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Home > Fluorides > 293754-55-9
293754-55-9 | Benzenesulfonamide, N-(2,2,2-trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-
CAS No: 293754-55-9 Catalog No: AG002Y7U MDL No:MFCD03412028
Product Description
Catalog Number:
AG002Y7U
Chemical Name:
Benzenesulfonamide, N-(2,2,2-trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-
CAS Number:
293754-55-9
Molecular Formula:
C17H12F9NO3S
Molecular Weight:
481.3327
MDL Number:
MFCD03412028
IUPAC Name:
N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-N-(2,2,2-trifluoroethyl)benzenesulfonamide
InChI:
InChI=1S/C17H12F9NO3S/c18-14(19,20)10-27(31(29,30)13-4-2-1-3-5-13)12-8-6-11(7-9-12)15(28,16(21,22)23)17(24,25)26/h1-9,28H,10H2
InChI Key:
SGIWFELWJPNFDH-UHFFFAOYSA-N
SMILES:
FC(CN(S(=O)(=O)c1ccccc1)c1ccc(cc1)C(C(F)(F)F)(C(F)(F)F)O)(F)F
UNII:
A07663A39I
Properties
Complexity:
684
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
481.039g/mol
Formal Charge:
0
Heavy Atom Count:
31
Hydrogen Bond Acceptor Count:
13
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
481.333g/mol
Monoisotopic Mass:
481.039g/mol
Rotatable Bond Count:
5
Topological Polar Surface Area:
66A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
4.9
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| Carboxylic acid based quinolines as liver X receptor modulators that have LXRbeta receptor binding selectivity. | Bioorganic & medicinal chemistry letters 20080101 |
| Liver X receptors (LXR) as therapeutic targets in dyslipidemia. | Cardiovascular therapeutics 20080101 |
| Chenodeoxycholic acid suppresses the activation of acetyl-coenzyme A carboxylase-alpha gene transcription by the liver X receptor agonist T0-901317. | Journal of lipid research 20071201 |
| Regulation of CYP3A4 and CYP2B6 expression by liver X receptor agonists. | Biochemical pharmacology 20071115 |
| Liver X receptors inhibit human monocyte-derived macrophage foam cell formation by inhibiting fluid-phase pinocytosis of LDL. | Journal of lipid research 20071101 |
| SIRT1 deacetylates and positively regulates the nuclear receptor LXR. | Molecular cell 20071012 |
| Regulation of 17beta-hydroxysteroid dehydrogenase type 2, type 4 and type 5 by calcitriol, LXR agonist and 5alpha-dihydrotestosterone in human prostate cancer cells. | The Journal of steroid biochemistry and molecular biology 20071001 |
| Conversion of the LXR-agonist TO-901317--from inverse to normal modulation of gamma-secretase by addition of a carboxylic acid and a lipophilic anchor. | Bioorganic & medicinal chemistry letters 20071001 |
| N-Acylthiadiazolines, a new class of liver X receptor agonists with selectivity for LXRbeta. | Journal of medicinal chemistry 20070823 |
| 2-Aryl-N-acyl indole derivatives as liver X receptor (LXR) agonists. | Bioorganic & medicinal chemistry letters 20070815 |
| Adipocyte fatty acid-binding protein (aP2), a newly identified LXR target gene, is induced by LXR agonists in human THP-1 cells. | Molecular and cellular biochemistry 20070801 |
| Effect of T0901317 on hepatic proinflammatory gene expression in apoE-/- mice fed a high-fat/high-cholesterol diet. | Inflammation 20070801 |
| Sterol regulatory element-binding protein-2- and liver X receptor-driven dual promoter regulation of hepatic ABC transporter A1 gene expression: mechanism underlying the unique response to cellular cholesterol status. | The Journal of biological chemistry 20070720 |
| A novel pathway to enhance adipocyte differentiation of 3T3-L1 cells by up-regulation of lipocalin-type prostaglandin D synthase mediated by liver X receptor-activated sterol regulatory element-binding protein-1c. | The Journal of biological chemistry 20070622 |
| Discovery and structure-activity relationship studies of indole derivatives as liver X receptor (LXR) agonists. | Bioorganic & medicinal chemistry letters 20070615 |
| Liver-X-receptor activator prevents homocysteine-induced production of IgG antibodies from murine B lymphocytes via the ROS-NF-kappaB pathway. | Biochemical and biophysical research communications 20070608 |
| The liver X receptor agonist T0901317 acts as androgen receptor antagonist in human prostate cancer cells. | Biochemical and biophysical research communications 20070601 |
| Inhibition of progesterone production in human luteinized granulosa cells treated with LXR agonists. | Molecular human reproduction 20070601 |
| Liver X receptors regulate dendritic cell phenotype and function through blocked induction of the actin-bundling protein fascin. | Blood 20070515 |
| T0901317 is a potent PXR ligand: implications for the biology ascribed to LXR. | FEBS letters 20070501 |
| Activation of liver X receptors and retinoid X receptors induces growth arrest and apoptosis in insulin-secreting cells. | Endocrinology 20070401 |
| The LXR agonist TO901317 selectively lowers hippocampal Abeta42 and improves memory in the Tg2576 mouse model of Alzheimer's disease. | Molecular and cellular neurosciences 20070401 |
| Immunomodulatory properties of increased levels of liver X receptor beta in peripheral blood mononuclear cells from multiple sclerosis patients. | Experimental neurology 20070401 |
| Crystal structure of the PXR-T1317 complex provides a scaffold to examine the potential for receptor antagonism. | Bioorganic & medicinal chemistry 20070301 |
| PXR induces CYP27A1 and regulates cholesterol metabolism in the intestine. | Journal of lipid research 20070201 |
| 24S-hydroxycholesterol induces cholesterol release from choroid plexus epithelial cells in an apical- and apoE isoform-dependent manner concomitantly with the induction of ABCA1 and ABCG1 expression. | Journal of neurochemistry 20070201 |
| Activation of LXRs prevents bile acid toxicity and cholestasis in female mice. | Hepatology (Baltimore, Md.) 20070201 |
| Inhibition of drug metabolism by blocking the activation of nuclear receptors by ketoconazole. | Oncogene 20070111 |
| The liver X receptor (LXR) and hepatic lipogenesis. The carbohydrate-response element-binding protein is a target gene of LXR. | The Journal of biological chemistry 20070105 |
| Liver X receptor inhibits the synthesis and secretion of apolipoprotein A1 by human liver-derived cells. | Biochemistry 20061219 |
| 22-Hydroxycholesterols regulate lipid metabolism differently than T0901317 in human myotubes. | Biochimica et biophysica acta 20061201 |
| Liver X receptor agonist T0901317 inhibition of glucocorticoid receptor expression in hepatocytes may contribute to the amelioration of diabetic syndrome in db/db mice. | Endocrinology 20061101 |
| The human myeloperoxidase gene is regulated by LXR and PPARalpha ligands. | Biochemical and biophysical research communications 20061020 |
| Discovery of phenyl acetic acid substituted quinolines as novel liver X receptor agonists for the treatment of atherosclerosis. | Journal of medicinal chemistry 20061019 |
| Insulin induction of glucokinase and fatty acid synthase in hepatocytes: analysis of the roles of sterol-regulatory-element-binding protein-1c and liver X receptor. | The Biochemical journal 20061015 |
| Synthesis and evaluation of anilinohexafluoroisopropanols as activators/modulators of LXRalpha and beta. | Bioorganic & medicinal chemistry letters 20061001 |
| Regulation of hepatic fatty acid elongase and desaturase expression in diabetes and obesity. | Journal of lipid research 20060901 |
| The chicken ovalbumin upstream promoter-transcription factors modulate genes and pathways involved in skeletal muscle cell metabolism. | The Journal of biological chemistry 20060825 |
| Identification of a lead pharmacophore for the development of potent nuclear receptor modulators as anticancer and X syndrome disease therapeutic agents. | Bioorganic & medicinal chemistry letters 20060815 |
| Sterol regulatory element-binding protein 1 mediates liver X receptor-beta-induced increases in insulin secretion and insulin messenger ribonucleic acid levels. | Endocrinology 20060801 |
| Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. | Toxicological sciences : an official journal of the Society of Toxicology 20060801 |
| The effects of ABCA1 on cholesterol efflux and Abeta levels in vitro and in vivo. | Journal of neurochemistry 20060801 |
| The liver X-receptor alpha controls hepatic expression of the human bile acid-glucuronidating UGT1A3 enzyme in human cells and transgenic mice. | Hepatology (Baltimore, Md.) 20060801 |
| Synergistic effect of peroxisome proliferator activated receptor-gamma and liver X receptor-alpha in the regulation of inflammation in macrophages. | Shock (Augusta, Ga.) 20060801 |
| Regulation of retinal dehydrogenases and retinoic acid synthesis by cholesterol metabolites. | The EMBO journal 20060712 |
| Glucose regulates LXRalpha subcellular localization and function in rat pancreatic beta-cells. | Cell research 20060701 |
| Inhibition of tumor growth and progression of LNCaP prostate cancer cells in athymic mice by androgen and liver X receptor agonist. | Cancer research 20060701 |
| [Liver X receptors mediate cholesterol efflux in mouse glomerular mesangial cells]. | Beijing da xue xue bao. Yi xue ban = Journal of Peking University. Health sciences 20060618 |
| ABCA1-dependent but apoA-I-independent cholesterol efflux mediated by fatty acid-bile acid conjugates (FABACs). | The Biochemical journal 20060615 |
| Assessing the effects of LXR agonists on cellular cholesterol handling: a stable isotope tracer study. | Journal of lipid research 20060601 |
| Liver X receptor agonist TO-901317 upregulates SCD1 expression in renal proximal straight tubule. | American journal of physiology. Renal physiology 20060501 |
| PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | Journal of lipid research 20060501 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Discovery and optimization of a novel series of liver X receptor-alpha agonists. | Bioorganic & medicinal chemistry letters 20060315 |
| Hepatic PCSK9 expression is regulated by nutritional status via insulin and sterol regulatory element-binding protein 1c. | The Journal of biological chemistry 20060310 |
| Oxysterols suppress inducible nitric oxide synthase expression in lipopolysaccharide-stimulated astrocytes through liver X receptor. | Neuroreport 20060206 |
| Regulatory effects of synthetic liver X receptor- and peroxisome-proliferator activated receptor agonists on sterol transport pathways in polarized cerebrovascular endothelial cells. | The international journal of biochemistry & cell biology 20060101 |
| Non-steroidal LXR agonists; an emerging therapeutic strategy for the treatment of atherosclerosis. | Recent patents on cardiovascular drug discovery 20060101 |
| Liver X receptors mediate inhibition of hCG secretion in a human placental trophoblast cell line. | Placenta 20051101 |
| The human ABCG1 gene: identification of LXR response elements that modulate expression in macrophages and liver. | Journal of lipid research 20051001 |
| Liver X receptor and retinoic X receptor agonists modulate the expression of genes involved in lipid metabolism in human endothelial cells. | International journal of molecular medicine 20051001 |
| Discovery of substituted maleimides as liver X receptor agonists and determination of a ligand-bound crystal structure. | Journal of medicinal chemistry 20050825 |
| Diet-dependent cardiovascular lipid metabolism controlled by hepatic LXRalpha. | Cell metabolism 20050501 |
| Pharmacological regulation of cholesterol efflux in human monocyte-derived macrophages in the absence of exogenous cholesterol acceptors. | Atherosclerosis 20050401 |
| Skeletal muscle lipid accumulation in type 2 diabetes may involve the liver X receptor pathway. | Diabetes 20050401 |
| Adipocytic differentiation and liver x receptor pathways regulate the accumulation of triacylglycerols in human vascular smooth muscle cells. | The Journal of biological chemistry 20050204 |
| Macrophage liver X receptor is required for antiatherogenic activity of LXR agonists. | Arteriosclerosis, thrombosis, and vascular biology 20050101 |
| Liver X receptor agonists suppress vascular smooth muscle cell proliferation and inhibit neointima formation in balloon-injured rat carotid arteries. | Circulation research 20041210 |
| LXR activation and cholesterol efflux from a lipoprotein depot in vivo. | Biochimica et biophysica acta 20041108 |
| Mimetics of caloric restriction include agonists of lipid-activated nuclear receptors. | The Journal of biological chemistry 20041029 |
| Nuclear oxysterol receptors, LXRs, are involved in the maintenance of mouse caput epididymidis structure and functions. | Journal of molecular endocrinology 20041001 |
| Post-transcriptional regulation of sterol regulatory element-binding protein-1 by ethanol induces class I alcohol dehydrogenase in rat liver. | The Journal of biological chemistry 20040702 |
| Coadministration of a liver X receptor agonist and a peroxisome proliferator activator receptor-alpha agonist in Mice: effects of nuclear receptor interplay on high-density lipoprotein and triglyceride metabolism in vivo. | The Journal of pharmacology and experimental therapeutics 20040601 |
| A liver X receptor and retinoid X receptor heterodimer mediates apolipoprotein E expression, secretion and cholesterol homeostasis in astrocytes. | Journal of neurochemistry 20040201 |
| Sitosterolemia in ABC-transporter G5-deficient mice is aggravated on activation of the liver-X receptor. | Gastroenterology 20040101 |
| CYP3A induction by liver x receptor ligands in primary cultured rat and mouse hepatocytes is mediated by the pregnane X receptor. | Drug metabolism and disposition: the biological fate of chemicals 20040101 |
| T0901317 is a dual LXR/FXR agonist. | Molecular genetics and metabolism 20040101 |
| Crystal structure of the human liver X receptor beta ligand-binding domain in complex with a synthetic agonist. | Journal of molecular biology 20031212 |
| The LXR ligand T0901317 induces severe lipogenesis in the db/db diabetic mouse. | Journal of lipid research 20031101 |
| Molecular determinants of LXRalpha agonism. | Journal of molecular graphics & modelling 20031101 |
| Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist. | The Journal of biological chemistry 20030919 |
| Crystal structure of the heterodimeric complex of LXRalpha and RXRbeta ligand-binding domains in a fully agonistic conformation. | The EMBO journal 20030915 |
| X-ray crystal structure of the liver X receptor beta ligand binding domain: regulation by a histidine-tryptophan switch. | The Journal of biological chemistry 20030718 |
| Cross-talk between peroxisome proliferator-activated receptor (PPAR) alpha and liver X receptor (LXR) in nutritional regulation of fatty acid metabolism. I. PPARs suppress sterol regulatory element binding protein-1c promoter through inhibition of LXR signaling. | Molecular endocrinology (Baltimore, Md.) 20030701 |
| Cross-talk between peroxisome proliferator-activated receptor (PPAR) alpha and liver X receptor (LXR) in nutritional regulation of fatty acid metabolism. II. LXRs suppress lipid degradation gene promoters through inhibition of PPAR signaling. | Molecular endocrinology (Baltimore, Md.) 20030701 |
| Angiopoietin-like protein 3 mediates hypertriglyceridemia induced by the liver X receptor. | The Journal of biological chemistry 20030613 |
| Relation between hepatic expression of ATP-binding cassette transporters G5 and G8 and biliary cholesterol secretion in mice. | Journal of hepatology 20030601 |
| Stimulation of cholesterol excretion by the liver X receptor agonist requires ATP-binding cassette transporters G5 and G8. | The Journal of biological chemistry 20030502 |
| Differential regulation of rat and human CYP7A1 by the nuclear oxysterol receptor liver X receptor-alpha. | Molecular endocrinology (Baltimore, Md.) 20030301 |
| Pharmacological evidence for a role of liver X receptors in atheroprotection. | FEBS letters 20030211 |
| T-0901317, a synthetic liver X receptor ligand, inhibits development of atherosclerosis in LDL receptor-deficient mice. | FEBS letters 20030211 |
| On the role of liver X receptors in lipid accumulation in adipocytes. | Molecular endocrinology (Baltimore, Md.) 20030201 |
| A chemical switch regulates fibrate specificity for peroxisome proliferator-activated receptor alpha (PPARalpha ) versus liver X receptor. | The Journal of biological chemistry 20030124 |
| Antidiabetic action of a liver x receptor agonist mediated by inhibition of hepatic gluconeogenesis. | The Journal of biological chemistry 20030110 |
| Polyunsaturated fatty acids decrease the expression of sterol regulatory element-binding protein-1 in CaCo-2 cells: effect on fatty acid synthesis and triacylglycerol transport. | The Biochemical journal 20021215 |
| Phospholipid transfer protein is regulated by liver X receptors in vivo. | The Journal of biological chemistry 20021018 |
| Stimulation of lipogenesis by pharmacological activation of the liver X receptor leads to production of large, triglyceride-rich very low density lipoprotein particles. | The Journal of biological chemistry 20020913 |
| Increased hepatobiliary and fecal cholesterol excretion upon activation of the liver X receptor is independent of ABCA1. | The Journal of biological chemistry 20020913 |
| LXR/RXR activation enhances basolateral efflux of cholesterol in CaCo-2 cells. | Journal of lipid research 20020701 |
| Identification of a nonsteroidal liver X receptor agonist through parallel array synthesis of tertiary amines. | Journal of medicinal chemistry 20020509 |
| Diminished hepatic response to fasting/refeeding and liver X receptor agonists in mice with selective deficiency of sterol regulatory element-binding protein-1c. | The Journal of biological chemistry 20020315 |
| Induction of human liver X receptor alpha gene expression via an autoregulatory loop mechanism. | Molecular endocrinology (Baltimore, Md.) 20020301 |
| Hypolipidemic effects of selective liver X receptor alpha agonists. | Steroids 20010901 |
| Role of LXRs in control of lipogenesis. | Genes & development 20001115 |
| Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands. | The Journal of biological chemistry 20000519 |
| Liver X receptor-alpha regulates proopiomelanocortin (POMC) gene transcription in the pituitary. | Molecular endocrinology (Baltimore, Md.) |
| Identification of MIG12 as a mediator for stimulation of lipogenesis by LXR activation. | Molecular endocrinology (Baltimore, Md.) |
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