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ChemicalBook >  Product Catalog >  Organic Chemistry >  Heterocyclic Compounds >  (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide

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(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide Basic information

Product Name:
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
Synonyms:
  • Sch 527123
  • (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)propylamino)-3
  • (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
  • 3-[[3-[(Dimethylamino)carbonyl]-2-hydroxyphenyl]amino]-4-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]cyclobut-3-ene-1,2-dione
  • SCH527123, Navarixin
  • Benzamide, 2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]-
  • 2-Hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl
CAS:
473727-83-2
MF:
C21H23N3O5
MW:
397.42
Mol File:
473727-83-2.mol
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(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide Chemical Properties

Melting point:
118-120℃
Boiling point:
548.7±60.0 °C(Predicted)
Density 
1.34
storage temp. 
Refrigerator
solubility 
DMSO (Slightly), Methanol (Slightly)
pka
7.93±0.50(Predicted)
form 
Solid
color 
Light Yellow to Yellow
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(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide Usage And Synthesis

Uses

Sch 527123 is a potent CXCR2 antagonist. It can potentially inhibits human colon cancer liver metastasis.

General Description

A cell-permeable, orally active, non-toxic, cyclobutenedione compound with anti-inflammatory properties. Acts as a specific, high-affinity, and potent allosteric antagonist of CXCR2 (IC50 = 2.6 nM for human; Kd = 49, 200, and 80 pM for human, rat, and cynomolgus, respectively). Also exhibits high potency against CXCR1 (IC50 = 36 nM for human, Kd = 3.9 and 41 nM for human and cynomolgus, respectively). Displays excellent selectivity over CXCR3, CCR5, and a large panel of GPCRs, enzymes and ion channels (~ 10 μM). Potently inhibits CXCL1- and CXCL8-induced chemotaxis in human neutrophils (hPMN; IC50<1 nM and 16 nM, respectively). Shown to suppress pulmonary neutrophilia (ED50 = 1.3 mg/kg), goblet cell hyperplasia (ED50 = 700 mg/kg), and increase bronchoalveolar lavage (BAL) mucin content (ED50 ≤ 1 mg/kg) in rats subjected to vanadium pentoxide induced pulmonary inflammation. Inhibits melanoma cell proliferation (~ 1 mg/ml) by suppressing the phosphorylation of ERK1/2. Diminishes the invasive potential of melanoma cells and blocks angiogenesis in mice (100 mg/kg, p.o., q.d for 21 days). Exhibits desirable pharmacokinetic properties.

Please note that the molecular weight for this compound is batch-specific due to variable water content.

Biological Activity

sch-527123 is a novel, selective cxc chemokine receptor 2 (cxcr2) antagonist.sch-527123 was able to suppress cxcr2-mediated signal transduction as shown through decreased phosphorylation of the nf-κb/mitogen-activated protein kinase (mapk)/akt pathway [1].cells were treated with increasing concentrations of sch-527123 for 72 hours and showed dose-dependent growth inhibitory activity with ic50 (72 h) values ranging from 18 to 40 μmol/l. importantly the il-8–overexpressing cells showed a higher ic50 (72 h) concentration of sch-527123 than parental cells [hct116 and e2 (p < 0.005): 28.9 ± 0.02 μmol/l and 39.5 ± 0.01 μmol/l, respectively; caco2 and iiie (p < 0.005): 18.8 ± 0.03 μmol/l and 25.5 ± 0.02 μmol/l, respectively]. therefore, sch-527123 decreased growth inhibitory activity in colorectal cancer cell lines [2].

Biochem/physiol Actions

Cell permeable: yes

target

CXCR1

References

[1]. holz o, khalilieh s, ludwig-sengpiel a et al. sch527123, a novel cxcr2 antagonist, inhibits ozone-induced neutrophilia in healthy subjects. holz o1, khalilieh s, ludwig-sengpiel a et al.
[2]. holz o1, khalilieh s, ludwig-sengpiel a et al. the cxcr2 antagonist, sch-527123, shows antitumor activity and sensitizes cells to oxaliplatin in preclinical colon cancer models. mol cancer ther. 2012 jun;11(6):1353-64.

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamideSupplier

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