Synthesis and carbonic anhydrase inhibitory properties of novel bromophenols including natural products


Balaydin H. T. , Soyut H., Ekinci D., GÖKSU S., Beydemir S., MENZEK A., ...More

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, vol.27, no.1, pp.43-50, 2012 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.3109/14756366.2011.574131
  • Title of Journal : JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Page Numbers: pp.43-50
  • Keywords: Bromophenols, diphenylmethane, carbonic anhydrase, glaucoma, enzyme inhibition, IN-VITRO, THERAPEUTIC APPLICATIONS, PHENOLS, PATTERNS, METALS, SERIES

Abstract

(2-Bromo-3,4-dimethoxyphenyl) (3,4-dimethoxyphenyl) methanone (10) and its derivatives with Br, one dibromide and isomeric three tribromides, were synthesized. Demethylation of these compounds afforded a series of new bromophenols. Inhibition of human cytosolic carbonic anhydrase II (hCA II) isozyme by these new bromophenols and naturally occurring 3,4,6-tribromo-5-(2,5-dibromo-3,4-dihydroxybenzyl) benzene-1,2-diol (3), and 5,5'-methylenebis(3,4,6-tribromo-benzene-1,2-diol) (4) was investigated. The synthesized compounds showed carbonic anhydrase inhibitory capacities with IC50 values in the range of 0.7-372 mu M against hCA II. Some bromophenols investigated here showed effective hCA II inhibitory activity and might be used as leads for generating novel carbonic anhydrase inhibitors which are valuable drug candidates for the treatment of glaucoma, epilepsy, gastric and duodenal ulcers, neurological disorders, or osteoporosis.