1340543-34-1

Basic information

• Product Name: (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate
• Synonyms: (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate
• CAS NO: 1340543-34-1
• Molecular Weight: 534.528
• Mol File: 1340543-34-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate(CAS DataBase Reference)
• NIST Chemistry Reference: (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate(1340543-34-1)
• EPA Substance Registry System: (6-(benzyloxy)-2-((((4-nitrobenzyl)oxy)carbonyl)amino)-9H-purin-9-yl)methyl pivalate(1340543-34-1)

Safety Data

• Hazardous Substances Data: 1340543-34-1(Hazardous Substances Data)

Upstream product

• 619-73-8 4-nitrobenzyl chloride 
• 152833-02-8 (2-amino-6-(benzyloxy)-9H-purin-9-yl)methyl pivalate 

Downstream Products

• 1340543-31-8 4-nitrobenzyl (6-(benzyloxy)-9H-purin-2-yl)carbamate 
• 19916-73-5 2-Amino-6-benzyloxypurine 

Relevant articles and documents

4-nitrobenzyloxycarbonyl derivatives of O 6-benzylguanine as hypoxia-activated prodrug inhibitors of O 6-alkylguanine-DNA alkyltransferase (AGT), which produces resistance to agents targeting the o -6 position of DNA guanine

A series of 4-nitrobenzyloxycarbonyl prodrug derivatives of O 6-benzylguanine (O6-BG), conceived as prodrugs of O 6-BG, an inhibitor of the resistance protein O6- alkylguanine-DNA alkyltransferase (AGT), were synthesized and evaluated for their ability to undergo bioreductive activation by reductase enzymes under oxygen deficiency. Three agents of this class, 4-nitrobenzyl (6-(benzyloxy)-9H-purin-2-yl)carbamate (1) and its monomethyl (2) and gem-dimethyl analogues (3), were tested for activation by reductase enzyme systems under oxygen deficient conditions. Compound 3, the most water-soluble of these agents, gave the highest yield of O6-BG following reduction of the nitro group trigger. Compound 3 was also evaluated for its ability to sensitize 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(methylamino)carbonyl] hydrazine (laromustine)-resistant DU145 human prostate carcinoma cells, which express high levels of AGT, to the cytotoxic effects of this agent under normoxic and oxygen deficient conditions. While 3 had little or no effect on laromustine cytotoxicity under aerobic conditions, significant enhancement occurred under oxygen deficiency, providing evidence for the preferential release of the AGT inhibitor O6-BG under hypoxia.