2-{3-[3,5-Bis[4-nitrobenzylidene]-4-oxopiperidin-1-yl]-3-oxopropylsulfanyl} ethanesulfonic acid | 1188338-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-{3-[3,5-Bis[4-nitrobenzylidene]-4-oxopiperidin-1-yl]-3-oxopropylsulfanyl} ethanesulfonic acid
• 英文别名: 2-[3-[3,5-bis[(4-nitrophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid
• CAS: 1188338-99-9
• 化学式: C₂₄H₂₃N₃O₉S₂
• 分子量: 561.593
• InChiKey: LDBYFUIDXJSVDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  217
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-哌啶酮 在 盐酸 、 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 以 溶剂黄146 为溶剂， 生成 2-{3-[3,5-Bis[4-nitrobenzylidene]-4-oxopiperidin-1-yl]-3-oxopropylsulfanyl} ethanesulfonic acid
  参考文献：
  名称：

  1-[3-(2-Hydroxyethylsulfanyl)propanoyl]-3,5-bis(benzylidene)-4-piperidones: A novel cluster of P-glycoprotein dependent multidrug resistance modulators

  摘要：

  A series of 1-[3-(2-hydroxyethylsulfanyl)propanoyl]-3,5-bis(benzylidene)-4-piperidones 4a-e display promising P-glycoprotein dependent multidrug resistance (MDR) revertant properties and are significantly more potent than a reference drug verapamil when evaluated against L-5178Y MDR lymphoma cells. These dienones may be referred to as dual agents having both MDR revertant properties and tumour-selective cytotoxicity. In particular, 3,5-bis(4-chlorobenzylidene)-1-[3-(2-hydroxyethylsulfanyl]propanoyl-4-piperidone 4d emerged as a lead molecule for further development based on its MDR revertant properties, cytotoxic potencies and tumour-selective toxicity. The structure-activity relationships reveal important structural requirements for further designing of potent MDR revertants. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.005

文献信息

• 1-[3-(2-Hydroxyethylsulfanyl)propanoyl]-3,5-bis(benzylidene)-4-piperidones: A novel cluster of P-glycoprotein dependent multidrug resistance modulators
  作者：Umashankar Das、Hari N. Pati、Zoltan Baráth、Ákos Csonka、Joseph Molnár、Jonathan R. Dimmock

  DOI：10.1016/j.bmcl.2016.01.005

  日期：2016.2

  A series of 1-[3-(2-hydroxyethylsulfanyl)propanoyl]-3,5-bis(benzylidene)-4-piperidones 4a-e display promising P-glycoprotein dependent multidrug resistance (MDR) revertant properties and are significantly more potent than a reference drug verapamil when evaluated against L-5178Y MDR lymphoma cells. These dienones may be referred to as dual agents having both MDR revertant properties and tumour-selective cytotoxicity. In particular, 3,5-bis(4-chlorobenzylidene)-1-[3-(2-hydroxyethylsulfanyl]propanoyl-4-piperidone 4d emerged as a lead molecule for further development based on its MDR revertant properties, cytotoxic potencies and tumour-selective toxicity. The structure-activity relationships reveal important structural requirements for further designing of potent MDR revertants. (C) 2016 Elsevier Ltd. All rights reserved.