Newly synthesized 3-sulfenylindole derivatives from 4-hydroxydithiocoumarin using an oxidative cross dehydrogenative coupling reaction (OCDCR): potential lead molecules for antiproliferative activity

Santa Mondal, Karuna Mahato, Neha Arora, Dheerendra Kankane, Umed Pratap Singh, Saghir Ali, Aftab Hossain Khan, Siddhartha S. Ghosh, Abu T. Khan

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

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% CuBr2as 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.

Original languageEnglish (US)
Pages (from-to)4104-4113
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume18
Issue number21
DOIs
StatePublished - Jun 7 2020
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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