70303-37-6

Basic information

• Product Name: 1-(4-carbethoxyphenyl)-3-hydroxymethyl-3-methyltriazene
• Synonyms: 1-(4-carbethoxyphenyl)-3-hydroxymethyl-3-methyltriazene
• CAS NO: 70303-37-6
• Molecular Formula: C₁₁H₁₅N₃O₃
• Molecular Weight: 237.26
• Mol File: 70303-37-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 73-75 °C
• Boiling Point: 362.1°C at 760 mmHg
• Flash Point: 172.8°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 7.07E-06mmHg at 25°C
• Refractive Index: 1.545
• PKA: 13.20±0.10(Predicted)
• CAS DataBase Reference: 1-(4-carbethoxyphenyl)-3-hydroxymethyl-3-methyltriazene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-carbethoxyphenyl)-3-hydroxymethyl-3-methyltriazene(70303-37-6)
• EPA Substance Registry System: 1-(4-carbethoxyphenyl)-3-hydroxymethyl-3-methyltriazene(70303-37-6)

Safety Data

• Hazardous Substances Data: 70303-37-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15N3O3/c1-3-17-11(16)9-4-6-10(7-5-9)12-13-14(2)8-15/h4-7,15H,3,8H2,1-2H3/b13-12+

Upstream product

• 114642-73-8 C₁₉H₂₁N₃O₅ 
• 50-00-0 formaldehyd 
• 94-09-7 p-aminoethylbenzoate 
• 74-89-5 methylamine 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 114642-76-1 C₁₈H₁₈N₄O₆ 
• 114642-75-0 C₁₈H₁₈ClN₃O₄ 
• 114642-74-9 C₁₉H₂₁N₃O₄ 
• 90476-13-4 C₁₈H₁₉N₃O₄ 

Downstream Products

• 54283-75-9 1-(4-ethoxycarbonylphenyl)-3-methyltriazene 
• 90476-13-4 1-p-ethoxycarbonylphenyl-3-methyl-3-benzoyloxymethyltriazene 
• 67-56-1 methanol 
• 94-09-7 p-aminoethylbenzoate 

Relevant articles and documents

Targeting gliomas with triazene-based hybrids: Structure-activity relationship, mechanistic study and stability

Herein we report novel hybrid compounds based on valproic acid and DNA-alkylating triazene moieties, 1, with therapeutic potential for glioblastoma multiforme chemotherapy. We identified hybrid compounds 1d and 1e to be remarkably more potent against glioma and more efficient in decreasing invasive cell properties than temozolomide and endowed with chemical and plasma stability. In contrast to temozolomide, which undergoes hydrolysis to release an alkylating metabolite, the valproate hybrids showed a low potential to alkylate DNA. Key physicochemical properties align for optimal CNS penetration, highlighting the potential of these effective triazene based-hybrids for enhanced anticancer chemotherapy.

Triazene Drug Metabolites. Part 4. Kinetics and Mechanism of the Decomposition of 1-Aryl-3-benzoyloxymethyl-3-methyltriazenes in Mixed Aqueous-Organic Solvents

Kinetic studies for the hydrolysis of 1-aryl-3-benzoyloxymethyl-3-methyltriazenes to 1-aryl-3-hydroxymethyl-3-methyltriazenes in mixed aqueous-organic media are reported.Reactions are first-order in the benzoyloxymethyltriazene, and are independent of pH above pH 8.Below pH 8, specific acid catalysis is observed.No nucleophilic catalysis is detected at any pH.The observed first-order rate constants, kobs, vary with the substituent in both the 1-aryl and benzoyl rings.Hammett ? values of 1.28 and 1.41 are obtained for substituents in the benzoyl group in 50percent MeCN-H2O and 60percent dioxane-H2O respectively.A Hammett ρ value of -1.84 is obtained in 50percent MeCN-H2O for substituents in the 1-aryl ring.Observed first-order rate constants also vary with the composition of aqueous dioxane mixtures and a linear correlation between log kobs and the Grunwald-Winstein Y parameter is found to give a slope of 0.99.The solvent deuterium isotope effect, kH2O/kD2O, is 1.26 for the 4-methoxybenzoyl derivative.Values of the activation parameters are ΔH(excit.) ca. 80 kJ mol-1 and ΔS(excit.) ca. -5 J K-1 mol-1.The data are best interpreted in terms of a unimolecular ionisation of the benzoyloxymethyltriazene to form a iminium cation and a benzoate anion.Hydroxymethyltriazene formation results from the capture of the intermediate iminium ion by water.Consistent with this mechanism, a common ion effect of the benzoate anion is observed, and the benzoate ion is ca. 75 times more effective than water at trapping the iminium ion.

Studies of the mode of action of antitumor triazenes and triazines. 6. 1-Aryl-3-(hydroxymethyl)-3-methyltriazenes: Synthesis, chemistry, and antitumor properties

1-Aryl-3-(hydroxymethyl)-3-alkyltriazenes [ArN=NN(CH3)CH2OH] have been synthesized by diazonium coupling to the carbinolamine (RNHCH2OH), generated in situ from the alkylamine and formaldehyde mixtures. The (hydroxymethyl)triazene structure has been confirmed by IR, NMR, and mass spectral analysis and also by the preparation of a crystalline benzoate derivative. The mass spectra of the (hydroxymethyl)triazenes suggest that they fragment by loss of formaldehyde to give the methyltriazene, which is also the product of hydrolysis in solution. The degradation of the (hydroxymethyl)triazenes in solution has been followed by UV spectroscopy and by HPLC analysis, and the half-lives were determined under a variety of conditions. The half-lives of the corresponding methyl- and (hydroxymethyl)triazenes are very similar. Both methyl- and (hydroxymethyl)triazenes decompose on silica plates during TLC analysis to give products consistent with known diazo-migration reactions. The (hydroxymethyl)triazenes have pronounced antitumor activity against the TLX5 tumor in vivo; in vivo-in vitro bioassay experiments suggest that the (hydroxymethyl)triazenes exert their in vivo antitumor activity via the degradation product, the alkyltriazene.