New quinoxalin-1,3,4-oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Mirzazadeh R., Asgari M. S., Barzegari E., Pedrood K., Mohammadi-Khanaposhtani M., Sherafati M., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.354, sa.9, 2021 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 354 Sayı: 9
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/ardp.202000471
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, International Pharmaceutical Abstracts, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: 1,3,4-oxadiazole, carbonic anhydrase, cholinesterase, quinoxalin, alpha-glucosidase, INHIBITORY PROPERTIES, CARBONIC-ANHYDRASE, CRYSTAL-STRUCTURE, AGENTS, SALTS
  • Atatürk Üniversitesi Adresli: Evet

Özet

A new series of quinoxalin-1,3,4-oxadiazole (10a-l) derivatives was synthesized and evaluated against some metabolic enzymes including human carbonic anhydrase (hCA) isoenzymes I and II (carbonic anhydrases I and II), cholinesterase (acetylcholinesterase and butyrylcholinesterase), and alpha-glucosidase. Obtained data revealed that all the synthesized compounds were more potent as compared with the used standard inhibitors against studied target enzymes. Among the synthesized compounds, 4-fluoro derivative (10f) against hCA I, 4-chloro derivative (10i) against hCA II, 3-fluoro derivative (10e) against acetylcholinesterase and butyrylcholinesterase, and 3-bromo derivative (10k) against alpha-glucosidase were the most potent compounds with inhibitory activity around 1.8- to 7.37-fold better than standard inhibitors. Furthermore, docking studies of these compounds were performed at the active site of their target enzymes.