Synthesis and antimicrobial activity evaluation of novel phosphorylated derivatives of Zidovudine
By S. Subba Reddy, V. Koteswara Rao, K. Venkataramana, C. Suresh Reddy, S. K. Ghosh and C. Naga Raju
ABSTRACT
A series of novel phosphorylated derivatives of zidovudine (5-15) were synthesized in two step process with high yields. In the first step zidovudine (1) was reacted with bis(2-chloroethyl) phosphoramidicdichloride/4-nitrophenylphosphorodichloridate/4-chloro phenyl phosphorodi-chloridate in presence of triethylamine (TEA) in dry tetrahydrofuran (THF) to yield the intermediates(2-4). They were further reacted with various compounds like monopotassium dihydrogenphosphate and amino acid esters to obtain the title compounds 5-15. The title compounds showed promising antimicrobial activity and it was greatly influenced by the presence of different bio-active groups at phosphorus.
Key words: Phosphorylated derivatives of zidovudine, gram positive bacteria, gram negative bacteria, antimicrobial activity, phosphoramidate monoesters
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