Synthesis and in vitro study of novel bis‐[3‐(2‐arylmethylidenimino‐1,3‐thiazol‐4‐yl)‐4‐hydroxy‐2H‐chromen‐2‐one‐6‐yl]methane and bis‐[3‐(2‐arylidenhydrazo‐1,3‐thiazol‐4‐yl)‐4‐hydroxy‐2H‐chromen‐2‐one‐6‐yl]methane as potential antimicrobial agents

Abstract

Abstract magnified imageA series of novel bis‐[3‐(2‐arylmethylidenimino‐1,3‐thiazol‐4‐yl)‐4‐hydroxy‐2H‐chromen‐2‐one‐6‐yl]methane 7a, 7b, 7c, 7d, 7e, 7f and bis‐[3‐(2‐arylidenhydrazo‐1,3‐thiazol‐4‐yl)‐4‐hydroxy‐2H‐chromen‐2‐one‐6‐yl]‐methane 8a, 8b, 8c, 8d, 8e, 8f were synthesized in good yields from bis‐[3‐(2‐bromoacetyl‐4‐hydroxy‐2H‐chromen‐2‐one‐6‐yl]methane 5. The chemical structures of the newly synthesized compounds were elucidated by their IR, 1H NMR, MS, and elemental analyses. Further, all the compounds were screened for their antimicrobial activity against Gram‐positive, Gram‐negative bacteria, and fungi. Among the synthesized compounds, 7c, 7e, and 8c were found to be the most active against almost all the test bacteria. The compound 8c displayed notable antibacterial activity against Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC6538p), Micrococcus luteus (IFC 12708), Proteus vulgaris (ATCC 3851) and Salmonella typhimurium (ATCC 14028), equal to that of ampicillin. Similarly these compounds also showed potent antifungal effect against Candida albicans (ATCC 10231), Aspergillus fumigatus (HIC 6094), Trichophyton rubrum (IFO 9185), and Trichophyton mentagrophytes (IFO 40996). J. Heterocyclic Chem., 46, 261 (2009).