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

Product Name
(R)-2-hydroxy-N,N-dimethyl-3-(2-(1-(5-methylfuran-2-yl)propylamino)-3,4-dioxocyclobut-1-enylamino)benzamide
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
Formula Weight
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 Property

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335May cause respiratory irritation

H341Suspected of causing genetic defects

H361Suspected of damaging fertility or the unborn child

H370Causes damage to organs

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

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

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

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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

Shaanxi Dideu Medichem Co. Ltd
Product
Sch 527123 473727-83-2
Price
US $0.00-0.00/KG
Min. Order
1g
Purity
99%
Supply Ability
2000tons
Release date
2019-12-31

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

  • 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