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4,5-Diaryl-1H-pyrrole-2-carboxylates as combretastatin A-4/lamellarin T hybrids: Synthesis and evaluation as anti-mitotic and cytotoxic agents

  1. Author:
    Banwell, M. G.
    Hamel, E.
    Hockless, D. C. R.
    Verdier-Pinard, P.
    Willis, A. C.
    Wong, D. J.

  2. Author Address

    Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia. NCI, Toxicol & Pharmacol Branch, Dev Therapeut Program, Div Canc Treatment & Diagnosis,NIH, Frederick, MD 21702 USA.;Banwell, MG, Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia.;mgb@rse.anu.edu.au
    1. Year: 2006
    2. Date: Jul
  2. Journal: Bioorganic & Medicinal Chemistry
    1. 14
    2. 13
    3. Pages: 4627-4638
  4. Type of Article: Article
  5. ISSN: 0968-0896
  1. Abstract:

    The 4,5-diarylated-1H-pyrrole-2-carboxylates 3-8 have each been prepared as hybrids of the potent anti-mitotic agent combretastatin A-4 (1) and the similarly active marine alkaloid lamellarin T (2). The key steps involved selective lithium-for-halogen exchange at C5 within the N-PMB protected 4,5-dibromopyrrole 22 and Negishi cross-coupling of the derived zincated species with the relevant aryl iodide. The ensuing 5-aryl-4-bromopyrrole then engaged in Suzuki-Miyaura cross-coupling with the appropriate arylboronic acid to give the 4,5-diarylated pyrroles 4, 6 and 8. TFA-promoted removal of the N-PMB group within these last compounds then gave the N-unsubstituted congeners 3, 5 and 7. Compounds 3-8 have all been evaluated for their anti-mitotic and cytotoxic properties and two of them, 3 and 5, display useful activities although they are less potent than combretastatin A-4. Crown Copyright (c) 2006 Published by Elsevier Ltd. All rights reserved.

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External Sources

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  2. DOI: 10.1016/j.bmc.2006.02.018
  3. View record in Web of Science®
  4. WOS: 000238182500028

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