Synthesis and Antitumor Activity of Pinanyl Thiazole Hydrazone Derivatives

Pinanyl thiazole hydrazone derivatives 4a~4n were synthesized from nopinone via addition, condensation and cyclization, and their structures were characterized by FTIR, 1HNMR, 13CNMR and HRMS. The antitumor activities of compounds 4a~4n against four human cancer cell lines including HepG2, RPMI-8226, A549 and MDA-MB-231 were evaluated in vitro. The results showed that compound 4a had the best antitumor activity against the above four cancer cell lines, the IC50 values against HepG2, RPMI-8226, A549 and MDA-MB-231 were as low as 5.8, 8.8, 7.1 and 10.6 μmol/L, respectively. Compound 4c also had stronger activity with the corresponding IC50 values of 8.9, 8.7, 7.3 and 9.7 μmol/L. Cell apoptosis and cell cycle experiments indicated that when the concentration of compound 4a increased from 0 to 40 μmol/L, the total apoptotic rate of A549 cells increased from 6.55% to 47.20%, and the number of cells in G2/M phase increased from 13.50% to 51.72%. It was found that compound 4a could induce apoptosis in A549 cells in a dose-dependent manner and arrest the cell cycle at the G2/M phase. © 2019, Editorial Office of FINE CHEMICALS. All right reserved.