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

Balaydiin H. T., SÖYÜT H., Ekinci D., GÖKSU S., BEYDEMİR Ş., Menzek A., ...More

Journal of Enzyme Inhibition and Medicinal Chemistry, vol.27, no.1, pp.43-50, 2012 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 1
  • Publication Date: 2012
  • Doi Number: 10.3109/14756366.2011.574131
  • Journal Name: Journal of Enzyme Inhibition and Medicinal Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.43-50
  • Keywords: Bromophenols, Carbonic anhydrase, Diphenylmethane, Enzyme inhibition, Glaucoma
  • Bilecik Şeyh Edebali University Affiliated: Yes

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 IC 50 values in the range of 0.7372 μM 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. © 2012 Informa UK, Ltd.