European Journal of Chemistry

Synthesis and bioactivity of phosphorylated derivatives of stavudine

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Alahari Janardhan Rao
Valasani Koteswara Rao
Pasupuleti Visweswara Rao
Chamarthi Naga Raju
Sunil Kumar Ghosh


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.


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Rao, A. J.; Rao, V. K.; Rao, P. V.; Raju, C. N.; Ghosh, S. K. Synthesis and Bioactivity of Phosphorylated Derivatives of Stavudine. Eur. J. Chem. 2010, 1, 297-301.

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