3-[Benzimidazo- and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents

A series of 3-[benzimidazo(1,2-c) quinazolin-5-yl]-2H-chromene-2-one (6a-6f) and 3-[benzothiadiazoleimidazo( 1,2-c) quinazolin-5-yl]-2H-chromene-2-one derivatives (7a-7f) that incorporate a variety of substituents at the 6-and/or 8-positions of the coumarin moieties have been synthesized utilizing cellulose sulfuric acid as an efficient catalyst under both conventional heating and microwave irradiation procedures. These analogs were evaluated for their antimicrobial activity against Bacillus subtilis, Staphylococcus aureus, Streptococcus pyogenes (Gram-positive bacteria), Escherichia Coli, Klebsiella pneumonia, Salmonella typhimurium (Gram-negative bacteria), and Aspergillus niger, Candida albicans, and Aspergillus flavus (Fungi). Two analogs, 6c (a 6,8-dichloro analog, MIC[SA] = 2.5 mu g/mL; MIC[ST] = 2.5 mu g/mL) and 7d (a 6,8-dibromo analog, MIC[ST] = 2.5 mu g/mL) were identified as potent antibacterial agents, and two analogs, 6b (a 6-bromo analog, MIC[AF] = 10 mu g/mL) and 6d (a 6,8-dibromo analog, MIC[AF] = 15 mu g/mL; MIC[CA] = 15 mu g/mL), were identified as potent antifungal agents. Based on the MIC data, analogs 6b, 6c, 6d, and 7d were identified as the most potent antimicrobial agents in the series. (C) 2010 Elsevier Ltd. All rights reserved.