(2E,4E,6E,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid | 1075731-56-4

• 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: (2E,4E,6E,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• CAS: 1075731-56-4
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: QZTGWEZSZARWSX-XHGCCUEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 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,4E,6E,8E)-9-(2-butyl-6,6-dimethylcyclohex-1-enyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以82%的产率得到(2E,4E,6E,8E)-9-(2-butyl-6,6-dimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
  参考文献：
  名称：

  Preparation and biological evaluation of 5-substituted retinoic acids

  摘要：

  Various 5-substituted retinoic acids were prepared by a palladium-catalyzed cross coupling reactions of vinyl nonaflates and E-or Z-3-tributylstannyl-2-beten-1-ol as a key reaction. These coupling products were then converted to the corresponding all-E-and 9Z-retinoic acid analogs via Horner -Emmons reaction and subsequent basic hydrolysis, and their biological activities were evaluated. The all-E-derivatives, 5-butyl and isobutyl analogs exhibited stronger effects for anti-proliferative and differentiation-inducing activities in HL-60 cells. In contrast, in 9Z-derivatives, none of the analogs showed any activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.025

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.
• Preparation and biological evaluation of 5-substituted retinoic acids
  作者：Akimori Wada、Naomi Matsuura、Yukari Mizuguchi、Kimie Nakagawa、Masayoshi Ito、Toshio Okano

  DOI：10.1016/j.bmc.2008.08.025

  日期：2008.9

  Various 5-substituted retinoic acids were prepared by a palladium-catalyzed cross coupling reactions of vinyl nonaflates and E-or Z-3-tributylstannyl-2-beten-1-ol as a key reaction. These coupling products were then converted to the corresponding all-E-and 9Z-retinoic acid analogs via Horner -Emmons reaction and subsequent basic hydrolysis, and their biological activities were evaluated. The all-E-derivatives, 5-butyl and isobutyl analogs exhibited stronger effects for anti-proliferative and differentiation-inducing activities in HL-60 cells. In contrast, in 9Z-derivatives, none of the analogs showed any activity. (C) 2008 Elsevier Ltd. All rights reserved.