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Chemistry

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Also known as: Sx-682, 1648843-04-2, Unii-h5212r2dpm, H5212r2dpm, (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
Molecular Formula
C19H14BF4N3O4S
Molecular Weight
467.2  g/mol
InChI Key
SDUDZBCEHIZMFZ-UHFFFAOYSA-N
FDA UNII
H5212R2DPM

SX-682
CXCR1/2 Inhibitor SX-682 is an orally bioavailable, selective and reversible antagonist of C-X-C motif chemokine receptors 1 (CXCR1) and 2 (CXCR2), with potential anti-inflammatory and antineoplastic activities. Upon administration CXCR1/2 inhibitor SX-682 selectively and allosterically binds to CXCR 1 and 2 and inhibits their activation by tumor-secreted chemokines. This inhibits CXCR1/2-mediated signaling, reduces both recruitment and migration of immunosuppressive myeloid-derived suppressor cells (MDSCs) and neutrophils in the tumor microenvironment (TME), inhibits inflammatory processes and abrogates the immunosuppressive-induced nature of the TME. This allows effector cells, such as natural killer (NK) cells and cytotoxic T-lymphocytes (CTLs), to kill and eliminate cancer cells. This inhibits tumor cell migration, metastasis, angiogenesis and tumor cell proliferation. CXCR1 and 2, G protein-coupled receptor proteins located on myeloid cells and certain tumor cells, play key roles in the immunosuppressive nature of the TME, tumor metastasis, therapy-resistance and myeloid cell suppression. They play a key role in inflammation and their expression is elevated in several inflammatory-driven diseases.
1 2D Structure

SX-682

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic acid
2.1.2 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)
2.1.3 InChI Key
SDUDZBCEHIZMFZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
B(C1=C(C=C(C=C1)OC(F)(F)F)CSC2=NC=C(C=N2)C(=O)NC3=CC=C(C=C3)F)(O)O
2.2 Other Identifiers
2.2.1 UNII
H5212R2DPM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (2-((5-((4-fluorophenyl)carbamoyl)pyrimidin-2-yl)sulfanylmethyl)-4-(trifluoromethoxy)phenyl)boronic Acid

2. Incb057643

2.3.2 Depositor-Supplied Synonyms

1. Sx-682

2. 1648843-04-2

3. Unii-h5212r2dpm

4. H5212r2dpm

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

6. [2-[[5-[(4-fluorophenyl)carbamoyl]pyrimidin-2-yl]sulfanylmethyl]-4-(trifluoromethoxy)phenyl]boronic Acid

7. (2-(((5-((4-fluorophenyl)carbamoyl)pyrimidin-2-yl)thio)methyl)-4-(trifluoromethoxy)phenyl)boronicacid

8. B-(2-(((5-(((4-fluorophenyl)amino)carbonyl)-2-pyrimidinyl)thio)methyl)-4-(trifluoromethoxy)phenyl)boronic Acid

9. Boronic Acid, B-(2-(((5-(((4-fluorophenyl)amino)carbonyl)-2-pyrimidinyl)thio)methyl)-4-(trifluoromethoxy)phenyl)-

10. Chembl4297480

11. Gtpl10165

12. Sx682

13. Bcp32154

14. Ex-a4295

15. Mfcd28502254

16. S8947

17. Sx 682; Sx682

18. Sb17394

19. Ac-36549

20. Hy-119339

21. Cs-0067128

22. D81536

2.4 Create Date
2015-02-16
3 Chemical and Physical Properties
Molecular Weight 467.2 g/mol
Molecular Formula C19H14BF4N3O4S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Exact Mass467.0734199 g/mol
Monoisotopic Mass467.0734199 g/mol
Topological Polar Surface Area130 Ų
Heavy Atom Count32
Formal Charge0
Complexity606
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


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