2-(5-氟-1H-吲哚-3-基)乙基溴 | 127561-10-8

• 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: 2-(5-氟-1H-吲哚-3-基)乙基溴
• 英文名称: 3-(2-bromoethyl)-5-fluoro-1H-indole
• 英文别名: 2-(5-fluoro-1H-indol-3-yl)ethyl bromide
• CAS: 127561-10-8
• 化学式: C₁₀H₉BrFN
• 分子量: 242.091
• InChiKey: RTWYIDGAQHNTSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(5-氟-1H-吲哚-3-基)乙基溴 在 ethyl acetate hydrochloride 、 potassium carbonate 、 potassium iodide 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-(4-(2-(5-fluoro-1H-indol-3-yl)ethyl)piperazin-1-yl)benzo[d]isothiazole hydrochloride
  参考文献：
  名称：

  靶向SSRI / 5-HT1A / 5-HT7的新型芳烷基哌嗪和哌啶衍生物的合成及抗抑郁作用。

  摘要：

  合成了一系列新型的芳烷基哌嗪和哌啶衍生物，并评估了它们对5-羟色胺再摄取的抑制作用和5-HT 1A / 5-HT 7受体的亲和力活性。使用强制游泳测试（FST）和尾部悬浮测试（TST）筛选了选择性化合物的体内抗抑郁活性。结果表明，化合物19a对5-HT 1A / 5-HT 7受体（5-HT 1A，K i  = 12 nM； 5-HT 7，K i  = 3.2 nM）表现出高亲和力，并具有有效的5-羟色胺再摄取抑制作用。 （IC 50 = 14 nM），并在FST和TST模型中显示出明显的抗抑郁样作用。

  DOI：

  10.1016/j.bmcl.2019.126703
• 作为产物：
  描述：

  5-氟吲哚-3-乙酸 在 lithium aluminium tetrahydride 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(5-氟-1H-吲哚-3-基)乙基溴
  参考文献：
  名称：

  Studies toward the Discovery of the Next Generation of Antidepressants. 3. Dual 5-HT_1A and Serotonin Transporter Affinity within a Class of N-Aryloxyethylindolylalkylamines

  摘要：

  N-Aryloxylethylindolealkylamines (5) having dual 5-HT transporter and 5-HT1A affinity are described. These compounds represent truncated analogues of our previously reported piperidinyl derivatives (3). Compounds in this investigation were found to have more similar affinities and functional activities for the 5-HT1A receptor and 5-HT transporter. Though 5-HT1A antagonism is not consistently observed throughout series 5, several molecular features were found to be essential to obtain high and balanced activities. The proper placement of a heteroatom in the aryl ring and the length of the linkage used to tether the indole moiety had significant influence on 5-HT1A and 5-HT transporter affinities. Introduction of a halogen into the aryl ring usually lowered intrinsic activity and in some cases led to full 5-HT1A antagonists. Compounds 33 and 34 were observed to be full 5-HT1A antagonists with K-i values of approximately 30 nM for the 5-HT1A receptor and K-i values of 5 and 0.5 nM for the 5-HT transporter, respectively. Unfortunately, similar to our previous series (3), compounds in this report also had high affinity for the alpha(1) receptor.

  DOI：

  10.1021/jm0304010

文献信息

• SUBSTITUTED HETEROARYL DERIVATIVES
  申请人：Zemolka Saskia

  公开号：US20100009986A1

  公开（公告）日：2010-01-14

  The invention relates to substituted heteroaryl derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted heteroaryl derivatives for producing medicaments.

  这项发明涉及替代杂环芳基衍生物，涉及其生产方法，含有该化合物的药物以及利用替代杂环芳基衍生物生产药物的用途。
• Synthesis and antidepressant-like activity of novel aralkyl piperazine derivatives targeting SSRI/5-HT 1A /5-HT 7
  作者：Zheng-Song Gu、Ai-nan Zhou、Ying Xiao、Qing-Wei Zhang、Jian-Qi Li

  DOI：10.1016/j.ejmech.2017.12.063

  日期：2018.1

  piperazine derivatives were synthesized, and evaluated for their serotonin reuptake inhibitory and 5-HT1A/5-HT7 receptors affinities activity. Antidepressant activities in vivo of the compounds were screened using the forced swimming test (FST) and tail suspension test (TST). The results indicated that compounds 21k (RUI, IC50 = 31 nM; 5-HT1A, 5-HT7, ki = 62, 12 nM) and 21n (RUI, IC50 = 25 nM; 5-HT1A, 5-HT7

  合成了一系列新型的芳烷基哌嗪衍生物，并对其5-羟色胺再摄取抑制和5-HT 1A / 5-HT 7受体亲和力活性进行了评估。使用强制游泳试验（FST）和尾部悬浮试验（TST）筛选了化合物的体内抗抑郁活性。结果表明化合物21k（RUI，IC 50  = 31 nM; 5-HT 1A，5-HT 7，k i  = 62，12 nM）和21n（RUI，IC 50  = 25 nM; 5-HT 1A，5 -HT 7，K我 = 28，3.3纳米）表现出高的亲和性对5-HT 1A/ 5-HT 7受体结合有效的5-羟色胺再摄取抑制作用。具体而言，最有前途的化合物21n具有良好的口服药代动力学特性和可接受的hERG谱，并且在FST和TST模型中显示出有效的抗抑郁样作用。
• [EN] SMALL MOLECULE INDUCERS OF GDNF AS POTENTIAL NEW THERAPEUTICS FOR NEUROPSYCHIATRIC DISORDERS<br/>[FR] PETITES MOLÉCULES INDUCTRICES DE GDNF COMME NOUVELLE THÉRAPEUTIQUE POSSIBLE DES TROUBLES NEUROPSYCHIATRIQUES
  申请人：UNIV COLUMBIA

  公开号：WO2013028999A1

  公开（公告）日：2013-02-28

  The invention provides a compound having the structure (I), wherein A is a substituted or unsubstituted ring; Z is present or absent and when present is (II), wherein n is 0, 1, 2, 3, or 4; Y is -(CR11R12)-, -NH(CR11R12)- or -O(CR11R12)- wherein R11 and R12 are each hydrogen or combine to form a carbonyl; and wherein R1 to R10 are herein as described.

  本发明提供了一种具有结构（I）的化合物，其中A是取代的或未取代的环；Z是否存在，如果存在则为（II），其中n为0，1，2，3或4；Y是-(CR11R12)-，-NH(CR11R12)-或-O(CR11R12)-，其中R11和R12分别是氢或结合形成一个羰基；以及其中R1至R10如本文所述。
• Constructing <i>Iboga</i> Alkaloids via C–H Bond Functionalization: Examination of the Direct and Catalytic Union of Heteroarenes and Isoquinuclidine Alkenes
  作者：Andrew C. Kruegel、Souvik Rakshit、Xiaoguang Li、Dalibor Sames

  DOI：10.1021/jo5018102

  日期：2015.2.20

  The iboga alkaloids have attracted considerable attention in both the scientific community and popular media due to their reported ability to reverse or markedly diminish cravings for, and self-administration of, the major drugs of abuse. We have developed three new intramolecular C–H functionalization procedures leading to the core seven-membered ring of the iboga skeleton, a cyclization that proved

  由于据报道，伊博加生物碱具有逆转或显着减少对主要滥用药物的渴望和自我管理的能力，因此在科学界和大众媒体中都引起了相当大的关注。我们已经开发了三种新的分子内C–H功能化程序，这些程序导致了iboga骨架的核心七元环，这种环化过程极具挑战性。亲电钯盐Pd（CH 3 CN）4（BF 4）2对多种N-（2-芳基乙基）异喹核苷，收率为10–35％。两步溴化还原型Heck反应方案对于以42％的产率合成ibogamine也是有效的。最后，直接的Ni（0）催化的C–H功能化提供了ibogamine（74％）和epi- ibogamine（38％）的苯并呋喃类似物。尽管每种方法都有明显的缺点，但结合起来，所描述的方法提供了通往各种异烟酰胺类似物的实用途径。
• Synthesis and Evaluation of Novel 2,3-Dihydrobenzo[<i>b</i>][1,4]dioxin- and Indolealkylamine Derivatives as Potential Antidepressants
  作者：Songlin Wang、Yin Chen、Xinghua Liu、Xiangqing Xu、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1002/ardp.201300238

  日期：2014.1

  A series of 2,3‐dihydrobenzo[b][1,4]dioxin‐ and indolealkylamine derivatives were synthesized and the target compounds were evaluated for their binding affinities at the 5‐HT1A receptor and serotonin transporter. Antidepressant‐like activities of the compounds were screened using the tail suspension and forced swim tests in mice. Preliminary results indicated that the target compounds exhibited high

  合成了一系列 2,3-二氢苯并[b][1,4]二恶英和吲哚烷基胺衍生物，并评估了目标化合物对 5-HT1A 受体和血清素转运蛋白的结合亲和力。使用尾悬和小鼠强迫游泳试验筛选化合物的抗抑郁样活性。初步结果表明，目标化合物对 5-HT1A 受体和血清素转运蛋白表现出高亲和力，并产生显着的抗抑郁样作用。本研究中最好的例子是化合物 5，它对 5-HT1A 受体 (Ki = 96 nM) 和血清素转运蛋白 (Ki = 9.8 nM) 表现出高结合亲和力。化合物 5 的内在活性显示出对 5-HT1A 受体的激动作用和对 5-HT 转运蛋白的抑制作用。此外，