Synthesis and biological evaluation of bromophenol derivatives with cyclopropyl moiety: Ring opening of cyclopropane with monoester

BOZTAS, Murat; TASLIMI, Parham; YAVARİ, Mirali Akbar; Gülçin, İlhami; Şahin, Ertan; MENZEK, Abdullah

doi:10.1016/j.bioorg.2019.103017

Makale Tam Makale Uluslararası 2019

Synthesis and biological evaluation of bromophenol derivatives with cyclopropyl moiety: Ring opening of cyclopropane with monoester

Murat BOZTAS, Parham TASLIMI, Mirali Akbar YAVARİ, İlhami Gülçin, Ertan Şahin, Abdullah MENZEK

Bioorganic Chemistry Cilt 89 · 01.08.2019

DOI ile aç

Özet

Trans-(1R*,2R*,3R*)-Ethyl 2-(3,4-dimethoxyphenyl)-3-methylcyclopropane-1-carboxylate (6) and its cis isomer 7 were obtained from the reaction of the methyl isoeugenol (5) with ethyl diazoacetate. The reduction and bromination reactions of the ester 6 and 7 together with the hydrolysis of all esters were carried out. Opening ring of cyclopropane was observed in the reaction of 7 with bromine. The opening of cyclopropane ring with COOR and synthesis of esters, alcohols and acids (6-26) are new. These obtained bromophenol derivatives (6-26) were effective inhibitors of the cytosolic carbonic anhydrase I and II isoforms (hCA I and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 7.8 +/- 0.9-58.3 +/- 10.3 nM for hCA I, 43.1 +/- 16.7-150.2 +/- 24.1 nM for hCA II, and 159.6 +/- 21.9-924.2 +/- 104.8 nM for AChE, respectively. Acetylcholinesterase inhibitors are the most popular drugs applied in the treatment of diseases such as Alzheimer's disease, Parkinson's disease, senile dementia, and ataxia, among others.

Anahtar kelimeler

ANTIOXIDANT ACTIVITY carbonic anhydrase Acetylcholinesterase enzyme inhibition TROUT ONCORHYNCHUS-MYKISS ISOENZYMES I CRYSTAL-STRUCTURE alpha-glycosidase Bromination Bromophenol Cyclopropane ANHYDRASE INHIBITORY PROPERTIES POTENT CARBONIC-ANHYDRASE INCLUDING NATURAL-PRODUCTS CYCLOHEXANONYL BROMOPHENOL CYCLOADDITION REACTIONS

Atıf için künye

BOZTAS, M., TASLIMI, P., YAVARİ, M. A., Gülçin, İ., Şahin, E., & MENZEK, A. (2019). Synthesis and biological evaluation of bromophenol derivatives with cyclopropyl moiety: Ring opening of cyclopropane with monoester. Bioorganic Chemistry, 89. https://doi.org/10.1016/j.bioorg.2019.103017

BibTeX

@article{boztas2019-66615,
  author = {BOZTAS, Murat and TASLIMI, Parham and YAVARİ, Mirali Akbar and Gülçin, İlhami and Şahin, Ertan and MENZEK, Abdullah},
  title = {Synthesis and biological evaluation of bromophenol derivatives with cyclopropyl moiety: Ring opening of cyclopropane with monoester},
  journal = {Bioorganic Chemistry},
  year = {2019},
  volume = {89},
  issn = {0045-2068},
  doi = {10.1016/j.bioorg.2019.103017},
  url = {https://akademik.atauni.edu.tr/yayinlar/66615-synthesis-and-biological-evaluation-of-bromophenol-derivatives-with-cyclopropyl}
}