2. Academic Validation
  3. Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities

Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities

  • Bioorg Med Chem. 2017 Jun 15;25(12):3206-3214. doi: 10.1016/j.bmc.2017.04.012.
John T Gupton 1,  Scott Yeudall 2,  Nakul Telang 2,  Megan Hoerrner 2,  Ellis Huff 2,  Evan Crawford 2,  Katie Lounsbury 2,  Michael Kimmel 2,  William Curry 2,  Andrew Harrison 2,  Wen Juekun 2,  Alex Shimozono 2,  Joe Ortolani 2,  Kristin Lescalleet 2,  Jon Patteson 2,  Veronica Moore-Stoll 2,  Cristina C Rohena 3,  Susan L Mooberry 3,  Ahmad J Obaidullah 4,  Glen E Kellogg 4,  James A Sikorski 5
Affiliations

Affiliations

  • 1 Department of Chemistry, University of Richmond, Richmond, VA 23173, USA. Electronic address: jgupton@richmond.edu.
  • 2 Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
  • 3 Department of Pharmacology and Cancer Therapy & Research Center, University of Texas Health Science Center at San Antonio, San Antonio, TX 78229, USA.
  • 4 Department of Medicinal Chemistry & Institute of Structural Biology, Drug Discovery and Development, Virginia Commonwealth University, Richmond, VA 23298, USA.
  • 5 Chemistry and Drug Discovery, Chesterfield, MO 63005, USA.
PMID: 28433513 DOI: 10.1016/j.bmc.2017.04.012
Abstract

New microtubule depolymerizing agents with potent cytotoxic activities have been prepared with a 5-cyano or 5-oximino group attached to a pyrrole core. The utilization of ortho activation of a bromopyrrole ester to facilitate successful Suzuki-Miyaura cross-coupling reactions was a key aspect of the synthetic methodology. This strategy allows for control of regiochemistry with the attachment of four completely different groups at the 2, 3, 4 and 5 positions of the pyrrole scaffold. Biological evaluations and molecular modeling studies are reported for these examples.

Keywords

Cytotoxic activity; Marine natural products; Microtubule inhibitors; Pyrrole; Suzuki-Miyaura cross-coupling.

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