SYNTHESIS, SPECTRAL CHARACTERIZATION, DFT, AND DOCKING STUDIES OF (4-AMINO-2-(PHENYLAMINO) THIAZOL-5-YL)(THIOPHENE-2-YL)
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SYNTHESIS, SPECTRAL CHARACTERIZATION, DFT, AND DOCKING STUDIES OF (4-AMINO-2-(PHENYLAMINO) THIAZOL-5-YL)(THIOPHENE-2-YL)METHANONE AND (4-AMINO-2-(4-CHLOROPHENYL)AMINO)THIAZOL5-YL)(THIOPHENE-2-YL)METHANONE M. F. Shahana1 and A. Yardily1*
Novel compounds (4-amino-2-(phenylamino)thiazol-5-yl)(thiophene-2-yl)methanone and (4-amino-2-(4chlorophenyl)amino)thiazol-5-yl)(thiophene-2-yl)methanone are synthesized and characterized by UV, IR, 1 H and 13C NMR, and high-resolution mass spectrometry. The structural optimization and the interpretation of theoretical vibrational spectra is made by the density functional theory calculation using Becke′s threeparameter exchange functional in combination with the Lee–Yang–Parr correlation Gaussian 09 program package with the standard 6-311G basis software set. The equilibrium geometry, various bonding features, and harmonic vibrational wave numbers of the titled compound are investigated using the density functional theory calculation. Structural changes in the molecule due to the substitution of the electron withdrawing group are also analyzed. The Mülliken population analysis on atomic charges is performed. The thermodynamic stability in the ground state and reactivity of the compounds in the excited state are explained by the HOMO–LUMO energy gap. The molecular docking study is carried out using Hex 8.0. This study aids to understand the antibacterial activity of the compound. DOI: 10.1134/S0022476620090036 Keywords: ketothiophene derivatives; computational studies; Mulliken charges; stability; Molecular docking.
INTRODUCTION Due to the sudden spread of contagious diseases, nowadays it is an urge to scientists to design and find out new drug molecules, which in all likelihood offers some of the finest hopes for success in the future era. Heterocyclic chemistry constitutes the essential and fundamental part of organic chemistry that has significantly impacted medicinal and biochemistry. Pharmaceutical chemistry has flourished at the advancements made inside synthetic heterocyclic chemistry in supplying heterocyclic systems which could mimic the structures and biotic activity of natural products [1]. Thiophene is one of the heterocyclic compounds with promising biological activities. Thiophene along with the carbonyl group possesses antibacterial, antifungal activities, is used in the treatment of Alzheimer′s disease [2, 3], and has DNA binding [4] and anticancer activities [5].
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Department of Chemistry and Research Center, Scott Christian College (Autonomous), Nagercoil, Manonmaniam Sundaranar University, Abhishekapatti, Tamil Nadu, Republic of India; *[email protected]. Original article submitted April 7, 2020; revised April 14, 2020; accepted April 14, 2020. 0022-4766/20/6109-1367 © 2020 by Pleiades Publishing, Ltd.
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On the way of doing our research on the synthesis of new heterocyclic compounds with expected biological activities, we reported the synthesis of two new ketothiophene derivatives, viz.(4-amino-2-(phenylamino)thiazol-5yl)(thiophene-2-yl)methanone (APT) and
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