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

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Oztaskin N., Göksu S., Demir Y., Maraş A., Gülçin İ.

MOLECULES, cilt.27, sa.21, 2022 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 27 Sayı: 21
  • Basım Tarihi: 2022
  • Doi Numarası: 10.3390/molecules27217426
  • Dergi Adı: MOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Biotechnology Research Abstracts, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, EMBASE, Food Science & Technology Abstracts, MEDLINE, Metadex, Veterinary Science Database, Directory of Open Access Journals, Civil Engineering Abstracts
  • Anahtar Kelimeler: bromophenol, diaryl methane, demethylation, carbonic anhydrase, acetylcholinesterase, BIOLOGICAL EVALUATION, ANTIMICROBIAL ACTIVITIES, ANTIOXIDANT PROPERTIES, ISOENZYMES I, METAL-IONS, HCA I, DERIVATIVES, BUTYRYLCHOLINESTERASE, ESTERASE, (3,4-DIHYDROXYPHENYL)(2,3,4-TRIHYDROXYPHENYL)METHANONE
  • Atatürk Üniversitesi Adresli: Evet

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.