Novel echinocandin antifungals. Part 2: Optimization of the side chain of the natural product FR901379. Discovery of micafungin

Bioorg Med Chem Lett. 2008 May 1;18(9):2886-90. doi: 10.1016/j.bmcl.2008.03.093. Epub 2008 Apr 8.

Abstract

Further optimization of the potent antifungal activity of side chain analogs of the natural product FR901379 led to the discovery of compound 8 with an excellent, well-balanced profile. Potent compounds with reduced hemolytic potential were designed based upon a disruption of the linearity of the terphenyl lipophilic side chain. The optimized compound (8, FK463, micafungin) displayed the best balance and was selected as the clinical candidate.

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Aspergillus fumigatus / drug effects*
  • Biological Products / chemical synthesis
  • Biological Products / pharmacology*
  • Candida albicans / drug effects*
  • Echinocandins / chemical synthesis
  • Echinocandins / pharmacology*
  • Lipopeptides
  • Lipoproteins
  • Micafungin
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Peptides, Cyclic / chemical synthesis
  • Peptides, Cyclic / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antifungal Agents
  • Biological Products
  • Echinocandins
  • FR 901379
  • Lipopeptides
  • Lipoproteins
  • Peptides, Cyclic
  • Micafungin