Microwave assisted, one-pot synthesis of 5-nitro- 2-aryl substituted-1H-benzimidazole libraries: Screeningin vitrofor antimicrobial activity
Open Access
- 29 July 2009
- journal article
- research article
- Published by Taylor & Francis Ltd in Journal of Enzyme Inhibition and Medicinal Chemistry
- Vol. 24 (5), 1095-1100
- https://doi.org/10.1080/14756360802632716
Abstract
The efficient and rapid synthesis of 5-nitro-2-aryl substituted-1H-benzimidazole libraries (1a-1j) has been established. Thus, both microwave and conventional cyclo-condensation of 4-nitro ortho-phenylenediamine with various phenoxyacetic acids were carried out in the presence of HCl catalyst. The microwave synthesis route afforded advantages, such as good to excellent yields, shorter reaction time (2.5–3.5 min), readily available starting material, and simple purification procedure, which distinguish the present protocol from other existing methods used for the synthesis of benzimidazole libraries. Bioassay indicated that all the compounds showed in vitro antimicrobial activity against Vancomycin resistant enteroccoccus, Staphylococcus aureus, Micrococcus, Bacillus subtilis (gram-positive bacteria) and Shigella dysentery, Escherichia coli (gram-negative bacteria) and Candida albicans, Aspergillus niger, Penicillium (fungi). The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards.Keywords
This publication has 16 references indexed in Scilit:
- Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazolesTetrahedron Letters, 2007
- Synthesis and Anti-Hepatitis B Virus Activity of Novel Benzimidazole DerivativesJournal of Medicinal Chemistry, 2006
- Copper-Catalyzed N-Arylation of Amines/Amides in Poly(ethylene glycol) as Recyclable Solvent MediumSynthesis, 2006
- Green Chemistry, a Pharmaceutical PerspectiveOrganic Process Research & Development, 2006
- Design, synthesis, and evaluation of novelly substituted benzimidazole compounds as angiotensin II receptor antagonistsBioorganic & Medicinal Chemistry Letters, 2005
- Comprehensive Survey of Combinatorial Library Synthesis: 2003Journal of Combinatorial Chemistry, 2004
- Synthesis and anthelmintic activity of 5(6)-[(benzimidazol-2-yl)carboxamido]- and (4-substituted piperazin-1-yl)benzimidazolesJournal of Medicinal Chemistry, 1985
- Antibacterial and antifungal activities of benzimidazole and benzoxazole derivativesAntimicrobial Agents and Chemotherapy, 1981
- Oxazolines. XXII. Nucleophilic aromatic substitution on aryl oxazolines. Efficient approach to unsymmetrically substituted biphenyls and o-alkyl benzoic acidsJournal of the American Chemical Society, 1975
- The Chemistry of the Benzimidazoles.Chemical Reviews, 1951