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    Chemistry

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    Also known as: Mpt0e028, 1338320-94-7, T65l58fi65, (e)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-n-hydroxyprop-2-enamide, 2-propenamide, 3-(2,3-dihydro-1-(phenylsulfonyl)-1h-indol-5-yl)-n-hydroxy-, Imofinostat
    Molecular Formula
    C17H16N2O4S
    Molecular Weight
    344.4  g/mol
    InChI Key
    MGTIFSBCGGAZDB-VQHVLOKHSA-N
    FDA UNII
    T65L58FI65
    Imofinostat
    Imofinostat is an orally bioavailable N-hydroxyacrylamide-derived inhibitor of both human pan-histone deacetylase (HDAC) enzymes and the serine/threonine protein kinase Akt (protein kinase B), with potential antineoplastic activity. Upon administration, imofinostat selectively binds to and inhibits HDACs, which inhibits deacetylation of histone proteins and leads to the accumulation of highly acetylated histones. This may result in both an induction of chromatin remodeling, and the selective transcription of tumor suppressor genes. This prevents cell division and induces both cell cycle arrest and apoptosis, which may inhibit the proliferation of susceptible tumor cells. In addition, imofinostat inhibits the phosphorylation and activation of Akt, which prevents the activation of downstream signaling pathways, independent of its HDAC inhibitory activity. HDACs, upregulated in many tumor cell types, are a family of enzymes that deacetylate histone proteins. Akt, overexpressed in many tumor cell types, plays a key role in tumor cell proliferation and survival.
    1 2D Structure

    Imofinostat

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-N-hydroxyprop-2-enamide
    2.1.2 InChI
    InChI=1S/C17H16N2O4S/c20-17(18-21)9-7-13-6-8-16-14(12-13)10-11-19(16)24(22,23)15-4-2-1-3-5-15/h1-9,12,21H,10-11H2,(H,18,20)/b9-7+
    2.1.3 InChI Key
    MGTIFSBCGGAZDB-VQHVLOKHSA-N
    2.2 Other Identifiers
    2.2.1 UNII
    T65L58FI65
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Mpt0e028

    2. 1338320-94-7

    3. T65l58fi65

    4. (e)-3-[1-(benzenesulfonyl)-2,3-dihydroindol-5-yl]-n-hydroxyprop-2-enamide

    5. 2-propenamide, 3-(2,3-dihydro-1-(phenylsulfonyl)-1h-indol-5-yl)-n-hydroxy-

    6. Imofinostat

    7. Unii-t65l58fi65

    8. Imofinostat [inn]

    9. Orb1706952

    10. Schembl2511433

    11. Mgtifsbcggazdb-vqhvlokhsa-n

    12. Glxc-04031

    13. Akos040742169

    14. Ms-25283

    15. Sy461501

    16. Hy-124295

    17. Cs-0086144

    18. G16985

    19. Q27289720

    20. (e)-n-hydroxy-3-[1-(phenylsulfonyl)indolin-5-yl]acrylamide

    21. (2e)-3-[1-(benzenesulfonyl)-2,3-dihydro-1h-indol-5-yl]-n-hydroxyprop-2-enamide

    2.4 Create Date
    2011-10-31
    3 Chemical and Physical Properties
    Molecular Weight 344.4 g/mol
    Molecular Formula C17H16N2O4S
    XLogP31.9
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass Da
    Monoisotopic Mass Da
    Topological Polar Surface Area95.1
    Heavy Atom Count24
    Formal Charge0
    Complexity578
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1

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