3-(3-溴丙基)-5-氟-1H-吲哚 | 191013-68-0

• 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: 3-(3-溴丙基)-5-氟-1H-吲哚
• 英文名称: 3-(3-Bromopropyl)-5-fluoro-1H-indole
• 英文别名: 3-(3-bromo-propyl)-5-fluoro-1H-indole；3 (3-bromopropyl)-5-fluoro-1H-indole；3-(5-fluoro-3-indolyl)propyl bromide；3-(5-fluoroindol-3-yl)propyl bromide；5-fluoro-3-(3-bromopropyl)indole
• CAS: 191013-68-0
• 化学式: C₁₁H₁₁BrFN
• 分子量: 256.117
• InChiKey: ZJNJOXXOZZFKCS-UHFFFAOYSA-N

物化性质

• 沸点：
  354.6±27.0 °C(Predicted)
• 密度：
  1.519±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-(3-溴丙基)-5-氟-1H-吲哚 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 60.0~90.0 ℃ 、344.74 kPa 条件下， 反应 49.0h， 生成 3-{2-[3-(5-fluoro-1H-indol-3-yl)propylamino]ethoxy}benzene-1,2-diamine
  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
• 作为产物：
  描述：

  4-氟苯肼盐酸盐 在 四溴化碳 、 硫酸 、 三苯基膦 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 17.03h， 生成 3-(3-溴丙基)-5-氟-1H-吲哚
  参考文献：
  名称：

  新型吲哚烷基哌嗪衍生物作为选择性5-HT1A受体激动剂的设计，合成和结构-活性关系研究。

  摘要：

  5-HT1A受体（5-HT1AR）激动剂已涉及多种中枢神经系统（CNS）疾病的治疗，例如抑郁症和焦虑症等。基于我们先前发现的通过虚拟筛选获得的化合物FW01（Ki = 51±16 nM），通过修饰FW01的酰胺尾基和吲哚基团设计并合成了一系列FW01衍生物。SAR探索发现，酰胺尾基和吲哚基团在确定对多巴胺和5-羟色胺受体亚型的结合亲和力和选择性中起着关键作用。在所有测试的化合物中，9_24的Ki值为5±0.6 nM，对5-HT1AR的选择性很好。[35S]GTPγS分析显示9_24是对5-HT1AR的完全激动剂，EC50值为0.059 nM，显示为266.2和146。对5-HT2A和D3的选择性是4倍。用5-HT1AR-9_24进行了分子动力学模拟和分子对接研究，以揭示其高活性和选择性的机理。最后，提出了5-HT1AR的逐步9_24诱导信号转导机制。

  DOI：

  10.1021/acs.jcim.9b00926

文献信息

• [EN] 3-AMINO CHOMAN AND 2-AMINO TETRALIN DERIVATIVES<br/>[FR] DERIVES 3-AMINO CHOMANE ET 2-AMINO TETRALINE
  申请人：WYETH CORP

  公开号：WO2005012291A1

  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.

  揭示了3-氨基色苷和2-氨基四氢萘衍生物以及含有这些化合物的组合物。还揭示了在治疗血清素失调症，如抑郁症和焦虑症中使用3-氨基色苷和2-氨基四氢萘化合物以及含有这些化合物的组合物的方法。
• 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，
• Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands
  申请人：Wyeth

  公开号：US20030171353A1

  公开（公告）日：2003-09-11

  The present invention provides a compound of formula I and the use thereof for the therapeutic treatment of disorders relating to or affected by the 5-HT6 receptor. 1

  本发明提供了一种I式化合物及其用于治疗与5-HT6受体相关或受其影响的疾病的用途。
• Synthesis and Biological Evaluation of Novel Compounds within a Class of 3-Aminochroman Derivatives with Dual 5-HT_1A Receptor and Serotonin Transporter Affinity
  作者：Nicole T. Hatzenbuhler、Deborah A. Evrard、Boyd L. Harrison、Donna Huryn、Jennifer Inghrim、Christina Kraml、James F. Mattes、Richard E. Mewshaw、Dahui Zhou、Geoffrey Hornby、Qian Lin、Deborah L. Smith、Kelly M. Sullivan、Lee E. Schechter、Chad E. Beyer、Terrance H. Andree

  DOI：10.1021/jm060218h

  日期：2006.7.1

  Compounds containing a 5-carbamoyl-8-fluoro-3-amino-3,4-dihydro-2H-1-benzopyran and a 3-alkylindole moiety linked through a common basic nitrogen were prepared and evaluated for 5-HT1A affinity, serotonin rat transporter affinity, and functional antagonist activity in vitro. 26a was found to be the most potent and selective compound in this series and was shown to possess neurochemical activity in vivo by

  制备了包含5-氨基甲酰基-8-氟-3-氨基-3,4-二氢-2H-1-苯并吡喃和通过共同碱性氮连接的3-烷基吲哚部分的化合物并评估了5-HT1A亲和力转运蛋白亲和力和体外功能拮抗剂活性。已发现26a是该系列中最有效和最具选择性的化合物，并通过在大鼠额叶皮层中产生5-HT急剧且快速的增加而显示其在体内具有神经化学活性。
• Palladium-catalyzed dearomative cyclization by a norbornene-mediated sequence: a route to spiroindolenine derivatives
  作者：Xin-Xing Wu、Yi Shen、Wen-Long Chen、Si Chen、Peng-Fei Xu、Yong-Min Liang

  DOI：10.1039/c5cc07411h

  日期：——

  Spiroindolenine derivatives bearing an all-carbon quaternary spirocenter are synthesizedviaa Pd-catalyzed norbornene-mediated tandemortho-alkylation dearomative cyclization reaction.

  螺环吲哚啉衍生物通过Pd催化的诺伯辛介导串联邻位烷基化脱芳环化反应合成，其中含有全碳季铵螺环中心。