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*****

^#Phone: +90-264-2953378; fax: +90-264-2953679; e-mail: [email protected]

*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

DOI: 10.7868/S0132342316050043

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.

Биоорг. химия 2016, 42 (5): 561-566