12-Amino-andrographolide analogues: synthesis and cytotoxic activity

Arch Pharm Res. 2013 Dec;36(12):1454-64. doi: 10.1007/s12272-013-0152-0. Epub 2013 May 25.

Abstract

Andrographolide, a diterpenoid lactone of the plant Andrographis paniculata, has been shown to be cytotoxic against various cancer cells in vitro. In the present study, a series of β-amino-γ-butyrolactone analogues has been synthesized from naturally occurring andrographolide via one pot tandem aza-conjugate addition-elimination reaction. By using economic procedure without any base or catalyst at room temperature, the products obtained were in fair to excellent yields with high stereoselectivity. The cytotoxicity of all new amino analogues were evaluated against six cancer cell lines and revealed their potential for being developed as promising anti-cancer agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Andrographis*
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cytotoxins / chemical synthesis*
  • Cytotoxins / isolation & purification
  • Cytotoxins / pharmacology
  • Diterpenes / chemical synthesis*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology
  • Drug Screening Assays, Antitumor / methods
  • Humans
  • MCF-7 Cells
  • Mice
  • Plant Components, Aerial*
  • Rats
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Cytotoxins
  • Diterpenes
  • andrographolide