Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A

Org Biomol Chem. 2014 Oct 14;12(38):7591-7. doi: 10.1039/c4ob01149j.

Abstract

Total synthesis of cryptocin, a fungus metabolite, was achieved based on the biosynthetic hypothesis. A variety of derivatives of cryptocin, equisetin and fusarisetin A were prepared, wherein the racemization of C-3 and diastereoselectivity of C-5 were investigated. We further examined their inhibitory effects on breast cancer cell survival and metastasis, and summarized the structure-activity relationship.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Chemistry Techniques, Synthetic
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Heterocyclic Compounds, 4 or More Rings / pharmacology*
  • Humans
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacology*
  • Oxidation-Reduction
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry
  • Pyrrolidinones / pharmacology*
  • Structure-Activity Relationship
  • Substrate Specificity
  • Tetrahydronaphthalenes / chemical synthesis*
  • Tetrahydronaphthalenes / chemistry
  • Tetrahydronaphthalenes / pharmacology*

Substances

  • Antineoplastic Agents
  • Heterocyclic Compounds, 4 or More Rings
  • Naphthalenes
  • Pyrroles
  • Pyrrolidinones
  • Tetrahydronaphthalenes
  • cryptocin
  • fusarisetin A
  • equisetin