The application of tandem aza-wittig reaction to synthesize artemisinin-guanidine hybrids and their anti-tumor activity

Arch Pharm (Weinheim). 2011 Oct;344(10):631-8. doi: 10.1002/ardp.201000363. Epub 2011 Aug 25.

Abstract

Three series of novel artemisinin-guanidine hybrids 4a-4f, 8a-8h and 9a-9h have been facilely synthesized via four-component reaction (aza-Wittig reaction) and evaluated for their anti-tumor activities against A549, HT-29 and MDA-MB-231 cell lines in vitro. All of the tested compounds showed enhanced anti-tumor activities with IC(50) values ranging from 0.02 µM to 12.0 µM as compared to DHA (dihydroartemisinin). Among them, artemisinin derived dimers, compounds 9b (IC(50) = 0.05 µM), 9d (IC(50) = 0.06 µM) and 9f (IC(50) = 0.02 µM) were found to be most active against HT29 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Artemisinins / chemistry*
  • Aza Compounds / chemistry*
  • Cell Culture Techniques
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • Guanidine / chemistry*
  • Humans
  • Molecular Structure
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Artemisinins
  • Aza Compounds
  • artemisinin
  • Guanidine