SYNTHESIS AND IN VITRO ANTIMICROBIAL EVALUATION OF PIPERAZINE SUBSTITUTED QUINAZOLINE-BASED THIOUREA/THIAZOLIDINONE/CHALCONE HYBRIDS

© 2015 D. R. Shah, H. P. Lakum, and K. H. Chikhalia^#

^#Tel: +91-79-26300969/9427155529, fax: +91-79-26308545; e-mail: [email protected]

Department of Chemistry, School of Sciences, Gujarat University, Ahmedabed, Gujarat, 380009 India

Received June 11, 2014; in final form , 23.07.2014

In frames of the search for new biological entities to fight against recent drug_resistant microbial strains, we report a library of quinazoline_based thiourea/4-thiazolidinone/chalcone hybrids. The newly synthesized compounds were studied for efficacy against several bacteria (Staphylococcus aureus, Bacillus cereus, Pseudomonas aeruginosa, and Klebsiella pneumoniae) and fungi (Candida albicans and Aspergillus clavatus) using the broth dilution technique. From the biological evaluation, (E)-3-(3,4-dimethoxyphenyl)-1-(4-((4-(4-ethylpiperazin-1-yl)quinazolin-2-yl)amino)phenyl)prop-2-en-1-one was found to be the most active analogue (microbial inhibition concentration 3.12 μg/mL) to inhibit the bacterial growth. The rest of the compounds showed equipotent efficacy (3.12–12.5 μg/mL) as compared to the standard. Final compounds were characterized by FT-IR, ¹H NMR, ¹³C NMR, mass spectroscopy, and elemental analysis.

Keywords: 4-thiazolidinone, antibacterial activity, antifungal activity, chalcone, quinazoline, thiourea.

Биоорг. химия 2015, 41(2): 235–248