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, K. Kövér, Tünde Zita Illyés, Attila Kiss-Szikszai, Balázs Balogh, T. Kurtán, S. Antus, P. Mátyus

Research output: Article

9 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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Cyclization
Hydrides
Enantiomers
Amyloid
Discrete Fourier transforms
Hydrogen Peroxide
Derivatives
Geometry
4,1-benzoxazepine
flavanone
1,2,3,4-tetrahydroquinoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- And diastereoselective domino knoevenagel-[1,5]-hydride shift cyclization reaction. / Tóth, László; Fu, Yan; Zhang, Hai Yan; Mándi, Attila; Kövér, K.; Illyés, Tünde Zita; Kiss-Szikszai, Attila; Balogh, Balázs; Kurtán, T.; Antus, S.; Mátyus, P.

In: Beilstein Journal of Organic Chemistry, Vol. 10, 06.11.2014, p. 2594-2602.

Research output: Article

Tóth, László ; Fu, Yan ; Zhang, Hai Yan ; Mándi, Attila ; Kövér, K. ; Illyés, Tünde Zita ; Kiss-Szikszai, Attila ; Balogh, Balázs ; Kurtán, T. ; Antus, S. ; Mátyus, P. / Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- And diastereoselective domino knoevenagel-[1,5]-hydride shift cyclization reaction. In: Beilstein Journal of Organic Chemistry. 2014 ; Vol. 10. pp. 2594-2602.
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