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Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022

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Synthesis and Docking Studies of Novel Bis(2-(Substituted(methyl)amino)-4-phenylthiazol-5-yl)methanone

https://doi.org/10.14233/ajchem.2022.24030
Pravin S. Kulkarni
Department of Chemistry, J.E.S. College, Jalna-431203, India
Amol U. Khandebharad
Department of Chemistry, J.E.S. College, Jalna-431203, India
Swapnil R. Sarda
Department of Chemistry, J.E.S. College, Jalna-431203, India
Brijmohan R. Agrawal
Department of Chemistry, J.E.S. College, Jalna-431203, India

Corresponding Author(s) : Pravin S. Kulkarni

kulkarnipravin205@gmail.com

Asian Journal of Chemistry, Vol. 34 No. 11 (2022): Vol 34 Issue 11, 2022

Abstract

A new series of novel synthesis of bis(2-(substituted(methyl)amino)-4-phenylthiazol-5-yl)methanone (PVS 1-9) is reported. The carbonyl isothiocyanate (3) was synthesized by a para-cleavage of C–Cl bond of benzoyl chloride (1) with ammonium thiocyanate (2). The presence of carbonyl group in acyl isothiocyanates enhance the reactivity of acyl isothiocyanates upon reaction with substituted secondary amine (4) give n-alkylated adduct (5), which upon the reaction with dichloro acetone give target compound 7. Substituted derivatives as inhibitors against lungs, breast and EJFR assist cancer based on virtual screening cellular evaluations with NSCLC H1975 harboring EGFR L858R/T790M double mutations indicated that the most active compound PVS-7 could inhibit the proliferation of two cell lines in one digital micromolar scale. The enzymatically results indicated that the compounds PVS-2, PVS-4 and PVS-9 were the most active inhibitor against EGFR T790M and above cancer activity with ~82%. All compounds were well characterized by spectroscopic techniques and their purity was confirmed by UV-HPLC.

Keywords

Bis-thiazole Substituted secondary amine Virtual computational study
S. Kulkarni, P., U. Khandebharad, A., R. Sarda, S., & R. Agrawal, B. (2022). Synthesis and Docking Studies of Novel Bis(2-(Substituted(methyl)amino)-4-phenylthiazol-5-yl)methanone. Asian Journal of Chemistry, 34(11), 3015–3020. https://doi.org/10.14233/ajchem.2022.24030
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