Regioselective Synthesis, Antibacterial, Molecular Docking and Fingerprint Applications of 1‐Benzhydrylpiperazine Derivatized 1,4‐Disubstituted 1,2,3‐Triazoles

Abstract

AbstractA series of ten 1,4‐Disubstituted 1,2,3‐Triazoles having 1‐benzhydrylpiperazine chemical scaffold were synthesized by one pot Cu (I) catalyzed click reaction and evaluated for their antibacterial activity against Escherichia Coli and Staphylococcus aureus by agar well diffusion method. Amongst all, 2‐chloro‐6‐fluorobenzyl substituted 1,2,3‐Triazole 7 e and 2,4‐dichlorobenzyl Triazole 7 f found to be more active compared to the Ciprofloxacin. To rationalize the binding interaction of compounds and the protein at active site, we performed Molecular docking study using a bacterial DNA Gyrase B protein. The docking energy of 2‐chloro‐6‐fluorobenzyl substituted Triazole 7 e and 2,4‐dichlorobenzyl Triazole 7 f was observed as −22.498 and −22.569 kcalmol−1 in comparison to reference drug Ciprofloxacin whose docking energy is −22.072 kcal mol−1. It also makes several hydrogen bonds with our conserved residue Ser55, Asp81 and Ile86. Furthermore, several hydrophobic contacts were also observed within the pocket. Finally, Latent fingerprint detection study indicated that the compound unsubstituted Triazole 7 a powder shows good adhesion and finger ridge details without back ground staining. The demonstrated method can be applied to detect fingerprints on all types of smooth surfaces and hence, it can be easily adopted for latent fingerprint detection. The in vitro and in silico activities conclusively revealed that our lead compounds may be used as a novel antibacterial agents.