An efficient synthesis and antifungal evaluation of natural product streptochlorin and its analogues

Fitoterapia. 2018 Mar:125:106-110. doi: 10.1016/j.fitote.2017.12.017. Epub 2017 Dec 19.

Abstract

Streptochlorin, a small indole alkaloid isolated from marine Streptomyces sp., exhibits a wide range of potent biological activities. An efficient and economic synthetic protocol for streptochlorin has been developed and validated, 4 steps from indole in a total yield of 45%, and further applied for the synthesis of its analogues. Biological testing showed that most of the target compounds exhibited potential antifungal activity in the primary assays, especially compounds 6, 7 and 9c were the most active ones, representing effective activity against the phytopathogenic fungi screened in preliminary test and might be explored for the study of mode of action in the future.

Keywords: Antifungal activities; Natural products; Streptochlorin; Synthesis.

MeSH terms

  • Fungi / drug effects
  • Fungicides, Industrial / chemical synthesis*
  • Fungicides, Industrial / pharmacology*
  • Indoles / chemical synthesis*
  • Indoles / pharmacology*
  • Molecular Structure
  • Oxazoles / chemical synthesis*
  • Oxazoles / pharmacology*
  • Streptomyces / chemistry
  • Structure-Activity Relationship

Substances

  • Fungicides, Industrial
  • Indoles
  • Oxazoles
  • streptochlorin