Phthalimide/Naphthalimide containing 1,2,3-triazole hybrids: Synthesis and Antimicrobial Evaluation

■A series of phthalimide/naphthalimide containing 1,2,3-triazole hybrids were synthesized.■Compound 6b has been also studied through single crystal X-ray crystallography.■Synergic biological potential of phthalimide and 1,2,3-triazole moiety have been explored in present work.■Most of the synthesized hybrids displayed moderate to good antimicrobial activity.■Docking simulation of potent 1,2,3-triazole hybrid 6e have been examined against antibacterial target. A series of twenty-eight Phthalimide/Naphthalimide containing 1,2,3-triazole hybrids (6a-6z2) have been synthesized based on hybrid pharmacophore concept through Click reaction of terminal alkynes (3a-3d) with aromatic azides (5a-5 g). All the synthesized Phthalimide/Naphthalimide containing 1,2,3-triazole hybrids were characterized utilizing various spectral techniques like 1D, 2D NMR, FTIR and HRMS. Further, the structure of synthesized compound 6b (CCDC 2,192,005) was also confirmed by Single Crystal X-ray Crystallography. Additionally, In vitro antimicrobial activity of the synthesized hybrids were performed against two Gram positive bacterial strains and two Gram negative bacterial strains as well as two parasitic strains by serial dilution technique. The compound 6e (MIC 0.0179 µmol/mL) demonstrated excellent antimicrobial potency due to presence of nitro group on phenyl ring against all tested strains. The binding conformation of the most potent Phthalimide/Naphthalimide containing 1,2,3-triazole hybrid 6e with E. coli topoisomerase II DNA gyrase B was ascertained by molecular docking studies. [Display omitted]