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Synthesis, Antitubulin, and Antiproliferative SAR of Analogues of 2-Methoxyestradiol-3,17-O,O-bis-sulfamate

  1. Author:
    Jourdan, F.
    Leese, M. P.
    Dohle, W.
    Hamel, E.
    Ferrandis, E.
    Newman, S. P.
    Purohit, A.
    Reed, M. J.
    Potter, B. V. L.

  2. Author Address

    [Jourdan, Fabrice; Leese, Mathew P.; Dohle, Wolfgang; Potter, Barry V. L.] Univ Bath, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England. [Jourdan, Fabrice; Leese, Mathew P.; Dohle, Wolfgang; Potter, Barry V. L.] Univ Bath, Sterix Ltd, Bath BA2 7AY, Avon, England. [Hamel, Ernest] NCI, Screening Technol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA. [Ferrandis, Eric] Inst Rech Henri Beaufour, F-91966 Les Ulis, France. [Purohit, Atul; Reed, Michael J.] Univ London Imperial Coll Sci Technol & Med, St Marys Hosp, London W2 1NY, England.;Potter, BVL, Univ Bath, Dept Pharm & Pharmacol, Bath BA2 7AY, Avon, England.;B.V.L.Potter@bath.ac.uk
    1. Year: 2010
    2. Date: Apr
  2. Journal: Journal of Medicinal Chemistry
    1. 53
    2. 7
    3. Pages: 2942-2951
  4. Type of Article: Article
  5. ISSN: 0022-2623
  1. Abstract:

    The synthesis and antiproliferative activity of analogues of estradiol 3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent reveal that an H-bond acceptor is essential for high antiproliferative activity. The local environment in which this H-bond acceptor lies can be varied to an extent. The C-17-oxygen linker can be deleted or substituted with an electronically neutral methylene group, and replacement of the terminal NH2 with a methyl group is also acceptable. Mesylates 10 and 14 prove equipotent to the E2bisMATEs 2 and 3, while sulfones 20 and 35 display enhanced in vitro antiproliferative activity. In addition, the SAR of 2-substituted estradiol-3-O-sulfamate derivatives as inhibitors of tubulin polymerization has been established for the first time. These agents inhibit the binding of radiolabeled colchicine to tubulin.

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External Sources

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  2. DOI: 10.1021/jm9018806
  3. View record in Web of Science®
  4. WOS: 000276096300022

Library Notes

  1. Fiscal Year: FY2009-2010
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