Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- And diastereoselective domino knoevenagel-[1,5]-hydride shift cyclization reaction

László Tóth, Yan Fu, Hai Yan Zhang, Attila Mándi, Katalin E. Kövér, Tünde Zita Illyés, Attila Kiss-Szikszai, Balázs Balogh, Tibor Kurtán, Sándor Antus, Péter Mátyus

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11 Citations (Scopus)

Abstract

Condensed O, N- heterocycles containing tetrahydro-1,4-benzoxazepine and tetrahydroquinoline moieties were prepared by a regio- and diastereoselective domino Knoevenagel-[1,5]-hydride shift cyclization reaction of a 4-aryl-2-phenyl-1,4-benzoxazepine derivative obtained from flavanone. The relative configuration of products were determined by the correlation of 3JH,H coupling data with the geometry of major conformers accessed by DFT conformational analysis. Separated enantiomers of the products were characterized by HPLC-ECD data, which allowed their configurational assignment on the basis of TDDFT-ECD calculation of the solution conformers. Two compounds showed neuroprotective activities against hydrogen peroxide ( H2O2 ) or β-amyloid 25- 35 ( Aβ25-35 )- induced cellular injuries in human neuroblastoma SH-SY5Y cells in the range of those of positive controls.

Original languageEnglish
Pages (from-to)2594-2602
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
Publication statusPublished - Nov 6 2014

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Keywords

  • 1,4-benzoxazepine
  • Diastereoselective domino knoevenagel-[1,5]-hydride shift cyclization
  • Neuroprotective
  • Tddft-ecd calculation
  • Tert-amino effect

ASJC Scopus subject areas

  • Organic Chemistry

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