Synthesis, Crystal Structure, Density Function Theory, Molecular Docking and Antimicrobial Studies of 2-(3-(4- phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione

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, wR_ref(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

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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.

Keywords
Isoindoline-1; 3-dione; X-ray analysis; Density function theory; Antimicrobial; Molecular docking