- Antitumor Imidazotetrazines. 1. Synthesis and Chemistry of 8-Carbamoyl-3-(2-chloroethyl)imidazo-1,2,3,5-tetrazin-4(3H)-one, a Novel Broad-Spectrum Antitumor Agent
-
Interaction of 5-diazoimidazole-4-carboxamide and alkyl and aryl isocyanates in the dark affords 8-carbamoyl-3-substituted-imidazo-1,2,3,5-tetrazin-4(3H)-ones.In cold methanol or ethanol, the 3-(2-chloroethyl) derivative 7a decomposes to afford 2-azahypoxanthine (14) and methyl and ethyl N-(2-chloroethyl)carbamates, respectively.Compound 7a has curative activity against L-1210 and P388 leukemia and may act as a prodrug modification of the acyclic triazene 5-imidazole-4-carboxamide (MCTIC), since it ring opens to form the triazene in aqueous sodium carbonate.
- Stevens, Malcolm F. G.,Hickman, John A.,Stone, Robert,Gibson, Neil W.,Baig, Ghouse Unissa,et al.
-
p. 196 - 201
(2007/10/02)
-
- Triazines and Related Products. Part 23. New Photo-products from 5-Diazoimidazole-4-carboxamide (Diazo-IC)
-
Photolysis of Diazo-IC in dilute aqueous solution affords products which differ according to the pH of the medium.At pH 1, or pH 7.4 - 12 the product is 2-azahypoxanthine (2): in the intervening pH range the product is 4-carbamoylimidazolium-5-olate (3).In the dark only 2-azahypoxanthine is formed.Photolysis of Diazo-IC in concentrated solution containing citric acid (1 mol equiv.) at pH 2.5 affords a marroon imidazolylazoimidazolium olate (8) and 2-azahypoxanthine.
- Horton, Julie K.,Stevens, Malcolm F. G.
-
p. 1433 - 1436
(2007/10/02)
-