IN VITRO INHIBITION EFFECTS ON ERYTHROCYTE CARBONIC ANHYDRASE I AND II AND STRUCTURE–ACTIVITY RELATIONSHIPS OF CUMARYLTHIAZOLE DERIVATIVES
© 2016 Belma Z. Kurt*, Fatih Sonmez**, #, Basak Gokce***, Adem Ergun****, Nahit Gencer****, Taki Demir**, Oktay Arslan****, and Mustafa Kucukislamoglu*****
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*Deparment of Medicinal Chemistry, Faculty of Pharmacy, Bezmialem Vakif University, Istanbul, 34093 Turkey; **Pamukova Vocational High School, Sakarya University, Sakarya, 54900 Turkey; ***Faculty of Pharmacy, Suleyman Demirel University, Isparta, 32260 Turkey; ****Department of Chemistry, Faculty of Art and Sciences, Balikesir University, Balikesir, 10145 Turkey; *****Department of Chemistry, Faculty of Arts and Science, Sakarya University, Sakarya, 54055 Turkey
Received October 23, 2015; in final form, April 1, 2016
Coumarin and heterocyclic compounds incorporating urea have clinical applications as antiepileptics, diuretics, and antiglaucoma agents due to their carbonic anhydrase inhibitory properties. We investigated inhibition of carbonic anhydrase I and II with a series of coumarylthiazole derivatives containing urea/thiourea groups. All the investigated compounds exhibited inhibitory activity on both hCA I and hCA II, with 1-(3-chlorophenyl)-3-(4-(2-oxo-2Hchromen-3-yl)thiazol-2-yl)urea being the strongest inhibitor. Structure–activity relationship study showed that most of urea derivatives were more inhibiting for hCA I and hCA II than thiourea derivatives. The electron-withdrawing groups at the phenyl ring increased the inhibitory activity compared to electron-donating groups.
Keywords: carbonic anhydrase, coumarin, inhibitor, structure–activity relationship.
Áčîîđă. őčěč˙ 2016, 42 (5): 561-566