Synthesis and carbonic anhydrase inhibitory properties of novel cyclohexanonyl bromophenol derivatives


Balaydin H. T. , Senturk M., MENZEK A.

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol.22, no.3, pp.1352-1357, 2012 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 3
  • Publication Date: 2012
  • Doi Number: 10.1016/j.bmcl.2011.12.069
  • Title of Journal : BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
  • Page Numbers: pp.1352-1357
  • Keywords: Carbonic anhydrase, Enzyme inhibition, Bromination, Bromophenols, Cyclohexanone with benzyl, Enamine, Esterification, Symphyoketone, IN-VITRO INHIBITION, ERYTHROCYTE GLUTATHIONE-REDUCTASE, ALGA SYMPHYOCLADIA-LATIUSCULA, AROMATIC/HETEROCYCLIC SULFONAMIDES, THERAPEUTIC APPLICATIONS, ODONTHALIA-CORYMBIFERA, PHENOLIC-COMPOUNDS, HUMAN SERUM, ISOZYME-II, PURIFICATION

Abstract

The Naturally occurring novel cyclohexanonyl bromophenol 2(R)-2-(2,3,6-tribromo-4,5-dihydroxybenzyl) cyclohexanone (4) was synthesized as a racemic compound. Cyclohexylphenyl methane derivatives (10-17) with Br, OMe, CO, and OH were also obtained. Inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I, II, IV, and VI, with compounds 2-4, 8, and 10-26 was investigated. These compounds were found to be promising carbonic anhydrase inhibitors and some of them showed interesting inhibitory activity. Some of the compounds investigated here showed effective hCA 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, and osteoporosis. (C) 2011 Elsevier Ltd. All rights reserved.