all-trans-N-Retinoylglycine ethyl ester | 81425-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: all-trans-N-Retinoylglycine ethyl ester
• 英文别名: ethyl 2-[[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoyl]amino]acetate
• CAS: 81425-66-3
• 化学式: C₂₄H₃₅NO₃
• 分子量: 385.547
• InChiKey: XQUXHEMMWYKMRG-DXJCHIHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  all-trans-N-Retinoylglycine ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以97%的产率得到all-trans-N-Retinoylglycine
  参考文献：
  名称：

  某些13-顺式和全反式视黄酰胺的合成和性质

  摘要：

  通过13-顺-视黄酰氯或13-顺-1-视黄基咪唑从13-顺-视黄酸合成了几种13-顺-视黄酰胺。由全反式视黄酰氯和甘氨酸乙酯制备全反式视黄酰甘氨酸。开发了用于制备其他全反式维甲酸酰胺的详细程序，以用于癌症化学预防的研究。

  DOI：

  10.1002/jps.2600730610
• 作为产物：
  描述：

  维A酸 在 sodium hydroxide 、 potassium carbonate 、 三氯化磷 作用下， 以 苯 为溶剂， 反应 5.0h， 生成 all-trans-N-Retinoylglycine ethyl ester
  参考文献：
  名称：

  某些13-顺式和全反式视黄酰胺的合成和性质

  摘要：

  通过13-顺-视黄酰氯或13-顺-1-视黄基咪唑从13-顺-视黄酸合成了几种13-顺-视黄酰胺。由全反式视黄酰氯和甘氨酸乙酯制备全反式视黄酰甘氨酸。开发了用于制备其他全反式维甲酸酰胺的详细程序，以用于癌症化学预防的研究。

  DOI：

  10.1002/jps.2600730610

文献信息

• Fenretinide Derivatives Act as Disrupters of Interactions of Serum Retinol Binding Protein (sRBP) with Transthyretin and the sRBP Receptor
  作者：José Angel Campos-Sandoval、Clara Redondo、Gemma K. Kinsella、Akos Pal、Geraint Jones、Gwen S. Eyre、Simon C. Hirst、John B. C. Findlay

  DOI：10.1021/jm200256g

  日期：2011.7.14

  Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.
• RETINOL DERIVATIVES, THEIR USE IN THE TREATMENT OF CANCER AND FOR POTENTIATING THE EFFICACY OF OTHER CYTOTOXIC AGENTS
  申请人：Ardenia Investments Ltd.

  公开号：EP1534672B1

  公开（公告）日：2013-05-01
• Synthesis and Properties of Some 13-cis- and All-trans-retinamides
  作者：Y. Fulmer Shealy、Jerry L. Frye、C. Allen O'Dell、Martha C. Thorpe、Marion C. Kirk、W.C. Coburn、Michael B. Sporn

  DOI：10.1002/jps.2600730610

  日期：1984.6

  chloride or 13-cis-1-retinoylimidazole. All-trans-retinoylglycine was prepared from all-trans-retinoyl chloride and ethyl glycinate. Detailed procedures were developed for the preparation of other all-trans-retinamides on a large scale for studies of the chemoprevention of cancer.

  通过13-顺-视黄酰氯或13-顺-1-视黄基咪唑从13-顺-视黄酸合成了几种13-顺-视黄酰胺。由全反式视黄酰氯和甘氨酸乙酯制备全反式视黄酰甘氨酸。开发了用于制备其他全反式维甲酸酰胺的详细程序，以用于癌症化学预防的研究。