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

doi:10.4314/TJPR.V15I2.23

Paper

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

Published Mar 4, 2016 · H. Ghabbour, Maha M. Qabeel

Tropical Journal of Pharmaceutical Research

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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 (C 21 H 23 N 3 O 2 ) 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) A, b = 6.0157 (2) A, c = 30.8571 (12) A, β = 90.105 (1) °, V = 1857.14 (11) A 3 , Z = 4, wR ref (F 2 ) = 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. Keywords: Isoindoline-1, 3-dione, X-ray analysis, Density function theory, Antimicrobial, Molecular docking

Study Snapshot

2-(3-(4-phenylpiperazin-1-yl) propyl) isoindoline-1,3-dione has moderate antimicrobial activity against S. aureus and C. albicans, with a good agreement in its optimized molecular structure.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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