the Ellman method, and the red blood cell lysis was defined by erythrotoxicity test. The results proved the pro-apoptosis properties of all tested compounds in normoxia and hypoxia. The DNA content assay showed that the benzimidazoles possess the ability to interrupt S phase of tumor cell cycle. The best activity in this action was presented by compound 1, especially in hypoxia, and it proves that the N-oxide analogs are predispositioned to the hypoxic target. In this study, the benzimidazoles were found as potentially biocompatible and their inhibition of acetylcholinesterase was lower than tirapazamine and much lower than tacrine which constitutes their desired effect of potential biological activity.
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