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182498-32-4,MFCD00954637
Catalog No.:AA0023UQ

182498-32-4 | Sb 225002

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1mg
98%
in stock  
$25.00   $18.00
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5mg
98%
in stock  
$63.00   $44.00
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10mg
98%
in stock  
$83.00   $58.00
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25mg
98%
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$109.00   $76.00
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50mg
98%
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$142.00   $100.00
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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:
AA0023UQ
Chemical Name:
Sb 225002
CAS Number:
182498-32-4
Molecular Formula:
C13H10BrN3O4
Molecular Weight:
352.1402
MDL Number:
MFCD00954637
SMILES:
O=C(Nc1ccccc1Br)Nc1ccc(cc1O)[N+](=O)[O-]
Properties
Computed Properties
 
Complexity:
390  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
2.6  

Downstream Synthesis Route

[1]Locationinpatent:experimentalpartBakshi,Pancham;Jin,Chao;Broutin,Pierre;Berhane,Beniam;Reed,Jon;Mullan,Michael[BioorganicandMedicinalChemistry,2009,vol.17,#23,p.8102-8112]

[2]CurrentPatentAssignee:GLAXOSMITHKLINEPLC-US5886044,1999,ACurrentPatentAssignee:GLAXOSMITHKLINEPLC-US5780483,1998,A

1592-00-3    121-88-0    182498-32-4   
CASUnavailable 

[1]CurrentPatentAssignee:GLAXOSMITHKLINEPLC-US6262113,2001,B1

Literature

Title: Adiponectin promotes human jaw bone marrow mesenchymal stem cell chemotaxis via CXCL1 and CXCL8.

Journal: Journal of cellular and molecular medicine 20170701

Title: Discovery of 2-[5-(4-Fluorophenylcarbamoyl)pyridin-2-ylsulfanylmethyl]phenylboronic Acid (SX-517): Noncompetitive Boronic Acid Antagonist of CXCR1 and CXCR2.

Journal: Journal of medicinal chemistry 20141023

Title: Chemokine receptor antagonists.

Journal: Journal of medicinal chemistry 20121126

Title: The role of CXCR2 chemokine receptors in the oral squamous cell carcinoma.

Journal: Investigational new drugs 20120801

Title: Epigenetic augmentation of the macrophage inflammatory protein 2/C-X-C chemokine receptor type 2 axis through histone H3 acetylation in injured peripheral nerves elicits neuropathic pain.

Journal: The Journal of pharmacology and experimental therapeutics 20120301

Title: CXCR2 antagonists block the N-Ac-PGP-induced neutrophil influx in the airways of mice, but not the production of the chemokine CXCL1.

Journal: European journal of pharmacology 20111015

Title: Simvastatin regulates CXC chemokine formation in streptococcal M1 protein-induced neutrophil infiltration in the lung.

Journal: American journal of physiology. Lung cellular and molecular physiology 20110601

Title: Simvastatin antagonizes CD40L secretion, CXC chemokine formation, and pulmonary infiltration of neutrophils in abdominal sepsis.

Journal: Journal of leukocyte biology 20110501

Title: CXCL1 and its receptor, CXCR2, mediate murine sickle cell vaso-occlusion during hemolytic transfusion reactions.

Journal: The Journal of clinical investigation 20110401

Title: Chemokine-related gene expression in the brain following ischemic stroke: no role for CXCR2 in outcome.

Journal: Brain research 20110204

Title: Cardiac glycosides are potent inhibitors of interferon-β gene expression.

Journal: Nature chemical biology 20110101

Title: Mechanisms involved in IL-6-induced muscular mechanical hyperalgesia in mice.

Journal: Pain 20101101

Title: The effects of the selective and non-peptide CXCR2 receptor antagonist SB225002 on acute and long-lasting models of nociception in mice.

Journal: European journal of pain (London, England) 20100101

Title: Structural optimization of a CXCR2-directed antagonist that indirectly inhibits gamma-secretase and reduces Abeta.

Journal: Bioorganic & medicinal chemistry 20091201

Title: The angiogenic effect of probiotic Bacillus polyfermenticus on human intestinal microvascular endothelial cells is mediated by IL-8.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20091101

Title: [Selective non-peptide CXCR2 antagonist SB225002 inhibits choroidal neovascularization in rat model].

Journal: [Zhonghua yan ke za zhi] Chinese journal of ophthalmology 20090801

Title: Novel role of CXCR2 in regulation of gamma-secretase activity.

Journal: ACS chemical biology 20081219

Title: The selective nonpeptide CXCR2 antagonist SB225002 ameliorates acute experimental colitis in mice.

Journal: Journal of leukocyte biology 20081001

Title: Hepatocyte signaling through CXC chemokine receptor-2 is detrimental to liver recovery after ischemia/reperfusion in mice.

Journal: Hepatology (Baltimore, Md.) 20081001

Title: CXCR2 chemokine receptor antagonism enhances DOP opioid receptor function via allosteric regulation of the CXCR2-DOP receptor heterodimer.

Journal: The Biochemical journal 20080601

Title: Secreted protein acidic, rich in cysteine induces pulp cell migration via alphavbeta3 integrin and extracellular signal-regulated kinase.

Journal: Oral diseases 20080501

Title: Comparison of N,N'-diarylsquaramides and N,N'-diarylureas as antagonists of the CXCR2 chemokine receptor.

Journal: Bioorganic & medicinal chemistry letters 20070315

Title: Differential calcium signaling in dairy cows with specific CXCR1 genotypes potentially related to interleukin-8 receptor functionality.

Journal: Immunogenetics 20070101

Title: Regulation of matrix metalloproteinase-9 release from IL-8-stimulated human neutrophils.

Journal: Journal of leukocyte biology 20050701

Title: IL-8 increases transmission of HIV type 1 in cervical explant tissue.

Journal: AIDS research and human retroviruses 20050301

Title: Beta 2-adrenergic receptor regulation of human neutrophil function is sexually dimorphic.

Journal: British journal of pharmacology 20041201

Title: Rabbit neutrophil chemotactic protein (NCP) activates both CXCR1 and CXCR2 and is the functional homologue for human CXCL6.

Journal: Biochemical pharmacology 20041115

Title: Cloning and pharmacological characterization of CXCR1 and CXCR2 from Macaca fascicularis.

Journal: The Journal of pharmacology and experimental therapeutics 20040701

Title: Characterization of the molecular interactions of interleukin-8 (CXCL8), growth related oncogen alpha (CXCL1) and a non-peptide antagonist (SB 225002) with the human CXCR2.

Journal: Biochemical pharmacology 20030301

Title: Nonpeptide CXCR2 antagonist prevents neutrophil accumulation in hyperoxia-exposed newborn rats.

Journal: The Journal of pharmacology and experimental therapeutics 20011001

Title: Identification of a potent, selective non-peptide CXCR2 antagonist that inhibits interleukin-8-induced neutrophil migration.

Journal: The Journal of biological chemistry 19980424

Title: White JR, et al. Identification of a potent, selective non-peptide CXCR2 antagonist that inhibits interleukin-8-induced neutrophil migration. J Biol Chem. 1998 Apr 24;273(17):10095-8.

Title: Wang B, et al. A growth-related oncogene/CXC chemokine receptor 2 autocrine loop contributes to cellular proliferation in esophageal cancer. Cancer Res. 2006 Mar 15;66(6):3071-7.

Title: Herz J, et al. Role of Neutrophils in Exacerbation of Brain Injury After Focal Cerebral Ischemia in Hyperlipidemic Mice. Stroke. 2015 Oct;46(10):2916-25.

Title: Wang LY, et al. CXCL5 signaling is a shared pathway of neuroinflammation and blood-brain barrier injury contributing to white matter injury in the immature brain. J Neuroinflammation. 2016 Jan 6;13:6.

Title: Shi ZR, et al. Decrease of galectin-3 in keratinocytes: A potential diagnostic marker and a critical contributor to the pathogenesis of psoriasis. J Autoimmun. 2018 May;89:30-40.

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