5-乙氧基吲哚-3-甲醛 | 169789-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-乙氧基吲哚-3-甲醛
• 英文名称: 5-ethoxy-1H-indole-3-carbaldehyde
• CAS: 169789-47-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: MSEZSIQZGXBEDM-UHFFFAOYSA-N

物化性质

• 沸点：
  381.8±22.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R36
• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  5-乙氧基吲哚-3-甲醛 在 哌啶 、 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 1-(5-乙氧基-1H-吲哚-3-基)丙烷-2-胺
  参考文献：
  名称：

  Synthesis and structure–activity relationship of novel conformationally restricted analogues of serotonin as 5-HT₆ receptor ligands

  摘要：

  5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structure-activity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the K-i of 23.4 and 20.5 nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

  DOI：

  10.3109/14756366.2011.595713
• 作为产物：
  描述：

  4-ethoxy-2-methyl-1-nitrobenzene 在 镍 盐酸 、 一水合肼 、 三氯氧磷 作用下， 反应 5.25h， 生成 5-乙氧基吲哚-3-甲醛
  参考文献：
  名称：

  The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists

  摘要：

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.

  DOI：

  10.1021/jm00013a010

文献信息

• Fluorinated indole-imidazole conjugates: Selective orally bioavailable 5-HT7 receptor low-basicity agonists, potential neuropathic painkillers
  作者：Adam S. Hogendorf、Agata Hogendorf、Katarzyna Popiołek-Barczyk、Agata Ciechanowska、Joanna Mika、Grzegorz Satała、Maria Walczak、Gniewomir Latacz、Jadwiga Handzlik、Katarzyna Kieć-Kononowicz、Evgeni Ponimaskin、Sophie Schade、Andre Zeug、Monika Bijata、Maciej Kubicki、Rafał Kurczab、Tomasz Lenda、Jakub Staroń、Ryszard Bugno、Beata Duszyńska、Bogusław Pilarski、Andrzej J. Bojarski

  DOI：10.1016/j.ejmech.2019.03.017

  日期：2019.5

  The 5-HT7 receptor has recently gained much attention due to its involvement in multiple physiological functions and diseases. The insufficient quality of the available molecular probes prompted design of fluorinated 3-(1-alkyl-1H-imidazol-5-yl)-1H-indoles as a new generation of selective 5-HT7 receptor agonists. A potent and drug-like agonist, 3-(1-ethyl-1H-imidazol-5-yl)-5-iodo-4-fluoro-1H-indole

  5-HT 7受体由于其参与多种生理功能和疾病而最近引起了广泛关注。现有分子探针质量不足，促使设计了氟化3-（1-烷基-1 H-咪唑-5-基）-1 H-吲哚作为新一代的选择性5-HT 7受体激动剂。有效和药物样激动剂，3-（1-乙基-1- ħ咪唑-5-基）-5-碘-4-氟-1- ħ -吲哚（AGH-192，35，ķ I 5-HT 7 - [R = 4 nM），是通过以Ser5.42作为假定的配偶体优化卤素键形成来鉴定的。该化合物的特点是优异的水溶性，对相关中枢神经系统靶标的高选择性，高代谢稳定性，口服生物利用度和低细胞毒性。 在小鼠腹腔注射（2.5 mg / kg）后发现迅速吸收到血液中，半衰期中等，大脑中的最高峰浓度C max = 1069 ng / g。因此，AGH-192可能是研究5-HT 7受体功能以及潜在的镇痛剂的长期寻求的工具化合物，这在神经性疼痛小鼠模型中观察到的抗伤害感受作用表明。
• PPAR active compounds
  申请人：Lin Jack

  公开号：US20070072904A1

  公开（公告）日：2007-03-29

  Compounds are described that are active on PPARs, including pan-active compounds and compounds selective for any one or any two of PPARα, PPARα and PPARδ. Also described are methods of use of the compounds in treating various diseases.

  描述了对PPARs活性的化合物，包括全谱活性化合物和选择性作用于PPARα、PPARα和PPARδ中的任何一个或两个的化合物。还描述了使用这些化合物治疗各种疾病的方法。
• 1,3-DISUBSTITUTED INDOLE DERIVATIVES FOR USE AS PPAR MODULATORS
  申请人：PLEXXIKON, INC.

  公开号：EP1943245A2

  公开（公告）日：2008-07-16
• [EN] PPAR ACTIVE COMPOUNDS<br/>[FR] COMPOSES ACTIFS SUR LES PPAR
  申请人：PLEXXIKON INC

  公开号：WO2007030559A2

  公开（公告）日：2007-03-15

  [EN] Compounds are described that are active on PPARs, including pan-active compounds and compounds selective for any one or any two of PPARa, PPAR? and PPARd. Also described are methods of use of the compounds in treating various diseases.
  [FR] L'invention concerne des composés qui sont actifs sur les PPAR, y compris les composés ayant une activité sur pan et des composés sélectifs pour un ou deux quelconques de PPARa, PPAR? et PPARd. L'invention concerne également des procédés d'utilisation de ces composés dans le traitement de diverses maladies.
• The Serotonin 5-HT4 Receptor. 2. Structure-Activity Studies of the Indole Carbazimidamide Class of Agonists
  作者：Karl-Heinz Buchheit、Rainer Gamse、Rudolf Giger、Daniel Hoyer、Francois Klein、Edgar Kloeppner、Hans-Juergen Pfannkuche、Henri Mattes

  DOI：10.1021/jm00013a010

  日期：1995.6

  A number of substituted indole carbazimidamides were prepared and evaluated as 5-HT4 receptor agonists by using the isolated field-stimulated guinea pig ileum preparation. Their selectivity for the 5-HT4 receptor was established by examining their affinity for other 5-HT receptors using radioligand-binding techniques. Several selective and highly potent full as well as partial agonists emerged from this study. For example, 1b,d were found to be the most potent, full 5-HT4 receptor agonists described so far (EC(50) = 0.5 and 0.8 nM, respectively), being 6 and 4 times more potent than serotonin itself. On the other hand, 5b and 1h appeared as partial 5-HT4 receptor agonists in the nonstimulated guinea pig ileum preparation with potencies, evaluated against serotonin action, respectively similar (5b, K-i = 12 nM) to and 300-fold higher (1h, K-i = 0.04 nM) than serotonin.