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

被引:6
作者
Ghabbour, Hazem A. [1 ,2 ]
Qabeel, Maha M. [3 ]
机构
[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, Riyadh 11451, Saudi Arabia
[2] Mansoura Univ, Fac Pharm, Dept Med Chem, Mansoura 35516, Egypt
[3] Mansoura Univ, Coll Med, Dept Clin Microbiol & Immunol, Mansoura 35516, Egypt
关键词
Isoindoline-1; 3-dione; X-ray analysis; Density function theory; Antimicrobial; Molecular docking; RECEPTORS; LIGANDS; AMINES; HOMO; LUMO;
D O I
10.4314/tjpr.v15i2.23
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
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) angstrom, b = 6.0157 (2) angstrom, c = 30.8571 (12) angstrom, beta = 90.105 (1) degrees, V = 1857.14 (11) angstrom(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-center dot center dot center dot 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.
引用
收藏
页码:385 / 392
页数:8
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