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Diversity synthesis of complex pyridines yields a probe of a neurotrophic signaling pathway.

Abstract
Recognizing the value of including complex pyridines in small-molecule screening collections, we developed a previously unexplored [2 + 2 + 2]-cycloaddition of silyl-tethered diynes with nitriles. The tether provides high regioselectivity, while the solvent THF allows catalytic CpCo(CO)(2) to be used without exogenous irradiation. One of the resulting bicyclic and monocyclic (desilylated) pyridines was identified as an inhibitor of neuregulin-induced neurite outgrowth (EC(50) = 0.30 microM) in a screen that probes a pathway likely to be involved in breast cancers and schizophrenia.
AuthorsB Lawrence Gray, Xiang Wang, W Colby Brown, Letian Kuai, Stuart L Schreiber
JournalOrganic letters (Org Lett) Vol. 10 Issue 13 Pg. 2621-4 (Jul 03 2008) ISSN: 1523-7060 [Print] United States
PMID18510333 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)
Chemical References
  • Nitriles
  • Pyridines
Topics
  • Animals
  • Catalysis
  • Molecular Structure
  • Neurons (drug effects, metabolism)
  • Nitriles (chemistry)
  • PC12 Cells
  • Pyridines (chemical synthesis, chemistry, pharmacology)
  • Rats
  • Signal Transduction (drug effects)

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