Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati, 781039 India.
Org Biomol Chem. 2020 Jun 7;18(21):4104-4113. doi: 10.1039/d0ob00054j. Epub 2020 May 20.
An expedient and efficient synthetic method was developed for the oxidative cross dehydrogenative coupling reaction between 4-hydroxydithiocoumarin and indole at the C-3 position regio-selectively using a combination of 10 mol% molecular iodine and TBHP in the presence of 10 mol% CuBr as an additive at room temperature. Mild reaction conditions, good yields and a broad substrate scope are some of the salient features of the present protocol. Additionally, the synthesized 3-sulfenylindoles derived from 4-hydroxydithiocoumarin were converted into biologically active sulfone derivatives. Interestingly, some of the compounds exhibit anti-cell proliferative activity on breast cancer (MCF-7) cells due to reactive oxygen species (ROS) mediated cell damage.
开发了一种简便高效的合成方法，用于在室温下，通过 10mol%分子碘和 TBHP 的组合，在 10mol%CuBr 作为添加剂的条件下，将 4-羟基二硫代香豆素与吲哚在 C-3 位进行区域选择性氧化交叉脱氢偶联反应。该方法具有温和的反应条件、良好的收率和广泛的底物范围等特点。此外，由 4-羟基二硫代香豆素衍生的 3-亚磺酰基吲哚可转化为具有生物活性的砜衍生物。有趣的是，由于活性氧（ROS）介导的细胞损伤，一些化合物对乳腺癌（MCF-7）细胞表现出抗增殖活性。
