Abstract
Alkyl/aralkyl/phenacyl thiotriazolyl isoindoline-1,3-diones were synthesized by the reaction of dipotassium cyanodithioimidocarbonate salt with hydrazine hydrate, phthalic anhydride and alkyl/aralkyl/phenacyl bromides using acetic acid and sodium acetate via a one-pot four-component synthesis. Alternatively, the same final products were also synthesized by the reaction of dipotassium cyanodithioimidocarbonate salt with hydrazine hydrate in presence of acetic acid to give intermediate 5-amino-4H-1,2,4-triazole-3-thiol [I]. This compound was further reacted with phthalic anhydride, followed by a reaction with alkyl/aralkyl/phenacyl bromides to give the title compounds in a two-step process. In this method, the yields are less compared to one-pot four-component synthesis. All the newly synthesized compounds were characterized by their spectral studies (FTIR, 1H-NMR, 13C-NMR, Mass). Further, the synthesized compounds were screened for their in-vitro anticancer activity. Compounds 5 m, 5p, 5r showed good cytotoxic assay against Hela cancer cell lines. Furthermore, compounds 5(a-t) were subjected to their docking analysis and DFT calculations.
Graphical Abstract
Acknowledgement
One of the authors (P.V.K) is thankful to Council of Scientific & Industrial Research (CSIR) – India for research fellowship. We thank the Director, National Institute of Technology, Warangal for providing research facilities. P.V.K is thanks to Dr. Ravinder Pawar (NITW) for study DFT calculations.
Disclosure statement
The authors declared that there is no conflict of interest.