40643-39-8

Usage

InChI:InChI=1/C7H8N4O2/c1-8-10-9-6-2-4-7(5-3-6)11(12)13/h2-5H,1H3,(H,8,9)

Upstream product

• 64-17-5 ethanol 
• 122779-51-5 C₉H₇F₃N₄O₃ 
• 76935-79-0 1-(4-nitrophenyl)-3-formyl-3-methyltriazene 
• 100-01-6 4-nitro-aniline 
• 74-89-5 methylamine 

Downstream Products

• 122779-51-5 C₉H₇F₃N₄O₃ 
• 540-67-0 ethyl methyl ether 
• 100-01-6 4-nitro-aniline 

Relevant academic research and scientific papers

Expedient synthesis and anticancer evaluation of dual-action 9-anilinoacridine methyl triazene chimeras

The efficient synthesis of molecular hybrids including a DNA-intercalating 9-anilinoacridine (9-AnA) core and a methyl triazene DNA-methylating moiety is described. Nucleophilic aromatic substitution (SNAr) and electrophilic aromatic substitution (EAS) reactions using readily accessible starting materials provide a quick entry to novel bifunctional anticancer molecules. The chimeras were evaluated for their anticancer activity. Chimera 7b presented the highest antitumor activity at low micromolar IC50 values in antiproliferative assays performed with various cancer cell lines. In comparison, compound 7b outperformed DNA-intercalating drugs like amsacrine and AHMA. Mechanistic studies of chimera 7b suggest a dual mechanism of action: methylation of the DNA-repairing protein MGMT associated with the triazene structural portion and Topo II inhibition by intercalation of the acridine core.

Triazene Drug Metabolites. Part 9. Base Catalysed Deacylation of 3-Acyl-3-alkyl-1-aryltriazenes in Ethanol.

3-Acyl-3-alkyl-1-aryltriazenes undergo a base-catalysed deacylation reaction to liberate the corresponding cytotoxic 3-alkyl-1-aryltriazene.Reaction are first-order in both and .Second-order rate constants, k2, depend on the structure of both the substrate and the base.The values of k2 for the deformylation of 1-aryl-3-formyl-3-methyltriazenes by piperidine follow the Hammett relationship giving ρ +2.9; a similar correlation, ρ +1.6, is observed for the morpholine catalysed deacylation of 1-aryl-3-methyl-3-trifluoroacetyltriazenes.For 1-(4-cyanophenyl)-3-methyl-3-trifluoroacetyltriazene, a correlation between the aqueous pKa of the base and k2 is obtained, giving a Broensted β value of 0.36.The solvent deuterium isotope effect, k2EtOH/k2EtOD, for the piperidine-catalysed deacylation of 1-(3-pyridyl)-3-formyl-3-methyltriazene is 2.2, and 2,2,6,6-tetramethylpiperidine is some 2.4 times more effective than piperidine at catalysing the deformylation of this compound.Rate constants for the deacylation of 3-alkyltriazenes diminish in the order Me > Pr > Et.Rate constants also vary with the nature of the acyl group: thus CF3CO > HCO > MeCO > C8H17CO.The data are interpreted in terms of a mechanism that involves a rate-determining, general-base-catalysed attack of a solvent ethanol molecule at the carbonyl carbon atom of the group, followed by rapid collapse of the tetrahedral intermediate to form the monoalkyltriazene.