Home Indole and Oxindoles 192820-78-3
192820-78-3,MFCD08690517
Catalog No.:AA002GB6

192820-78-3 | 1H-Indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-

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25mg
95%
1 week  
$732.00   $513.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002GB6
Chemical Name:
1H-Indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-
CAS Number:
192820-78-3
Molecular Formula:
C18H16N2O6
Molecular Weight:
356.3294
MDL Number:
MFCD08690517
SMILES:
COC1=CC(=O)c2c(C1=O)c(COc1ccc(cc1)[N+](=O)[O-])c(n2C)C
Properties
Properties
 
Form:
Solid  
Storage:
2-8℃;  

Computed Properties
 
Complexity:
620  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Rotatable Bond Count:
4  
XLogP3:
2.4  

Downstream Synthesis Route

[1]Beall,HowardD.;Winski,Shannon;Swann,Elizabeth;Hudnott,AnnaR.;Cotterill,AnnS.;O'Sullivan,Noeleen;Green,StephenJ.;Bien,Richard;Siegel,David;Ross,David;Moody,ChristopherJ.[JournalofMedicinalChemistry,1998,vol.41,#24,p.4755-4766]

110-91-8    192820-78-3   
1,2-dimethyl-5-(morpholin-1-yl)-3-(4-nitrophenoxy)methylindole-4,7-dione 

[1]Everett,StevenA.;Naylor,MatthewA.;Barraja,Paola;Swann,Elizabeth;Patel,KantilalB.;Stratford,MichaelR.L.;Hudnott,AnnaR.;Vojnovic,Borivoj;Locke,RosalindJ.;Wardman,Peter;Moody,ChristopherJ.[Perkin2,2001,#5,p.843-860]

67-63-0    192820-78-3    100-02-7    161518-24-7   
3-(isopropoxy)methyl-5-methoxy-1,2-dimethylindole-4,7-dione 

[1]Swann;Moody;Stratford;Patel;Naylor;Vojnovic;Wardman;Everett[Perkin2,2001,#8,p.1340-1345]

[1]Beall,HowardD.;Winski,Shannon;Swann,Elizabeth;Hudnott,AnnaR.;Cotterill,AnnS.;O'Sullivan,Noeleen;Green,StephenJ.;Bien,Richard;Siegel,David;Ross,David;Moody,ChristopherJ.[JournalofMedicinalChemistry,1998,vol.41,#24,p.4755-4766]

Literature

Title: Role for NAD(P)H:quinone oxidoreductase 1 and manganese-dependent superoxide dismutase in 17-(allylamino)-17-demethoxygeldanamycin-induced heat shock protein 90 inhibition in pancreatic cancer cells.

Journal: The Journal of pharmacology and experimental therapeutics 20110301

Title: ES936 stimulates DNA synthesis in HeLa cells independently on NAD(P)H:quinone oxidoreductase 1 inhibition, through a mechanism involving p38 MAPK.

Journal: Chemico-biological interactions 20100730

Title: NAD(P)H:quinone oxidoreductase 1-compromised human bone marrow endothelial cells exhibit decreased adhesion molecule expression and CD34+ hematopoietic cell adhesion.

Journal: The Journal of pharmacology and experimental therapeutics 20100701

Title: Synthesis and evaluation of 3-aryloxymethyl-1,2-dimethylindole-4,7-diones as mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1) activity.

Journal: Journal of medicinal chemistry 20071115

Title: Development of indolequinone mechanism-based inhibitors of NAD(P)H:quinone oxidoreductase 1 (NQO1): NQO1 inhibition and growth inhibitory activity in human pancreatic MIA PaCa-2 cancer cells.

Journal: Biochemistry 20070522

Title: Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen.

Journal: Toxicology 20070212

Title: The highly expressed and inducible endogenous NAD(P)H:quinone oxidoreductase 1 in cardiovascular cells acts as a potential superoxide scavenger.

Journal: Cardiovascular toxicology 20070101

Title: The bioreduction of a series of benzoquinone ansamycins by NAD(P)H:quinone oxidoreductase 1 to more potent heat shock protein 90 inhibitors, the hydroquinone ansamycins.

Journal: Molecular pharmacology 20061001

Title: 5-Methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione, a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1, exhibits activity against human pancreatic cancer in vitro and in vivo.

Journal: Molecular cancer therapeutics 20060701

Title: The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol.

Journal: Biochemistry 20060523

Title: Formation of 17-allylamino-demethoxygeldanamycin (17-AAG) hydroquinone by NAD(P)H:quinone oxidoreductase 1: role of 17-AAG hydroquinone in heat shock protein 90 inhibition.

Journal: Cancer research 20051101

Title: Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism.

Journal: Biochemical pharmacology 20050601

Title: RH1 induces cellular damage in an NAD(P)H:quinone oxidoreductase 1-dependent manner: relationship between DNA cross-linking, cell cycle perturbations, and apoptosis.

Journal: The Journal of pharmacology and experimental therapeutics 20050501

Title: NAD(P)H:quinone oxidoreductase 1: role as a superoxide scavenger.

Journal: Molecular pharmacology 20040501

Title: Biochemical, cytotoxic, and genotoxic effects of ES936, a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1, in cellular systems.

Journal: Molecular pharmacology 20030901

Title: Kinetics of NAD(P)H:quinone oxidoreductase I (NQO1) inhibition by mitomycin C in vitro and in vivo.

Journal: The Journal of pharmacology and experimental therapeutics 20030601

Title: Characterization of a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1 by biochemical, X-ray crystallographic, and mass spectrometric approaches.

Journal: Biochemistry 20011218

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Tags:192820-78-3 Molecular Formula|192820-78-3 MDL|192820-78-3 SMILES|192820-78-3 1H-Indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-