Synthesis and bioactivity of phosphorylated derivatives of stavudine

Novel phosphorylated derivatives of stavudine were synthesized by the reaction of bis(2-chloroethyl)phosphoramidic dichloride/4-nitrophenyl phosphorodichloridate with various cyclic amines and amino acid esters in the presence of triethylamine in dry tetrahydrofuran through the corresponding monochl...

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Bibliographic Details
Published in:European journal of chemistry 2010-12, Vol.1 (4), p.297-301
Main Authors: Rao, Alahari Janardhan, Rao, Valasani Koteswara, Rao, Pasupuleti Visweswara, Raju, Chamarthi Naga, Ghosh, Sunil Kumar
Format: Article
Language:English
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Summary:Novel phosphorylated derivatives of stavudine were synthesized by the reaction of bis(2-chloroethyl)phosphoramidic dichloride/4-nitrophenyl phosphorodichloridate with various cyclic amines and amino acid esters in the presence of triethylamine in dry tetrahydrofuran through the corresponding monochloride intermediates 2a-l. Further reaction of the intermediates 2a-l with stavudine in tetrahydrofuran and pyridine in the presence of triethylamine formed the title compounds 4a-l. Their structures were characterized by IR, 1H-, 13C-, 31P-NMR and mass spectral data analyses. They exhibited good antibacterial and antioxidant activities. Their bioactivity was greatly influenced by the different groups present at the phosphorus.
ISSN:2153-2249
2153-2257
DOI:10.5155/eurjchem.1.4.297-301.20