The first synthesis of 4-phenylbutenone derivative bromophenols including natural products and their inhibition profiles for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase enzymes

BAYRAK C., TASLIMI P., GÜLÇİN İ., MENZEK A.

BIOORGANIC CHEMISTRY, cilt.72, ss.359-366, 2017 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 72
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.bioorg.2017.03.001
  • Dergi Adı: BIOORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.359-366
  • Anahtar Kelimeler: Bromination, Bromophenols, Carbonic anhydrase, Acetylcholinesterase, Butyrylcholinesterase, Enzyme inhibition, Phenylbutenone, Natural products, TROUT ONCORHYNCHUS-MYKISS, ERYTHROCYTES IN-VITRO, ISOENZYMES HCA I, ANTIOXIDANT ACTIVITY, ANTICHOLINERGIC PROPERTIES, ISOZYMES I, PURIFICATION, LACTOPEROXIDASE, SULFAMIDES, ESTERASE
  • Atatürk Üniversitesi Adresli: Evet

Özet

The first synthesis of (E)-4-(3-bromo-4,5-dihydroxyphenyl) but-3-en-2-one (1), (E)-4-(2-bromo-4,5-dihy droxyphenyl) but-3-en-2-one (2), and (E)-4-(2,3-dibromo-4,5-dihydroxyphenyl) but-3-en-2-one (3) was realized as natural bromophenols. Derivatives with mono OMe of 2 and 3 were obtained from the reactions of their derivatives with di OMe with AlCl3. These novel 4-phenylbutenone derivatives were effective inhibitors of the cytosolic carbonic anhydrase I and II isoenzymes (hCA I and II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) with Ki values in the range of 158.07-404.16 pM for hCA I, 107.63-237.40 pM for hCA II, 14.81-33.99 pM for AChE and 5.64-19.30 pM for BChE. The inhibitory effects of the synthesized novel 4-phenylbutenone derivatives were compared to acetazolamide as a clinical hCA I and II isoenzymes inhibitor and tacrine as a clinical AChE and BChE enzymes inhibitor. (C) 2017 Elsevier Inc. All rights reserved.