A concise and diversity-oriented approach to the synthesis of SAG derivatives

J Comb Chem. 2008 Nov-Dec;10(6):825-34. doi: 10.1021/cc800025n. Epub 2008 Aug 28.

Abstract

An efficient and rapid solution-phase combinatorial synthesis of the SAG library was developed. The salient features for this library synthesis is the application of carbothioamide-derived palladacycle-catalyzed Suzuki coupling reactions for the parallel synthesis of a series of pyridine-based biaryl aldehydes under aerobic conditions and a direct N-alkylation of carbamates using NaH as base in DMF in the presence of catalytic amount of water. The resultant library has been submitted to biological screening to evaluate their potential role in the regulation of Hedgehog pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Carbamates / chemistry
  • Combinatorial Chemistry Techniques*
  • Cyclohexylamines / chemical synthesis*
  • Cyclohexylamines / pharmacology
  • Hedgehog Proteins / drug effects
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis
  • Small Molecule Libraries
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacology

Substances

  • Carbamates
  • Cyclohexylamines
  • Hedgehog Proteins
  • Heterocyclic Compounds, 4 or More Rings
  • SAG compound
  • Small Molecule Libraries
  • Thiophenes