Baylis-Hillman reaction: convenient ascending syntheses and biological evaluation of acyclic deoxy monosaccharides as potential antimycobacterial agents

Bioorg Med Chem. 2002 Oct;10(10):3187-96. doi: 10.1016/s0968-0896(02)00210-9.

Abstract

A series of acyclic deoxy carbohydrate derivatives from easily available carbohydrate enals 1, 2, 3 or 5 were prepared involving the Baylis-Hillman reaction. These newly formed carbohydrate based Baylis-Hillman adducts and their amino derivatives were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H(37)R(v). Among the compounds evaluated for their antimycobacterial activity, compound (10) showed the desired activity in the range of 3.125 microg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylonitrile / chemistry
  • Amino Sugars / chemical synthesis
  • Amino Sugars / pharmacology
  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / pharmacology
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / pharmacology
  • Butanones / chemistry
  • Deoxy Sugars / chemical synthesis*
  • Deoxy Sugars / pharmacology
  • Mycobacterium tuberculosis / drug effects
  • Structure-Activity Relationship

Substances

  • Amino Sugars
  • Anti-Bacterial Agents
  • Antitubercular Agents
  • Butanones
  • Deoxy Sugars
  • 3-buten-2-one
  • Acrylonitrile