2-[3-[(3E,5E)-3,5-bis[(4-nitrophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid | 1009817-68-8

• 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-nitrophenyl)methylidene]-4-oxopiperidin-1-yl]-3-oxopropyl]sulfanylethanesulfonic acid
• CAS: 1009817-68-8
• 化学式: C₂₄H₂₃N₃O₉S₂
• 分子量: 561.593
• InChiKey: LDBYFUIDXJSVDH-IWGRKNQJSA-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：

  sodium 2-[3-(4-oxopiperidin-1-yl)-3-oxo-propylsulfanyl]ethanesulfonate 、 对硝基苯甲醛 在 盐酸 、 溶剂黄146 作用下， 反应 8.0h， 以75%的产率得到2-[3-[(3E,5E)-3,5-bis[(4-nitrophenyl)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

• NUCLEIC ACIDS ENCODING REPETITIVE AMINO ACID SEQUENCES RICH IN PROLINE AND ALANINE RESIDUES THAT HAVE LOW REPETITIVE NUCLEOTIDE SEQUENCES
  申请人：XL-protein GmbH

  公开号：EP3394266A1

  公开（公告）日：2018-10-31
• [EN] NUCLEIC ACIDS ENCODING REPETITIVE AMINO ACID SEQUENCES RICH IN PROLINE AND ALANINE RESIDUES THAT HAVE LOW REPETITIVE NUCLEOTIDE SEQUENCES<br/>[FR] ACIDES NUCLÉIQUES CODANT POUR DES SÉQUENCES D'ACIDES AMINÉS RÉPÉTITIVES RICHES EN RÉSIDUS PROLINE ET ALANINE COMPORTANT DES SÉQUENCES DE NUCLÉOTIDES À FAIBLE RÉPÉTITIVITÉ
  申请人：XL-PROTEIN GMBH

  公开号：WO2017109087A1

  公开（公告）日：2017-06-29

  The present invention relates to a nucleic acid molecule comprising a low repetitive nucleotide sequence encoding a proline/alanine-rich amino acid repeat sequence. The encoded polypeptide comprises a repetitive amino acid sequence that forms a random coil. The nucleic acid molecule comprising said low repetitive nucleotide sequences can further comprise a nucleotide sequence encoding a biologically or pharmacologically active protein. Further, the present invention provides for selection means and methods to identify said nucleic acid molecule comprising said low repetitive nucleotide sequence. The present invention also relates to a method for preparing said nucleic acid molecules. Also provided herein are methods for preparing the encoded polypeptide or drug conjugates with the encoded polypeptide using the herein provided nucleic acid molecules. The drug conjugate may comprise a biologically or pharmacologically active protein or a small molecule drug. Also provided herein are vectors and hosts comprising such nucleic acid molecules.
• 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.