Design, synthesis and biological evaluation of new substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones. Pharmacophore models for antifungal activity

Abstract

As a part of our ongoing studies in developing new derivatives as antimicrobial agents we describe the synthesis of novel substituted 5-benzylideno-2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones.The twenty-five newly synthesized compounds were tested for their antimicrobial and antifungal activity. All compounds have shown antibacterial properties with compounds 1–9 showing the lowest activity, followed by compounds 10–14 while compounds 15–25 the highest antibacterial activity. Specific compounds appeared to be more active than ampicillin in most studied strains and in some cases more active than streptomycin. Antifungal activity in most cases also was better than that of reference drugs ketoconazole and bifonazole. Elucidating the relation of molecular properties to antimicrobial activity as well as generation of pharmacophore model for antifungal activity of two fungal species Aspergillus fumigatus and Candida albicans were performed. Keywords: Adamantlythiazoles, Anti-inflammatory, Antibacterial, Antifungal, Pharmacophore, SAR