Synthesis, crystal structure, and biological evaluation of optically active 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-3-carbonitriles: Antiepileptic, antidiabetic, and anticholinergics potentials

MAHARRAMOV A., KAYA R., TASLIMI P., KURBANOVA M., SADİGOVA A., Farzaliyev V., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.352, sa.2, 2019 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 352 Sayı: 2
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1002/ardp.201800317
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Anahtar Kelimeler: antidiabetic potential, asymmetric synthesis, carbonic anhydrase, metabolic enzymes, optically active 4H-chromenes, ANHYDRASE INHIBITORY PROPERTIES, CARBONIC-ANHYDRASE, ALPHA-GLUCOSIDASE, NATURAL-PRODUCTS, 1ST SYNTHESIS, ISOENZYMES I, ACETYLCHOLINESTERASE, DERIVATIVES, BUTYRYLCHOLINESTERASE, BROMOPHENOLS
  • Atatürk Üniversitesi Adresli: Evet

Özet

In the presence of chiral organic catalysts, the optically active 4H-chromine was synthesized from the multicomponent condensation of 5,5-dimethylcyclohexane-1,3-dione with malononitrile and methylene-active compound, and the specific angle of rotation of the compounds was determined in the AUTOPOL-III polarimeter and their structures were confirmed by the X-ray spectroscopic analysis method. These optically active 2-amino-4-aryl-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromen-3-carbonitriles were effective inhibitors of alpha-glycosidase, the cytosolic carbonic anhydrase I and II isoforms (hCA I and II), and acetylcholinesterase (AChE) enzymes with K-i values in the range of 21.33 +/- 1.11 to 40.24 +/- 10.78 mu M for hCA I, 28.91 +/- 6.51 to 59.97 +/- 15.62 mu M for hCA II, 18.16 +/- 3.18 to 66.57 +/- 1.36 mu M for alpha-glycosidase, and 8.68 +/- 0.93 to 102.61 +/- 24.96 mu M for AChE.