3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

Base Information

• Chemical Name: 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
• CAS No.: 27314-97-2
• Molecular Formula: C7H6N4O2
• Molecular Weight: 178.15
• Mol file: 27314-97-2.mol

Synonyms:1,2,4-Benzotriazine,3-amino-, 1,4-dioxide (6CI,8CI);3-Amino-1,2,4-benzotriazine 1,4-dioxide;SR259075;SR 4233;Tirazone;Win 59075;

Chemical Property of 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

Chemical Property:

• Appearance/Colour: Orange needles
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 220 °C dec.
• Refractive Index: 1.777
• Boiling Point: 493.6 °C at 760 mmHg
• PKA: 1.51±0.30(Predicted)
• Flash Point: 252.3 °C
• PSA: 89.83000
• Density: 1.68 g/cm³
• LogP: 1.25520
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Amino-1,2,4-benzotriazine 1,4-dioxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 3-Amino-1,2,4-benzotriazine-1,4-dioxide (also known as tirapazamine or SR 4233) is a hypoxia-selective cytotoxin structurally related to tricyclic [1,2,4]triazine 1,4-dioxides (TTOs). It exhibits preferential cytotoxicity under hypoxic conditions, making it a promising candidate for targeting oxygen-deficient tumors that are resistant to conventional therapies. 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE’s efficacy is linked to its ability to undergo selective metabolic activation in low-oxygen environments, generating reactive intermediates that damage tumor cells. Structural optimization studies suggest that derivatives with fused cycloalkyl rings and specific 3-aminoalkyl or 3-alkyl substituents enhance hypoxic metabolism and tissue diffusion, improving their potential as clinical agents for hypoxic tumor treatment.

Technology Process of 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

There total 14 articles about 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

→ 3-amino-1,2,4-benzotriazine-1,4-dioxide (27314-97-2)

Guidance literature:

Reference yield: 82.0%

3-amino-1,2,4-benzotriazine 1-oxide (5424-06-6) → 3-amino-1,2,4-benzotriazine-1,4-dioxide (27314-97-2)

Guidance literature:

With dihydrogen peroxide; In acetic acid; at 60 - 70 ℃; for 10h;

DOI:10.1055/s-1997-1283

Reference yield: 73.0%

3-CH3CONH-1,2,4-benzotriazine-1-oxide (20028-79-9) → 3-amino-1,2,4-benzotriazine-1,4-dioxide (27314-97-2)

Guidance literature:

With acetonitrile complex of hypofluorous acid; In dichloromethane; at 0 ℃;

DOI:10.1016/j.tet.2012.08.017

upstream raw materials:

SR 4330

3-amino-1,2,4-benzotriazine 1-oxide

3-CH₃CONH-1,2,4-benzotriazine-1-oxide

2-nitro-aniline

Downstream raw materials:

3-amino-1,2,4-benzotriazine 1-oxide

2H-<1,2,4>oxadiazolo<3,2-c><1,2,4>benzotriazin-2-one-5-oxide

SR 4330

3-amino-1,2,4-benzotriazine 4-oxide

Refernces

Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins

10.1021/jm800967h

The research presents the design and synthesis of novel tricyclic [1,2,4]triazine 1,4-dioxides (TTOs), which are hypoxia-selective cytotoxins related to tirapazamine. The purpose of this study was to develop TTO analogues that display hypoxia-selective cytotoxicity in vitro, with the aim of improving the treatment of hypoxic tumors, which are associated with resistance to therapy and aggressive tumor behavior. The researchers synthesized a series of TTOs with various structural arrangements, including cycloalkyl, oxygen-, and nitrogen-containing saturated rings fused to the triazine core, along with different side chains linked to either hemisphere. They optimized the rates of hypoxic metabolism and tissue diffusion coefficients, and used pharmacokinetic/pharmacodynamic model predictions to identify 12 TTO analogues predicted to be active in vivo, contingent upon achieving adequate plasma pharmacokinetics. The chemicals used in the process included a range of amines, cyanamide, peracetic acid, trifluoroacetic acid, and various nitroanilines and their derivatives, among others, to construct the diverse TTO analogues. The study concluded that the fused cycloalkyl rings, in combination with 3-aminoalkyl or 3-alkyl substituents linked to weakly basic soluble amines, resulted in TTOs with optimal hypoxic metabolism and diffusion coefficients, highlighting the potential of these compounds as clinical agents that selectively target hypoxia in tumors.