all-trans-retinal dimer | 193532-21-7

• 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: all-trans-retinal dimer
• 英文别名: Retinal dimer；6-methyl-4,6-bis[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]cyclohexa-1,3-diene-1-carbaldehyde
• CAS: 193532-21-7
• 化学式: C₄₀H₅₄O
• 分子量: 550.868
• InChiKey: JHCJKXALYCOPEL-OELGEJODSA-N

物化性质

• 沸点：
  668.4±55.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  13-顺式视黄醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 all-trans-retinal dimer
  参考文献：
  名称：

  Condensation of all-E-retinal

  摘要：

  A novel base induced self condensation product of all-E-retinal is presented. The scope of the reaction is investigated with three analogous alpha,beta-unsaturated aldehydes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01171-4

文献信息

• Substituted Cyclohexadienals - Syntheses and Applications
  申请人：Watanabe Coran M. H.

  公开号：US20070232813A1

  公开（公告）日：2007-10-04

  The present invention is generally directed to the use of L-proline and certain derivatives thereof to catalyze the asymmetric self-condensation of α,β-unsaturated aldehydes to form homodimer and heterodimer cyclohexadienals. Reaction conditions are mild and yet amenable to a variety of different substrates yielding molecules with complex scaffolds from simple precursors. This approach allows for diversification and synthesis of this structural class of compounds in sufficient quantity, purity and enantioselectivity for, e.g., biological investigations and use as fluorescent probes, anti-cancer agents, anti-bacterial agents, and/or anti-fungal agents. The present invention is also generally directed to the cyclohexadienals produced.

  本发明通常涉及利用L-脯氨酸及其某些衍生物催化α,β-不饱和醛进行不对称自缩合，形成同二聚体和杂二聚体环己二烯醛。反应条件温和，且适用于多种不同的底物，从简单的原料生成具有复杂支架的分子。这种方法允许以足够的数量、纯度和对映选择性多样化合成这类结构的化合物，例如用于生物学研究以及作为荧光探针、抗癌剂、抗菌剂和/或抗真菌剂。本发明还一般涉及所生产的环己二烯醛。
• Aberrant Buildup of All-<i>Trans</i>-Retinal Dimer, a Nonpyridinium Bisretinoid Lipofuscin Fluorophore, Contributes to the Degeneration of the Retinal Pigment Epithelium
  作者：Junli Zhao、Yi Liao、Jingmeng Chen、Xinran Dong、Zhan Gao、Houjian Zhang、Xiaodan Wu、Zuguo Liu、Yalin Wu

  DOI：10.1167/iovs.16-20734

  日期：2017.2.13

  deleterious lipofuscin of RPE are involved in pathological mechanisms leading to the degeneration of RPE in AMD. A2E, a major component of RPE lipofuscin, could cause damage to RPE cells. Nevertheless, all-trans-retinal dimer (atRAL dimer) was found to be much more abundant than that of A2E in eyes of Abca4-/-Rdh8-/- double-knockout (DKO) mice, a rodent model showing the typical characteristics of retinopathies

  目的积聚为RPE的有害脂褐素的不可降解的荧光团与导致AMD中RPE变性的病理机制有关。A2E是RPE脂褐素的主要成分，可能会损坏RPE细胞。然而，在Abca4-/-Rdh8-/-双敲除（DKO）小鼠的眼睛中发现，全反式视网膜二聚体（atRAL二聚体）比A2E丰富得多，这是一种啮齿动物模型，显示了AcaE4-D视网膜病变在AMD患者中。我们的目的是阐明atRAL二聚体诱导的RPE变性的作用和机制。方法用HPLC检查从C57BL / 6J野生型（WT）和Abca4-/-Rdh8-/-DKO小鼠中收获的眼睛。细胞摄取，亚细胞定位，5-溴-2-脱氧尿苷（BrdU），Cdc25C，DNA链断裂，线粒体膜电位（ΔΨm），通过荧光显微镜分析细胞色素c。通过乳酸脱氢酶（LDH）测定和死细胞染色测定细胞毒性。通过流式细胞术检测细胞凋亡和细胞周期阶段。此外，通过免疫印迹测定法测量了与细胞周期和细胞凋亡相关的蛋
• OCTAHYDROCYCLOPENTAPYRROLES, THEIR PREPARATION AND USE
  申请人：PETRUKHIN Konstantin

  公开号：US20160024007A1

  公开（公告）日：2016-01-28

  The present invention provides Octahydrocyclopentapyrrole compounds having the structure: (structurally represented) wherein psi is absent or present, and when present is a bond; R1, R2, R3, R4, and R5 are each independently H, halogen, CF, or C1-C4 alkyl; R6 is absent or present, and when present is H, OH, or halogen; A is absent or present, and when present is C(O) or C(O)NH; B is substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, benzyl, CO2H or (C1-C4 alkyl)-CO2H, wherein when B is CO2H, then A is present and is C(O); and when psi is present, then R6 is absent and when psi is absent, then R6 is present, or a pharmaceutically acceptable salt thereof, for treatment of diseases characterized by excessive lipofuscin accumulation in the retina.

  本发明提供了八氢环戊吡咯化合物，其结构如下：（结构式表示），其中psi不存在或存在，当存在时为键；R1、R2、R3、R4和R5各自独立地为H、卤素、CF或C1-C4烷基；R6不存在或存在，当存在时为H、OH或卤素；A不存在或存在，当存在时为C（O）或C（O）NH；B为取代或未取代的单环、双环、杂单环、杂双环、苄基、CO2H或（C1-C4烷基）-CO2H，其中当B为CO2H时，A存在且为C（O）；当psi存在时，R6不存在，当psi不存在时，R6存在，或其药学上可接受的盐，用于治疗以视网膜过多脂褐质沉积为特征的疾病。
• OCTAHYDROPYRROLOPYRROLES THEIR PREPARATION AND USE
  申请人：PETRUKHIN Konstantin

  公开号：US20160046632A1

  公开（公告）日：2016-02-18

  The present invention provides compounds comprising variously substituted octahydropyrrolopyrroles, their synthesis, methods of making, methods of using, compositions and formulations thereof.

  本发明提供了包含各种取代的八氢吡咯吡咯化合物，它们的合成方法，制备方法，使用方法，以及它们的组成和配方。
• N-ALKYL-2-PHENOXYETHANAMINES, THEIR PREPARATION AND USE
  申请人：PETRUKHIN Konstantin

  公开号：US20160046649A1

  公开（公告）日：2016-02-18

  The present invention provides a compound having the structure: (structurally represented) wherein R1, R2, R3, R4, and R5 are each independently H, halogen, CF3 or C1-C4 alkyl; R6 is alkyl; A is absent or present, and when present is —C(O)— or —C(O)NH—; B is substituted or unsubstituted monocycle, bicycle, heteromonocycle, heterobicycle, benzyl, CO2H or (C1-C4 alkyl)-CO2H, wherein when B is CO2H, then A is present and is —C(O)—, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有以下结构的化合物：（结构表示）其中R1、R2、R3、R4和R5各自独立地为H、卤素、CF3或C1-C4烷基；R6为烷基；A不存在或存在，当存在时为—C（O）—或—C（O）NH—；B为取代或未取代的单环、双环、杂单环、杂双环、苄基、CO2H或（C1-C4烷基）-CO2H，其中当B为CO2H时，A存在且为—C（O）—，或其药学上可接受的盐。