Synthesis of models of metabolites: Oxidation of variously substituted chromenes including acronycine, by a porphyrin catalytic system

The influence of chemical neighbouring on oxidation of substituted 2,2‐dimethylchromenes derivatives 5‐8 by a biomimetic catalytic system was first studied. It was then applied to acronycine an anti‐cancer drug in order to obtain in one single step oxidized products resulting from the reactivity of...

Full description

Saved in:
Bibliographic Details
Published in:Journal of heterocyclic chemistry 2005-11, Vol.42 (7), p.1267-1272
Main Authors: Akagah, Bernardin, Estour, François, Vérité, Philippe, Seguin, Elisabeth, Lafont, Olivier, Tillequin, François
Format: Article
Language:English
Subjects:
Chemical Sciences
Life Sciences
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:The influence of chemical neighbouring on oxidation of substituted 2,2‐dimethylchromenes derivatives 5‐8 by a biomimetic catalytic system was first studied. It was then applied to acronycine an anti‐cancer drug in order to obtain in one single step oxidized products resulting from the reactivity of the 1,2‐double bond in the pyranic D‐ring. These 2,2‐dimethylchromenes constitute the structural moiety responsible for the activity of acronycine. This oxidation showed the sensitivity of the ethylenic bond, leading to the formation of the corresponding epoxides, diols and/or ketoalcohol. In the case of 5‐dimethylamino‐2,2‐dimethylchromene 8, the double bond was not sensitive to oxidation, but the N‐methyl groups reacted to lead to the formamide derivative 16 and an imino‐alcohol 17. This methodology applied to acronycine molecule 1, allowed to obtain in one step, two oxidized compounds, a trans‐diol 3 and a ketoalcohol 4 under preparative conditions.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570420704