473727-83-2

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
• CAS NO: 473727-83-2
• Molecular Formula: C₂₁H₂₃N₃O₅
• Molecular Weight: 397.42442
• Mol File: 473727-83-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 118-120℃
• Boiling Point: 548.67 °C at 760 mmHg
• Flash Point: 285.626 °C
• Appearance: /
• Density: 1.34
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.93±0.50(Predicted)
• CAS DataBase Reference: (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide(473727-83-2)
• EPA Substance Registry System: (R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide(473727-83-2)

Safety Data

• Hazardous Substances Data: 473727-83-2(Hazardous Substances Data)

Usage

Description

(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide, also known as SCH 527123, is a potent CXCR2 antagonist. It is a chemical compound with a complex structure that has been synthesized for specific biological applications. SCH 527123 has the ability to modulate the activity of the CXCR2 receptor, which plays a crucial role in various physiological and pathological processes.

Uses

Used in Pharmaceutical Industry:
SCH 527123 is used as a potent CXCR2 antagonist for inhibiting human colon cancer liver metastasis. By targeting the CXCR2 receptor, it can potentially disrupt the signaling pathways that promote the growth and spread of cancer cells, particularly in the context of liver metastasis from colon cancer.
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide's ability to inhibit the CXCR2 receptor suggests that it may have therapeutic potential in the treatment of other conditions where this receptor is implicated, such as inflammatory diseases and other types of cancer. However, further research and clinical trials are necessary to fully understand the scope of SCH 527123's applications and to determine its safety and efficacy in various medical contexts.

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

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.

Upstream product

• 473732-10-4 2-hydroxy-3-(2-methoxy-3,4-dioxo-cyclobut-1-enylamino)-N,N-dimethyl-benzamide 
• 473732-94-4 (R)-1-(5-methylfuran-2-yl)propan-1-amine 
• 464913-33-5 3-((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)-2-hydroxy-N,N-dimethylbenzamide 
• 464913-11-9 3-amino-2-hydroxy-N,N-dimethylbenzamide 
• 473733-74-3 3-ethoxy-4-[1-(5-methylfuran-2-yl)propylamino]cyclobut-3-en-1,2-dione 
• 66952-65-6 2-hydroxy-N,N-dimethyl-3-nitrobenzamide 
• 620-02-0 5-Methylfurfural 
• 35748-36-8 2-hydroxy-3-nitrobenzoyl chloride 
• 85-38-1 3-nitrosalicylic acid 

Downstream Products

• 862464-58-2 C₂₁H₂₃N₃O₅*H₂O 

Relevant articles and documents

PROCESS FOR CONTROLLED CRYSTAL SIZE IN 1,2-SUBSTITUTED 3,4-DIOXO-1-CYCLOBUTENE COMPOUNDS

This application discloses a novel process for the preparation of 2-Hydroxy-N,N-dimethyl-3-[[2-[[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide, which has utility, for example, in the treatment of CXC chemokine-mediated diseases.

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

Structure-activity studies on lead cyclobutenedione 3 led to the discovery of 4 (SCH 527123), a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist with excellent cell-based activity. Compound 4 displayed good oral bioavailability in rat and may be a potential therapeutic agent for the treatment of various inflammatory diseases.