2,4-bis(4-chlorobenzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one | 1121978-98-0

• 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: 2,4-bis(4-chlorobenzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one
• 英文别名: (2E,4E)-2,4-Bis[(4-chlorophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octan-3-one
• CAS: 1121978-98-0
• 化学式: C₂₂H₁₉Cl₂NO
• 分子量: 384.305
• InChiKey: YILQAVVQOZRPNH-KLCVKJMQSA-N

物化性质

• 熔点：
  183 °C(Solvent: Ethanol)
• 沸点：
  566.0±50.0 °C(predicted)
• 密度：
  1.325±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  托品酮 、 4-氯苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以85%的产率得到2,4-bis(4-chlorobenzylidene)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-one
  参考文献：
  名称：

  The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones

  摘要：

  This study demonstrated that replacement of the axial protons on the C2 and C6 atoms of various 1-methyl-3,5-bis(benzylidene)-4-piperidones 3 by a dimethylene bridge leading to series 2 lowered cytotoxic potencies. Four compounds 2a and 3a-c emerged as lead molecules based on their toxicity towards different neoplasms and their selective toxicity for malignant rather than normal cells. Some possible reasons for the disparity between the IC50 values in the two series of compounds are presented based on molecular modeling, log P values and respiration in rat liver mitochondria. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.015

文献信息

• The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones
  作者：Hari N. Pati、Umashankar Das、Swagatika Das、Brian Bandy、Erik De Clercq、Jan Balzarini、Masami Kawase、Hiroshi Sakagami、J. Wilson Quail、James P. Stables、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2008.03.015

  日期：2009.1

  This study demonstrated that replacement of the axial protons on the C2 and C6 atoms of various 1-methyl-3,5-bis(benzylidene)-4-piperidones 3 by a dimethylene bridge leading to series 2 lowered cytotoxic potencies. Four compounds 2a and 3a-c emerged as lead molecules based on their toxicity towards different neoplasms and their selective toxicity for malignant rather than normal cells. Some possible reasons for the disparity between the IC50 values in the two series of compounds are presented based on molecular modeling, log P values and respiration in rat liver mitochondria. (C) 2008 Elsevier Masson SAS. All rights reserved.