Synthesis, Characterization, Carbonic Anhydrase Inhibitor Activity, and Docking Studies of phenylthiazol-2 (3h)-ylidene-isoquinoline-5-amine Derivatives

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Berber N., Şahutoğlu A. S., Gökçe B., Çıkrıkçı K., Gençer N.

JOURNAL OF MOLECULAR STRUCTURE, vol.1291, no.2023, pp.1-11, 2023 (SCI-Expanded)

  • Publication Type: Article / Article
  • Volume: 1291 Issue: 2023
  • Publication Date: 2023
  • Journal Name: JOURNAL OF MOLECULAR STRUCTURE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Page Numbers: pp.1-11
  • Çanakkale Onsekiz Mart University Affiliated: Yes

Abstract

Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives(5a-r) were easily prepared from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives in the presence of triethylamine in tetrahydrofuran (THF), and dimethyl formamide (DMF) in two steps. In the first step, thiourea was synthesized in THF reflux, 24 h and then in the second step, the formation of thiazole ring was ensured in EtOH-DMF (5:5 v/v), reflux, 24 h. The newly synthesized compounds were characterized using 1 H NMR, 13C NMR, IR, and elemental analysis. The inhibitory effects of 18 newly synthesized compounds (5a-r) on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro.