3,5-bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3,5-bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone
• 英文别名: (3E,5E)-3,5-bis[4-(diethylamino)benzylidene]-1-methylpiperidin-4-one；3,5-bis((E)-4-(diethylamino)benzylidene)-1-methylpiperidin-4-one；(3E,5E)-3,5-bis[[4-(diethylamino)phenyl]methylidene]-1-methylpiperidin-4-one
• 化学式: C₂₈H₃₇N₃O
• 分子量: 431.621
• InChiKey: CSZGWTIIEDCAOM-SIHVKLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  盐酸氨基脲 、 3,5-bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 6.0h， 以84%的产率得到(E)-7-(4-(diethylamino)benzylidene)-3-(4-diethylamino)phenyl-4,5,6,7-tetrahydro-5-methyl pyrazole[4,3-c]pyridine-2-carboxamide
  参考文献：
  名称：

  Aruna, S.; Girija, R.; Saamanthi, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 5, p. 746 - 754

  摘要：

  DOI：
• 作为产物：
  描述：

  N-甲基-4-哌啶酮 、 N,N-二乙基-4-氨基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 18.25h， 生成 3,5-bis[4-(diethylamino)benzylidene]-1-methyl-4-piperidone
  参考文献：
  名称：

  Synthesis, cytotoxicity, and structure–activity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones

  摘要：

  Twenty-one NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidone analogs of curcumin, 12 of which are novel, were synthesized and evaluated for their cytotoxicity against B16 (murine melanoma) and L1210 (murine lymphoma) cells grown in culture. These curcumin analogs are related to a known anticancer STAT3 inhibitor 3,5-bis-(4-fluorobenzyl)-4-piperidone (3). The compounds showed remarkable cytotoxicity, especially against B16 cells. The dimethoxy substituted analogs 4e and 4f and dihydroxy analog 4i emerged as the most active compounds with IC50 values in the range of 0.2-2.3 mu M. 4e, f, and i were about 10-times more cytotoxic against both cell lines than 3. Analysis of the results demonstrates that the position of the hydroxyl group is crucial for cytotoxicity. Amino-containing analogs are generally less active than their halogenated and oxygen-containing analogs, and N-substitution in the 4-piperidone moiety adds value to the cytotoxicity of the compounds.

  DOI：

  10.1007/s00044-013-0557-9

文献信息

• Synthesis, cytotoxicity, and structure–activity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones
  作者：Matthew Gregory、Armaan Dandavati、Megan Lee、Samuel Tzou、Mia Savagian、Kimberly A. Brien、Vijay Satam、Pravin Patil、Moses Lee

  DOI：10.1007/s00044-013-0557-9

  日期：2013.11

  Twenty-one NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidone analogs of curcumin, 12 of which are novel, were synthesized and evaluated for their cytotoxicity against B16 (murine melanoma) and L1210 (murine lymphoma) cells grown in culture. These curcumin analogs are related to a known anticancer STAT3 inhibitor 3,5-bis-(4-fluorobenzyl)-4-piperidone (3). The compounds showed remarkable cytotoxicity, especially against B16 cells. The dimethoxy substituted analogs 4e and 4f and dihydroxy analog 4i emerged as the most active compounds with IC50 values in the range of 0.2-2.3 mu M. 4e, f, and i were about 10-times more cytotoxic against both cell lines than 3. Analysis of the results demonstrates that the position of the hydroxyl group is crucial for cytotoxicity. Amino-containing analogs are generally less active than their halogenated and oxygen-containing analogs, and N-substitution in the 4-piperidone moiety adds value to the cytotoxicity of the compounds.
• Synthesis and anti-tumor activity of EF24 analogues as IKKβ inhibitors
  作者：Rong Jin、Qiuxiang Chen、Song Yao、Encheng Bai、Weitao Fu、Ledan Wang、Jiabing Wang、Xiaojing Du、Tao Wei、Haineng Xu、Chengxi Jiang、Peihong Qiu、Jianzhang Wu、Wulan Li、Guang Liang

  DOI：10.1016/j.ejmech.2017.11.077

  日期：2018.1

  EF24 is an IKK beta inhibitor (IC50: 72 mu M) containing various anti-tumor activities. In this study, a series of EF24 analogs targeting IKK beta were designed and synthesized. Several IKK beta inhibitors with better activities than EF24 were screened out and B3 showed best IKK beta inhibitory (IC50: 6.6 mu M). Molecular docking and dynamic simulation experiments further confirmed this inhibitory effect. B3 obviously suppressed the viability of Hela229, A549, SGC-7901 and MGC-803 cells. Then, in SGC-7901 and MGC-803 cells, B3 blocked the NF-kappa B signal pathway by inhibiting IKK beta phosphorylation, and followed arrested the cell cycle at G2/M phase by suppressing the Cyclin B1 and Cdc2 p34 expression, induced the cell apoptosis by down-regulating Bcl-2 protein and up-regulating cleaved-caspase3. Moreover, B3 significantly reduced tumor growth and suppressed the IKK beta-NF-kappa B signal pathway in SGC-7901 xenograft model. In total, this study present a potential IKK beta inhibitor as anti-tumor precursor. (C) 2017 Published by Elsevier Masson SAS.
• Aruna, S.; Girija, R.; Saamanthi, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2021, vol. 60, # 5, p. 746 - 754
  作者：Aruna, S.、Girija, R.、Saamanthi, M.、Vinod, D.

  DOI：——

  日期：——