Novel spirobicyclic artemisinin analogues (artemalogues)

Synthesis and antitumor activities

Gang Liu, Shanshan Song, Shiqi Shu, Zehong Miao, Ao Zhang, Chunyong Ding

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The sesquiterpene lactone framework of artemisinin was used as a drug repositioning prototype for the development of novel antitumor drugs. Several series of novel artemisinin analogues (artemalogues) were designed and synthesized through 1,3-dipolar cycloaddition of artemisitene with nitrile oxides or nitrones. The isoxazolidine-containing spirobicyclic artemalogue 11b turns out to be the most potent with low micromolar IC50 values against all three tumor cells, which were at least 4-to 14-fold more potent than the parent artemisinin.

Original languageEnglish (US)
Pages (from-to)17-28
Number of pages12
JournalEuropean Journal of Medicinal Chemistry
Volume103
DOIs
StatePublished - Oct 20 2015
Externally publishedYes

Fingerprint

Drug Repositioning
Nitriles
Cycloaddition
Sesquiterpenes
Cycloaddition Reaction
Lactones
Antineoplastic Agents
Oxides
Inhibitory Concentration 50
Tumors
Cells
Pharmaceutical Preparations
artemisinine
Neoplasms
artemisitene
nitrones

Keywords

  • 1 3-dipolar cycloaddition
  • Antiprolifereative effect
  • Artemisinin
  • Spirobicyclic artemalogues
  • Stereoconfiguration

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Novel spirobicyclic artemisinin analogues (artemalogues) : Synthesis and antitumor activities. / Liu, Gang; Song, Shanshan; Shu, Shiqi; Miao, Zehong; Zhang, Ao; Ding, Chunyong.

In: European Journal of Medicinal Chemistry, Vol. 103, 20.10.2015, p. 17-28.

Research output: Contribution to journalArticle

Liu, Gang ; Song, Shanshan ; Shu, Shiqi ; Miao, Zehong ; Zhang, Ao ; Ding, Chunyong. / Novel spirobicyclic artemisinin analogues (artemalogues) : Synthesis and antitumor activities. In: European Journal of Medicinal Chemistry. 2015 ; Vol. 103. pp. 17-28.
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