Synthesis, anticancer evaluation in vitro, DFT, Hirshfeld surface analysis of some new 4-(1,3-benzothiazol-2-yl)-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one derivatives

A new method for synthesizing compounds having benzothiazole and pyrazole moieties in their backbone has been successfully performed, based on the rearrangement of pyrazolylylidene-pyranopyrazolone in the presence of o-aminothiophenol in hot n-butanol. The new compound has been alkylated with different alkylating agents under phase transfer catalysis conditions. A Hirshfeld surface analysis for visually analyzing intermolecular interactions in crystal structures employing molecular surface contours and 2D fingerprint plots has been used to examine molecular shapes. The gas-phase geometries of the new compound and one alkylated derivative were studied by the DFT-B3LYP method. The anticancer properties of the compounds obtained have been evaluated. In this study, the use of pyrazololylide-pyranopyrazolone rearrangement has been shown to be a new synthetic route for new heterocyclic systems containing benzothiazole and pyrazole moieties. [Display omitted] •A new method for synthesizing compounds having benzothiazole and pyrazole moieties in the backbones is introduced.•This method is based on the rearrangement of pyrazolylylidene-pyranopyrazolone.•The anticancer activity of the new (un)alkylated compounds were tested.