27238-35-3

Basic information

• Product Name: 1,2,4-BENZOTRIAZIN-3-AMINE, 7-METHOXY-, 1-OXIDE
• Synonyms: 1,2,4-BENZOTRIAZIN-3-AMINE, 7-METHOXY-, 1-OXIDE;7-Methoxybenzo[1,2,4]triazin-3-ylaMine-1-oxide;7-methoxy-1,2,4-Benzotriazin-3-amine 1-oxide;7-methoxy-1-oxido-1,2,4-benzotriazin-1-ium-3-amine
• CAS NO: 27238-35-3
• Molecular Formula: C₈H₈N₄O₂
• Molecular Weight: 192.17
• Mol File: 27238-35-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 458.6°C at 760 mmHg
• Flash Point: 231.2°C
• Appearance: /
• Density: 1.54g/cm³
• Vapor Pressure: 1.35E-08mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: 1,2,4-BENZOTRIAZIN-3-AMINE, 7-METHOXY-, 1-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-BENZOTRIAZIN-3-AMINE, 7-METHOXY-, 1-OXIDE(27238-35-3)
• EPA Substance Registry System: 1,2,4-BENZOTRIAZIN-3-AMINE, 7-METHOXY-, 1-OXIDE(27238-35-3)

Safety Data

• Hazardous Substances Data: 27238-35-3(Hazardous Substances Data)

Usage

General Description

1,2,4-Benzotriazin-3-amine, 7-methoxy-, 1-oxide is a chemical compound that is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. It is a derivative of benzotriazole, a heterocyclic compound containing a triazole ring. This chemical is known for its ability to act as a reactive intermediate in organic synthesis, and it possesses potential applications in the development of new drugs and pesticides. Its unique structure and reactivity make it a valuable building block for the production of diverse chemical compounds, and it has been the subject of research in medicinal chemistry and agrochemical development.

InChI:InChI=1/C8H8N4O2/c1-14-5-2-3-6-7(4-5)12(13)11-8(9)10-6/h2-4H,1H3,(H2,9,10,11)

Upstream product

• 420-04-2 CYANAMID 
• 96-96-8 4-methoxy-2-nitroaniline 
• 27314-99-4 7-methoxy-1,4-dioxy-benzo[e][1,2,4]triazin-3-ylamine 
• 104-94-9 4-methoxy-aniline 
• 51-66-1 4-methoxyacetanilide 
• 119-81-3 4-methoxy-2-nitroacetanilide 
• 119707-93-6 2-nitro-4-methoxyphenylguanidine 

Downstream Products

• 1096161-90-8 3-((1-phenylethoxy)methylamino)-7-methoxy-1,2,4-benzotriazine 1,4-dioxide 
• 1096161-86-2 3-(benzyloxymethylamino)-7-methoxy-1,2,4-benzotriazine 1,4-dioxide 
• 1096162-04-7 3-(benzyloxymethylamino)-7-methoxy-1,2,4-benzotriazine 1-oxide 
• 1096162-08-1 3-((1-phenylethoxy)methylamino)-7-methoxy-1,2,4-benzotriazine 1-oxide 
• 27238-40-0 7-methoxy-benzo[e][1,2,4]triazin-3-ylamine 

Relevant articles and documents

Exploiting the Inherent Photophysical Properties of the Major Tirapazamine Metabolite in the Development of Profluorescent Substrates for Enzymes That Catalyze the Bioreductive Activation of Hypoxia-Selective Anticancer Prodrugs

Hypoxia-selective cytotoxins (HSCs) seek to exploit the oxygen-poor nature of tumor tissue for therapeutic gain. Typically, HSCs require activation by one-electron bioreductive enzymes such as NADPH:cytochrome P450 reductase (CYPOR). Thus, successful clinical deployment of HSCs may be facilitated by the development and implementation of diagnostic probes that detect the presence of relevant bioreductive enzymes in tumor tissue. The work described here develops analogues of the well-studied HSC tirapazamine (3-amino-1,2,4-benzotriazine 1,4-di-N-oxide, TPZ) as profluorescent substrates of the one-electron reductases involved in bioactivation of HSCs. Hypoxic metabolism of TPZ or 7-fluoro-TPZ by one-electron reductases releases inherently fluorescent mono-N-oxide metabolites that may serve as indicators, probes, markers, or stains for the detection of the enzymes involved in the bioactivation of HSCs. In particular, profluorescent compounds of this type can provide a foundation for fluorescence-based bioassays that help identify tumors responsive to HSCs.

Synthesis, hypoxia-selective cytotoxicity of new 3-amino-1,2,4- benzotriazine-1,4-dioxide derivatives

We reported the synthesis, hypoxic cytotoxic activities and selectivities of 18 new 3-(alkoxymethylamino)-1,2,4-benzotriazine 1,4-dioxides. The synthesized compounds were screened in vitro against 5 cell lines: K562, SMMC-7721, A549, PC-3 and KB in hypoxia and in normoxia. Some of them showed higher or similar cytotoxic activity when compared to tirapazamine. Physico-chemical study showed the positive correlation between hypoxic activity and lipophilicity within a certain range. Preliminary mechanism study on the potent derivatives 4b, 4l and 4m indicated that the cytotoxic activities of these compounds might be mediated by inducing apoptosis.

Benzoazine mono-N-oxides and benzoazine 1,4 dioxides and compositions therefrom for the therapeutic use in cancer treatments

The present invention relates to a synergetistic composition comprising one or more benzoazine-mono-N-oxides, and one or more benzoazine 1,4 dioxides for use in cancer therapy. The invention also provides a range of novel 1,2,4 benzoazine-mono-N-oxides and related analogues. These can be used as potentiators of the cytotoxicity of existing anticancer drugs and therapies for cancer treatment.