(Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylic acid | 40244-46-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylic acid
• 英文别名: 7-cis-β-Cyclocitrylidenessigsaeure；(Z)-3-(2,6,6-trimethylcyclohexen-1-yl)prop-2-enoic acid
• CAS: 40244-46-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: RCVGWZAQWMJQHG-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl (2E)-3-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-propenoate 在 sodium hydroxide 、 维生素 B2 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 28.0h， 生成 (Z)-3-(2,6,6-trimethylcyclohex-1-en-1-yl)acrylic acid
  参考文献：
  名称：

  β-离子基衍生物的光催化E → Z异构化

  摘要：

  据报道，使用廉价的（-）-核黄素（维生素B 2），在402 nm的辐射下，基于视网膜固有的β-离子基，活化二烯的操作简单的E → Z异构化。从光激发的（-）-核黄素到起始E-异构体的选择性能量转移实现了几何异构化。由于与Z-异构体的类似过程效率低下，因此可避免微观可逆性，从而实现定向异构化以生成反热力学产物（产率高达99％，Z / E高达99：1））。谨慎选择光催化剂可使分子间和分子内系统实现化学选择性异构化。从这项研究中建立的原理，以及分子编辑方法，已经促进了基于视网膜支架的截短的三烯的区域选择性异构化的发展。

  DOI：

  10.1021/acs.orglett.9b03842

文献信息

• Methods and compositions for the treatment of proliferative disorders
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US10265288B2

  公开（公告）日：2019-04-23

  The invention features methods of treating a proliferative disorder characterized by elevated Pin1 marker levels and/or reduced Pin1 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 Pin1 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 Pin1 inhibitors.

  本发明的特点是通过施用维甲酸化合物治疗增殖性疾病的方法，该增殖性疾病的特征是受试者体内Pin1标记物水平升高和/或Pin1 Ser71磷酸化降低。此外，本发明还具有通过施用维甲酸化合物与另一种抗增殖化合物联合治疗增殖性疾病（例如，以Pin1标记物水平升高为特征的增殖性疾病）的方法。最后，本发明还包括发现和验证 Pin1 抑制剂的高通量筛选方法。
• Enhanced ATRA-related compounds for the treatment of proliferative diseases, autoimmune diseases, and addiction conditions
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US10548864B2

  公开（公告）日：2020-02-04

  The invention features all-trans retinoic acid (ATRA)-related compounds capable of associating with Pin1 and methods of treating a proliferative disorder characterized by elevated Pin1 marker levels, Pin1 degradation, and/or reduced Pin1 Ser71 phosphorylation in a subject by administering an ATRA-related compound. The invention also 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 an ATRA-related compound in combination with another therapeutic compound.

  本发明的特征是能够与Pin1结合的全反式维甲酸（ATRA）相关化合物，以及通过施用ATRA相关化合物治疗以Pin1标记物水平升高、Pin1降解和/或Pin1 Ser71磷酸化降低为特征的增殖性疾病的方法。本发明的另一个特点是通过施用 ATRA 相关化合物与另一种治疗化合物联合治疗增殖性疾病、自身免疫性疾病和成瘾病症（例如，以 Pin1 标记水平升高为特征的疾病、病症和病症）的方法。
• Arsenic trioxide for treatment of PIN1-associated disorders
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US10980835B2

  公开（公告）日：2021-04-20

  The present invention relates to the treatment of Pin1-associated disorders (e.g., disorders characterized by elevated Pin1 activity) with arsenic trioxide, optionally in combination with a retinoic acid compound. Pin1-associated disorders may include, for example, proliferative disorders (e.g., cancers), inflammatory conditions, and autoimmune disorders associated with aberrant levels of Pin1 activity.

  本发明涉及用三氧化二砷治疗Pin1相关疾病（例如，以Pin1活性升高为特征的疾病），可选择与维甲酸化合物联合使用。Pin1相关疾病可包括与Pin1活性异常水平相关的增殖性疾病（如癌症）、炎症和自身免疫性疾病等。
• METHODS AND COMPOSITIONS FOR THE TREATMENT OF PROLIFERATIVE DISORDERS
  申请人：Lu Kun Ping

  公开号：US20140086909A1

  公开（公告）日：2014-03-27

  The invention features methods of treating a proliferative disorder characterized by elevated Pin1 marker levels and/or reduced Pin1 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 Pin1 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 Pin1 inhibitors.
• ENHANCED ATRA-RELATED COMPOUNDS DERIVED FROM STRUCTURE-ACTIVITY RELATIONSHIPS AND MODELING FOR INHIBITING PIN1
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US20170112792A1

  公开（公告）日：2017-04-27

  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.