5-氟-N,N-二甲基色胺 | 22120-36-1

• 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-氟-N,N-二甲基色胺
• 英文名称: 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethanamine
• 英文别名: 2-(5-fluoro-1H-indol-3-yl)-N,N-dimethylethylamine；N,N-dimethyl-3-(2-aminoethyl)-5-fluoro-1H-indole；N,N-Dimethyl-5-fluoro-1H-indole-3-ethanamine；[2-(5-fluoro-indol-3-yl)-ethyl]-dimethyl-amine；N,N-dimethyl-3-(2-aminoethyl)-5-fluoro-[1H]-indole；5-Fluor-N,N-dimethyl-tryptamin；5-Fluoro-N,N-dimethyltryptamine
• CAS: 22120-36-1
• 化学式: C₁₂H₁₅FN₂
• 分子量: 206.263
• InChiKey: BXYDWQABVPBLBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氟-N,N-二甲基色胺 、 1-bromo-4-chloro-2-(chloromethyl)benzene 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(1-(2-bromo-5-chlorobenzyl)-5-fluoro-1H-indol-3-yl)-N,N-dimethylethan-1-amine
  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：

  4-二甲胺基丁醛缩二甲醇 、 4-氟苯肼盐酸盐 在 硫酸 作用下， 反应 2.0h， 以100%的产率得到5-氟-N,N-二甲基色胺
  参考文献：
  名称：

  Improved Fischer Indole Reaction for the Preparation of N,N-Dimethyltryptamines: Synthesis of L-695,894, a Potent 5-HT1D Receptor Agonist

  摘要：

  DOI：

  10.1021/jo00092a046

文献信息

• 吲哚衍生物及其在药物上的应用
  申请人：广东东阳光药业有限公司

  公开号：CN104276993B

  公开（公告）日：2019-03-15

  本发明提供一些吲哚衍生物或其立体异构体，互变异构体，氮氧化物，溶剂化物，代谢产物，药学上可接受的盐或前药，用于治疗阿尔茨海默症。本发明还公开了含有这样的化合物的药物组合物和使用本发明化合物或其药物组合物治疗阿尔茨海默症的方法。
• [EN] METHODS OF TREATING PSYCHOLOGICAL CONDITIONS<br/>[FR] PROCÉDÉS DE TRAITEMENT DE TROUBLES PSYCHOLOGIQUES
  申请人：UNIV OKLAHOMA STATE

  公开号：WO2010151258A1

  公开（公告）日：2010-12-29

  A method and composition for inducing in a subject a tolerance to a psychoactive substance or for treating an abnormal mental condition in a subject. The composition used in the method comprises in one embodiment a 5-HT2B receptor agonist disposed within a pharmaceutically-acceptable vehicle or carrier.

  一种用于诱导受试者对精神活性物质产生耐受性或用于治疗受试者异常精神状况的方法和组合物。该方法中使用的组合物在一个实施例中包括一个5-HT2B受体激动剂，该激动剂被置于药学上可接受的载体或载体中。
• 3-ALKYL-5-FLUOROINDOLE DERIVATIVES AS MYELOPEROXIDASE INHIBITORS
  申请人：Soubhye Jalal

  公开号：US20120122948A1

  公开（公告）日：2012-05-17

  The invention relates to a compound of formula (Ia) wherein n is an integer between 2 and 10, R 1 and R 2 independently represent a substituent selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 3 -C 10 cycloalkyl and aminoalkyl, or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a four to ten-membered heterocycle, R 5 represents independently in each of the n units a substituent selected from the group consisting of hydrogen, C 1 -C 10 alkyl, halogen, alkoxy, aminoalkyl and alkylamino; or a pharmaceutically acceptable salt thereof, with the proviso that the 5-fluorotryptamine is excluded, for the treatment or the prophylaxis of neuroinflammatory diseases or disorders. The invention also relates to a pharmaceutical composition, a method for inhibiting myeloperoxidase enzyme activity, to a method for inhibiting Low density lipoproteins oxidation.

  该发明涉及一个化合物，其化学式为（Ia），其中n为2到10之间的整数，R1和R2分别代表从氢、C1-C10烷基、C3-C10环烷基和氨基烷基组成的基团，或者R1和R2与它们所连接的氮原子一起形成一个由四到十个成员的杂环，R5在每个n个单位中独立地代表从氢、C1-C10烷基、卤素、烷氧基、氨基烷基和烷基氨基组成的基团；或其药学上可接受的盐，但排除5-氟色胺，用于治疗或预防神经炎性疾病或紊乱。该发明还涉及一种制药组合物，一种抑制髓过氧化物酶酶活性的方法，以及一种抑制低密度脂蛋白氧化的方法。
• [EN] COMPOUNDS FOR INCREASING NEURAL PLASTICITY<br/>[FR] COMPOSÉS POUR L'AUGMENTATION DE LA PLASTICITÉ NEURONALE
  申请人：UNIV CALIFORNIA

  公开号：WO2018064465A1

  公开（公告）日：2018-04-05

  The present invention provides a method of using non-hallucinogenic analogs of psychedelic compounds for increasing neural plasticity of the neuronal cell, and a method of using thereof for treating a brain disorder.

  本发明提供了一种利用非致幻类似物治疗神经元细胞的神经可塑性增加的方法，以及利用该方法治疗脑部疾病的方法。
• Structure-Based Design, Synthesis, and Pharmacological Evaluation of 3-(Aminoalkyl)-5-fluoroindoles as Myeloperoxidase Inhibitors
  作者：Jalal Soubhye、Martine Prévost、Pierre Van Antwerpen、Karim Zouaoui Boudjeltia、Alexandre Rousseau、Paul G. Furtmüller、Christian Obinger、Michel Vanhaeverbeek、Jean Ducobu、Jean Nève、Michel Gelbcke、Franc¸ois Dufrasne

  DOI：10.1021/jm1009988

  日期：2010.12.23

  Oxidized low-density lipoproteins (LDLs) accumulate in the vascular wall and promote local inflammation, which contributes to the progression of the atheromatous plaque. The key role of myeloperoxidase (MPO) in this process is related to its ability to modify APO B-100 in the intima and at the surface of endothelial cells. A series of 3-(aminoalkyl)-5-fluoroindole analogues was designed and synthesized by exploiting the structure-based docking of 5-fluorotryptamine, a known MPO inhibitor. In vitro assays were used to study the effects of these compounds on the inhibition of MPO-mediated taurine chlorination and oxidation of LDLs. The kinetics of the interaction between the MPO redox intermediates, Compounds I and II, and these inhibitors was also investigated. The most potent molecules possessed a 4- or 5-carbon aminoalkyl side chain and no substituent on the amino group. The mode of binding of these analogues and the mechanism of inhibition is discussed with respect to the structure of MPO and its halogenation and peroxidase cycles.