Synthesis and Biological Activity of Diazaphospholo-Iminophosphorane Derivatives of Zidovudine (Azt) Through Staudinger Reaction

Abstract

Synthesis of a series of novel iminophosphorane derivatives of Zidovudine (AZT) was accomplished through Staudinger reaction. In the first step PBr3 was reacted with various substituted phenolic and amino compounds in the presence of triethylamine (TEA) in dry tetrahydrofuran (THF) under nitrogen atmosphere followed by cyclisation of (±) 2-aminomethyl piperidine, afforded diazaphosphole P(III) intermediates (3al).They were further reacted with zidovudine to obtain iminophosphorane derivatives 4a-l. They  showed promising antioxidant activitiy. Their antioxidant activitiy was greatly influenced by the presence of different bio-active groups at phosphorus.