Synthesis of antitumor marine alkaloid discorhabdin A oxa analogues

Org Lett. 2009 Sep 17;11(18):4048-50. doi: 10.1021/ol901471r.

Abstract

Discorhabdin A (1) exhibits a strong cytotoxic activity in vitro, but it is difficult to synthesize and handle due to the instability of its highly strained N,S-acetal structure. We then designed the analogues of discorhabdin A which also have strong cytotoxic activity and stability. The synthesis and examination of the biological activity of various types of stable discorhabdin A oxa analogues (2) were achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals
  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Drug Screening Assays, Antitumor*
  • Marine Biology*
  • Oxytocin / analogs & derivatives*
  • Oxytocin / chemical synthesis
  • Oxytocin / chemistry
  • Quinones / chemical synthesis*
  • Quinones / chemistry
  • Quinones / pharmacology
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship
  • Thiazepines / chemical synthesis*
  • Thiazepines / chemistry
  • Thiazepines / pharmacology

Substances

  • Acetals
  • Alkaloids
  • Antineoplastic Agents
  • Quinones
  • Spiro Compounds
  • Thiazepines
  • discorhabdin A
  • Oxytocin
  • oxytocin, Asp(5)-