13-顺式-芬维A胺 | 75686-07-6

• 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
• 中文名称: 13-顺式-芬维A胺
• 英文名称: (2Z,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenamide
• 英文别名: 13-cis-N-(4-Hydroxyphenyl)retinamide；13-cis-fenretinide；(2Z,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• CAS: 75686-07-6
• 化学式: C₂₆H₃₃NO₂
• 分子量: 391.554
• InChiKey: AKJHMTWEGVYYSE-DRYRGIGMSA-N

物化性质

• 熔点：
  >181°C (dec.)
• 溶解度：
  可溶于DMSO（少许）、乙酸乙酯（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  异维A酸	13-cis-retinoic acid	4759-48-2	C20H28O2	300.441
  ——	13-cis-retinoyl chloride	73174-99-9	C20H27ClO	318.887

反应信息

• 作为产物：
  描述：

  异维A酸 在 三氯化磷 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 13-顺式-芬维A胺
  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

• Insulin-producing cells derived from stem cells
  申请人：Hori Yuichi

  公开号：US20070154981A1

  公开（公告）日：2007-07-05

  The disclosure provides, among other things, insulin-producing cells derived from stem cells, such as human stem cells and neural stem cells. The disclosure discloses a relationship between caudalizing factors and the differentiation of insulin-producing cells.

  该披露提供了从干细胞（如人类干细胞和神经干细胞）衍生出的胰岛素产生细胞，其中包括其他内容。该披露揭示了尾端因子与胰岛素产生细胞分化之间的关系。
• Use of retinoids to treat high blood pressure and other cardiovascular disease
  申请人：——

  公开号：US20030008919A1

  公开（公告）日：2003-01-09

  This invention provides methods of treating a disease in a mammal where the disease is characterized by a symptom ameliorated by inhibition of cellular calcium influx. The methods involve administering to the mammal an effective amount of a retinoid and a pharmacologically acceptable excipient.

  本发明提供了治疗哺乳动物疾病的方法，该疾病的特征是通过抑制细胞钙离子流入而改善症状。这些方法包括向哺乳动物施用有效量的维甲酸和药理学上可接受的赋形剂。
• 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.
• Process for preparing retinoyl chlorides
  申请人：McNeilab, Inc.

  公开号：EP0261911B1

  公开（公告）日：1991-08-21
• PREVENTION OF RETINOPATHY BY INHIBITION OF THE VISUAL CYCLE
  申请人：Larsen, Lars, Michael

  公开号：EP1727529B1

  公开（公告）日：2016-03-02