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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02375821
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Submitted on : Friday, November 22, 2019 - 11:10:36 AM
Last modification on : Thursday, July 30, 2020 - 3:06:50 AM

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Bernardin Akagah, François Estour, Philippe Vérité, Elisabeth Seguin, Olivier Lafont, et al.. Synthesis of models of metabolites: Oxidation of variously substituted chromenes including acronycine, by a porphyrin catalytic system. Journal of Heterocyclic Chemistry, Wiley, 2005, 42 (7), pp.1267-1272. ⟨10.1002/jhet.5570420704⟩. ⟨hal-02375821⟩

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