Synthesis, crystal structure, density function theory, molecular docking and antimicrobial studies of 2-(3-(4- phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione

Abstract

Purpose: To determine the exact structure and antimicrobial activity of 2-(3-(4-phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione. Methods: 2-(3- (4-Phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione (C21H23N3O2) was synthesized by the reaction of phthalimide with 1,3-dibromopropane to form 2-(3-bromopropyl) isoindoline-1,3-dione, and was then treated with 1-phenylpiperazine in acetonitrile. The structure of the title compound, 2-(3- (4-phenylpiperazin-1-yl)propyl)isoindoline-1,3-dione, was characterized by proton nuclear magnetic resonance spectroscopy (NMR) and single crystal x-ray diffraction method. The target compound was tested for its antimicrobial activities and computational studies including density function test (DFT) and docking studies were performed. Results: The crystal structure is monoclinic, P21/n, a = 10.0047 (3) Å, b = 6.0157 (2) Å, c = 30.8571 (12) Å, β = 90.105 (1) °, V = 1857.14 (11) Å3, Z = 4, wRref(F2) = 0.158, T = 296 K. The molecules are packed in the crystal structure by non-classical intermolecular C–H….O interactions. Besides HOMO– LUMO energy gap was performed at B3LYP/6-31G (d,p) level of theory. The compound exhibited good activity against S. aureus and C. albicans with zones of inhibition of 15 cm and 18 cm, respectively Conclusion: The test compound has a moderate antimicrobial activity and the optimized molecular structure of the studied compound using B3LYP/6-31G (d,p) method showed good agreement with the reported x-ray structure.