74829-45-1Relevant articles and documents
Fujiwara et al.
, p. 701,705 (1973)
Antitumour imidazotetrazines. Part 36. Conversion of 5-aminoimidazole-4-carboxamide to imidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-ones and imidazo[1,5-a][1,3,5]triazin-4(3H)-ones related in structure to the antitumour agents temozolomide and mitozolomide
Wang, Yongfeng,Wheelhouse, Richard T.,Zhao, Linxiang,Langnel, David A. F.,Stevens, Malcolm F. G.
, p. 1669 - 1675 (2007/10/03)
Novel 3-substituted imidazo[5,1-d][1,2,3,5]tetrazinones 3 have been prepared by two routes: reaction of 5-diazoimidazole-4-carboxamide 2 and isocyanates, and nitrosative cyclisation of 5-amino-1-carbamoylimidazole-4-carboxamides 7. The latter cyclisations do not proceed efficiently when the 1-carbamoyl group bears an electron-donating alkyl group. 5-Amino-1-carbamoylimidazole-4-carboxamides 7 cyclise with triethyl orthoformate or triethyl orthobenzoate to yield imidazo[1,5-a][1,3,5]triazinones 15. A 1H NMR study of the decomposition of 8-carbamoyl-3-ethylimidazo[5,1-d][1,2,3,5]tetrazin-4(3H)-one 3c in deuteriated phosphate buffer has shown that its ethylating capacity is attenuated by the unproductive generation of ethene. This observation explains why the ethylimidazotetrazine possesses weaker antitumour properties than the clinically-used congener temozolomide 3a.
Mass Spectral Characteristics of the Sulfur-containing Ketoxime Carbamates Thiofanox and Metabolites
Corkins, H. G.,Mannion, J. J.,Storace, L.
, p. 185 - 191 (2007/10/02)
Deuterium labeling and high resolution mass spectroscopy have been used to determine the modes of electron impact fragmentation of 3,3-dimethyl-1-methylthio-2-butanone O-oxime, thiofanox and its metabolites, the sulfoxide and sulfone.The mass spectra of the corresponding oximes were also examined.The carbamates fragmented chiefly by two competing pathways-the loss of CH3N=C-O or the sulfur-containing moiety.The favored process was dependent on the oxidation state at sulfur.Several unusual rearrangements were noted.
