Home Aminos (R)-2-Hydroxy-N,N-dimethyl-3-((2-((1-(5-methylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)benzamide

(R)-2-Hydroxy-N,N-dimethyl-3-((2-((1-(5-methylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)benzamide

CAS No.:
473727-83-2
Catalog Number:
AG0070RI
Molecular Formula:
C21H23N3O5
Molecular Weight:
397.4244
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98+%
1 week
United States
$139
- +
10mg
98+%
1 week
United States
$207
- +
50mg
98%
1 week
United States
$682
- +
100mg
98%
1 week
United States
$1098
- +
Product Description
Catalog Number:
AG0070RI
Chemical Name:
(R)-2-Hydroxy-N,N-dimethyl-3-((2-((1-(5-methylfuran-2-yl)propyl)amino)-3,4-dioxocyclobut-1-en-1-yl)amino)benzamide
CAS Number:
473727-83-2
Molecular Formula:
C21H23N3O5
Molecular Weight:
397.4244
MDL Number:
MFCD16628072
IUPAC Name:
2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobuten-1-yl]amino]benzamide
InChI:
InChI=1S/C21H23N3O5/c1-5-13(15-10-9-11(2)29-15)22-16-17(20(27)19(16)26)23-14-8-6-7-12(18(14)25)21(28)24(3)4/h6-10,13,22-23,25H,5H2,1-4H3/t13-/m1/s1
InChI Key:
RXIUEIPPLAFSDF-CYBMUJFWSA-N
SMILES:
CC[C@H](c1ccc(o1)C)NC1=C(C(=O)C1=O)Nc1cccc(c1O)C(=O)N(C)C
Properties
Complexity:
704  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
397.164g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
397.431g/mol
Monoisotopic Mass:
397.164g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
112A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.1  
Literature
Title Journal
International Union of Basic and Clinical Pharmacology. [corrected]. LXXXIX. Update on the extended family of chemokine receptors and introducing a new nomenclature for atypical chemokine receptors. Pharmacological reviews 20140101
Chemokine receptor antagonists. Journal of medicinal chemistry 20121126
LPS challenge in healthy subjects: an investigation of neutrophil chemotaxis mechanisms involving CXCR1 and CXCR2. International immunopharmacology 20120701
Safety and efficacy of a CXCR2 antagonist in patients with severe asthma and sputum neutrophils: a randomized, placebo-controlled clinical trial. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20120701
The CXCR2 antagonist, SCH-527123, shows antitumor activity and sensitizes cells to oxaliplatin in preclinical colon cancer models. Molecular cancer therapeutics 20120601
Attenuation of leukocyte recruitment via CXCR1/2 inhibition stops the progression of PAH in mice with genetic ablation of endothelial BMPR-II. Blood 20111027
Small molecule antagonists for CXCR2 and CXCR1 inhibit human colon cancer liver metastases. Cancer letters 20110128
A common intracellular allosteric binding site for antagonists of the CXCR2 receptor. British journal of pharmacology 20100401
SCH527123, a novel CXCR2 antagonist, inhibits ozone-induced neutrophilia in healthy subjects. The European respiratory journal 20100301
Neutrophils in chronic inflammatory airway diseases: can we target them and how? The European respiratory journal 20100301
CXCR2 inverse agonism detected by arrestin redistribution. Journal of biomolecular screening 20091001
Diaminocyclobutenediones as potent and orally bioavailable CXCR2 receptor antagonists: SAR in the phenolic amide region. Bioorganic & medicinal chemistry letters 20090801
Small-molecule antagonists for CXCR2 and CXCR1 inhibit human melanoma growth by decreasing tumor cell proliferation, survival, and angiogenesis. Clinical cancer research : an official journal of the American Association for Cancer Research 20090401
Synthesis and structure-activity relationships of new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists. Bioorganic & medicinal chemistry letters 20080315
Future therapeutic treatment of COPD: struggle between oxidants and cytokines. International journal of chronic obstructive pulmonary disease 20070901
A novel, orally active CXCR1/2 receptor antagonist, Sch527123, inhibits neutrophil recruitment, mucus production, and goblet cell hyperplasia in animal models of pulmonary inflammation. The Journal of pharmacology and experimental therapeutics 20070801
Pharmacological characterization of Sch527123, a potent allosteric CXCR1/CXCR2 antagonist. The Journal of pharmacology and experimental therapeutics 20070801
C(4)-alkyl substituted furanyl cyclobutenediones as potent, orally bioavailable CXCR2 and CXCR1 receptor antagonists. Bioorganic & medicinal chemistry letters 20070701
Discovery of 2-hydroxy-N,N-dimethyl-3-{2-[[(R)-1-(5- methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobut-1-enylamino}benzamide (SCH 527123): a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist. Journal of medicinal chemistry 20061228
Properties