Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives

Some derivatives of benzimidazole were synthesized by nucleophilic substitution of 2-substituted-1 H-benzimidazole. The resulting ethyl (2-substituted-1 H-benzimidazol-1-yl) acetate on treatment with hydrazine hydrate yielded 2-(2-substituted-1 H-benzimidazol-1-yl) acetohydrazide, which on further r...

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Veröffentlicht in:European journal of medicinal chemistry 2009-10, Vol.44 (10), p.4028-4033
Hauptverfasser: Ansari, K.F., Lal, C.
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Lal, C.
description Some derivatives of benzimidazole were synthesized by nucleophilic substitution of 2-substituted-1 H-benzimidazole. The resulting ethyl (2-substituted-1 H-benzimidazol-1-yl) acetate on treatment with hydrazine hydrate yielded 2-(2-substituted-1 H-benzimidazol-1-yl) acetohydrazide, which on further reaction with one equivalent of different aliphatic or aromatic carboxylic acids in the presence of phosphoryl chloride afforded the corresponding target compounds, 2-substituted-1-[{(5-substituted alkyl/aryl)-1,3,4-oxadiazol-2-yl} methyl]-1 H-benzimidazole. The structures of the synthesized compounds were evaluated by spectral and elemental methods of analyses. All the synthesized compounds were screened for their antimicrobial activities. All of the derivatives showed good activity towards Gram-positive bacteria and negligible activity towards Gram-negative bacteria. Some of the synthesized compounds showed moderate activity against tested fungi. [Display omitted] The synthesis, characterization, physicochemical properties and antimicrobial effects of some new benzimidazole derivatives were reported.
doi_str_mv 10.1016/j.ejmech.2009.04.037
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The resulting ethyl (2-substituted-1 H-benzimidazol-1-yl) acetate on treatment with hydrazine hydrate yielded 2-(2-substituted-1 H-benzimidazol-1-yl) acetohydrazide, which on further reaction with one equivalent of different aliphatic or aromatic carboxylic acids in the presence of phosphoryl chloride afforded the corresponding target compounds, 2-substituted-1-[{(5-substituted alkyl/aryl)-1,3,4-oxadiazol-2-yl} methyl]-1 H-benzimidazole. The structures of the synthesized compounds were evaluated by spectral and elemental methods of analyses. All the synthesized compounds were screened for their antimicrobial activities. All of the derivatives showed good activity towards Gram-positive bacteria and negligible activity towards Gram-negative bacteria. Some of the synthesized compounds showed moderate activity against tested fungi. 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The resulting ethyl (2-substituted-1 H-benzimidazol-1-yl) acetate on treatment with hydrazine hydrate yielded 2-(2-substituted-1 H-benzimidazol-1-yl) acetohydrazide, which on further reaction with one equivalent of different aliphatic or aromatic carboxylic acids in the presence of phosphoryl chloride afforded the corresponding target compounds, 2-substituted-1-[{(5-substituted alkyl/aryl)-1,3,4-oxadiazol-2-yl} methyl]-1 H-benzimidazole. The structures of the synthesized compounds were evaluated by spectral and elemental methods of analyses. All the synthesized compounds were screened for their antimicrobial activities. All of the derivatives showed good activity towards Gram-positive bacteria and negligible activity towards Gram-negative bacteria. Some of the synthesized compounds showed moderate activity against tested fungi. [Display omitted] The synthesis, characterization, physicochemical properties and antimicrobial effects of some new benzimidazole derivatives were reported.</description><subject>1,3,4-Oxadiazole</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal activity</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Bacteria - drug effects</subject><subject>Benzimidazole</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Fungi - drug effects</subject><subject>General aspects</subject><subject>Lipophilicity</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pharmacology. 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Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal activity</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial activity</topic><topic>Bacteria - drug effects</topic><topic>Benzimidazole</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - chemistry</topic><topic>Benzimidazoles - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Fungi - drug effects</topic><topic>General aspects</topic><topic>Lipophilicity</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ansari, K.F.</creatorcontrib><creatorcontrib>Lal, C.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ansari, K.F.</au><au>Lal, C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2009-10-01</date><risdate>2009</risdate><volume>44</volume><issue>10</issue><spage>4028</spage><epage>4033</epage><pages>4028-4033</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Some derivatives of benzimidazole were synthesized by nucleophilic substitution of 2-substituted-1 H-benzimidazole. The resulting ethyl (2-substituted-1 H-benzimidazol-1-yl) acetate on treatment with hydrazine hydrate yielded 2-(2-substituted-1 H-benzimidazol-1-yl) acetohydrazide, which on further reaction with one equivalent of different aliphatic or aromatic carboxylic acids in the presence of phosphoryl chloride afforded the corresponding target compounds, 2-substituted-1-[{(5-substituted alkyl/aryl)-1,3,4-oxadiazol-2-yl} methyl]-1 H-benzimidazole. The structures of the synthesized compounds were evaluated by spectral and elemental methods of analyses. All the synthesized compounds were screened for their antimicrobial activities. All of the derivatives showed good activity towards Gram-positive bacteria and negligible activity towards Gram-negative bacteria. Some of the synthesized compounds showed moderate activity against tested fungi. 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subjects 1,3,4-Oxadiazole
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antifungal activity
Antifungal agents
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Antimicrobial activity
Bacteria - drug effects
Benzimidazole
Benzimidazoles - chemical synthesis
Benzimidazoles - chemistry
Benzimidazoles - pharmacology
Biological and medical sciences
Fungi - drug effects
General aspects
Lipophilicity
Medical sciences
Microbial Sensitivity Tests
Molecular Structure
Pharmacology. Drug treatments
Structure-Activity Relationship
title Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives
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