Home Other Building Blocks 1,2,4-benzotriazin-3-amine

1,2,4-benzotriazin-3-amine

CAS No.:
20028-80-2
Catalog Number:
AG002CN7
Molecular Formula:
C7H6N4
Molecular Weight:
146.1493
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Product Description
Catalog Number:
AG002CN7
Chemical Name:
1,2,4-benzotriazin-3-amine
CAS Number:
20028-80-2
Molecular Formula:
C7H6N4
Molecular Weight:
146.1493
MDL Number:
MFCD00054599
IUPAC Name:
1,2,4-benzotriazin-3-amine
InChI:
InChI=1S/C7H6N4/c8-7-9-5-3-1-2-4-6(5)10-11-7/h1-4H,(H2,8,9,11)
InChI Key:
BHHRGAKNBXQGIO-UHFFFAOYSA-N
SMILES:
Nc1nnc2c(n1)cccc2
EC Number:
243-470-4
NSC Number:
286693
Properties
Complexity:
138  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
146.059g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
146.153g/mol
Monoisotopic Mass:
146.059g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
64.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.3  
Literature
Title Journal
Novel Phenazine 5,10-Dioxides Release OH in Simulated Hypoxia and Induce Reduction of Tumour Volume In Vivo. ISRN pharmacology 20110101
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. Bioorganic & medicinal chemistry letters 20101101
Characterization of radicals formed following enzymatic reduction of 3-substituted analogues of the hypoxia-selective cytotoxin 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine). Journal of the American Chemical Society 20100303
Cell death by the quinoxaline dioxide DCQ in human colon cancer cells is enhanced under hypoxia and is independent of p53 and p21. Radiation oncology (London, England) 20100101
Initiation of DNA strand cleavage by 1,2,4-benzotriazine 1,4-dioxide antitumor agents: mechanistic insight from studies of 3-methyl-1,2,4-benzotriazine 1,4-dioxide. Journal of the American Chemical Society 20090128
DNA strand damage product analysis provides evidence that the tumor cell-specific cytotoxin tirapazamine produces hydroxyl radical and acts as a surrogate for O(2). Journal of the American Chemical Society 20071024
Complete 1H, 13C and 15N NMR assignment of tirapazamine and related 1,2,4-benzotriazine N-oxides. Magnetic resonance in chemistry : MRC 20061001
Potentiation of the cytotoxicity of the anticancer agent tirapazamine by benzotriazine N-oxides: the role of redox equilibria. Journal of the American Chemical Society 20060111
Radical properties governing the hypoxia-selective cytotoxicity of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides. Organic & biomolecular chemistry 20050607
Oxidation of 2-deoxyribose by benzotriazinyl radicals of antitumor 3-amino-1,2,4-benzotriazine 1,4-dioxides. Journal of the American Chemical Society 20040630
DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine). Journal of the American Chemical Society 20030924
A mass spectrometry study of tirapazamine and its metabolites. insights into the mechanism of metabolic transformations and the characterization of reaction intermediates. Journal of the American Society for Mass Spectrometry 20030801
Photochemical and photobiological studies of tirapazamine (SR 4233) and related quinoxaline 1,4-Di-N-oxide analogues. Chemical research in toxicology 20030201
Activation of 3-amino-1,2,4-benzotriazine 1,4-dioxide antitumor agents to oxidizing species following their one-electron reduction. Journal of the American Chemical Society 20030122
Structure-activity relationships of 1,2,4-benzotriazine 1,4-dioxides as hypoxia-selective analogues of tirapazamine. Journal of medicinal chemistry 20030102
Oxidative DNA base damage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine). Bioorganic & medicinal chemistry letters 20020902
Redox-activated, hypoxia-selective DNA cleavage by quinoxaline 1,4-di-N-oxide. Bioorganic & medicinal chemistry 20010901
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). The Journal of organic chemistry 20010112
Properties