Home Other Building Blocks 1,2,4-Benzotriazin-3-amine, 1,4-dioxide

1,2,4-Benzotriazin-3-amine, 1,4-dioxide

CAS No.:
27314-97-2
Catalog Number:
AG01CBL3
Molecular Formula:
C7H6N4O2
Molecular Weight:
178.1481
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
10mg
≥98%
1 week
United States
$125
- +
50mg
99%
1 week
United States
$157
- +
100mg
99%
1 week
United States
$240
- +
200mg
99%
1 week
United States
$390
- +
250mg
≥98%
1 week
United States
$397
- +
Product Description
Catalog Number:
AG01CBL3
Chemical Name:
1,2,4-Benzotriazin-3-amine, 1,4-dioxide
CAS Number:
27314-97-2
Molecular Formula:
C7H6N4O2
Molecular Weight:
178.1481
MDL Number:
MFCD00132954
IUPAC Name:
1,4-dioxido-1,2,4-benzotriazine-1,4-diium-3-amine
InChI:
InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
InChI Key:
ORYDPOVDJJZGHQ-UHFFFAOYSA-N
SMILES:
[O-][n+]1nc(=N)n(c2c1cccc2)O
UNII:
1UD32YR59G
Properties
Complexity:
191  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
178.049g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
178.151g/mol
Monoisotopic Mass:
178.049g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
89.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.3  
Literature
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Phase I trial of tirapazamine and cyclophosphamide in children with refractory solid tumors: a pediatric oncology group study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20040415
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The importance of DT-diaphorase and hypoxia in the cytotoxicity of RH1 in human breast and non-small cell lung cancer cell lines. Anti-cancer drugs 20040101
Efficacy of cytotoxic agents used in the treatment of testicular germ cell tumours under normoxic and hypoxic conditions in vitro. British journal of cancer 20031201
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Enhanced conversion of DNA radical damage to double strand breaks by 1,2,4-benzotriazine 1,4-dioxides linked to a DNA binder compared to tirapazamine. Chemical research in toxicology 20031101
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Professor Tom Connors and the development of novel cancer therapies by the Phase I/II Clinical Trials Committee of Cancer Research UK. British journal of cancer 20030804
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
A simple method of producing low oxygen conditions with oxyrase for cultured cells exposed to radiation and tirapazamine. American journal of clinical oncology 20030801
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Comparison of the comet assay and the oxygen microelectrode for measuring tumor oxygenation in head-and-neck cancer patients. International journal of radiation oncology, biology, physics 20030601
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Antagonism of buthionine sulfoximine cytotoxicity for human neuroblastoma cell lines by hypoxia is reversed by the bioreductive agent tirapazamine. Cancer research 20030401
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
Potential of alpha-amino alcohol p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, regarding its enantiomers. Journal of cancer research and clinical oncology 20030101
Usefulness of combined treatment with mild temperature hyperthermia and/or tirapazamine in the treatment of solid tumors: its independence of p53 status. Cancer science 20030101
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Therapeutic advantage from combining paclitaxel with the hypoxia-selective cytotoxin NLCQ-1 in murine tumor- or human xenograft-bearing mice. Cancer chemotherapy and pharmacology 20021201
Platinum drugs in the treatment of non-small-cell lung cancer. British journal of cancer 20021007
Therapeutic advantage from combining 5-fluorouracil with the hypoxia-selective cytotoxin NLCQ-1 in vivo; comparison with tirapazamine. Cancer chemotherapy and pharmacology 20021001
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Carbogen breathing after irradiation enhances the effectiveness of tirapazamine in SiHa tumors but not SCCVII tumors in mice. Radiation research 20020701
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Photochemical electron transfer reactions of tirapazamine. Photochemistry and photobiology 20020401
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The effect of functional groups on reduction and activation of quinone bioreductive agents by DT-diaphorase. Cancer chemotherapy and pharmacology 20020201
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Synergistic enhancement of the antitumor effect of taxol by the bioreductive compound NLCQ-1, in vivo: comparison with tirapazamine. Oncology research 20020101
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Metabolism of tirapazamine by multiple reductases in the nucleus. Biochemical pharmacology 20011101
Optimizing the use of combined radioimmunotherapy and hypoxic cytotoxin therapy as a function of tumor hypoxia. International journal of cancer 20011101
Evaluation of the potential of p-boronophenylalaninol as a boron carrier in boron neutron capture therapy, referring to the effect on intratumor quiescent cells. Japanese journal of cancer research : Gann 20010901
Indications for chemotherapy in stage IV non-small cell lung cancer. Lung cancer (Amsterdam, Netherlands) 20010901
Modeling the action of an antitumor drug: a density functional theory study of the mechanism of tirapazamine. Journal of the American Chemical Society 20010801
Effects of anticancer drugs on the metabolism of the anticancer drug 5,6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes. British journal of clinical pharmacology 20010801
The chemopotentiation of cisplatin by the novel bioreductive drug AQ4N. British journal of cancer 20010801
Schedule-dependent potentiation of chemotherapeutic drugs by the bioreductive compounds NLCQ-1 and tirapazamine against EMT6 tumors in mice. Cancer chemotherapy and pharmacology 20010801
Selective interaction of tirapazamine with DNA bases and DNA. A comparison of cyclic voltammetry and electrolysis techniques. Free radical research 20010801
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Phase I trial of i.v. administered tirapazamine plus cyclophosphamide. Anti-cancer drugs 20010701
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Triplet combination chemotherapy and targeted therapy regimens. Oncology (Williston Park, N.Y.) 20010301
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Phase I trial of concurrent tirapazamine, cisplatin, and radiotherapy in patients with advanced head and neck cancer. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20010115
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
Analysis of DNA damage in individual cells. Methods in cell biology 20010101
An investigation of the molecular basis for the synergistic interaction of tirapazamine and cisplatin. International journal of radiation oncology, biology, physics 20010101
Mitochondrial dysfunction after aerobic exposure to the hypoxic cytotoxin tirapazamine. Cancer research 20010101
Cytotoxicity of bioreductive drug tirapazamine is increased by application of electric pulses in SA-1 tumours in mice. Anticancer research 20010101
4-[3-(2-Nitro-1-imidazolyl)propylamino]-7-chloroquinoline hydrochloride (NLCQ-1), a novel bioreductive agent as radiosensitizer in vitro and in vivo: comparison with tirapazamine. Oncology research 20010101
Hypoxia and oxidative stress. Tumour hypoxia--therapeutic considerations. Breast cancer research : BCR 20010101
Targeting hypoxia in head and neck cancer. Acta oncologica (Stockholm, Sweden) 20010101
Combination of the bioreductive drug tirapazamine with the chemotherapeutic prodrug cyclophosphamide for P450/P450-reductase-based cancer gene therapy. Cancer research 20000715
Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. British journal of cancer 19950401
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