Synthesis, characterization, carbonic anhydrase inhibitor activity, and docking studies of phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine Derivatives

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 syn...

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Bibliographic Details
Published in:Journal of molecular structure 2023-11, Vol.1291, p.136061, Article 136061
Main Authors: Berber, Nurcan, Şahutoğlu, Arif Sercan, Gökçe, Başak, Çıkrıkçı, Kübra, Gençer, Nahit
Format: Article
Language:English
Subjects:
Carbonic anhydrase
Enzyme inhibitor
Isoquinoline
Thiazole
Thiourea
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Summary: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 1H 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. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2023.136061