85623-02-5

Basic information

• Product Name: 3-Benzyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
• Synonyms: 3-Benzyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
• CAS NO: 85623-02-5
• Molecular Weight: 270.25
• Mol File: 85623-02-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-Benzyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Benzyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide(85623-02-5)
• EPA Substance Registry System: 3-Benzyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide(85623-02-5)

Safety Data

• Hazardous Substances Data: 85623-02-5(Hazardous Substances Data)

Upstream product

• 3173-56-6 benzyl isothiocyanate 
• 100-51-6 benzyl alcohol 
• 188612-59-1 5-Amino-1-(N-benzylcarbamoyl)imidazole-4-carboxamide 
• 7008-85-7 5-diazoimidazole-4-carboxamide 

Downstream Products

• 360-97-4 5-Aminoimidazole-4-carboxamide 

Relevant articles and documents

Synthesis and growth-inhibitory activities of imidazo?5,1-d]-1,2,3,5-tetrazine-8-carboxamides related to the anti-tumour drug temozolomide, with appended silicon, benzyl and heteromethyl groups at the 3-position

A series of 3-(benzyl-substituted)-imidazo?5,1-d]-1,2,3,5-tetrazines (13) and related derivatives with 3-heteromethyl groups has been synthesised and screened for growth-inhibitory activity in vitro against two pairs of glioma cell lines with temozolomide-sensitive and -resistant phenotypes dependent on the absence/presence of the DNA repair protein O6-methylguanine-DNA methyltransferase (MGMT). In general the compounds had low inhibitory activity with GI50 values >50 μM against both sets of cell lines. Two silicon-containing derivatives, the TMS-methylimidazotetrazine (9) and the SEM-analogue (10), showed interesting differences: compound (9) had a profile very similar to that of temozolomide with the MGMT+ cell lines being 5 to 10-fold more resistant than MGMT- isogenic partners; the SEM-substituted compound (10) showed potency across all cell lines irrespective of their MGMT status.

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

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.

Synthetic studies of 8-carbamoylimidazo-[5,1-D]-1,2,3,5-tetrazin-4(3H)-one: A key derivative of antitumor drug temozolomide

5-Diazoimidazole-4-carboxamide 4 reacted with trimethylsilyl isocyanate in acetonitrile to afford 8-carbamoylimidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one 1, which was undergoing a methylation to give antitumour drug temozolomide 2; while 1,5-dicarbamoyl aminoimidazole 6 failed in an azo-cyclization to give 1 but accomplished a carbon-cyclization to produce 8-carbamoylimidazo[1,5-a] s-triazin-4(3H)-one 7.