Home Nitro Compounds 21919-05-1
21919-05-1,MFCD00869490
Catalog No.:AA007OQO

21919-05-1 | Benzamide,5-(1-aziridinyl)-2,4-dinitro-

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  • Technical Information
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA007OQO
Chemical Name:
Benzamide,5-(1-aziridinyl)-2,4-dinitro-
CAS Number:
21919-05-1
Molecular Formula:
C9H8N4O5
Molecular Weight:
252.1836
MDL Number:
MFCD00869490
SMILES:
NC(=O)c1cc(N2CC2)c(cc1[N+](=O)[O-])[N+](=O)[O-]
NSC Number:
115829
Properties
Computed Properties
 
Complexity:
385  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
2  

Downstream Synthesis Route
21919-05-1   
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide 

[1]Palmer;VanZijl;Denny;Wilson[JournalofMedicinalChemistry,1995,vol.38,#7,p.1229-1241]

[2]Chen,Shiuan;Knox,Richard;Lewis,AlexanderD.;Friedlos,Frank;Workman,Paul;Deng,PaulisS.K.;Fung,Maisie;Ebenstein,Donna;Wu,Kebin;Tsai,Ta-Ming[MolecularPharmacology,1995,vol.47,#5,p.934-939]

[3]AbuKhader,Majed;Heap,John;DeMatteis,Cristina;Kellam,Barrie;Doughty,StephenW.;Minton,Nigel;Paoli,Massimo[JournalofMedicinalChemistry,2005,vol.48,#24,p.7714-7719]

21919-05-1   
5-(aziridin-1-yl)-2-nitro-4-nitrosobenzamide 

[1]AbuKhader,Majed;Heap,John;DeMatteis,Cristina;Kellam,Barrie;Doughty,StephenW.;Minton,Nigel;Paoli,Massimo[JournalofMedicinalChemistry,2005,vol.48,#24,p.7714-7719]

21919-05-1   
5-(aziridin-1-yl)-2-hydroxylamino-4-nitrobenzamide 

[1]Jackson,JenniferC.;Duffy,SeanP.;Hess,KennethR.;Mehl,RyanA.[JournaloftheAmericanChemicalSociety,2006,vol.128,#34,p.11124-11127]

21919-05-1   
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide 
 
5-(aziridin-1-yl)-2-hydroxylamino-4-nitrobenzamide 

[1]CurrentPatentAssignee:GORDIANPHARMA-WO2007/74344,2007,A1Locationinpatent:Page/Pagecolumn63-65

21919-05-1   
4-aminometabolite 
  61837-26-1   
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide 
 
5-(aziridin-1-yl)-2-hydroxylamino-4-nitrobenzamide 

[1]Çelik,Ayhan;Yetiş,Gülden[BioorganicandMedicinalChemistry,2012,vol.20,#11,p.3540-3550]

[2]Ball,Patrick;Thompson,Emma;Anderson,Simon;Gwenin,Vanessa;Gwenin,Chris[EuropeanJournalofPharmaceuticalSciences,2019,vol.127,p.217-224]

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Title: The NprA nitroreductase required for 2,4-dinitrophenol reduction in Rhodobacter capsulatus is a dihydropteridine reductase.

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Title: E. coli nitroreductase/CB1954 gene-directed enzyme prodrug therapy: role of arylamine N-acetlytransferase 2.

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Title: Optimized clostridium-directed enzyme prodrug therapy improves the antitumor activity of the novel DNA cross-linking agent PR-104.

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Title: Gene therapy for the treatment of hip prosthesis loosening: adverse events in a phase 1 clinical study.

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Title: Metabolic activation of the antitumor drug 5-(Aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) by NO synthases.

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Title: Escherichia coli nitroreductase plus CB1954 enhances the effect of radiotherapy in vitro and in vivo.

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Title: SALMON: solvent accessibility, ligand binding, and mapping of ligand orientation by NMR spectroscopy.

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Title: Combining gene and immunotherapy for prostate cancer.

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Title: Hepatic nitroreduction, toxicity and toxicokinetics of the anti-tumour prodrug CB 1954 in mouse and rat.

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Title: Synthesis of cryptolepine analogues as potential bioreducible anticancer agents.

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Title: Validation of nitroreductase, a prodrug-activating enzyme, mediated cell death in embryonic zebrafish (Danio rerio).

Journal: Comparative medicine 20070601

Title: Ablation of central nervous system progenitor cells in transgenic rats using bacterial nitroreductase system.

Journal: Journal of neuroscience research 20070501

Title: Kinetic and structural characterisation of Escherichia coli nitroreductase mutants showing improved efficacy for the prodrug substrate CB1954.

Journal: Journal of molecular biology 20070427

Title: Direct positive selection for improved nitroreductase variants using SOS triggering of bacteriophage lambda lytic cycle.

Journal: Gene therapy 20070401

Title: Synthesis and structure-activity relationships for 2,4-dinitrobenzamide-5-mustards as prodrugs for the Escherichia coli nfsB nitroreductase in gene therapy.

Journal: Journal of medicinal chemistry 20070322

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Title: Repeated cycles of Clostridium-directed enzyme prodrug therapy result in sustained antitumour effects in vivo.

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Title: Reduction of mitomycin C is catalysed by human recombinant NRH:quinone oxidoreductase 2 using reduced nicotinamide adenine dinucleotide as an electron donating co-factor.

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Title: Nitroreductase-based therapy of prostate cancer, enhanced by raising expression of heat shock protein 70, acts through increased anti-tumour immunity.

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Title: Delivery of the bacterial nitroreductase gene into endothelial cells prolongs the survival of tumour-bearing mice by bystander mechanisms.

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Title: New enzyme for reductive cancer chemotherapy, YieF, and its improvement by directed evolution.

Journal: Molecular cancer therapeutics 20060101

Title: Aerobic 2- and 4-nitroreduction of CB 1954 by human liver.

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Title: Binding of the anticancer prodrug CB1954 to the activating enzyme NQO2 revealed by the crystal structure of their complex.

Journal: Journal of medicinal chemistry 20051201

Title: Late expression of nitroreductase in an oncolytic adenovirus sensitizes colon cancer cells to the prodrug CB1954.

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Title: Bacillus amyloliquefaciens orthologue of Bacillus subtilis ywrO encodes a nitroreductase enzyme which activates the prodrug CB 1954.

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Title: Telomerase-specific suicide gene therapy vectors expressing bacterial nitroreductase sensitize human cancer cells to the pro-drug CB1954.

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Title: High-level, beta-catenin/TCF-dependent transgene expression in secondary colorectal cancer tissue.

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Title: Appropriate subcellular localisation of prodrug-activating enzymes has important consequences for suicide gene therapy.

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Title: Conditional ablation of neurones in transgenic mice.

Journal: Journal of neurobiology 20010605

Title: Inducible ablation of astrocytes shows that these cells are required for neuronal survival in the adult brain.

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Title: Combined adenovirus-mediated nitroreductase gene delivery and CB1954 treatment: a well-tolerated therapy for established solid tumors.

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Tags:21919-05-1 Molecular Formula|21919-05-1 MDL|21919-05-1 SMILES|21919-05-1 Benzamide,5-(1-aziridinyl)-2,4-dinitro-