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N,N‘-Bisbenzylidenebenzene-1,4-diamines and N,N‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors

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    N,N‘-Bisbenzylidenebenzene-1,4-diamines and N,N‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors
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    Department of Pharmaceutical Chemistry and Department of Neuroscience and Neurology, University of Kuopio, P.O. Box 1627, 70211 Kuopio, Finland, and Department of Neurology, Kuopio University Hospital, P.O. Box 1777, 70211 Kuopio, Finland
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2006, 49, 26, 7907–7911
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    https://doi.org/10.1021/jm060566j
    Published December 6, 2006
    Copyright © 2006 American Chemical Society
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    Abstract

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    A series of N,N‘-bisbenzylidenebenzene-1,4-diamine and N,N‘-bisbenzylidenenaphthalene-1,4-diamine derivatives were synthesized as inhibitors for human sirtuin type 2 (SIRT2). The design of the new compounds was based on two earlier reported hits from molecular modeling and virtual screening. The most potent compound was N,N‘-bis(2-hydroxybenzylidene)benzene-1,4-diamine, which was equipotent with the most potent hit compound and well-known SIRT2 inhibitor sirtinol.

    Copyright © 2006 American Chemical Society

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     To whom correspondence should be addressed. Phone:  +358-17-163714. Fax:  +358-17-162456. E-mail:  [email protected].

    †

     Department of Pharmaceutical Chemistry, University of Kuopio.

    §

     Department of Neuroscience and Neurology, University of Kuopio.

    #

     Current location:  AstraZeneca R&D Mölndal, SC2, Pepparedsleden 1, 431 83 Mölndal, Sweden.

    ‡

     Kuopio University Hospital.

    Supporting Information Available

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    Detailed experimental procedures for the syntheses, NMR spectra, ESI-MS results, and elemental analysis data for the new compounds, in vitro assay for SIRT2 activity, and the docking procedure. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2006, 49, 26, 7907–7911
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm060566j
    Published December 6, 2006
    Copyright © 2006 American Chemical Society
    Request reuse permissions

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