Home Nitros 1H-Indole-4,7-dione, 5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]-

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

CAS No.:
192820-78-3
Catalog Number:
AG002GDY
Molecular Formula:
C18H16N2O6
Molecular Weight:
356.3294
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Product Description
Catalog Number:
AG002GDY
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
IUPAC Name:
5-methoxy-1,2-dimethyl-3-[(4-nitrophenoxy)methyl]indole-4,7-dione
InChI:
InChI=1S/C18H16N2O6/c1-10-13(9-26-12-6-4-11(5-7-12)20(23)24)16-17(19(10)2)14(21)8-15(25-3)18(16)22/h4-8H,9H2,1-3H3
InChI Key:
IBLWSLZYYZHSRG-UHFFFAOYSA-N
SMILES:
COC1=CC(=O)c2c(C1=O)c(COc1ccc(cc1)[N+](=O)[O-])c(n2C)C
UNII:
1XI90I177M
Properties
Complexity:
620  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
356.101g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
356.334g/mol
Monoisotopic Mass:
356.101g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
103A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4  
Literature
Title Journal
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. The Journal of pharmacology and experimental therapeutics 20110301
ES936 stimulates DNA synthesis in HeLa cells independently on NAD(P)H:quinone oxidoreductase 1 inhibition, through a mechanism involving p38 MAPK. Chemico-biological interactions 20100730
NAD(P)H:quinone oxidoreductase 1-compromised human bone marrow endothelial cells exhibit decreased adhesion molecule expression and CD34+ hematopoietic cell adhesion. The Journal of pharmacology and experimental therapeutics 20100701
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 of medicinal chemistry 20071115
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. Biochemistry 20070522
Role of NAD(P)H:quinone oxidoreductase 1 in clofibrate-mediated hepatoprotection from acetaminophen. Toxicology 20070212
The highly expressed and inducible endogenous NAD(P)H:quinone oxidoreductase 1 in cardiovascular cells acts as a potential superoxide scavenger. Cardiovascular toxicology 20070101
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. Molecular pharmacology 20061001
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. Molecular cancer therapeutics 20060701
The crystal structure of NAD(P)H quinone oxidoreductase 1 in complex with its potent inhibitor dicoumarol. Biochemistry 20060523
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. Cancer research 20051101
Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism. Biochemical pharmacology 20050601
RH1 induces cellular damage in an NAD(P)H:quinone oxidoreductase 1-dependent manner: relationship between DNA cross-linking, cell cycle perturbations, and apoptosis. The Journal of pharmacology and experimental therapeutics 20050501
NAD(P)H:quinone oxidoreductase 1: role as a superoxide scavenger. Molecular pharmacology 20040501
Biochemical, cytotoxic, and genotoxic effects of ES936, a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1, in cellular systems. Molecular pharmacology 20030901
Kinetics of NAD(P)H:quinone oxidoreductase I (NQO1) inhibition by mitomycin C in vitro and in vivo. The Journal of pharmacology and experimental therapeutics 20030601
Characterization of a mechanism-based inhibitor of NAD(P)H:quinone oxidoreductase 1 by biochemical, X-ray crystallographic, and mass spectrometric approaches. Biochemistry 20011218
Properties