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 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.

Automated summary

Phenylthiazol-2(3h)-ylidene-isoquinoline-5-amine derivatives (5a-r) were easily synthesized using a two-step method from 5-aminoisoquinoline, thioisocyanate, and phenacyl bromide derivatives. The newly synthesized compounds were characterized using 1H NMR, 13C NMR, IR, and elemental analysis. Their inhibitory effects on hydratase and esterase activities of carbonic anhydrase isoenzymes (hCA I, II, IX, and X) were studied in vitro.