5-Triazolyl-2-methylisoxazolidin-3-yl 3-phosphonates have been synthesized by 1,3-dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and vinyl triazoles. The process showed a complete regioselectivity and a nearly exclusive cis stereoselectivity. M062X/6-31G(d,p) calculations rationalize the regio- and the stereochemical results. The formation of a hydrogen bond along a particular reaction channel significantly stabilizes both transition states and products related to cis-adducts. Biological tests indicate that the obtained compounds do not show relevant antiviral and anticancer activity.

5-3-Phosphonated 1H-123-triazol-4-ylisoxazolidines synthesis DFT studies and biological properties

GAROZZO, Adriana;CAMPISI, Agatina;LANZA, GIUSEPPE;CHIACCHIO, MARIA ASSUNTA ROSSELLA
2015-01-01

Abstract

5-Triazolyl-2-methylisoxazolidin-3-yl 3-phosphonates have been synthesized by 1,3-dipolar cycloaddition of N-methyl-C-diethoxyphosphorylnitrone and vinyl triazoles. The process showed a complete regioselectivity and a nearly exclusive cis stereoselectivity. M062X/6-31G(d,p) calculations rationalize the regio- and the stereochemical results. The formation of a hydrogen bond along a particular reaction channel significantly stabilizes both transition states and products related to cis-adducts. Biological tests indicate that the obtained compounds do not show relevant antiviral and anticancer activity.
2015
DFT studies; stereoselectivity; phosphonated Cnucleosides
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/17827
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