Synthesis and antimalarial activities of optically active labdane-type diterpenes

An efficient method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8 is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9, and synthetic hydroxybutenolides 6 and 7 via a furan photosensitised oxygenation reaction of labdafuran...

Full description

Saved in:
Bibliographic Details
Published in:Natural product research 2009-01, Vol.23 (10), p.891-902
Main Authors: Villamizar, José, Pittelaud, Jean P., Rodrigues, Juan R., Gamboa, Neira, Canudas, Nieves, Tropper, Eleonora, Salazar, Franklin, Fuentes, Juan
Format: Article
Language:English
Subjects:
Animals
antimalarial activities
Antimalarials - chemical synthesis
Antimalarials - chemistry
Antimalarials - pharmacology
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - pharmacology
Hedychium coronarium
labdane-type diterpenes
Magnetic Resonance Spectroscopy
Male
Mice
Molecular Structure
Plasmodium berghei - drug effects
synthesis
Zingiberaceae - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:An efficient method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8 is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9, and synthetic hydroxybutenolides 6 and 7 via a furan photosensitised oxygenation reaction of labdafuran (14). Compounds 5, 6, 7 and 9 were evaluated as inhibitors of the β-haematin formation and globin proteolysis, and then were assayed in a malarial murine model. Compound 9 was the most promising compound, showing a positive correlation between in vitro and in vivo activities.
ISSN:1478-6419
1478-6427
DOI:10.1080/14786410802164048