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

BAYRAK, Cetin; TASLIMI, Parham; Gülçin, İlhami; MENZEK, Abdullah

doi:10.1016/j.bioorg.2017.03.001

Makale Tam Makale Uluslararası 2017

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

Cetin BAYRAK, Parham TASLIMI, İlhami Gülçin, Abdullah MENZEK

Bioorganic Chemistry Cilt 72 · ss. 359–366 · 01.06.2017

DOI ile aç

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.

Anahtar kelimeler

ANTIOXIDANT ACTIVITY carbonic anhydrase Acetylcholinesterase Butyrylcholinesterase enzyme inhibition Natural products TROUT ONCORHYNCHUS-MYKISS ERYTHROCYTES IN-VITRO ISOZYMES I PURIFICATION SULFAMIDES BROMOPHENOLS Bromination Lactoperoxidase ISOENZYMES HCA I ESTERASE ANTICHOLINERGIC PROPERTIES Phenylbutenone

Atıf için künye

BAYRAK, C., TASLIMI, P., Gülçin, İ., & MENZEK, A. (2017). The first synthesis of 4-phenylbutenone derivative bromophenols including natural products and their inhibition profiles for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase enzymes. Bioorganic Chemistry, 72, 359–366. https://doi.org/10.1016/j.bioorg.2017.03.001

BibTeX

@article{bayrak2017-68060,
  author = {BAYRAK, Cetin and TASLIMI, Parham and Gülçin, İlhami and MENZEK, Abdullah},
  title = {The first synthesis of 4-phenylbutenone derivative bromophenols including natural products and their inhibition profiles for carbonic anhydrase, acetylcholinesterase and butyrylcholinesterase enzymes},
  journal = {Bioorganic Chemistry},
  year = {2017},
  volume = {72},
  pages = {359--366},
  issn = {0045-2068},
  doi = {10.1016/j.bioorg.2017.03.001},
  url = {https://akademik.atauni.edu.tr/yayinlar/68060-the-first-synthesis-of-4-phenylbutenone-derivative-bromophenols-including}
}