Developing novel C-4 analogues of pyrrole-based antitubulin agents: Weak but critical hydrogen bonding in the colchicine site

Chenxiao Da, Nakul Telang, Kayleigh Hall, Emily Kluball, Peter Barelli, Kara Finzel, Xin Jia, John T. Gupton, Susan L. Mooberry, Glen E. Kellogg

Research output: Contribution to journalArticle

11 Scopus citations

Abstract

The synthesis, biological evaluation and molecular modeling of a series of pyrrole compounds related to 3,5-dibromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2- carboxylic acid that evaluates and optimizes C-4 substituents are reported. The key factor for microtubule depolymerization activity appears to be the presence of an appropriately positioned acceptor for Cys241β in the otherwise hydrophobic subpocket A.

Original languageEnglish (US)
Pages (from-to)417-421
Number of pages5
JournalMedChemComm
Volume4
Issue number2
DOIs
StatePublished - Feb 2013

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry

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    Da, C., Telang, N., Hall, K., Kluball, E., Barelli, P., Finzel, K., Jia, X., Gupton, J. T., Mooberry, S. L., & Kellogg, G. E. (2013). Developing novel C-4 analogues of pyrrole-based antitubulin agents: Weak but critical hydrogen bonding in the colchicine site. MedChemComm, 4(2), 417-421. https://doi.org/10.1039/c2md20320k