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A diaryl sulfide, sulfoxide, and sulfone bearing structural similarities to combretastatin A-4

  1. Author:
    Barbosa, E. G.
    Bega, L.
    Beatriz, A.
    Sarkar, T.
    Hamel, E.
    do Amaral, M. S.
    de Lima, D. P.

  2. Author Address

    Barbosa, Euzebio G.; Bega, Luis A. S.; Beatriz, Adilson, de Lima, Denis Pires] Univ Fed Mato Grosso do Sul, Dept Quim, CCET, Lab LP4, BR-79070900 Campo Grande, MS, Brazil. [Sarkar, Taradas, Hamel, Ernest] NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diag,NIH, Frederick, MD 21702 USA. [do Amaral, Marcos S.] Univ Fed Mato Grosso do Sul, Dept Fis, CCET, LAB2M, BR-79070900 Campo Grande, MS, Brazil.
    1. Year: 2009
  2. Journal: European Journal of Medicinal Chemistry
    1. 44
    2. 6
    3. Pages: 2685-2688
  4. Type of Article: Article
  1. Abstract:

    Studies examining various spacer groups that link the two aromatic rings of combretastatin A-4 (CA4) have shown that the biological activity of analogs does not require the cis-stilbene configuration of CA4. Oxygen or nitrogen, carbonyl, methylene and ethylene spacers, for example, are present in CA4 analogs that show good activity. Up to now sulfur was not tested for this purpose. In this article we describe the synthesis of sulfide, sulfoxide and sulfone spacers between two aromatic rings comparable to those of CA4. We also compared them with CA4 for inhibitory effects on cell growth, tubulin polymerization, and the binding of [H-3]colchicine to tubulin. We found that the sulfide is highly active and may be a lead compound for the preparation of antitumor compounds. (C) 2008 Elsevier Masson SAS. All rights reserved.

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  2. DOI: 10.1016/j.ejmech.2008.12.018
  3. PMID: 19135763

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