157871-29-9Relevant academic research and scientific papers
Purines. LXX. An extension of the 'Phenacylamine route' to the syntheses of the 7-N-oxides of 6-mercaptopurine and 6-methylthiopurine, and antileukemic activity of some purine N-oxides
Fujii,Ogawa,Itaya,Date,Inagaki,Nohara
, p. 408 - 413 (2007/10/02)
A full account is given of the first syntheses of 6-mercaptopurine 7-N-oxide (4) and 6-methylthiopurine 7-N-oxide (5), The synthesis of 4 followed a 'phenacylamine route', which started from condensation of 4,6-dichloro-5-nitropyrimidine (15) with N-(4-methoxybenzyl)phenacylamine to form the phenacylaminopyrimidine derivative (11) and proceeded through conversion into the mercapto derivative, intramolecular cyclization between the NO2 nitrogen atom and the phenacyl carbanion to give 6-mercapto-9-(4-methoxybenzyl)purine 7-N-oxide (12), and removal of the 4-methoxybenzyl group, S-Methylation of 12 and removal of the 4-methoxybenzyl group afforded 5, The location of the oxygen function in 4, 5, and 12 was confirmed by X-ray crystallographic analysis of 5 · H2O, which was shown to exist in the N(7)-OH form (19). A UV spectroscopic approach suggested that the neutral species of 4 exists in H2O as the N(7)-OH tautomer (21), whereas that of 5 exists as an equilibrated mixture of the N(7)-oxide (5) and the N(7)-OH (19) tautomers. In the in vitro bioassay of antileukemic activity against murine L5178Y cells, the N-oxides 4 and 12 were found to be weakly cytotoxic.
Syntheses of the 7-N-Oxides of 6-Mercaptopurine and 6-Methylthiopurine
Ogawa, Kazuo,Itaya, Taisuke,Fujii, Tozo
, p. 1225 - 1228 (2007/10/02)
6-Mercaptopurine 7-N-oxide (6) has been synthesized for the first time from 4,6-dichloro-5-nitropyrimidine (12) by following a "phenacylamine route" through the intermediates (8) and (9).Methylation of 9 and removal of the p-methoxybenzyl group provided 6
