1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-one | 1293995-10-4

• 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: 1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-one
• 英文别名: 1-[3-(2-Hydroxyethylsulfanyl)propanoyl]piperidin-4-one
• CAS: 1293995-10-4
• 化学式: C₁₀H₁₇NO₃S
• 分子量: 231.316
• InChiKey: JXQQTEUZHPKEJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-one 、 对甲基苯甲醛 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 1-[3-(2-hydroxyethylsulfanyl)propanoyl]-3,5-bis[(4-methylphenyl)methylidene]piperidin-4-one
  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
• 作为产物：
  描述：

  4-哌啶酮 在 四丁基溴化铵 、 potassium carbonate 、 三乙胺 作用下， 生成 1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-one
  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

• 3,5-Bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones: A Novel Cluster of Potent Tumor-Selective Cytotoxins
  作者：Umashankar Das、Hari N. Pati、Hiroshi Sakagami、Ken Hashimoto、Masami Kawase、Jan Balzarini、Erik De Clercq、Jonathan R. Dimmock

  DOI：10.1021/jm101595p

  日期：2011.5.12

  Novel 3,5-bis(benzylidene)-1-[3-(2-hydroxyethylthio)propanoyl]piperidin-4-ones (3a-e) display potent cytotoxicity and a preferential lethality toward various neoplasms compared to some normal cells. The corresponding sulfonic acid analogues 5a−e and an isostere 4 demonstrated substantially lower activity. The leads 3d and 3e possess very high activity against colon cancer and leukemia cell lines, caused

  与一些正常细胞相比，新型 3,5-双(亚苄基)-1-[3-(2-羟乙硫基)丙酰基]哌啶-4-酮 ( 3a-e)显示出有效的细胞毒性和对各种肿瘤的优先致死率。相应的磺酸类似物5a - e和等排体4表现出显着较低的活性。3d和3e导联对结肠癌和白血病细胞系具有非常高的活性，导致 DNA 断裂，并激活 HL-60 细胞中的 caspase-3。在小鼠的短期毒性筛选中，烯酮3b - e具有良好的耐受性。
• 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.