Synthesis, Antimicrobial Evaluation, and Molecular Docking Study of New Thiazole-5-phenylpropenone Derivatives
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ynthesis, Antimicrobial Evaluation, and Molecular Docking Study of New Thiazole-5-phenylpropenone Derivatives P. S. Patila, S. L. Kasarea, A. D. Badara, R. S. Kulkarnia, P. P. Dixitb, J. A. Kulkarnic, P. B. Choudharid, and K. P. Havala,* a Department
of Chemistry, Dr. Babasaheb Ambedkar Marathwada University SubCampus, Osmanabad, 413501 India of Microbiology, Dr. Babasaheb Ambedkar Marathwada University SubCampus, Osmanabad, 413501 India c Department of Biotechnology, Dr. Babasaheb Ambedkar Marathwada University SubCampus, Osmanabad, 413501 India d Department of Pharmaceutical Chemistry, Bharati Vidyapeeth College of Pharmacy, Kolhapur, 416013 India *e-mail: [email protected] b Department
Received April 29, 2020; revised June 29, 2020; accepted August 5, 2020
Abstract—A series of new (E)-1-[2-(2-ethylpyridin-4-yl)-4-methylthiazol-5-yl]-3-phenylprop-2-en-1-one derivatives have been synthesized starting from the antitubercular drug, ethionamide. The synthesized compounds have been tested for their in vitro antimicrobial activity, and five of those have demonstrated promising activity. According to molecular docking study the active compounds have display high binding affinity towards DNA Gyrase and Lumazine Synthase. Keywords: thiazole, chalcone, claisen-schmidt condensation, antimicrobial activity, molecular docking study, ADME prediction
DOI: 10.1134/S1070363220080216 INTRODUCTION Chalcone derivatives have attracted close attention due to their broad spectrum of biological activities [1, 2] including antimicrobial, anticancer [3], antibacterial [4], and anti-tubercular [5]. Thiazole-chalcone hybrid molecules with antibacterial [6], anticancer [7–9], antioxidant [10], antimicrobial [11, 12], and many more have been reported. In view of the above observations and based on our earlier approaches to synthesis of pyridylthiazolyl clubbed bioactive compounds [13, 14], herein a new series of thiazole- 5-phenylpropenone derivatives have been synthesized and evaluated for their biological activities. RESULTS AND DISCUSSION Synthesis of the target thiazole-5-phenylpropenone derivatives 5a–5j was accomplished as presented in Scheme 1. In the first step 2-ethylpyridine-4carbothioamide (1) was reacted with 3-chloropentane2,4-dione (2) to give formation of 1-[2-(2-ethylpyridin4-yl)-4-methylthiazol-5-yl]ethanone (3) with 92% yield. The following Claisen-Schmidt condensation of the intermediate 3 with various aromatic aldehydes 4a–4j under basic conditions furnished the corresponding chalcones 5a–5j with 70–80% yield.
Structures of the newly synthesized thiazole-5phenylpropenone derivatives 5a–5j were elucidated from IR, 1H, and 13C NMR, and HRMS spectra. In IR spectrum of compound 5a, the characteristic band at 1644 cm–1 indicated the presence of α,β-unsaturated ketone. In 1 H NMR spectrum of 5a, a singlet at 2.88 ppm indicated CH3 attached to thiazole ring. Two doublets of vinylic protons were recorded at 7.22 and 7.77 ppm with coupling constants 15.6 and 15.2 Hz and indicated the trans conformation. 13C NMR and HRMS spectra
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