Publication Date:
2014-11-07
Description:
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 3 J H,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 (H 2 O 2 ) or β-amyloid 25–35 (Aβ 25–35 )-induced cellular injuries in human neuroblastoma SH-SY5Y cells in the range of those of positive controls. Beilstein J. Org. Chem. 2014, 10, 2594–2602. doi:10.3762/bjoc.10.272
Keywords:
1,4-benzoxazepinediastereoselective domino Knoevenagel–[1,5]-hydride shift cyclizationneuroprotectivetert-amino effectTDDFT-ECD calculation
Electronic ISSN:
1860-5397
Topics:
Chemistry and Pharmacology
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