N-((4-DIMETHYLAMINO)PHENYL(HYDROXY)METHYL)MORPHOLINE -4-CARBOTHIOHYDRAZIDE: SYNTHESIS, STRUCTURAL ANALYSIS AND ANTITUMOUR ESSAY

Tóm tắt

N(4)- substituted thiosemicarbazone was a potential class of organic compounds due to its effective bioactivities. In this study, the condensation of 4-dimethylaminobenzaldehyde (4–DB) and N(4)- morpholinylthiosemicarbazide (MT) was conducted in ethanol/glacial acetic acid as a catalyst with the molar 4–DB - MT ratio of 0.89:1 at 750C for 90 mins to obtain N-((dimethylamino)phenyl(hydroxy)methyl) morpholine-4-carbothiohydrazide (H2K), instead of the target thiosemicarbazone. The structure of H2K was analyzed by IR, UV-Vis, 1H ,13C-NMR, HSQC, HMBC, and HRMS. H2K existed the thioketone form in the solid state. In ethanol, there was an equilibrium of thioketone and thiol of H2K. The literature mechanism of the condensation showed that H2K was supposed to be an intermediate prior to the dehydration leading to imine formation. The antitumour performance of H2K for lung cancer (IC50 = 9.37 μg/mL) was greater than that of liver cancer (IC50 = 40.95 μg/mL). Therefore, H2K possesses a comparable antitumour performance in comparison with thiosemicarbozones.