Synthesis of Methoxy Analogues of Coenzyme Q10 Metabolites from Parsley Seed Extracts via Baeyer–Villiger Rearrangement of Carbonyl-Substituted Polyalkoxybenzenes

Synthesis Pub Date : 2024-06-18 DOI:10.1055/s-0043-1775368
Dmitry V. Demchuk, Olga I. Adaeva, Dmitry V. Tsyganov, Darina I. Nasyrova, Roman A. Dolotov, Еgor А. Muravsky, Alexander E. Varakutin, Alexander V. Samet, Victor V. Semenov
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Abstract

Based on the parsley seed main component, apiol, efficient approach to polymethoxyquinone C3- and C4-acids was developed. The key step of this approach is Baeyer–Villiger rearrangement of carbonyl-substituted polyalkoxybenzenes derived from parsley seed extracts. These acids are the MeO-analogues of natural antioxidants – metabolites of ubiquinone and idebenone. Due to antioxidant properties, they are the potential therapeutic candidates for the treatment of mitochondrial dysfunction.

Abstract Image

通过羰基取代的多烷氧基苯的拜尔-维利格重排从欧芹籽提取物中合成辅酶 Q10 代谢物的甲氧基类似物
以欧芹种子的主要成分芹醇为基础,开发出了一种高效的 C3- 和 C4-酸多甲氧基醌方法。该方法的关键步骤是对从欧芹籽提取物中提取的羰基取代的多烷氧基苯进行拜耳-维利格重排。这些酸是天然抗氧化剂--泛醌和idebenone的代谢物--的MeO-类似物。由于具有抗氧化特性,它们是治疗线粒体功能障碍的潜在候选疗法。
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