Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

Bayrak C., Taslimi P., Kilinc N., GÜLÇİN İ., MENZEK A.

Chemistry and Biodiversity, cilt.20, sa.8, 2023 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20 Sayı: 8
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1002/cbdv.202300469
  • Dergi Adı: Chemistry and Biodiversity
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Agricultural & Environmental Science Database, Aquatic Science & Fisheries Abstracts (ASFA), CAB Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: Brominating, condensation, enzyme inhibition, molecular docking, natural bromophenol
  • Atatürk Üniversitesi Adresli: Evet

Özet

In addition to the first synthesis of the natural bromophenol butyl 2-(3,5-dibromo-4-hydroxyphenyl)acetate (1), indene derivatives 34 and 35 were synthesized from 3-phenylpropenal derivatives in BBr3 medium. Five known natural bromophenols and some derivatives were synthesized by known methods. Cholinesterase (ChEs) inhibitors reduce the breakdown of acetylcholine and are used in the treatment of Alzheimer's disease (AD) and dementia symptoms. The inhibition effects of all obtained compounds were examined towards acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and α-glycosidase enzymes. All synthesized compounds demonstrated the strong inhibition effects against both cholinergic enzymes. For determination of Ki values of novel bromophenols Lineweaver-Burk graphs were obtained. Ki values were found in the ranging of 0.13–14.74 nM for AChE, 5.11–23.95 nM for BChE, and 63.96–206.78 nM for α-glycosidase, respectively. All bromophenols and their derivatives exhibit effective inhibition profile when compared to positive controls.