1,5-Diaryl-3-oxo-1,4-pentadienes based on (4-oxopiperidin-1-yl)(aryl)methyl phosphonate scaffold: synthesis and antitumor properties

详细信息    查看全文

• 作者：Mikhail V. Makarov ; Ekaterina Yu. Rybalkina230
• 关键词：3 ; 5 ; Bis(arylidene) ; 4 ; piperidones ; Antitumor activity ; Aminophosphonates ; Aryl(methyl) phosphonates ; 1 ; 5 ; Diaryl ; 3 ; oxo ; 1 ; 4 ; pentadienes
• 刊名：Medicinal Chemistry Research
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：26
• 期：1
• 页码：140-152
• 全文大小：
• 刊物主题：Pharmacology/Toxicology; Biochemistry, general; Cell Biology;
• 出版者：Springer US
• ISSN：1554-8120
• 卷排序：26

文摘

Novel 3,5-bis(arylidene)-4-piperidones modified with diethyl[(aryl)methyl]phosphonate moiety attached to the piperidone nitrogen atom have been synthesized by crotonic condensation of aromatic aldehydes with diethyl[(4-oxopiperidin-1-yl)(aryl)methyl]phosphonates in the presence of LiClO₄/Et₃N system or acetonitrile solution of boron trifluoride etherate. The synthesized phosphonate derivatives of 3,5-bis(arylidene)-4-piperidone series displayed inhibitory properties toward RD, PC3, HCT116, and MCF7 human cancer cell lines with IC₅₀ values in the range of 2.5–8.5 μM, as assessed by an in vitro 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay.