Synthesis, theoretical calculation and alpha-glucosidase inhibition of new chalcone oximes

FANDAKLI S., DOĞAN İ. S., SELLİTEPE H. E., YAŞAR A., YAYLI N.

ORGANIC COMMUNICATIONS, cilt.11, sa.1, ss.23-34, 2018 (ESCI) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 11 Sayı: 1
  • Basım Tarihi: 2018
  • Doi Numarası: 10.25135/acg.oc.38.18.02.067
  • Dergi Adı: ORGANIC COMMUNICATIONS
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.23-34
  • Anahtar Kelimeler: Chalcone, chalcone oxime, alpha-glucosidase inhibition, BIOLOGICAL EVALUATION, ANTIMICROBIAL ACTIVITY, SULFONAMIDE CHALCONE, MOLECULAR DOCKING, DERIVATIVES, AGENTS, DISCOVERY
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

A series of eleven hydroxy and methoxy substituted new chalcone oximes (2a-2k) were synthesized by the condensation of chalcone (1a-1k) with hydroxylamine hydrochloride in pyridine. Structures of the synthesized compounds were characterized using NMR (1D; H-1, C-13/APT and 2D H-1-H-1 COSY, NOESY and ROESY), FT-IR, UV, LC-MS spectral data and elemental analysis. These synthetic compounds (2a-k) were screened for their a-glucosidase inhibition. The most a-glucosidase inhibitory activity were observe on compounds 2a and 2b with in the range of 1.61-3.36 mu M (IC50 values) which were more active then acarbose (IC50, 13,34 mu M). IC50 values of other synthesized compounds 2c-2h are within the range of 7,25-25,55 mu M which were more or as active as acarbose, but, IC50 values for compounds 2j-2k were not observed. The geometric isomers of compounds 2a-2k were calculated theoretically. Experimental and theoretical calculations showed that cisoid 1E,2E is the most stable geometrical isomer of all.