11,12-dehydro-9-cis-retinoic acid | 166373-38-2

• 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: 11,12-dehydro-9-cis-retinoic acid
• 英文别名: (2E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,6,8-trien-4-ynoic acid
• CAS: 166373-38-2
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: IIUMHUDUINJHPZ-YDUQNZCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  11,12-dehydro-9-cis-retinoic acid 在 Wilkinson's catalyst 超重氢 作用下， 以 乙醇 、 苯 为溶剂， 反应 16.0h， 生成 <11,12-3H>-9-cis-retinoic acid
  参考文献：
  名称：

  A preparation of high specific activity [11,12-3H]-9-cis-retinoic acid

  摘要：

  描述了一种具有特定活性为46 Ci/mmol的[11,12-3H]-9-顺式-视黄酸1的选择性全合成方法。通过两步高效地从容易获得的起始材料制备得到的炔4，与氘气和氚气部分还原得到9,11-二顺式-视黄酸3。讨论了3到1的选择性异构化，以及4到1的非选择性直接转化。

  DOI：

  10.1002/jlcr.2580360610
• 作为产物：
  描述：

  methyl-3-methyl-hex-6-al-4-yn-2-enoate 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 反应 4.17h， 生成 11,12-dehydro-9-cis-retinoic acid
  参考文献：
  名称：

  A preparation of high specific activity [11,12-3H]-9-cis-retinoic acid

  摘要：

  描述了一种具有特定活性为46 Ci/mmol的[11,12-3H]-9-顺式-视黄酸1的选择性全合成方法。通过两步高效地从容易获得的起始材料制备得到的炔4，与氘气和氚气部分还原得到9,11-二顺式-视黄酸3。讨论了3到1的选择性异构化，以及4到1的非选择性直接转化。

  DOI：

  10.1002/jlcr.2580360610

文献信息

• [EN] METHODS AND COMPOSITIONS FOR THE TREATMENT OF PROLIFERATIVE DISORDERS<br/>[FR] MÉTHODES ET COMPOSITIONS POUR LE TRAITEMENT DE TROUBLES PROLIFÉRATIFS
  申请人：BETH ISRAEL HOSPITAL

  公开号：WO2012125724A1

  公开（公告）日：2012-09-20

  The invention features methods of treating a proliferative disorder characterized by elevated Pinl marker levels and/or reduced Pinl Ser71 phosphorylation in a subject by administering a retinoic acid compound. Additionally, the invention features methods of treating proliferative disorders (e.g., proliferative disorders characterized by elevated Pinl marker levels) by administering a retinoic acid compound in combination with another anti-proliferative compound. Finally, the invention also features methods including high-throughput screens for discovering and validating Pinl inhibitors.
• [EN] ENHANCED ATRA-RELATED COMPOUNDS DERIVED FROM STRUCTURE-ACTIVITY RELATIONSHIPS AND MODELING FOR INHIBITING PIN1<br/>[FR] DÉRIVÉS PERFECTIONNÉS DE COMPOSÉS APPARENTÉS À L'ATRA À PARTIR DE RELATIONS STRUCTURE-ACTIVITÉ ET MODÉLISATION D'INHIBITION DE PIN1
  申请人：BETH ISRAEL HOSPITAL

  公开号：WO2015143190A1

  公开（公告）日：2015-09-24

  The invention features all-trans retinoic acid (ATRA)-related compounds capable of associating with Pin1 and methods of identifying the same. The invention also provides methods of treating a condition selected from the group consisting of a proliferative disorder, an autoimmune disease, and an addiction condition characterized by elevated Pin1 marker levels, Pin1 degradation, and/or reduced Pin1 Ser71 phosphorylation in a subject by administering a retinoic acid compound. Additionally, the invention features methods of treating proliferative disorders, autoimmune diseases, and addiction conditions (e.g., diseases, disorders, and conditions characterized by elevated Pin1 marker levels) by administering a retinoic acid compound in combination with another therapeutic compound. The invention also features a co-crystal including Pin1 and a retinoic acid compound. Finally, the invention also provides methods of developing and identifying enhanced Pin1 -targeted ATRA-related compounds based on the newly defined unique binding pockets in the Pin1 active site revealed from the co-crystal structure, structure-activity relationship, and structural modeling.
• A preparation of high specific activity [11,12-3H]-9-cis-retinoic acid
  作者：Jotham W. Coe、Calvin R. Hawes、Patrick Towers

  DOI：10.1002/jlcr.2580360610

  日期：1995.6

  A selective total synthesis of [11,12-3H]-9-cis-retinoic acid 1 at a specific activity of 46 Ci/mmole is described. The alkyne 4, efficiently prepared in two steps from readily available starting materials, was partially reduced to 9,11-di-cis-retinoic acid 3 with both deuterium and tritium gas. Selective isomerization of 3 to 1 is discussed, as well as non-selective direct conversions of 4 to 1.

  描述了一种具有特定活性为46 Ci/mmol的[11,12-3H]-9-顺式-视黄酸1的选择性全合成方法。通过两步高效地从容易获得的起始材料制备得到的炔4，与氘气和氚气部分还原得到9,11-二顺式-视黄酸3。讨论了3到1的选择性异构化，以及4到1的非选择性直接转化。