123002-39-1

Usage

InChI:InChI=1/C10H14N6O6S/c11-10-14-7-4(8(15-10)23(12,20)21)13-2-16(7)9-6(19)5(18)3(1-17)22-9/h2-3,5-6,9,17-19H,1H2,(H2,11,14,15)(H2,12,20,21)/t3-,5-,6-,9-/m1/s1

Upstream product

• 85-31-4 6-thioguanosine 
• 123002-38-0 2-amino-9-β-D-ribofuranosylpurine-6-sulfenamide 

Relevant academic research and scientific papers

6-sulfenamide, 6-sulfinamide and 6-sulfonamide purines, purine nucleosides, purine nucleotides, pharmaceutical compositions, and processes of making

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.

Synthesis and in vivo antitumor activity of 2-amino-9H-purine-6-sulfenamide, -sulfinamide, and -sulfonamide and related purine ribonucleosides

A number of 6-sulfenamide, 6-sulfinamide, and 6-sulfonamide derivatives of 2-aminopurine and certain related purine ribonucleosides have been synthesized and evaluated for antileukemic activity in mice. Amination of 6-mercaptopurine ribonucleiside (7a) and 6-thioguanosine (7b) with chloramine solution gave 9-β-D-ribofuranosylpurine-6-sulfenamide (8a) and 2-amino-9-β-D-ribofuranosylpurine-6-sulfenamide-sulfenosine, 8b), respectively. Selective oxidation of 8a and 8b with 3-chloroperoxybenzoic acid (MCPBA) gave (R,S)-9-β-D-ribofuranosylpurine-6-sulfinamide (9a) and (R,S)-2-amino-9-β-D-ribofuranosylpurine-6-sulfinamide (sulfinosine, 9b), respectively. However, oxidation of 8a and 8b with excess of MCPBA gave 9-β-D-ribofuranosylpurine-6-sulfonamide (10a) and 2-amino-9-β-D-ribofuranosylpurine-6-sulfonamide (sulfonosine, 10b), respectively. Similarly, amination of 5'-deoxy-6-thioguanosine (7c) afforded the 6-sulfenamide derivative (8c), which on controlled oxidation gave (R,S)-2-amino-9-(5-deoxy-β-D-ribofuranosyl)purine-6-sulfinamide (9c) and the corresponding 6-sulfonamide derivative (10c). Treatment of 6-thioguanine (12) with aqueous chloramine solution gave 2-amino-9H-purine-6-sulfenamide (13). Oxidation of 13 with 1 molar equiv of MCPBA afforded (R,S)-2-amino-9H-purine-6-sulfinamide (14), whereas the use of 4 molar equiv of MCPBA furnished 2-amino-9H-purine-6-sulfonamide (15). The resolution of R and S diastereomers of sulfinosine (9b) was accomplished by HPLC techniques. The structures of (R)-9b and 10b were assigned by single-crystal X-ray diffraction studies. (R)-9b exists in the crystal structure in four crystallographically independent conformations. Of the 18 compounds evaluated, 13 exhibited very significant anti-L1210 activity in mice. Sulfenosine (8b) at 22 mg/kg per day x 1 showed a T/C of 170, whereas sulfinosine (9b) at 173 mg/kg per day x 1 showed a T/C of 167 against L1210 leukemia. The 5'-deoxy analogue of sulfinosine (9c) at 104 mg/kg per day also showed a T/C of 167 against L1210 leukemia. The 5'-deoxy analogue of sulfinosine (9c) at 104 mg/kg per day also showed a T/C of 172. A single treatment with 8b, 9b, and 9c reduced body burdens of viable L1210 cells by more than 99.8%.