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Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam.

Abstract
An improvement of the synthesis of biphenyl-carbamate 2a, the most active analogue of rhazinilam 1 so far, was performed using the Pd-catalyzed borylation/Suzuki coupling (BSC) method developed in our laboratories. The preparation of A-ring analogues of 2a bearing electron-withdrawing or donating groups is reported according to this new synthetic scheme. The antitubulin properties as well as the cytotoxicity of these compounds toward human cancer cell lines were evaluated in comparison with rhazinilam and 2a.
AuthorsOlivier Baudoin, Fabien Claveau, Sylviane Thoret, Audrey Herrbach, Daniel Guénard, Françoise Guéritte
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 10 Issue 11 Pg. 3395-400 (Nov 2002) ISSN: 0968-0896 [Print] England
PMID12213452 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Alkaloids
  • Antineoplastic Agents
  • Indicators and Reagents
  • Indolizines
  • Lactams
  • rhazinilam
  • Palladium
Topics
  • Alkaloids (chemical synthesis, pharmacology)
  • Antineoplastic Agents (chemical synthesis, pharmacology)
  • Catalysis
  • Drug Screening Assays, Antitumor
  • Humans
  • Indicators and Reagents
  • Indolizines
  • Lactams
  • Microtubules (drug effects)
  • Palladium
  • Tumor Cells, Cultured

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