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., ...Daha Fazla

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.27, sa.1, ss.43-50, 2012 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 1
  • Basım Tarihi: 2012
  • Doi Numarası: 10.3109/14756366.2011.574131
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.43-50
  • Anahtar Kelimeler: Bromophenols, diphenylmethane, carbonic anhydrase, glaucoma, enzyme inhibition, IN-VITRO, THERAPEUTIC APPLICATIONS, PHENOLS, PATTERNS, METALS, SERIES
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Hayır

Özet

(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.