Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities.

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.

• Authors: Gang Liu, Shanshan Song, Shiqi Shu, Zehong Miao, Ao Zhang, Chunyong Ding
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 103 Pg. 17-28 (Oct 20 2015) ISSN: 1768-3254 [Electronic] France
• PMID: 26318055 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2015 Elsevier Masson SAS. All rights reserved.

Chemical References

• Antineoplastic Agents
• Artemisinins
• Spiro Compounds
• artemisinin

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Artemisinins (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Humans
• Models, Molecular
• Molecular Structure
• Spiro Compounds (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship