3-(4-aminobutyl)-5-fluoro-1H-indole | 724463-88-1

• 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
• 英文名称: 3-(4-aminobutyl)-5-fluoro-1H-indole
• 英文别名: 3-(4-aminobutyl)-5-fluoro-[1H]-indole；4-(5-fluoro-1H-indol-3-yl)-butylamine；4-(5-fluoro-1H-indol-3-yl)butan-1-amine
• CAS: 724463-88-1
• 化学式: C₁₂H₁₅FN₂
• 分子量: 206.263
• InChiKey: PMRAIFHQGIJTTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-quinaldine dioxine brosylate 、 3-(4-aminobutyl)-5-fluoro-1H-indole 在 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 生成 N-[4-(5-fluoro-1H-indol-3-yl)butyl]-N-(8-methyl-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-2-ylmethyl)amine
  参考文献：
  名称：

  [EN] ANTIDEPRESSANT INDOLEALKYL DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXAN METHYLAMINES
  [FR] DERIVES INDOLEALKYLE D'HETEROCYCLE DE BENZODIOXAN FUSIONNES METHYLAMINES EN TANT QU'ANTIDEPRESSEURS

  摘要：

  这个公式的化合物对治疗抑郁症（包括但不限于重性抑郁障碍、儿童抑郁症和慢性抑郁症）非常有用。焦虑、恐慌障碍、创伤后应激障碍、经前期失调性障碍（也称为经前综合征）、注意力缺陷障碍（伴有或不伴有多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖、厌食症、暴食症、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病均有一定疗效。

  公开号：

  WO2004024734A1
• 作为产物：
  描述：

  4-(5-fluoro-1H-indol-3-yl)butanamide 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 3-(4-aminobutyl)-5-fluoro-1H-indole
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and Pharmacological Evaluation of 3-(Aminoalkyl)-5-fluoroindoles as Myeloperoxidase Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm1009988

文献信息

• 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。
• Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines
  申请人：——

  公开号：US20040138222A1

  公开（公告）日：2004-07-15

  Compounds of the formula: 1 are useful for the treatment of depression (including but not limited to major depressive disorder, childhood depression and dysthymia), anxiety, panic disorder, post-traumatic stress disorder, premenstrual dysphoric disorder (also known as pre-menstrual syndrome), attention deficit disorder (with and without hyperactivity), obsessive compulsive disorder, social anxiety disorder, generalized anxiety disorder, obesity, eating disorders such as anorexia nervosa, bulimia nervosa, vasomotor flushing, cocaine and alcohol addiction, sexual dysfunction and related illnesses.

  公式1的化合物对于治疗抑郁症（包括但不限于重度抑郁症、儿童抑郁症和慢性低落情绪）、焦虑症、惊恐障碍、创伤后应激障碍、经前期不良情绪障碍（也称为经前综合征）、注意力缺陷过动症（带或不带多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖症、饮食障碍如厌食症、贪食症、潮红、可卡因和酒精成瘾、性功能障碍以及相关疾病具有治疗作用。
• 3-Amino chroman and 2-amino tetralin derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050032873A1

  公开（公告）日：2005-02-10

  3-Amino chroman and 2-amino tetralin derivatives and compositions containing such compounds are disclosed. Methods of using the 3-amino chroman and 2-amino tetralin compounds and compositions containing such compounds in the treatment of serotonin disorders, such as depression and anxiety, are also disclosed.

  本文披露了3-氨基色满和2-氨基四氢萘衍生物及含有这些化合物的组合物。还披露了使用3-氨基色满和2-氨基四氢萘化合物及含有这些化合物的组合物治疗血清素失调症，如抑郁和焦虑的方法。
• Piperidine und Piperazine, die Wirkungen auf das z.n.s. Zeigen
  申请人：MERCK PATENT GmbH

  公开号：EP0648767B1

  公开（公告）日：1997-05-28
• ANTIDEPRESSANT INDOLEALKYL DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXAN METHYLAMINES
  申请人：Wyeth

  公开号：EP1537122A1

  公开（公告）日：2005-06-08