14-Ethylretinoic acid | 138093-41-1

• 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: 14-Ethylretinoic acid
• 英文别名: (2E,4E,6E,8E)-2-ethyl-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
• CAS: 138093-41-1
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: SGXIMFHLTCOFPV-XEZQCVTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  维A酸 在 六甲基磷酰三胺 、 氢氧化钾 、 sodium methylate 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 27.83h， 生成 14-Ethylretinoic acid
  参考文献：
  名称：

  视黄酸的碱催化异构化。14-烷基化的全反式，13-顺式和20,14-复古-视黄酸的合成和诱导分化的活性。

  摘要：

  视黄酸（1）通过过量的二异丙基氨基锂（LDA）进行区域选择性异构化，得到20,14-复古视黄酸（3）。视黄酸的中间二价阴离子的烷基化得到3的14-烷基化衍生物。通过在碱性条件下烷基化的逆向异构体的异构化，合成了几种14-烷基-全反式和-13-顺式-视黄酸。基于诱导人早幼粒细胞白血病细胞系HL-60分化的能力，检查了这些衍生物的类维生素A活性。20,14-复古视黄酸（3）的活性是视黄酸（1）的1/50。虽然14-甲基-20,14-复古-视黄酸（4）具有3的活性，但将14-甲基引入全反式和13-顺式-视黄酸会降低活性。

  DOI：

  10.1021/jm00081a020

文献信息

• ENCAPSULATED COSMETIC MATERIALS
  申请人：DSM IP Assets B.V.

  公开号：EP1838428A1

  公开（公告）日：2007-10-03
• Encapsulated Cosmetic Materials
  申请人：Van Benthem A. Rudolfus

  公开号：US20080031909A1

  公开（公告）日：2008-02-07

  Cosmetic materials, e.g., sunscreen agents are encapsulated by means of a compound of the formula (I) where X is O or NR 5 ; EWG is an electron-withdrawing group; R 1 , R 2 , R 3 , R 5 are equal to an H, alykl, cycloalkyl, aryl, or heterocyclic group; or R 1 , R 2 and R 5 or R 1 , R 2 and R 3 together form a heterocyclic group; and wherein at least one NH or NH 2 group, attached to an electron-attracting atom or to an atom that is connected to electron-attracting atom or group such as oxygen, nitrogen and sulphur, is present.
• [EN] ENCAPSULATED COSMETIC MATERIALS<br/>[FR] SUBSTANCES COSMETIQUES ENCAPSULEES
  申请人：DSM IP ASSETS BV

  公开号：WO2006061124A1

  公开（公告）日：2006-06-15

  [EN] Cosmetric materials, e.g., sunscreen agents are encapsulated by means of a compound of the formula (I) where X is O or NR₅; EWG is an electron-withdrawing group; R₁, R₂, R₃ R₅ are equal to an H, alykl, cycloalkyl, aryl, or heterocyclic group; or R₁, R₂ and R₅ or R₁, R₂ and R₃ together form a heterocyclic group; and wherein at least one NH or NH₂ group, attached to an electron-attracting atom or to an atom that is connected to electron-attracting atom or group such as oxygen, nitrogen and sulphur, is present.
  [FR] L'invention concerne des substances cosmétiques, par exemple, des agents de crème solaire, encapsulées au moyen d'un composé de formule (I), dans laquelle X désigne O ou NR₅; EWG représente un groupe de retrait d'électrons; R₁, R₂, R₃ R₅ représentent un groupe H, alkyle, cycloalkyle, aryle ou hétérocyclique; ou R₁, R₂ et R₅ ou R₁, R₂ et R₃ forment ensemble un groupe hétérocyclique; et au moins un groupe NH ou NH_2, fixé sur un atome attirant les électrons ou sur un atome connecté à un atome attirant les électrons ou un groupe, tel que l'oxygène, l'azote et le soufre est présent.
• [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.