Novel chiral ferrocenylpyrazolo[1,5-a][1,4]diazepin-4-one derivatives - Synthesis, characterization and inhibition against lung cancer cells

作者：Shen, Shi-Li; Shao, Jin-Hui; Luo, Ji-Zhuang; Liu, Jin-Ting; Miao, Jun-Ying^*; Zhao, Bao-Xiang

来源：European Journal of Medicinal Chemistry, 2013, 63: 256-268.

DOI：10.1016/j.ejmech.2013.02.016

• Pyrazole
• Ferrocene
• Chiral diazepinone
• Lung cancer cells
• Cell cycle arrest
• Apoptosis

A series of novel 2-ferrocenyl-7-hydroxy-5-phenethyl-5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one derivatives with optical activity (2) was synthesized in the microwave-assisted condition and characterized by means of IR, H-1 NMR and mass spectroscopy, and furthermore confirmed by X-ray analysis of a representative compound (R)-2a. Preliminary biological evaluation showed that some compounds could suppress the growth of A549, H322 and H1299 lung cancer cells. Among the tested compounds, 2b-d were more effective and might perform their action through cell cycle arrest for A549 cell. Whereas these compounds inhibited growth of H1299 and H322 cells by inducing apoptosis. The anti-tumor activities of these compounds were related to the nature of substituents in benzene moiety. In addition, the results indicated also that compounds 2b-d possessed notable cytotoxicity and selectivity for A549 vs H1299 and H322 lung cancer cells.

• 出版日期2013-5
• 单位山东大学