Year: 2025
Type: article
Abstract: A BF 3 ·OEt 2 catalyzed chemo‐ and regioselective Michael type addition of indoles with α,β‐unsaturated oxindole esters has been developed to synthesize new designed 3‐indolylmethyl oxindole scaffolds in excellent yields (61%–88%). Notably, the reaction exhibits high site‐selectivity, favoring C‐3 indole addition to the β‐position of the enone moiety while retaining full tolerance to the ester functionality. This metal‐free protocol offers the first selective access to biologically important NH‐free indolyl frameworks in a single step, relevant to naturally occurring indole alkaloids, including those isolated from the indole‐3‐carbinol‐induced culture of Daldinia eschscholzii . In silico studies of the synthesized compounds revealed strong binding affinities to key bacterial enzymes ( Staphylococcus aureus FtsZ, Sortase A, Thioredoxin Reductase) and cancer‐related human proteins (Bcl‐2, KSP, EGFR). Several compounds showed dual‐targeting potential, highlighting their promise as multifunctional therapeutic candidates.
Source: ChemistrySelect
Authors: Supriya Sharma, Amar Nath Singh Chauhan, Ajay Kumar, Rohan D. Erande
Institution: Indian Institute of Technology Jodhpur
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4415629518