Synthesis of two phloroglucinol derivatives with cinnamyl moieties as inhibitors of the carbonic anhydrase isozymes I and II: an in vitro study

Abstract

Two cinnamyl-substituted phloroglucinols, 4-p-methoxycinnamyl phloroglucinol (9) and 4,6-bis-p-methoxycinnamyl phloroglucinol (10) were synthesized. Two carbonic anhydrases, human carbonic anhydrase I and II (hCA I and II), were purified. Kinetic interactions between these isozymes with 9 and 10 were investigated. These new compounds exhibited inhibitory effects on the hCA I and II enzymes’ activity in vitro. The combination of the inhibitory effects of both phloroglucinol and p-coumaric acid groups in a single compound was explored. However, relative to the inhibitory effects of the two groups separately, compounds 9 and 10 demonstrated comparable inhibitory effects. More effective inhibitors of CAs could be created by testing these compounds on other CA isozymes.

Keywords:

• Enzyme inhibition, human CAI, human CAII, phloroglucinol, synthesis

Declaration of interest

The authors report no declarations of interest. We thank the Scientific and Technological Research Council of Turkey (TUBITAK, Project number: 114Z554) and Erzincan University (Project number: FEN-A-300614–0098) for their financial supports of this work.

Supplementary material available online