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    SX-682

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    DIGITAL CONTENT

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    2D Structure
    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
    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

    2D Structure

    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.)