20028-80-2

Basic information

• Product Name: 1,2,4-benzotriazin-3-amine
• Synonyms: 1,2,4-benzotriazin-3-amine;3-amino-1,2,4-benzotriazine;Benzo[1,2,4]triazin-3-ylamine;SR-4330;Win-60109
• CAS NO: 20028-80-2
• Molecular Formula: C₇H₆N₄
• Molecular Weight: 146.14934
• EINECS: 243-470-4
• Product Categories: pharmacetical;Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 20028-80-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 205-208 °C
• Boiling Point: 373.6°Cat760mmHg
• Flash Point: 207.6°C
• Appearance: /
• Density: 1.385g/cm³
• Vapor Pressure: 8.86E-06mmHg at 25°C
• Refractive Index: 1.741
• PKA: 2.00±0.40(Predicted)
• CAS DataBase Reference: 1,2,4-benzotriazin-3-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-benzotriazin-3-amine(20028-80-2)
• EPA Substance Registry System: 1,2,4-benzotriazin-3-amine(20028-80-2)

Safety Data

• Hazardous Substances Data: 20028-80-2(Hazardous Substances Data)

Usage

Description

1,2,4-Benzotriazin-3-amine is an organic compound with the molecular formula C7H7N5. It is a heterocyclic amine that features a benzene ring fused to two triazine rings, with an amine group attached to the third nitrogen atom. 1,2,4-Benzotriazin-3-amine has potential applications in the pharmaceutical industry due to its unique chemical structure and properties.

Uses

Used in Pharmaceutical Industry:
1,2,4-Benzotriazin-3-amine is used as a potential intermediate in the synthesis of aminoindazole PDK1 inhibitors for the treatment of cancer. It has been identified through fragment-based drug discovery methods, which involve screening small molecular fragments to identify potential drug candidates.
In the pharmaceutical industry, 1,2,4-Benzotriazin-3-amine serves as a key building block for the development of novel therapeutic agents targeting the PDK1 enzyme. PDK1 (Phosphoinositide-dependent protein kinase-1) is an important enzyme involved in various cellular processes, including cell survival, growth, and metabolism. Inhibition of PDK1 has been shown to have potential anti-cancer effects, making it an attractive target for drug development.
By incorporating 1,2,4-Benzotriazin-3-amine into the molecular structure of aminoindazole PDK1 inhibitors, researchers can potentially enhance the potency, selectivity, and pharmacokinetic properties of these compounds. This, in turn, may lead to the development of more effective cancer treatments with fewer side effects.

Synthesis Reference(s)

The Journal of Organic Chemistry, 42, p. 542, 1977 DOI: 10.1021/jo00423a032

InChI:InChI=1/C7H6N4/c8-7-9-5-3-1-2-4-6(5)10-11-7/h1-4H,(H2,8,9,11)

Upstream product

• 99072-85-2 benzo[e][1,2,4]triazin-3-yl-carbamic acid ethyl ester 
• 856070-90-1 1-(2-nitro-phenyl)-thiosemicarbazide 
• 91669-21-5 3-chlorobenzo[e][1,2,4]triazine 
• 5424-06-6 3-amino-1,2,4-benzotriazine 1-oxide 
• 29540-87-2 1,2-diaminobenzimidazole 
• 27314-97-2 3-amino-1,2,4-benzotriazine-1,4-dioxide 
• 88-74-4 2-nitro-aniline 
• 98555-24-9 benzo[e][1,2,4]triazine-3-carboxylic acid hydrazide 
• 99185-60-1 ethyl benzo[e][1,2,4]triazine-3-carboxylate 
• 98556-75-3 benzo[e][1,2,4]triazine-3-carbonyl azide 
• 99056-01-6 1,4-dihydro-benzo[e][1,2,4]triazine-3-carboxylic acid ethyl ester 
• 114098-35-0 amino-(2-nitro-phenylhydrazono)-acetic acid ethyl ester 
• 110181-37-8 bromo-(2-nitro-phenylhydrazono)-acetic acid ethyl ester 
• 119-66-4 2-nitrobenzenediazonium chloride 

Downstream Products

• 110422-84-9 2,3-diphenyl-benz[e]imidazo[1,2-b][1,2,4]triazine 
• 27314-97-2 3-amino-1,2,4-benzotriazine-1,4-dioxide 
• 5424-06-6 3-amino-1,2,4-benzotriazine 1-oxide 
• 27238-43-3 3-amino-1,2,4-benzotriazine 2-oxide 
• 251322-95-9 3-amino-1,2,4-benzotriazine 4-oxide 
• 254-87-5 1,2,4-benzotriazene 
• 67692-91-5 3-chloro-1,2,4-benzotriazine 1-oxide 
• 916890-53-4 1-benzo[1,2,4]triazin-3-yl-3-[5-chloro-2-(3-dimethylaminopropoxy)phenyl]urea 
• 91669-21-5 3-chlorobenzo[e][1,2,4]triazine 
• 127845-06-1 3-phenylaminobenzo[e][1,2,4]triazine 
• 77475-32-2 ethyl 2-(benzo[e][1,2,4]triazin-3-yl)acetate 

Relevant articles and documents

3-amino-1,2,4-benzotriazine 4-oxide: Characterization of a new metabolite arising from bioreductive processing of the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine)

Tirapazamine (1) is a promising antitumor agent that selectively causes DNA damage in hypoxic tumor cells, following one-electron bioreductive activation. Surprisingly, after more than 10 years of study, the products arising from bioreductive metabolism of tirapazamine have not been completely characterized. The two previously characterized metabolites are 3-amino-1,2,4-benzotriazine 1-oxide (3) and 3-amino-1,2,4-benzotriazine (5). In this work, 3-amino-1,2,4-benzotriazine 4-oxide (4) is identified for the first time as a product resulting from one-electron activation of the antitumor agent tirapazamine by the enzymes xanthine/xanthine oxidase and NADPH:cytochrome P450 oxidoreductase. As part of this work, the novel N-oxide (4) was unambiguously synthesized and characterized using NMR spectroscopy, UV-vis spectroscopy, LC/MS, and X-ray crystallography. Under conditions where the parent drug tirapazamine is enzymatically activated, the metabolite 4 is produced but readily undergoes further reduction to the benzotriazine (5). Thus, under circumstances where extensive reductive metabolism occurs, the yield of the 4-oxide (4) decreases. In contrast, the isomeric two-electron reduction product 3-amino-1,2,4-benzotriazine 1-oxide (3) does not readily undergo enzymatic reduction and, therefore, is found as a major bioreductive metabolite under all conditions. Finally, the ability of the 4-oxide metabolite (4) to participate in tirapazamine-mediated DNA damage is considered.

ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME

The present invention relates to a novel organic compound and an organic electroluminescent device using the same. An organic electroluminescent device is provided to improve luminous efficiency, driving voltage and lifetime by including an organic compound having excellent luminous efficiency, electron transporting capability, electrochemical stability, and thermal stability.

Reaction of N-Nitro-benzotriazole with nucleophiles

N-Nitro-benzotriazole 1 reacts with various C-nucleophiles 2 in tetrahydrofuran at room temperature to afford o-nitramidophenylazo-compounds 3a-f and o-nitramidophenyl hydrazones 3g-l, respectively. Reaction of 1 with sodium azide in aqueous acetonitrile gives a reactive 2-azidophenylnitramide intermediate 4 which is trapped by Cu-catalyzed 1,3-dipolar cycloadition with phenyl acetylene to afford 1-o-nitramidophenyl-4-phenyl-1,2,3-triazole 5. Reaction of 1 with trimethylsilylcyanide affords 3-amino-benzo[e][1,2,4]triazine 6. Copyright Taylor & Francis Group, LLC.