(2E,4E)-8-methyl-2,4-bis((pyridin-3-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one | 1251531-75-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: (2E,4E)-8-methyl-2,4-bis((pyridin-3-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one
• 英文别名: (2E,4E)-8-Methyl-2,4-bis[(pyridin-3-YL)methylidene]-8-azabicyclo[3.2.1]octan-3-one；(2E,4E)-8-methyl-2,4-bis(pyridin-3-ylmethylidene)-8-azabicyclo[3.2.1]octan-3-one
• CAS: 1251531-75-5
• 化学式: C₂₀H₁₉N₃O
• 分子量: 317.39
• InChiKey: GZYDXLNQYNGTGS-OTYYAQKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-吡啶甲醛 、 托品酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 以85%的产率得到(2E,4E)-8-methyl-2,4-bis((pyridin-3-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  Synthesis and cytotoxic potential of heterocyclic cyclohexanone analogues of curcumin

  摘要：

  A series of 18 heterocyclic cyclohexanone analogues of curcumin have been synthesised and screened for their activity in both adherent and non-adherent cancer cell models. Cytotoxicity towards MBA-MB-231 breast cancer cells, as well as ability to inhibit NF-kappa B transactivation in non-adherent K562 leukemia cells were investigated. Three of these analogues 3,5-bis(pyridine-4-yl)-1-methylpiperidin-4-one B1, 3,5-bis(3,4,5-trimethoxybenzylidene)-1-methylpiperidin-4-one B10, and 8-methyl-2,4-bis((pyridine-4-yl)methylene)-8-aza-bicyclo[3.2.1]octan-3-one C1 showed potent cytotoxicity towards MBA-MB-231, MDA-MB-468, and SkBr3 cell lines with EC50 values below 1 mu M and inhibition of NF-kappa B activation below 7.5 mu M. The lead drug candidate, B10, was also able to cause 43% of MDA-MB-231 cells to undergo apoptosis after 18 h. This level of activity warrants further investigation for the treatment of ER-negative breast cancer and/or chronic myelogenous leukemia as prototypical cellular models for solid and liquid tumors. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.063