Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms.,The Journal of Organic Chemistry

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Mechanisms of Orthogonal Photodecarbonylation Reactions of 3-Hydroxyflavone-Based Acid-Base Forms.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-01-24 , DOI: 10.1021/acs.joc.9b03248
Marina Russo ₁ , Peter Štacko ₁ , Dana Nachtigallová ₂ , Petr Klán ₁

Affiliation

Carbon monoxide is a naturally occurring gasotransmitter combining inherent toxicity with a remarkable therapeutic potential and arduous administration. Photoactivatable carbon monoxide-releasing molecules (photoCORMs) are chemical agents that allow for precise spatial and temporal control over the CO release. In this work, we present a comprehensive mechanistic study of the photochemical CO release from 3-hydroxy-2-phenyl-4H-chromen-4-one, a π-extended 3-hydroxyflavone photoCORM, in methanol using steady-state and transient absorption spectroscopies and quantum chemical calculations. The multiplicity of the productive excited states and the role of oxygen (O2) in the CO production are emphasized, revealing a photoreaction dichotomy of the 3-hydroxyflavone acid and base forms. The utilization of three major orthogonal mechanistic pathways, all of which lead to the CO release, can fuel future endeavors to improve the CO release efficacy of 3-hydroxyflavone-based derivatives and refine their potential medical applications as photoCORMs.

中文翻译：

3-羟基黄酮基酸基形式的正交光脱羰反应机理

一氧化碳是一种天然存在的气体递质，具有固有的毒性，显着的治疗潜力和艰巨的给药方式。可光激活的一氧化碳释放分子（photoCORM）是化学试剂，可对CO释放进行精确的时空控制。在这项工作中，我们使用稳态和瞬态吸收技术，对甲醇中π扩展的3-羟基黄酮photoCORM的3-羟基-2-苯基-4H-铬n-4-one释放光化学CO的机理进行了全面的研究。光谱学和量子化学计算。强调了生产激发态的多样性以及氧气（O2）在CO生产中的作用，揭示了3-羟基黄酮酸和碱形式的光反应二分法。利用三种主要的正交机制途径，

更新日期：2020-01-26

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