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177172-49-5 | Benzenepropanamine, 2-chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-, hydrochloride (1:1)
CAS No: 177172-49-5 Catalog No: AG002552 MDL No:
Product Description
Catalog Number:
AG002552
Chemical Name:
Benzenepropanamine, 2-chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-, hydrochloride (1:1)
CAS Number:
177172-49-5
Molecular Formula:
C18H23Cl2NO
Molecular Weight:
340.2873
IUPAC Name:
3-(2-chlorophenyl)-N-[(1R)-1-(3-methoxyphenyl)ethyl]propan-1-amine;hydrochloride
InChI:
InChI=1S/C18H22ClNO.ClH/c1-14(16-8-5-10-17(13-16)21-2)20-12-6-9-15-7-3-4-11-18(15)19;/h3-5,7-8,10-11,13-14,20H,6,9,12H2,1-2H3;1H/t14-;/m1./s1
InChI Key:
YJXUXANREVNZLH-PFEQFJNWSA-N
SMILES:
COc1cccc(c1)[C@H](NCCCc1ccccc1Cl)C.Cl
UNII:
3HP28R98LC
Properties
Complexity:
286
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
339.116g/mol
Formal Charge:
0
Heavy Atom Count:
22
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
340.288g/mol
Monoisotopic Mass:
339.116g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
21.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Biased allosteric modulation at the CaS receptor engendered by structurally diverse calcimimetics. | British journal of pharmacology 20150101 |
| Enhanced Ca(2+)-sensing receptor function in idiopathic pulmonary arterial hypertension. | Circulation research 20120803 |
| Calcium-sensing receptor inhibits secretagogue-induced electrolyte secretion by intestine via the enteric nervous system. | American journal of physiology. Gastrointestinal and liver physiology 20120701 |
| The regulation of K- and L-cell activity by GLUT2 and the calcium-sensing receptor CasR in rat small intestine. | The Journal of physiology 20120615 |
| Positive and negative allosteric modulators promote biased signaling at the calcium-sensing receptor. | Endocrinology 20120301 |
| Negative cross-talk between calcium-sensing receptor and β-catenin signaling systems in colonic epithelium. | The Journal of biological chemistry 20120106 |
| Calcimimetic R-568 and its enantiomer S-568 increase nitric oxide release in human endothelial cells. | PloS one 20120101 |
| Calcium-sensing receptor modulates cell adhesion and migration via integrins. | The Journal of biological chemistry 20111125 |
| Stimulation of the calcium-sensing receptor stabilizes the podocyte cytoskeleton, improves cell survival, and reduces toxin-induced glomerulosclerosis. | Kidney international 20110901 |
| Calcimimetics inhibit renal pathology in rodent nephronophthisis. | Kidney international 20110901 |
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| Effects of calcimimetic combined with an angiotensin-converting enzyme inhibitor on uremic cardiomyopathy progression. | American journal of nephrology 20110101 |
| Calcimimetic R-568 effects on activity of R990G polymorphism of calcium-sensing receptor. | Journal of molecular endocrinology 20101001 |
| Calcium-sensing receptor biosynthesis includes a cotranslational conformational checkpoint and endoplasmic reticulum retention. | The Journal of biological chemistry 20100625 |
| Expression of calcium-sensing receptor in quail granulosa explants: a key to survival during folliculogenesis. | Anatomical record (Hoboken, N.J. : 2007) 20100501 |
| Functional expression of the extracellular-Ca2+-sensing receptor in mouse taste cells. | Journal of cell science 20100315 |
| Residue 826 in the calcium-sensing receptor is implicated in the response to calcium and to R-568 calcimimetic compound. | Calcified tissue international 20100301 |
| Differential modulation of intracellular Ca2+ responses associated with calcium-sensing receptor activation in renal collecting duct cells. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101 |
| Effect of the calcimimetic R-568 [3-(2-chlorophenyl)-N-((1R)-1-(3-methoxyphenyl)ethyl)-1-propanamine] on correcting inactivating mutations in the human calcium-sensing receptor. | The Journal of pharmacology and experimental therapeutics 20091201 |
| Discovery and optimization of substituted 1-(1-phenyl-1H-pyrazol-3-yl)methanamines as potent and efficacious type II calcimimetics. | Journal of medicinal chemistry 20091112 |
| Calcium-sensing receptors modulate renin release in vivo and in vitro in the rat. | Journal of hypertension 20091001 |
| Human PTH gene regulation in vivo using transgenic mice. | American journal of physiology. Renal physiology 20090901 |
| R-568 reduces ectopic calcification in a rat model of chronic kidney disease-mineral bone disorder (CKD-MBD). | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090801 |
| The calcimimetic R-568 retards uremia-enhanced vascular calcification and atherosclerosis in apolipoprotein E deficient (apoE-/-) mice. | Atherosclerosis 20090701 |
| Acute cardiovascular effects of the calcimimetic R-568 and its enantiomer S-568 in rats. | Pediatric nephrology (Berlin, Germany) 20090701 |
| The corpuscles of Stannius, calcium-sensing receptor, and stanniocalcin: responses to calcimimetics and physiological challenges. | Endocrinology 20090701 |
| Calcimimetic inhibits late-stage cyst growth in ADPKD. | Journal of the American Society of Nephrology : JASN 20090701 |
| Type II calcimimetics and polycystic kidney disease: unanswered questions. | Journal of the American Society of Nephrology : JASN 20090701 |
| Interstitial fibrosis and microvascular disease of the heart in uremia: amelioration by a calcimimetic. | Laboratory investigation; a journal of technical methods and pathology 20090501 |
| Regulation of PTH mRNA stability by the calcimimetic R568 and the phosphorus binder lanthanum carbonate in CKD. | American journal of physiology. Renal physiology 20090401 |
| Effect of calcium-sensing receptor activation in models of autosomal recessive or dominant polycystic kidney disease. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20090201 |
| Calcification is associated with loss of functional calcium-sensing receptor in vascular smooth muscle cells. | Cardiovascular research 20090201 |
| The new role of calcimimetics as vasculotropic agents. | Kidney international 20090101 |
| A calcimimetic (R-568), but not calcitriol, prevents vascular remodeling in uremia. | Kidney international 20090101 |
| Calcimimetics normalize the phosphate-induced stimulation of PTH secretion in vivo and in vitro. | Journal of nephrology 20090101 |
| The calcimimetic R-568 induces apoptotic cell death in prostate cancer cells. | Journal of experimental & clinical cancer research : CR 20090101 |
| [Calcimimetic or calcitriol? A new class struggle]. | Giornale italiano di nefrologia : organo ufficiale della Societa italiana di nefrologia 20090101 |
| Regulation of mouse lung development by the extracellular calcium-sensing receptor, CaR. | The Journal of physiology 20081215 |
| The extracellular Ca2+-sensing receptor branches out--a new role in lung morphogenesis. | The Journal of physiology 20081215 |
| Novel inactivating mutations of the calcium-sensing receptor: the calcimimetic NPS R-568 improves signal transduction of mutant receptors. | The Journal of clinical endocrinology and metabolism 20081201 |
| Calcimimetic R-568 or calcitriol: equally beneficial on progression of renal damage in subtotally nephrectomized rats. | American journal of physiology. Renal physiology 20080401 |
| N-isopropylsulfinylimines as useful intermediates in the synthesis of chiral amines: expeditive asymmetric synthesis of the calcimimetic (+)-NPS R-568. | The Journal of organic chemistry 20080118 |
| Destabilization of parathyroid hormone mRNA by extracellular Ca2+ and the calcimimetic R-568 in parathyroid cells: role of cytosolic Ca and requirement for gene transcription. | Journal of molecular endocrinology 20080101 |
| CKD-MBD: impact on management of kidney disease. | Clinical and experimental nephrology 20071201 |
| Activation of calcium-sensing receptor accelerates apoptosis in hyperplastic parathyroid cells. | Biochemical and biophysical research communications 20071012 |
| The calcimimetic R-568 increases vitamin D receptor expression in rat parathyroid glands. | American journal of physiology. Renal physiology 20070501 |
| Calcium sensing receptor activators: calcimimetics. | Current medicinal chemistry 20070101 |
| Calcification inhibitors and Wnt signaling proteins are implicated in bovine artery smooth muscle cell calcification in the presence of phosphate and vitamin D sterols. | Calcified tissue international 20061201 |
| Activation of the extracellular calcium-sensing receptor initiates insulin secretion from human islets of Langerhans: involvement of protein kinases. | The Journal of endocrinology 20060901 |
| [Calcium receptor/calcium-sensing receptor]. | Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20060901 |
| Meta-analysis of biochemical and patient-level effects of calcimimetic therapy. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20060501 |
| Pharmacological and clinical properties of calcimimetics: calcium receptor activators that afford an innovative approach to controlling hyperparathyroidism. | Pharmacology & therapeutics 20060301 |
| Acute blood pressure effects and chronic hypotensive action of calcimimetics in uremic rats. | Journal of the American Society of Nephrology : JASN 20060301 |
| Calcimimetic R-568 decreases extraosseous calcifications in uremic rats treated with calcitriol. | Journal of the American Society of Nephrology : JASN 20060301 |
| Increased parathyroid hormone gene expression in secondary hyperparathyroidism of experimental uremia is reversed by calcimimetics: correlation with posttranslational modification of the trans acting factor AUF1. | Journal of the American Society of Nephrology : JASN 20060101 |
| Pharmacological activity of calcimimetic NPS R-568 administered intravenously in rats: dose dependency. | Pharmacological reports : PR 20060101 |
| Role of calcium-phosphorous disorders in the progression of renal failure. | Kidney international. Supplement 20051201 |
| Calindol, a positive allosteric modulator of the human Ca(2+) receptor, activates an extracellular ligand-binding domain-deleted rhodopsin-like seven-transmembrane structure in the absence of Ca(2+). | The Journal of biological chemistry 20051104 |
| [Calcimimetics, mechanisms of action and therapeutic applications]. | Presse medicale (Paris, France : 1983) 20050910 |
| [Apoptosis: a possible mechanism of suppressing parathyroid hyperplasia by calcimimetics]. | Clinical calcium 20050901 |
| [Management of secondary hyperparathyroidism]. | Clinical calcium 20050901 |
| Calcimimetics: a new tool for management of hyperparathyroidism and renal osteodystrophy in patients with chronic kidney disease. | Kidney international. Supplement 20050601 |
| [Calcimimetics--a new treatment for hyperparathyroidism?]. | Polski merkuriusz lekarski : organ Polskiego Towarzystwa Lekarskiego 20050501 |
| Functional proteins involved in regulation of intracellular Ca(2+) for drug development: the extracellular calcium receptor and an innovative medical approach to control secondary hyperparathyroidism by calcimimetics. | Journal of pharmacological sciences 20050301 |
| Calcimimetic NPS R-568 induces hypotensive effect in spontaneously hypertensive rats. | American journal of hypertension 20050301 |
| Calcimimetics and the treatment of primary and secondary hyperparathyroidism. | The Annals of pharmacotherapy 20041101 |
| Calcimimetic compound upregulates decreased calcium-sensing receptor expression level in parathyroid glands of rats with chronic renal insufficiency. | Journal of the American Society of Nephrology : JASN 20041001 |
| Calcimimetics and hyperparathyroidism. | Current opinion in investigational drugs (London, England : 2000) 20041001 |
| Calcimimetic agents for the treatment of secondary hyperparathyroidism. | Seminars in nephrology 20040901 |
| Enantioselective synthesis of primary 1-(aryl)alkylamines by nucleophilic 1,2-addition of organolithium reagents to hydroxyoxime ethers and application to asymmetric synthesis of G-protein-coupled receptor ligands. | The Journal of organic chemistry 20040820 |
| Modulation and action of the calcium-sensing receptor. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20040801 |
| A novel cation-sensing mechanism in osteoblasts is a molecular target for strontium. | Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20040501 |
| Calcimimetic and calcilytic drugs: just for parathyroid cells? | Cell calcium 20040301 |
| [Bone status in primary hyperparathyroidism]. | Nihon rinsho. Japanese journal of clinical medicine 20040201 |
| Calcimimetic agents and secondary hyperparathyroidism: rationale for use and results from clinical trials. | Pediatric nephrology (Berlin, Germany) 20031201 |
| Calcyclin mediates serum response element (SRE) activation by an osteoblastic extracellular cation-sensing mechanism. | Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20031001 |
| Calcimimetic agents: review and perspectives. | Kidney international. Supplement 20030601 |
| Beneficial effects of calcimimetics on progression of renal failure and cardiovascular risk factors. | Journal of the American Society of Nephrology : JASN 20030401 |
| [Calcimimetic agents in the treatment of hyperparathyroidism secondary to chronic renal failure]. | Medicina 20030101 |
| [Calcimimmetic and calcilytics: new perspectives of correction of abnormal parathormone (PTH) secretion]. | Przeglad lekarski 20030101 |
| Calcium sensing receptor activation by a calcimimetic suggests a link between cooperativity and intracellular calcium oscillations. | The Journal of biological chemistry 20021220 |
| Calcimimetics: therapeutic potential in hyperparathyroidism. | Current opinion in pharmacology 20021201 |
| Calcimimetics in the treatment of primary hyperparathyroidism. | Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20021101 |
| Physiological and pharmacological agonists of the extracellular Ca2+-sensing receptor. | European journal of pharmacology 20020705 |
| Future role of calcimimetics in end-stage renal disease. | Advances in renal replacement therapy 20020701 |
| Evidence for distinct cation and calcimimetic compound (NPS 568) recognition domains in the transmembrane regions of the human Ca2+ receptor. | The Journal of biological chemistry 20020524 |
| [Bone changes in primary hyperparathyroidism]. | Nihon rinsho. Japanese journal of clinical medicine 20020301 |
| Calcimimetic agents and secondary hyperparathyroidism: treatment and prevention. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020201 |
| Treatment of secondary hyperparathyroidism with vitamin D derivatives and calcimimetics before and after start of dialysis. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020101 |
| Criteria for calcimimetic agent in the treatment of more severe secondary hyperparathyroidism. | Kidney international 20010101 |
| Prevention of uremic bone disease using calcimimetic compounds. | Annual review of medicine 20010101 |
| Effects of a calcimimetic compound and naturally activating mutations on the human Ca2+ receptor and on Ca2+ receptor/metabotropic glutamate chimeric receptors. | Endocrinology 20001101 |
| Calcimimetics with potent and selective activity on the parathyroid calcium receptor. | Proceedings of the National Academy of Sciences of the United States of America 19980331 |
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