Solution-phase synthesis of a combinatorial library of 3-[4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides

Molecules. 2005 Feb 28;10(2):444-56. doi: 10.3390/10020444.

Abstract

The parallel solution-phase synthesis of a new combinatorial library of 3-[4-(R1-coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acid amides 9 has been developed. The synthesis involves two steps: 1) the synthesis of core building blocks - 3- [4-(coumarin-3-yl)-1,3-thiazol-2-ylcarbamoyl]propanoic acids, 6 - by the reaction of 3-(omega-bromacetyl)coumarins 1 with 3-amino(thioxo)methylcarbamoylpropanoic acid (5); 2) the synthesis of the corresponding 3-[4-(coumarin-3-yl)-1,3-thiazol-2-yl- carbamoyl]propanoic acids amides 9 using 1,1'-carbonyldimidazole as a coupling reagent. The advantages of the method compared to existing ones are discussed.

Publication types

  • Comparative Study
  • Evaluation Study

MeSH terms

  • Amides / chemical synthesis*
  • Combinatorial Chemistry Techniques*
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Models, Biological
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Small Molecule Libraries / chemical synthesis*
  • Solutions / chemistry*

Substances

  • Amides
  • Coumarins
  • Propionates
  • Small Molecule Libraries
  • Solutions