Synthesis and carbonic anhydrase isoenzymes I and II inhibitory effects of novel benzylamine derivatives

ÇETİNKAYA Y., Gocer H., GÖKSU S., GÜLÇİN İ.

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, cilt.29, sa.2, ss.168-174, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 29 Sayı: 2
  • Basım Tarihi: 2014
  • Doi Numarası: 10.3109/14756366.2012.763163
  • Dergi Adı: JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.168-174
  • Anahtar Kelimeler: Benzylamine, carbonic anhydrase, enzyme inhibition, sulfonamide, ERYTHROCYTE ISOZYMES I, VITRO, ACETAZOLAMIDE, PERSPECTIVE, TARGETS, SERIES
  • Atatürk Üniversitesi Adresli: Evet

Özet

Synthesis and carbonic anhydrase inhibitory properties of novel diarylmethylamines 22-25 and sulfonamide derivatives 26-28 were investigated. Acylation of methoxy-substituted benzenes with benzene carboxylic acids, reduction of ketones with NaBH4, conversion of alcohols to azides, Pd-C catalyzed hydrogenation of azides afforded title compounds 22-25. Compounds 22, 24 and 25 were converted to sulfonamide derivatives 26-28 with MeSO2Cl. The inhibitory effects of novel benzylamine derivatives 22-28 were tested on human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes hCA I and II. The results demonstrated that compound 28 was found to be the best inhibitor against both hCA I (K-i: 3.68 mM) and hCA II (K-i: 9.23 mM).