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133208-93-2 | Phosphonic acid, [[4-[[(4-bromo-2-cyanophenyl)amino]carbonyl]phenyl]methyl]-, diethyl ester
CAS No: 133208-93-2 Catalog No: AG0014EG MDL No:
Product Description
Catalog Number:
AG0014EG
Chemical Name:
Phosphonic acid, [[4-[[(4-bromo-2-cyanophenyl)amino]carbonyl]phenyl]methyl]-, diethyl ester
CAS Number:
133208-93-2
Molecular Formula:
C19H20BrN2O4P
Molecular Weight:
451.2509
IUPAC Name:
N-(4-bromo-2-cyanophenyl)-4-(diethoxyphosphorylmethyl)benzamide
InChI:
InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
InChI Key:
KPRTURMJVWXURQ-UHFFFAOYSA-N
SMILES:
CCOP(=O)(Cc1ccc(cc1)C(=O)Nc1ccc(cc1C#N)Br)OCC
UNII:
07H1561618
Properties
Complexity:
576
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
450.034g/mol
Formal Charge:
0
Heavy Atom Count:
27
Hydrogen Bond Acceptor Count:
5
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
451.257g/mol
Monoisotopic Mass:
450.034g/mol
Rotatable Bond Count:
8
Topological Polar Surface Area:
88.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.5
Literature
| Title | Journal |
|---|---|
| NO-1886 ameliorates glycogen metabolism in insulin-resistant HepG2 cells by GSK-3β signalling. | The Journal of pharmacy and pharmacology 20120201 |
| Pioglitazone-induced body weight gain is prevented by combined administration with the lipoprotein lipase activator NO-1886. | European journal of pharmacology 20111015 |
| Activation of lipoprotein lipase increases serum high density lipoprotein 2 cholesterol and enlarges high density lipoprotein 2 particles in rats. | European journal of pharmacology 20111001 |
| Ibrolipim attenuates high glucose-induced endothelial dysfunction in cultured human umbilical vein endothelial cells via PI3K/Akt pathway. | Die Pharmazie 20111001 |
| Hepatic gene expression profiles are altered by dietary unsalted korean fermented soybean (chongkukjang) consumption in mice with diet-induced obesity. | Journal of nutrition and metabolism 20110101 |
| Preventive effect of Ibrolipim on suppressing lipid accumulation and increasing lipoprotein lipase in the kidneys of diet-induced diabetic minipigs. | Lipids in health and disease 20110101 |
| Ibrolipim increases ABCA1/G1 expression by the LXRα signaling pathway in THP-1 macrophage-derived foam cells. | Acta pharmacologica Sinica 20101001 |
| NO-1886 suppresses diet-induced insulin resistance and cholesterol accumulation through STAT5-dependent upregulation of IGF1 and CYP7A1. | The Journal of endocrinology 20100101 |
| NO-1886 up-regulates Niemann-Pick C1 protein (NPC1) expression through liver X receptor alpha signaling pathway in THP-1 macrophage-derived foam cells. | Cardiovascular drugs and therapy 20090601 |
| Pharmacological approaches to modifying HDL: more basic science to understand HDL metabolism is necessary. Editorial to: 'NO-1886 up-regulates Niemann-Pick C1 protein (NPC1) expression through liver X receptor alpha signaling pathway in THP-1 macrophage-derived foam cells' by Xin Ma et al. | Cardiovascular drugs and therapy 20090601 |
| Evaluation of induction potency of new drug candidates on CYP1A2 and CYP3A4 using real-time one-step RT-PCR in primary cultures of cryopreserved human hepatocytes. | Drug metabolism and pharmacokinetics 20090101 |
| NO-1886, a lipoprotein lipase activator, attenuates contraction of rat intestinal ring preparations. | The journal of medical investigation : JMI 20080201 |
| Lipoprotein lipase activator ameliorates the severity of dietary steatohepatitis. | Biochemical and biophysical research communications 20070427 |
| NO-1886, a lipoprotein lipase activator, attenuates vascular smooth muscle contraction in rat aorta. | European journal of pharmacology 20070112 |
| NO-1886 upregulates ATP binding cassette transporter A1 and inhibits diet-induced atherosclerosis in Chinese Bama minipigs. | Journal of lipid research 20060901 |
| Effects of NO-1886 on inflammation-associated cytokines in high-fat/high-sucrose/high-cholesterol diet-fed miniature pigs. | European journal of pharmacology 20060701 |
| Concomitant suppression of hyperlipidemia and intestinal polyp formation by increasing lipoprotein lipase activity in Apc-deficient mice. | Biological chemistry 20060401 |
| NO-1886 (ibrolipim), a lipoprotein lipase-promoting agent, accelerates the expression of UCP3 messenger RNA and ameliorates obesity in ovariectomized rats. | Metabolism: clinical and experimental 20060201 |
| Assessment of induction of cytochrome P450 by NO-1886 (ibrolipim), a lipoprotein lipase-promoting agent, in primary cultures of human hepatocytes and in female rat liver. | Drug metabolism and pharmacokinetics 20060201 |
| Uncoupling proteins, dietary fat and the metabolic syndrome. | Nutrition & metabolism 20060101 |
| NO-1886 (ibrolipim), a lipoprotein lipase activator, increases the expression of uncoupling protein 3 in skeletal muscle and suppresses fat accumulation in high-fat diet-induced obesity in rats. | Metabolism: clinical and experimental 20051201 |
| Effects of NO-1886 (Ibrolipim), a lipoprotein lipase-promoting agent, on gene induction of cytochrome P450s, carboxylesterases, and sulfotransferases in primary cultures of human hepatocytes. | Drug metabolism and pharmacokinetics 20041201 |
| NO-1886 inhibits size of adipocytes, suppresses plasma levels of tumor necrosis factor-alpha and free fatty acids, improves glucose metabolism in high-fat/high-sucrose-fed miniature pigs. | Pharmacological research 20040301 |
| NO-1886 decreases ectopic lipid deposition and protects pancreatic beta cells in diet-induced diabetic swine. | The Journal of endocrinology 20040301 |
| Lipoprotein lipase activator NO-1886 improves fatty liver caused by high-fat feeding in streptozotocin-induced diabetic rats. | Metabolism: clinical and experimental 20040201 |
| Lipoprotein lipase activator NO-1886 (ibrolipim) accelerates the mRNA expression of fatty acid oxidation-related enzymes in rat liver. | Metabolism: clinical and experimental 20031201 |
| Pharmacokinetics and metabolism of NO-1886, a lipoprotein lipase-promoting agent, in cynomolgus monkey. | Xenobiotica; the fate of foreign compounds in biological systems 20031201 |
| Lipoprotein lipase and atherosclerosis. | Current vascular pharmacology 20030301 |
| A lipoprotein lipase-promoting agent, NO-1886, improves glucose and lipid metabolism in high fat, high sucrose-fed New Zealand white rabbits. | International journal of experimental diabesity research 20030101 |
| Lipoprotein lipase activator NO-1886. | Cardiovascular drug reviews 20030101 |
| A lipoprotein lipase activator, NO-1886 prevents impaired endothelium-dependent relaxation of aorta caused by exercise in aged rats. | Experimental gerontology 20020701 |
| Correlation between lipid and glycogen contents in liver and insulin resistance in high-fat-fed rats treated with the lipoprotein lipase activator NO-1886. | Metabolism: clinical and experimental 20020601 |
| Phosphonate O-deethylation of [4-(4-bromo-2-cyano-phenylcarbamoyl) benzyl]-phosphonic acid diethyl ester, a lipoprotein lipase-promoting agent, catalyzed by cytochrome P450 2C8 and 3A4 in human liver microsomes. | Drug metabolism and disposition: the biological fate of chemicals 20020301 |
| Effects of the lipoprotein lipase activator NO-1886 as a suppressor agent of atherosclerosis in aorta of mild diabetic rabbits. | Arzneimittel-Forschung 20020101 |
| [Lipid-lowering drugs]. | Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20011201 |
| Discovery of novel mesangial cell proliferation inhibitors using a three-dimensional database searching method. | Journal of medicinal chemistry 20010705 |
| Effect of lipoprotein lipase activators bezafibrate and NO-1886, on B16 melanoma-induced cachexia in mice. | Anticancer research 19990101 |
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