950664-86-5Relevant academic research and scientific papers
Synthesis of 1-(alkyl)-5-dimethylamino-6-phenethyluracils as potent nonnucleoside HIV-1 RT inhibitors
Wang, Xiaowei,Chen, Yanli,Guo, Ying,Li, Amin,Ma, Xiaoyan,Liu, Junyi
, p. 2421 - 2431 (2007)
1-(Alkyl)-5-dimethylamino-6-phenethyl uracils (1) and (2) are analogs of MKC-442, which is a very potent inhibitor of HIV-1 reverse transcriptase. The target compound 1 was synthesized by the first approach, from the corresponding 1,3-dibenzyl-5-(dimethylamino)-6-phenethylpyrimidine-2,4(1H,3H)-dione (7), which was synthesized in four steps from 6-methyluracil (3) by nitration, benzylation, reduction, and methylation of the amino group. Compound 7 was then debenzylated to give the complete deprotected compound 8 with very low yield. To improve the yield, another pathway was developed for introducing the ethoxymethyl group at N-1 of the uracil ring first. The result of adjusting reaction sequences increased the overall yield dramatically. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity was found for target compound 1. Copyright Taylor & Francis Group, LLC.
