ethyl 14-<(ethylamino)carbonyl>-13-cis-retinoic acid | 113214-81-6

• 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
• 英文名称: ethyl 14-<(ethylamino)carbonyl>-13-cis-retinoic acid
• 英文别名: ethyl 14-[(ethylamino)carbonyl]-13-cis-retinoic acid；(2Z,4E,6E,8E)-2-(ethylcarbamoyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 113214-81-6
• 化学式: C₂₃H₃₃NO₃
• 分子量: 371.52
• InChiKey: BOPGZYTZIJQPIR-PKBUNJFLSA-N

物化性质

• 沸点：
  598.1±42.0 °C(predicted)
• 密度：
  1.054±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (7E,9E)-beta-离子亚基乙醛 在 氢氧化钾 、 sodium amide 、 三氯化磷 作用下， 以 乙醇 、 氨 、 甲苯 、 苯 为溶剂， 反应 5.17h， 生成 ethyl 14-<(ethylamino)carbonyl>-13-cis-retinoic acid
  参考文献：
  名称：

  Terminal bifunctional retinoids. Synthesis and evaluations related to cancer chemopreventive activity

  摘要：

  Retinoids that have two functional groups at the side-chain terminus have been synthesized. The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups. The synthesis route is based on the sodium amide catalyzed condensation of (E,E)-beta-ionylideneacetaldehyde with diethyl isopropylidenemalonate. Ethyl 14-carboxyretinoate (6), the initial bifunctional analogue, undergoes isomerization in unbuffered aqueous ethanol and reaches a state of equilibrium with ethyl 14-carboxy-13-cis-retinoate. Both of the possible amide-esters and amide-acids were obtained. The structures of the isomeric bifunctional analogues were established by studies of nuclear Overhauser effects. The bifunctional analogues induce differentiation of mouse embryonal carcinoma cells, and those analogues that have a free carboxyl group bind to cellular retinoic acid binding protein.

  DOI：

  10.1021/jm00401a011

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。
• SHEALY, Y. FULMER;KRAUTH, CHARLES A.;RIORDAN, JAMES M.;SANI, BRAHMA P., J. MED. CHEM., 31,(1988) N 6, 1124-1130
  作者：SHEALY, Y. FULMER、KRAUTH, CHARLES A.、RIORDAN, JAMES M.、SANI, BRAHMA P.

  DOI：——

  日期：——
• 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
• Prevention of Retinopathy by Inhibition of the Visual Cycle
  申请人：Larsen Michael Lars

  公开号：US20070249713A1

  公开（公告）日：2007-10-25

  The invention relates to compounds capable of inhibiting the visual cycle and/or dark adaptation and their use for treatment and prevention of non-degenerative retinal diseases with specific emphasis on the prevention and treatment of diabetic retinopathy, retinopathy of prematurity, branch retinal vein occlusion, central retinal vein occlusion, open-angle glaucoma, veovascular glaucoma, and other diseases of the retinal and/or optic nerve where an imbalance between metabolic demand and blood supply contribute to the development of tissue damage. The invention furthermore relates to pharmaceutical compositions comprising such compounds.