Efficient Routes to a Diverse Array of Amino Alcohol-Derived Chiral Fragments

ACS Comb Sci. 2016 Sep 12;18(9):569-74. doi: 10.1021/acscombsci.6b00050. Epub 2016 Aug 12.

Abstract

Efficient syntheses of chiral fragments derived from chiral amino alcohols are described. Several unique scaffolds were readily accessed in 1-5 synthetic steps leading to 45 chiral fragments, including oxazolidinones, morpholinones, lactams, and sultams. These fragments have molecular weights ranging from 100 to 255 Da and are soluble in water (0.085 to >15 mM).

Keywords: amino alcohols; chiral fragments; drug discovery; fragment-based lead discovery.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Alcohols / analysis*
  • Amino Alcohols / chemistry*
  • Drug Discovery
  • Humans
  • Lactams / chemistry
  • Molecular Weight
  • Morpholines / chemistry
  • Naphthalenesulfonates / chemistry
  • Oxazolidinones / chemistry
  • Stereoisomerism

Substances

  • Amino Alcohols
  • Lactams
  • Morpholines
  • Naphthalenesulfonates
  • Oxazolidinones
  • naphthosultone