9,10-Dibromo-N-aryl-9,10-dihydro-9,10-[3,4]epipyrroloanthracene-12,14-diones: Synthesis and Investigation of Their Effects on Carbonic Anhydrase Isozymes I, II, IX, and XII

Goksu H., Topal M., KESKIN A., GÜLTEKİN M. S., ÇELİK M., GÜLÇİN İ., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.349, sa.6, ss.466-474, 2016 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 349 Sayı: 6
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1002/ardp.201600047
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.466-474
  • Anahtar Kelimeler: Carbonic anhydrase, Enzyme inhibition, Enzyme purification, Isoenzyme, TROUT ONCORHYNCHUS-MYKISS, ACETYLCHOLINE ESTERASE INHIBITORS, ISOENZYMES HCA I, THERAPEUTIC APPLICATIONS, ENZYME-ACTIVITY, MYCOBACTERIUM-TUBERCULOSIS, SULFONAMIDE DERIVATIVES, SELECTIVE INHIBITORS, TUMOR-GROWTH, VIVO
  • Atatürk Üniversitesi Adresli: Evet

Özet

N-substituted maleimides were synthesized from maleic anhydride and primary amines. 1,4-Dibromodibenzo[e,h]bicyclo-[2,2,2]octane-2,3-dicarboximide derivatives (4a-f) were prepared by the [4+2] cycloaddition reaction of dibromoanthracenes with the N-substituted maleimide derivatives. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory effects of the new derivatives were assayed against the human (h) isozymes hCA I, II, IX, and XII. All tested bicyclo dicarboximide derivatives exhibited excellent inhibitory effects in the nanomolar range, with K-i values in the range of 117.73-232.87 nM against hCA I and of 69.74-111.51 nM against hCA II, whereas they were low micromolar inhibitors against hCA IX and XII.