(2E,4E,6E,8E)-N-(2-羟基乙基)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺 | 33631-47-9

• 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: (2E,4E,6E,8E)-N-(2-羟基乙基)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺
• 英文名称: all-trans-N-(2-hydroxyethyl)retinamide
• 英文别名: N-(2-Hydroxyethyl)retinamide；(2E,4E,6E,8E)-N-(2-hydroxyethyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide
• CAS: 33631-47-9
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: JOSHOGBFUULHNI-LYKFAKFTSA-N

物化性质

• 沸点：
  478.76°C (rough estimate)
• 密度：
  1.0455 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E,8E)-N-(2-羟基乙基)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 20.42h， 生成 N-(all-trans-retinoyl)-o-phospho-2-aminoethanol
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1015388429085
• 作为产物：
  描述：

  维A酸 在 三氯化磷 作用下， 以 苯 为溶剂， 反应 4.75h， 生成 (2E,4E,6E,8E)-N-(2-羟基乙基)-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯基)壬-2,4,6,8-四烯酰胺
  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

• [EN] METHODS OF USE FOR OPSIN BINDING LIGANDS<br/>[FR] PROCÉDÉS D'UTILISATION DE LIGANDS DE LIAISON DE L'OPSINE
  申请人：BIKAM PHARMACEUTICALS INC

  公开号：WO2010074746A1

  公开（公告）日：2010-07-01

  Methods of use of compounds of the Formula I1 II, III, IV and/or V are disclosed for treating ophthalmic conditions related to the production of toxic visual cycle products that accumulate in the eye, and are associated with reactions of the visual cycle during medical procedures that expose the eye to light, most commonly the various forms of ophthalmic surgery and stabilize the proper folding of mutant opsins. Compounds and compositions useful in the these methods, either alone or in combination with other therapeutic agents, are also described, along with methods of screening for new agents useful in said treatments.

  公开了利用公式I1 II、III、IV和/或V的化合物治疗与在眼睛中积聚的有毒视觉循环产物有关的眼科疾病的方法，这些产物与暴露于光线的医疗程序期间的视觉循环反应有关，最常见的是各种形式的眼科手术，并稳定突变视蛋白的正确折叠。还描述了在这些方法中有用的化合物和组合物，无论是单独使用还是与其他治疗剂结合使用，以及筛选用于上述治疗的新药物的方法。
• Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases
  申请人：Scaramuzzino, Giovanni

  公开号：EP1336602A1

  公开（公告）日：2003-08-20

  New pharmaceutical compounds of general formula (I): F-(X)q where q is an integer from 1 to 5, preferably 1; -F is chosen among drugs described in the text, -X is chosen among 4 groups -M, -T, -V and -Y as described in the text. The compounds of general formula (I) are nitrate prodrugs which can release nitric oxide in vivo in a controlled and selective way and without hypotensive side effects and for this reason they are useful for the preparation of medicines for prevention and treatment of inflammatory, ischemic, degenerative and proliferative diseases of musculoskeletal, tegumental, respiratory, gastrointestinal, genito-urinary and central nervous systems.

  通式（I）的新药物化合物：F-（X）q，其中q是1到5的整数，最好是1；-F是在文本中描述的药物中选择的，-X是在文本中描述的4个组-M，-T，-V和-Y中选择的。通式（I）的化合物是硝酸盐前药，可以在体内以受控和选择性的方式释放一氧化氮，而不会产生降压副作用，因此它们非常适用于制备用于预防和治疗肌肉骨骼，皮肤，呼吸，消化，泌尿和中枢神经系统的炎症，缺血，退行性和增生性疾病的药物。
• 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.
• EP0498883A4
  申请人：——

  公开号：EP0498883A4

  公开（公告）日：1993-03-10
• 3-SUBSTITUTED AND 3,3-DISUBSTITUTED 4-OXORETINOIC ACIDS AND THEIR ESTERS
  申请人：SOUTHERN RESEARCH INSTITUTE

  公开号：EP0498883A1

  公开（公告）日：1992-08-19