New class of potent antitumor acylhydrazone derivatives containing furan

A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50 = 16.4 μM) was better than doxorubicin (IC50 = 53.3 μM) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery.

Graphical abstractA pair of N-acylhydrazones I and II were synthesized in excellent yields. The antitumor bioassay revealed some compounds exhibited excellent activity. Their toxicities were predicted by in silico methods.Figure optionsDownload full-size imageDownload as PowerPoint slide