124508-99-2

6-Sulfenamide, 6-sulfinamide and 6-sulfonamide purines, purine nucleosides, purine nucleotides and 3 and 7 deaza and 8 aza derivatives thereof of structure: STR1 wherein Z is H or --NH2 ; X is --S--NH2, STR2 T is C--H, G is N and Q is N; or T is C--H, G is N and Q is C--H; or T is N, G is N and Q is C--H; or T is C--H, G is C--H and Q is N; Y is H or an α-pentofuranose or β-pentofuranose of the formula: STR3 wherein R1 and R2 independently are H, OH, --O-acyl or STR4 or together R1 and R2 are STR5 and R3 and R4 are H or one of R3 or R4 is OH and the other is H; provided that when Y is H, Z is --NH2 ; and acceptable salt thereof are prepared and are useful as antitumor agents or they are intermediates for compounds which are antitumor agents. The compounds are used to treat an affected warm blooded host by serving as the active ingredients of suitable pharmaceutical compositions.

7-Deaza (pyrrolopyrimidine) and 3-deaza (imidazopyridine congeners of sulfenosine (5a and 9), sulfinosine (6a and 10), and sulfonosine (7a) have been prepared and evaluated for their antileukemic activity in mice.Amination of 2-amino-7-β-D-ribofuranosylpyrrolopyrimidine-4(3H)-thione (4a) and its 2'-deoxy analogue (4c) with a chloramine solution gave the corresponding 4-sulfenamides (5a and 5c, respectively), which on selective oxidation with m-chloroperoxybenzoic acid (MCPBA) gave the respective diastereomeric 2-amino-7-β-D-ribofuranosylpyrrolopyrimidine-4-sulfinamide (7-deazasulfinosine, 6a) and its 2'-deoxy derivative (6c).A similar amination of 7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolopyrimidine-4(3H)-thione (4b) gave the corresponding 4-sulfenamide derivative (5b).Oxidation of 5b with 1 molar equiv of MCPBA furnished (R,S)-7-(2-deoxy-β-D-erythro-pentofuranosyl)pyrrolopyrimidine-4-sulfinamide (6b), whereas use of excess of MCPBA afforded the corresponding sulfonamide derivative (7b).Treatment of 3-deaza-6-thioguanosine (8) with a chloramine solution gave 3-deazasulfenosine (6-amino-1-β-D-ribofuranosylimidazopyridine-4-sulfenamide, 9).Controlled oxidation of 9 with MCPBA afforded 3-deazasulfinosine (10).As gauged by increases in the mean postinoculation life spans of L1210 inoculated mice, none of these nucleosides exhibited biologically significant activity (T/C 125).Even so, antileukemic activity appeared to be influenced, albeit not uniformly, by structural modifications in the base and carbohydrate moieties of sulfenosine and sulfinosine.Thus, while several of the compounds were lacking in cytotoxic activity, eight others (4c, 5a, 5c, 6a, 6b, 7b, 9, and 10) were estimated to have reduced body burdens of viable L1210 cells by 16-77percent.