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ChemicalBook >> CAS DataBase List >>(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

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide Structure
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide structure
CAS No.
473727-83-2
Chemical Name:
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
Synonyms
Sch 527123;SCH527123, Navarixin;Navarixin (SCH-527123);(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3;inhibit,CXC chemokine receptors,Inhibitor,MK 7123,Navarixin,SCH527123,SCH-527123,MK7123,CXCR;2-Hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl;(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)propyl)aMino)-3,4-dioxocyclobut-1-en-1-yl)aMino)benzaMide;Benzamide, 2-hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]-;3-[[3-[(Dimethylamino)carbonyl]-2-hydroxyphenyl]amino]-4-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]cyclobut-3-ene-1,2-dione
CBNumber:
CB82516091
Molecular Formula:
C21H23N3O5
Molecular Weight:
397.42
MDL Number:
MFCD16628072
MOL File:
473727-83-2.mol
MSDS File:
SDS
Last updated:2024-11-20 17:10:26
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(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide 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
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
InChIKey RXIUEIPPLAFSDF-CYBMUJFWSA-N
SMILES C(N(C)C)(=O)C1=CC=CC(NC2C(=O)C(=O)C=2N[C@@H](C2=CC=C(C)O2)CC)=C1O
FDA UNII 4GMU5HUX5I

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS05,GHS08,GHS07
Signal word  Danger
Hazard statements  H315-H318-H334-H317-H341-H361-H370-H335-H413
Precautionary statements  P201-P202-P260-P264-P270-P272-P273-P280-P284-P302+P352-P304+P341-P305+P351+P338-P310-P308+P313-P321-P362+P364-P333+P313-P342+P311-P363-P405-P501
NFPA 704
0
3 0

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide price More Price(20)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 5.32283 CXCR2 Antagonist IV, Sch527123 - CAS 473727-83-2 - Calbiochem 473727-83-2 5mg $254 2023-01-07 Buy
Cayman Chemical 27800 SCH 527123 473727-83-2 1mg $56 2024-03-01 Buy
Cayman Chemical 27800 SCH 527123 473727-83-2 25mg $1068 2024-03-01 Buy
Cayman Chemical 27800 SCH 527123 473727-83-2 5mg $241 2024-03-01 Buy
Cayman Chemical 27800 SCH 527123 473727-83-2 10mg $455 2024-03-01 Buy
Product number Packaging Price Buy
5.32283 5mg $254 Buy
27800 1mg $56 Buy
27800 25mg $1068 Buy
27800 5mg $241 Buy
27800 10mg $455 Buy

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

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)benzamide Preparation Products And Raw materials

Raw materials

Preparation Products

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

Global( 76)Suppliers
Supplier Tel Email Country ProdList Advantage
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32956 60
Alchem Pharmtech,Inc. 		8485655694 sales@alchempharmtech.com United States 63687 58
CONIER CHEM AND PHARMA LIMITED 		+8618523575427 sales@conier.com China 49374 58
Shaanxi Dideu Medichem Co. Ltd 		+86-29-87569262 +86-15003564040 1087@dideu.com China 3154 58
TargetMol Chemicals Inc. 		+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 32161 58
NINGBOBENKANGJS PHARMTECHCO., LTD 		+8615990591583 15990591583 CHINA 2029 58
InvivoChem 		+1-708-310-1919 +1-13798911105 sales@invivochem.cn United States 6391 58
Hangzhou MolCore BioPharmatech Co.,Ltd. 		+86-057181025280; +8617767106207 sales@molcore.com China 49734 58
TargetMol Chemicals Inc. 		support@targetmol.com United States 38631 58
GIHI CHEMICALS CO.,LIMITED 		+8618058761490 info@gihichemicals.com China 49977 58
Supplier Advantage
ATK CHEMICAL COMPANY LIMITED
60
Alchem Pharmtech,Inc. 		58
CONIER CHEM AND PHARMA LIMITED 		58
Shaanxi Dideu Medichem Co. Ltd 		58
TargetMol Chemicals Inc. 		58
NINGBOBENKANGJS PHARMTECHCO., LTD 		58
InvivoChem 		58
Hangzhou MolCore BioPharmatech Co.,Ltd. 		58
TargetMol Chemicals Inc. 		58
GIHI CHEMICALS CO.,LIMITED 		58

View Lastest Price from (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sch 527123 pictures 2025-01-03 Sch 527123
473727-83-2
 US $0.00-0.00 / KG 1g 99% 2000tons Shaanxi Dideu Medichem Co. Ltd
Navarixin pictures 2024-11-19 Navarixin
473727-83-2
 US $34.00-123.00 / mg 98.63% 10g TargetMol Chemicals Inc.
  • Sch 527123 pictures
  • Sch 527123
    473727-83-2
  • US $0.00-0.00 / KG
  • 99%
  • Shaanxi Dideu Medichem Co. Ltd
  • Navarixin pictures
  • Navarixin
    473727-83-2
  • US $34.00-123.00 / mg
  • 98.63%
  • TargetMol Chemicals Inc.

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

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide(473727-83-2)1HNMR

473727-83-2((R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide)Related Search:

Pyrazinecarboxamide, 3-amino-6-chloro-5-[(3S)-4-[1-[(4-chlorophenyl)methyl]-4-piperidinyl]-3-ethyl-1-piperazinyl]- (9CI) R(+)-7-CHLORO-8-HYDROXY-3-METHYL-1-PHENYL-2,3,4,5-TETRAHYDRO-1H-3-BENZAZEPINE HYDROCHLORIDE 2-(2-FURANYL)-7-[3-(4-METHOXYPHENYL)PROPYL]-7H-PYRAZOLO[4,3-E][1,2,4]TRIAZOLO[1,5-C]PYRIMIDIN-5-AMINE N,N-Dimethylaniline 2,6-Dimethylaniline
2,6-Lutidine

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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 inhibit,CXC chemokine receptors,Inhibitor,MK 7123,Navarixin,SCH527123,SCH-527123,MK7123,CXCR Navarixin (SCH-527123) 473727-83-2