151239-26-8Relevant articles and documents
Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives
Chen, Wenbin,Deng, Zhaohui,Chen, Kuangyu,Dou, Daolei,Song, Fanbo,Li, Luyuan,Xi, Zhen
, p. 172 - 181 (2015)
The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poo
Synthesis, Bioactivity and Anti-HIV Activity of the Bis(4-acyloxybenzyl) and Mono(4-acylaoxybenzyl) Esters of the 5'-Monophosphate of AZT
Thomson, William,Nicholls, Dave,Irwin, William J.,Al-Mushadani, Julian S.,Freeman, Sally,et al.
, p. 1239 - 1246 (2007/10/02)
To investigate the design of prodrugs of antiviral nucleosides for targeting to the central nervous system, the bis(4-acyloxybenzyl) esters of the 5'-monophosphate of AZT 5 (R = Me, Et, Pri or But) have been prepared.The reaction of the appropriate bis(4-acyloxybenzyl) N,N-diisopropylphosphoramidite 10 (R = Me, Et, Pri or But) with AZT in the presence of 1H-tetrazole, followed by oxidation of the PIII intermediate with 3-chloroperoxybenzoic acid gave the required triesters 5 in good yield.The lithium salts of the mono(4-acycloxybenzyl) esters of the 5'-phosphate of AZT 7 (R = Me, Et, Pri or But) were prepared by treatment of the triesters 5 with lithium iodide.In the presence of porcine liver carboxyesterase the triesters 5 and diesters 7 decomposed readily to the 5'-monophosphate of AZT 9.The anti-HIV activities of the triesters 5 and diesters 7 were, with one exception, comparable to that of AZT, but the greater cytotoxicity of certain compounds in particular types of cell significantly reduced their selectivity indices.
