2-[3-[(3E,5E)-3,5-bis[(4-chlorophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid | 1009817-67-7

• 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-[(3E,5E)-3,5-bis[(4-chlorophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid
• CAS: 1009817-67-7
• 化学式: C₂₄H₂₃Cl₂NO₅S₂
• 分子量: 540.488
• InChiKey: ZNCCDPXEQRDBCN-IWGRKNQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 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：
  125
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  sodium 2-[3-(4-oxopiperidin-1-yl)-3-oxo-propylsulfanyl]ethanesulfonate 、 4-氯苯甲醛 在 盐酸 、 溶剂黄146 作用下， 反应 8.0h， 以85%的产率得到2-[3-[(3E,5E)-3,5-bis[(4-chlorophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid
  参考文献：
  名称：

  Cytotoxic 3,5-bis(benzylidene)piperidin-4-ones and N-acyl analogs displaying selective toxicity for malignant cells

  摘要：

  A series of 3,5-bis(benzylidene)piperidin-4-ones 1, 1-acryloyl-3,5-bis(benzylidene)piperidin-4-ones 2 and adducts of 2 with sodium 2-mercaptoethanesulfonate (mesna), namely series 3, were prepared as candidate cytotoxic agents. These compounds were examined against neoplastic HSC-2, HSC-4 and HL-60 cells as well as HGF, HPC and HPLF normal cell lines and many of the compounds displayed selective toxicity for malignant cells. The CC50 values of the analogs in series 2 towards the cancer cell lines were mainly submicromolar. The relative potencies, selectivity and log P values were in the order of 2 > 1 > 3. The sulfonic acid group of a representative compound in series 3 was replaced by a thiol function to produce 4 leading to substantial increases in cytotoxic potencies and hydrophobicity indicating that the presence of a hydrophilic sulfonic acid group was disadvantageous in terms of potency. Molecular modeling suggested that the superior cytotoxicity of various members of series 1-3 over an acyclic analog 5 may have been due to the greater torsion angles theta(1) and theta(2) created between the arylidene aryl rings and the adjacent olefinic groups in series 1-3. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.010

文献信息

• Cytotoxic 3,5-bis(benzylidene)piperidin-4-ones and N-acyl analogs displaying selective toxicity for malignant cells
  作者：Hari N. Pati、Umashankar Das、J. Wilson Quail、Masami Kawase、Hiroshi Sakagami、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2007.03.010

  日期：2008.1

  A series of 3,5-bis(benzylidene)piperidin-4-ones 1, 1-acryloyl-3,5-bis(benzylidene)piperidin-4-ones 2 and adducts of 2 with sodium 2-mercaptoethanesulfonate (mesna), namely series 3, were prepared as candidate cytotoxic agents. These compounds were examined against neoplastic HSC-2, HSC-4 and HL-60 cells as well as HGF, HPC and HPLF normal cell lines and many of the compounds displayed selective toxicity for malignant cells. The CC50 values of the analogs in series 2 towards the cancer cell lines were mainly submicromolar. The relative potencies, selectivity and log P values were in the order of 2 > 1 > 3. The sulfonic acid group of a representative compound in series 3 was replaced by a thiol function to produce 4 leading to substantial increases in cytotoxic potencies and hydrophobicity indicating that the presence of a hydrophilic sulfonic acid group was disadvantageous in terms of potency. Molecular modeling suggested that the superior cytotoxicity of various members of series 1-3 over an acyclic analog 5 may have been due to the greater torsion angles theta(1) and theta(2) created between the arylidene aryl rings and the adjacent olefinic groups in series 1-3. (C) 2007 Elsevier Masson SAS. All rights reserved.