Format

Send to

Choose Destination
J Org Chem. 2002 Feb 8;67(3):609-19.

Alkylating capacity and reaction products of antimalarial trioxanes after activation by a heme model.

Author information

1
Laboratoire de Chimie de Coordination du CNRS, 205, route de Narbonne, F-31077 Toulouse Cedex 4, France.

Abstract

The reactivity of 1,2,4-trioxane molecules 2-5, structurally related to the antimalarial drug artemisinin, with a heme model, manganese(II) tetraphenylporphyrin, is reported. With the pharmacologically active drugs 2-4, covalent adducts were obtained by addition of a drug-derived radical onto the porphyrin macrocycle, whereas no reaction was obtained with the nonactive compound 5. This confirms that alkylation is probably one of the key factors of the pharmacological activity of endoperoxide-based antimalarial drugs.

PMID:
11855997
DOI:
10.1021/jo010688d
[Indexed for MEDLINE]

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center