59708-26-8

Basic information

• Product Name: 4-[(2E)-3-methyltriaz-2-en-1-yl]benzamide
• CAS NO: 59708-26-8
• Molecular Formula: C₈H₁₀N₄O
• Molecular Weight: 178.1912
• Mol File: 59708-26-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 329.8°C at 760 mmHg
• Flash Point: 153.2°C
• Density: 1.27g/cm³
• Vapor Pressure: 0.000174mmHg at 25°C
• Refractive Index: 1.61
• CAS DataBase Reference: 4-[(2E)-3-methyltriaz-2-en-1-yl]benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(2E)-3-methyltriaz-2-en-1-yl]benzamide(59708-26-8)
• EPA Substance Registry System: 4-[(2E)-3-methyltriaz-2-en-1-yl]benzamide(59708-26-8)

Safety Data

• Hazardous Substances Data: 59708-26-8(Hazardous Substances Data)

Upstream product

• 2835-68-9 4-aminobenzamide 
• 70346-61-1 C₉H₁₂N₄O₂ 
• 1407791-39-2 C₁₄H₁₇N₅O₆ 

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.

Synthesis and evaluation of N-acylamino acids derivatives of triazenes. Activation by tyrosinase in human melanoma cell lines

In this research work we report the synthesis of a new series of triazene prodrugs designed for Melanocyte-Directed Enzyme Prodrug Therapy (MDEPT). These compounds are derived from the N-acyltyrosine amino acid - a good enzyme substrate for the tyrosinase enzyme, which is significantly overexpressed in melanoma cells. We analysed their chemical stability and plasma enzymatic hydrolysis, and we also evaluated the release of the antitumoral drug in the presence of the tyrosinase. Subsequently, we performed the evaluation of the prodrug cytotoxicity in melanoma cell lines with different levels of tyrosinase activity. Prodrug 5c showed the highest cytotoxicity against melanoma cell lines, and this effect correlated well with the tyrosinase activity suggesting that prodrug cytotoxicity is tyrosinase-dependent.