diisopropyl 4-(hexadecyloxy)-3-(S)-methoxy-1-(E)-butenephosphonate | 692732-28-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diisopropyl 4-(hexadecyloxy)-3-(S)-methoxy-1-(E)-butenephosphonate
• CAS: 692732-28-8
• 化学式: C₂₇H₅₅O₅P
• 分子量: 490.704
• InChiKey: AGYQJCYSMQYFOM-NDLSKRMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  33.0
• 可旋转键数：
  24.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diisopropyl 4-(hexadecyloxy)-3-(S)-methoxy-1-(E)-butenephosphonate 在 吡啶 、 三甲基溴硅烷 、 三氯乙腈 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 [(E,3S)-4-hexadecoxy-3-methoxybut-1-enyl]-[2-(trimethylazaniumyl)ethoxy]phosphinate
  参考文献：
  名称：

  Synthesis and Use of Novel Ether Phospholipid Enantiomers To Probe the Molecular Basis of the Antitumor Effects of Alkyllysophospholipids:  Correlation of Differential Activation of c-Jun NH₂-Terminal Protein Kinase with Antiproliferative Effects in Neuronal Tumor Cells

  摘要：

  The enantiomers of a novel unsaturated phosphonocholine antitumor ether lipid were synthesized and found to have differential antiproliferative effects against epithelial cancer cell lines. The basis of the enantioselective effects on the cells was investigated in SK-N-MC and SK-N-SH neuroblastoma tumor cells. Our results indicate that the enantioselective antiproliferative potency arises primarily from the activation of the JNK signaling pathway by the ether lipids.

  DOI：

  10.1021/jm0302748
• 作为产物：
  描述：

  十六基甲基甘油 在 草酰氯 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 diisopropyl 4-(hexadecyloxy)-3-(S)-methoxy-1-(E)-butenephosphonate
  参考文献：
  名称：

  Synthesis and Use of Novel Ether Phospholipid Enantiomers To Probe the Molecular Basis of the Antitumor Effects of Alkyllysophospholipids:  Correlation of Differential Activation of c-Jun NH₂-Terminal Protein Kinase with Antiproliferative Effects in Neuronal Tumor Cells

  摘要：

  The enantiomers of a novel unsaturated phosphonocholine antitumor ether lipid were synthesized and found to have differential antiproliferative effects against epithelial cancer cell lines. The basis of the enantioselective effects on the cells was investigated in SK-N-MC and SK-N-SH neuroblastoma tumor cells. Our results indicate that the enantioselective antiproliferative potency arises primarily from the activation of the JNK signaling pathway by the ether lipids.

  DOI：

  10.1021/jm0302748

文献信息

• Enanitomers of unsaturated alkyllysophosphonocholines and use as anti-neoplastics
  申请人：Bittman Robert

  公开号：US20050014971A1

  公开（公告）日：2005-01-20

  Unsaturated alkyllysophosphonocholines compounds of formula (I) or (II): or pharmaceutically-acceptable salts, prodrugs or isomers thereof. The compounds of the invention have anti-neoplastic activity, and accordingly have utility in treating cancer and related diseases. The invention also provides enantiomers of these compounds, as well as synthetic methods for producing an enantiomer, substantially free of the other enantiomer. Also disclosed are pharmaceutical compositions, as well methods for treating cancer with the pharmaceutical compositions.

  式 (I) 或 (II) 的不饱和烷基膦酰胆碱化合物： 或其药学上可接受的盐、原药或异构体。本发明的化合物具有抗肿瘤活性，因此可用于治疗癌症及相关疾病。本发明还提供了这些化合物的对映体，以及生产基本上不含另一种对映体的对映体的合成方法。本发明还公开了药物组合物以及用药物组合物治疗癌症的方法。
• ENANTIOMERS OF UNSATURATED ALKYLLYSOPHOSPHONOCHOLINES AND USE AS ANTI-NEOPLASTICS
  申请人：The Research Foundation Of the City University of New York

  公开号：EP1387847A2

  公开（公告）日：2004-02-11
• EP1387847A4
  申请人：——

  公开号：EP1387847A4

  公开（公告）日：2005-06-29
• US7323601B2
  申请人：——

  公开号：US7323601B2

  公开（公告）日：2008-01-29
• [EN] ENANTIOMERS OF UNSATURATED ALKYLLYSOPHOSPHONOCHOLINES AND USE AS ANTI-NEOPLASTICS<br/>[FR] ENANTIOMERES D'ALKYLLYSOPHOSPHONOCHOLINES NON SATUREES ET LEUR UTILISATION COMME ANTI-NEOPLASIQUES
  申请人：UNIV CITY

  公开号：WO2002067855A2

  公开（公告）日：2002-09-06

  Unsaturated alkyllysophosphonocholines compounds of formula (I) or (II):or pharmaceutically-acceptable salts, prodrugs or isomers thereof. The compounds of the invention have anti-neoplastic activity, and accordingly have utility in treating cancer and related diseases. The invention also provides enantiomers of these compounds, as well as synthetic methods for producing an enantiomer, substantially free of the other enantiomer. Also disclosed are pharmaceutical compositions, as well methods for treating cancer with the pharmaceutical compositions.