Dithiocarbamation of spiro-aziridine oxindoles: a facile access to C3-functionalised 3-thiooxindoles as apoptosis inducing agents

Autor:	Shankaraiah Nagula, Jay Prakash Soni, Akash P. Sakla, Biswajit Panda, Kritika Laxmikeshav, Sonal Bhandari, Chandraiah Godugu
Rok vydání:	2021
Předmět:	A549 cell Migration Assay Chemistry Organic Chemistry Acridine orange Aziridine Biochemistry Combinatorial chemistry Oxindoles chemistry.chemical_compound Cell culture DAPI Physical and Theoretical Chemistry Clonogenic assay Ethidium bromide
Zdroj:	Organic & Biomolecular Chemistry. 19:10622-10634
ISSN:	1477-0539 1477-0520
Popis:	Herein, we report the first dithiocarbamation of spiro-aziridine oxindoles involving regiospecific ring-opening by in situ generated nucleophilic dithiocarbamates as an instant source of sulfur. This approach afforded C3-functionalised-3-thiooxindoles in good to excellent yields with wide substrate scope under catalyst-free, and mild reaction conditions. These compounds were screened for their anticancer activity on a panel of human cancer cell lines, wherein compound 3u exhibited significant cytotoxic activity on human lung cancer cells with an IC50 value of 4.31±1.88 μM. Phase contrast microscopy as well as different staining assays such as acridine orange/ethidium bromide (AO/EB), DAPI and DCFDA demonstrated induction of apoptosis in A549 lung cancer cells after the treatment of compound 3u. In addition, clonogenic assay and migration assay ascertained ability of compound 3u to inhibit colony formation and cell migration, respectively in A549 cells in a dose-dependent manner.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c758640c6603c3a51356c655f9182e5a https://doi.org/10.1039/d1ob02102h Zobrazit plný text záznamu