Synthesis of Novel Bromophenol with Diaryl Methanes-Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase

Oztaskin, Necla; Göksu, Süleyman; Demir, Yeliz; Maraş, Ahmet; Gülçin, İlhami

doi:10.3390/molecules27217426

Makale Tam Makale Uluslararası 2022 Açık erişimli

Synthesis of Novel Bromophenol with Diaryl Methanes-Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase

Necla Oztaskin, Süleyman Göksu, Yeliz Demir, Ahmet Maraş, İlhami Gülçin

MOLECULES Cilt 27 · Sayı 21 · 01.11.2022

DOI ile aç

Özet

In this work, nine new bromophenol derivatives were designed and synthesized. The alkylation reactions of (2-bromo-4,5-dimethoxyphenyl)methanol (7) with substituted benzenes 8-12 produced new diaryl methanes 13-17. Targeted bromophenol derivatives 18-21 were synthesized via the O-Me demethylation of diaryl methanes with BBr3. Moreover, the synthesized bromophenol compounds were tested with some metabolic enzymes such as acetylcholinesterase (AChE), carbonic anhydrase I (CA I), and II (CA II) isoenzymes. The novel synthesized bromophenol compounds showed Ki values that ranged from 2.53 +/- 0.25 to 25.67 +/- 4.58 nM against hCA I, from 1.63 +/- 0.11 to 15.05 +/- 1.07 nM against hCA II, and from 6.54 +/- 1.03 to 24.86 +/- 5.30 nM against AChE. The studied compounds in this work exhibited effective hCA isoenzyme and AChE enzyme inhibition effects. The results show that they can be used for the treatment of glaucoma, epilepsy, Parkinson's as well as Alzheimer's disease (AD) after some imperative pharmacological studies that would reveal their drug potential.

Anahtar kelimeler

carbonic anhydrase DERIVATIVES Acetylcholinesterase Butyrylcholinesterase ISOENZYMES I BIOLOGICAL EVALUATION ANTIMICROBIAL ACTIVITIES HCA I metal ions 3 Bromophenol demethylation Antioxidant properties 4-DIHYDROXYPHENYL)(2 4-TRIHYDROXYPHENYL)METHANONE ESTERASE diaryl methane

Atıf için künye

Oztaskin, N., Göksu, S., Demir, Y., Maraş, A., & Gülçin, İ. (2022). Synthesis of Novel Bromophenol with Diaryl Methanes-Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase. MOLECULES, 27(21). https://doi.org/10.3390/molecules27217426

BibTeX

@article{oztaskin2022-67973,
  author = {Oztaskin, Necla and Göksu, Süleyman and Demir, Yeliz and Maraş, Ahmet and Gülçin, İlhami},
  title = {Synthesis of Novel Bromophenol with Diaryl Methanes-Determination of Their Inhibition Effects on Carbonic Anhydrase and Acetylcholinesterase},
  journal = {MOLECULES},
  year = {2022},
  volume = {27},
  number = {21},
  issn = {1420-3049},
  doi = {10.3390/molecules27217426},
  url = {https://akademik.atauni.edu.tr/yayinlar/67973-synthesis-of-novel-bromophenol-with-diaryl-methanes-determination-of-their}
}