Prodrugs of 3-amido bearing pseudomycin analogues: novel antifungal agents

Bioorg Med Chem Lett. 2001 Jul 23;11(14):1881-4. doi: 10.1016/s0960-894x(01)00335-3.

Abstract

With the aim of identifying safer pseudomycin derivatives, we synthesized and evaluated a number of N-acyloxymethyl carbamate linked prodrugs of 3-amido pseudomycin analogues. To our satisfaction, all of the prodrug-amide combinations prepared exhibited good in vivo efficacy against murine Candidiasis. When evaluated in a dose elevation study, all of the newly synthesized combinations (e.g., 4A, 6A, 8A, and 8B) demonstrated improved toxicity profiles in comparison to their corresponding 3-amides as well as the parent pseudomycin B.

MeSH terms

  • Amides / chemistry
  • Amides / pharmacology
  • Animals
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Antifungal Agents / toxicity
  • Aspergillus fumigatus / drug effects
  • Candida albicans / drug effects
  • Candidiasis / drug therapy*
  • Carbamates / chemistry
  • Cryptococcosis / drug therapy*
  • Cryptococcus neoformans / drug effects
  • Disease Models, Animal
  • Mice
  • Microbial Sensitivity Tests
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacology*
  • Peptides, Cyclic / toxicity
  • Prodrugs / chemical synthesis
  • Prodrugs / pharmacology*
  • Prodrugs / toxicity

Substances

  • Amides
  • Antifungal Agents
  • Carbamates
  • Peptides, Cyclic
  • Prodrugs
  • pseudomycin B
  • methyl carbamate