A series of new deoxybenzoin based bis 1,2,3‐triazole analogues were synthesized and reported in the present communication. Synthesis of analogues were accomplished by a convenient 3 step protocol incorporating Friedel craft acetylation, propargylation and copper‐catalyzed click chemistry in final step to afford 1,2,3‐triazole moiety. The title compounds were screened for antimicrobial activity against two gram positive bacteria viz. S. aureus, B. cereus and two gram negative bacteria viz. E. coli, P. aeruginosa, and three fungus viz. C. albicans, A. niger, A. flavus strains. Compound containing 4‐fluoro substitution (7a) showed slightly superior in‐vitro antimicrobial activity than reference drugs Ciprofloxacin and Fluconazole. SAR of developed hybrids with reference to antimicrobial activity was predicted and presented. In‐silico bioactivity is investigated by molecular docking studies against the crystal structures of glucosamine‐6‐phospate synthase (PDB ID: 2VF5) and secreted aspartic proteinase (PDB ID: 2QZW) which endorsed good binding interactions.
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