The chemistry and biology of febrifugine and halofuginone.

Abstract

The trans-2,3-disubstituted piperidine, quinazolinone-containing natural product febrifugine (also known as dichroine B) and its synthetic analogue, halofuginone, possess antimalarial activity. More recently studies have also shown that halofuginone acts as an agent capable of reducing fibrosis, an indication with clinical relevance for several disease states. This review summarizes historical isolation studies and the chemistry performed which culminated in the correct structural elucidation of naturally occurring febrifugine and its isomer isofebrifugine. It also includes the range of febrifugine analogues prepared for antimalarial evaluation, including halofuginone. Finally, a section detailing current opinion in the field of halofuginone's human biology is included.

• Authors: Noel P McLaughlin, Paul Evans, Mark Pines
• Journal: Bioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 22 Issue 7 Pg. 1993-2004 (Apr 01 2014) ISSN: 1464-3391 [Electronic] England
• PMID: 24650700 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Review)
• Copyright: Copyright © 2014 Elsevier Ltd. All rights reserved.

Chemical References

• Antimalarials
• Piperidines
• Quinazolines
• Quinazolinones
• febrifugine
• halofuginone

Topics

• Antimalarials (chemistry, isolation & purification, pharmacology)
• Humans
• Molecular Structure
• Parasitic Sensitivity Tests
• Piperidines (chemistry, isolation & purification, pharmacology)
• Plasmodium (drug effects)
• Quinazolines (chemistry, isolation & purification, pharmacology)
• Quinazolinones (chemistry, isolation & purification, pharmacology)
• Structure-Activity Relationship