Synthesis, crystal structural determination and in silco biological studies of 3,3 '-ethane-1,2-diylbis(2-benzylidene-1,3-thiazolidin-4-one

doi:10.1016/j.molstruc.2021.130997

中山醫學大學機構典藏 CSMUIR > 中山醫學大學研究成果 > 期刊論文 > Item 310902500/24097

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Title:	Synthesis, crystal structural determination and in silco biological studies of 3,3 '-ethane-1,2-diylbis(2-benzylidene-1,3-thiazolidin-4-one
Authors:	Abdel-Rahman, LH;Mohamed, SK;El Bakri, Y;Ahmad, S;Lai, CH;Amer, AA;Mague, JT;Abdalla, EM
Keywords:	Thiourea;Bis thiourea;Thiazolidinones;Crystal structure;DFT calculations;Molecular docking;Molecular dynamics simulations
Date:	2021
Issue Date:	2022-08-05T09:47:46Z (UTC)
Publisher:	ELSEVIER
ISSN:	0022-2860
Abstract:	A new thiazolidine derivative, 3,3'-ethane-1,2-diylbis(2-benzylidene-1,3-thiazolidin-4-one (4) was synthesized and the product obtained was characterized by NMR, IR and mass spectral studies, and the structure was confirmed by single crystal X-ray diffraction studies. The title compound crystallizes in the monoclinic space group P21/n, the unit cell parameters are a = 15.9505(8) angstrom, b = 6.6818(3) angstrom, c = 18.1799(9) angstrom, beta = 94.249(2) degrees and Z = 4 at 150 K. In the title molecule, C20H18N4O2S2, the thiazolidine rings adopt a pincer conformation with the phenylimino substituents extending outwards on both sides. A layer structure is formed in the crystal by C-H center dot center dot center dot N and C-H center dot center dot center dot O hydrogen bonds. A Hirshfeld surface analysis was used to explore the nature of the intermolecular interactions in the crystal structure employing molecular surface contours and 2D fingerprint plots have been used to examine molecular shapes. The frontier orbital analysis shows that 4 should be more sensitive to a nucleophilic attack than an electrophilic attack. Molecular docking, followed by molecular dynamics simulation and MM-GBSA binding free energy was carried out to predict the binding affinity of 4 for alpha-amylase enzyme. These analyses revealed good intermolecular stability of the complex with stable high affinity intermolecular complex formation of high equilibrium nature. (C) 2021 Elsevier B.V. All rights reserved.
URI:	http://dx.doi.org/10.1016/j.molstruc.2021.130997 https://www.webofscience.com/wos/woscc/full-record/WOS:000702917000018 https://ir.csmu.edu.tw:8080/handle/310902500/24097
Relation:	JOURNAL OF MOLECULAR STRUCTURE ,2021,v1245
Appears in Collections:	[中山醫學大學研究成果] 期刊論文

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