ChemicalBook > CAS DataBase List > [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid

[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid

Product Name: [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid
CAS No.: 1648843-04-2
Chemical Name: [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid
Synonyms: SX-682;SX-682, 10 mM in DMSO;2-[[[5-[(4-Fluorophenyl)carbamoyl]-2-pyrimidinyl]thio]methyl]-4-(trifluoromethoxy)phenylboronic Acid;(2-(((5-((4-fluorophenyl)carbamoyl)pyrimidin-2-yl)thio)methyl)-4-(trifluoromethoxy)phenyl)boronic acid;[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid;Boronic acid, B-[2-[[[5-[[(4-fluorophenyl)amino]carbonyl]-2-pyrimidinyl]thio]methyl]-4-(trifluoromethoxy)phenyl]-;cells,SX-682,allosteric,SX 682,recruitment,suppressor,Inhibitor,tumor,CXCR,CXC chemokine receptors,SX682,immunity,MDSCs,inhibit,myeloid-derived,antitumor
CBNumber: CB24840361
Molecular Formula: C19H14BF4N3O4S
Formula Weight: 467.2
MOL File: 1648843-04-2.mol

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[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid Property

Density: 1.53±0.1 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (>25 mg/ml)
pka: 8.18±0.53(Predicted)
form: solid
color: Off-white
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI: InChI=1S/C19H14BF4N3O4S/c21-13-1-3-14(4-2-13)27-17(28)12-8-25-18(26-9-12)32-10-11-7-15(31-19(22,23)24)5-6-16(11)20(29)30/h1-9,29-30H,10H2,(H,27,28)
InChIKey: SDUDZBCEHIZMFZ-UHFFFAOYSA-N
SMILES: B(C1=CC=C(OC(F)(F)F)C=C1CSC1=NC=C(C(NC2=CC=C(F)C=C2)=O)C=N1)(O)O

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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

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N-Bromosuccinimide Price

ChemScene

Product number: CS-0067128
Product name: SX-682
Purity: 98.52%
Packaging: 5mg
Price: $150
Updated: 2021/12/16

ChemScene

Product number: CS-0067128
Product name: SX-682
Purity: 98.52%
Packaging: 10mg
Price: $270
Updated: 2021/12/16

ChemScene

Product number: CS-0067128
Product name: SX-682
Purity: 98.52%
Packaging: 25mg
Price: $540
Updated: 2021/12/16

ChemScene

Product number: CS-0067128
Product name: SX-682
Purity: 98.52%
Packaging: 50mg
Price: $870
Updated: 2021/12/16

ChemScene

Product number: CS-0067128
Product name: SX-682
Purity: 98.52%
Packaging: 100mg
Price: $1300
Updated: 2021/12/16

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[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid Chemical Properties,Usage,Production

Description

SX-682 is a novel CXCR1/2 inhibitor (IC50s: CXCR1 = 42 nM, CXCR2 = 20 nM).1?It displayed robust synergistic activity with immune checkpoint blockade against castration resistant prostate cancer.2 It significantly reduced tumor burden in a Ptenfl/fl/Lkb1fl/fl mouse model of lung squamous cell cancer when used in combination with anti-PD1 therapy.3 SX-682 significantly inhibited trafficking of neutrophilic myeloid-derived suppressor cells (PMN-MDSCs) enhancing anti-PD1 immune checkpoint blockade, T cell-based immunotherapy, and NK-cell immunotherapy.4,5

Uses

SX-682 is an orally bioavailable, potent allosteric inhibitor of CXCR1 and CXCR2. SX-682 can block tumor myeloid-derived suppressor cells (MDSCs) recruitment and enhance T cell activation and antitumor immunity[1].

in vivo

SX-682 (50 mg/kg; orally; twice a day on a Monday through Friday) has Meager to moderate effects as single agents on CRPC progression was observed, yet combination with ICB produced strong efficacy^[2].

Animal Model:	C57BL/6NTac-Tyr^tm1Arte?female mice^[2]
Dosage:	50 mg/kg
Administration:	Orally; twice a day on a Monday through Friday
Result:	Has Meager to moderate effects on CRPC progression.

IC 50

CXCR1; CXCR2

References

[1] C. BOSS C R. Substituted cyclopentanes, tetrahydrofurans and pyrrolidines as orexin-1-receptor antagonists for treatment of various CNS disorders (WO2015/055994; WO2015/124932; WO2015/124934)[J]. Expert Opinion on Therapeutic Patents, 2016, 26 1: 409-415. DOI:10.1517/13543776.2016.1124087
[2] XIN LU. Effective combinatorial immunotherapy for castration-resistant prostate cancer[J]. Nature, 2017, 543 7647: 728-732. DOI:10.1038/nature21676
[3] JULIA KARGL. Neutrophil content predicts lymphocyte depletion and anti-PD1 treatment failure in NSCLC.[J]. JCI insight, 2019. DOI:10.1172/jci.insight.130850
[4] LILLIAN SUN. Inhibiting myeloid-derived suppressor cell trafficking enhances T cell immunotherapy.[J]. JCI insight, 2019, 4 7. DOI:10.1172/jci.insight.126853
[5] SARAH GREENE. Inhibition of MDSC Trafficking with SX-682, a CXCR1/2 Inhibitor, Enhances NK-Cell Immunotherapy in Head and Neck Cancer Models.[J]. Clinical Cancer Research, 2020: 1420-1431. DOI:10.1158/1078-0432.ccr-19-2625

[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid Suppliers

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1648843-04-2, [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acidRelated Search:

KU57788(NU7441) Dequalinium chloride BI 2536 Imiquimod

[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid

SX-682

Boronic acid, B-[2-[[[5-[[(4-fluorophenyl)amino]carbonyl]-2-pyrimidinyl]thio]methyl]-4-(trifluoromethoxy)phenyl]-

(2-(((5-((4-fluorophenyl)carbamoyl)pyrimidin-2-yl)thio)methyl)-4-(trifluoromethoxy)phenyl)boronic acid

cells,SX-682,allosteric,SX 682,recruitment,suppressor,Inhibitor,tumor,CXCR,CXC chemokine receptors,SX682,immunity,MDSCs,inhibit,myeloid-derived,antitumor

2-[[[5-[(4-Fluorophenyl)carbamoyl]-2-pyrimidinyl]thio]methyl]-4-(trifluoromethoxy)phenylboronic Acid

SX-682, 10 mM in DMSO

1648843-04-2

C19H14BF4N3O4S