Indolizines Enabling Rapid Uncaging of Alcohols and Carboxylic Acids by Red Light-Induced Photooxidation.,Organic Letters

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Indolizines Enabling Rapid Uncaging of Alcohols and Carboxylic Acids by Red Light-Induced Photooxidation.
Organic Letters ( IF 4.9 ) Pub Date : 2020-07-03 , DOI: 10.1021/acs.orglett.0c01799
Kenji Watanabe ₁ , Nodoka Terao ₁ , Isao Kii _{1,

2,

3} , Reiko Nakagawa ₄ , Takashi Niwa ₁ , Takamitsu Hosoya _{1,

5}

Affiliation

The irradiation of red light-emitting-diode light (λ = 660 nm) to 3-acyl-2-methoxyindolizines in the presence of a catalytic amount of methylene blue triggered the photooxidation of the indolizine ring, resulting in a nearly quantitative release of alcohols or carboxylic acids within a few minutes. The method was applicable for photouncaging various functional molecules such as a carboxylic anticancer drug and a phenolic fluorescent dye from the corresponding indolizine conjugates, including an insulin–indolizine–dye conjugate.

中文翻译：

吲哚嗪使红光诱导的光氧化作用迅速释放出醇和羧酸。

在催化量的亚甲基蓝的存在下，将红色发光二极管光（λ= 660 nm）照射到3-酰基-2-甲氧基吲哚并引发吲哚嗪环的光氧化，从而导致几乎定量地释放出醇类或在几分钟内用羧酸。该方法适用于从相应的吲哚利嗪缀合物（包括胰岛素-吲哚嗪-染料缀合物）中对各种功能分子（例如羧酸抗癌药和酚类荧光染料）进行光解开。

更新日期：2020-07-17

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