Synthesis and chemical structure elucidation of [(E)-2-(2,6-dichlorobenzylidene)-N-ethylhydrazinecarbothioamide] and cytotoxicity activity against human cancer cells

• Published in: Journal of molecular structure 2024-06, Vol.1305, p.137792, Article 137792
• Main Authors: Briñez-Ortega, Edwin, Chaves, Sebastián, Aguilar-Muñoz, Gonzalo Andrés, Sandoval-Hernández, Adrián G., Viasus Pérez, Camilo J., Burgos, A.E.
• Format: Article
• Language: English
• Subjects: Cancer cells; Cytotoxicity; Drug resistance; Schiff bases; Thiosemicarbazones
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2024.137792

•[(E)-2-(2,6-dichlorobenzylidene)-N-ethylhydrazinecarbothioamide] from solvent free reaction.•Crystallization of the E-isomer as plates generated its stability in a solid state.•E-isomer inhibit the A549 and PC3 human cancer cells growth.•E-isomer is cytotoxic to PC3 (IC50 = 2,51 ± 0,575 µM) and A549 (IC50 = 4.75 ± 1.68 µM) cells. The E-isomer derived from thiosemicarbazone was obtained by reacting 4-ethylthiosemicarbazide with 2,6-dichlorobenzaldehyde. This compound was characterized by UV, IR and NMR spectrometry and its crystal structure was determined by single-crystal XRD. The cytotoxic activity of the compound was determined against PC3 (prostate cancer), A549 (human lung carcinoma) and U87MG (human glioblastoma) cells. The compound [(E)-2-(2,6-dichlorobenzylidene)-N-ethylhydrazinecarbothiamide] inhibited the growth of PC3 (IC50 = 2.51 ± 0.575 µM) and A549 (IC50 = 4.75 ± 1.68 µM) cells. Compared with Ceramide (IC50 = 10 µM) the thiosemicarbazone-induced inhibition of both cancer cell lines was found to be significant.