3-(5-氟-1H-3-吲哚)-1-丙醇 | 141071-80-9

• 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-(5-氟-1H-3-吲哚)-1-丙醇
• 中文别名: 3-(5-氟-1H-吲哚-3-基)丙-1-醇
• 英文名称: 3-(5-fluoro-1H-indol-3-yl)propan-1-ol
• 英文别名: 5-fluoro-3-(3 hydroxypropyl)-1H-indole；3-(5-fluoro-1H-3-indolyl)-1-propanol
• CAS: 141071-80-9
• 化学式: C₁₁H₁₂FNO
• mdl: MFCD08705788
• 分子量: 193.221
• InChiKey: JXNVVCPTZHQWFO-UHFFFAOYSA-N

物化性质

• 沸点：
  381.0±27.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿；二氯甲烷；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  36
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-氟-1H-3-吲哚)-1-丙醇 在 palladium on activated charcoal sodium azide 、 四溴化碳 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 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 51.0h， 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：

  3-(5-fluoro-1H-indol-3-yl)propyl acetate 在 甲醇 、 氢氧化钾 作用下， 生成 3-(5-氟-1H-3-吲哚)-1-丙醇
  参考文献：
  名称：

  A direct and simple approach for the synthesis of indole-3-propanol and its acetates from dihydropyran

  摘要：

  A general method was developed for the one-pot synthesis of highly functionalized indoles from simple, commercially available phenylhydrazine hydrochlorides and dihydropyran. Synthesis of indole-3-propanol and its acetates was studied extensively for appropriate acetic acid and water mixture as the solvent.

  DOI：

  10.1007/s00706-008-0945-x

文献信息

• [EN] SUBSTITUTED PIPERAZINE COMPOUNDS AND METHODS AND USE THEREOF<br/>[FR] COMPOSÉS PIPÉRAZINIQUES SUBSTITUÉS, PROCÉDÉS ET UTILISATION ASSOCIÉS
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2015169180A1

  公开（公告）日：2015-11-12

  Provided herein are novel piperazine compounds acting as selective serotonin reuptake inhibitors and/or the 5-HT1A receptor agonists. The invention also relates to the methods of preparing the compound and pharmaceutical composition, and the use of treating central nervous system dysfunction in mammals especially in humans.

  本文提供了作为选择性血清素再摄取抑制剂和/或5-HT1A受体激动剂的新型哌嗪化合物。该发明还涉及制备该化合物和药物组合物的方法，以及用于治疗哺乳动物中枢神经系统功能障碍，特别是人类的用途。
• 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。
• Synthesis, Structure−Activity Relationships, and Biological Properties of 1-Heteroaryl-4-[ω-(1<i>H</i>-indol-3-yl)alkyl]piperazines, Novel Potential Antipsychotics Combining Potent Dopamine D₂ Receptor Antagonism with Potent Serotonin Reuptake Inhibition
  作者：Pieter Smid、Hein K. A. C. Coolen、Hiskias G. Keizer、Rolf van Hes、Jan-Peter de Moes、Arnold P. den Hartog、Bob Stork、Rob H. Plekkenpol、Leonarda C. Niemann、Cees N. J. Stroomer、Martin Th. M. Tulp、Herman H. van Stuivenberg、Andrew C. McCreary、Mayke B. Hesselink、Arnoud H. J. Herremans、Chris G. Kruse

  DOI：10.1021/jm050148z

  日期：2005.11.1

  A series of novel bicyclic 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines was synthesized and evaluated on binding to dopamine D(2) receptors and serotonin reuptake sites. This class of compounds proved to be potent in vitro dopamine D(2) receptor antagonists and in addition were highly active as serotonin reuptake inhibitors. Some key representatives showed potent pharmacological in vivo activities

  合成了一系列新颖的双环1-杂芳基-4- [ω-（1H-吲哚-3-基）烷基]哌嗪，并评估了与多巴胺D（2）受体和5-羟色胺再摄取位点的结合。这类化合物被证明是有效的体外多巴胺D（2）受体拮抗剂，此外还具有作为5-羟色胺再摄取抑制剂的高活性。一些主要代表在口服阿扑吗啡诱导的爬升的拮抗作用和5-HTP诱导的小鼠行为的拮抗作用中均显示出口服给药后体内的有效药理活性。根据临床前数据，8- 4- [3-（5-氟-1H-吲哚-3-基）丙基]哌嗪-1-基} -4H-苯并[1,4]恶嗪-（R选择）-2-甲基-3-酮（45c，SLV314）进行临床开发。体外和体内研究表明45c具有良好的药代动力学特性和较高的CNS血浆比例。
• Indolylalkyl derivatives of pyrimidinylpiperazine for treating vascular
  申请人：Bristol-Myers Squibb Company

  公开号：US05300506A1

  公开（公告）日：1994-04-05

  A series of novel indol-3-ylalkyl derivatives of alkoxypyrimidinylpiperazines are disclosed as Formula I. ##STR1## These compounds are intended to be useful agents for alleviation of vascular headache on the basis of their potent affinity and agonist activity at 5-HT1D binding sites.

  一系列新颖的吲哚-3-基烷基衍生物的烷氧基嘧啶基哌嗪被披露为公式I。这些化合物旨在通过它们在5-HT1D结合位点的强亲和力和激动剂活性来缓解血管性头痛。
• INDOLYLALKYL DERIVATIVES OF PYRIMIDINYLPIPERAZINE AND METABOLITES THEREOF FOR TREATMENT OF ANXIETY, DEPRESSION, AND SEXUAL DYSFUNCTION
  申请人：KRAMER Stephen J.

  公开号：US20090281114A1

  公开（公告）日：2009-11-12

  The present invention relates to a method for alleviation, prevention, and treatment of anxiety, depression, and sexual dysfunction by administering certain indolylalkyl derivatives of pyrimidinylpiperazine or metabolites thereof. A preferred embodiment is of the following formula:

  本发明涉及通过给予某些吡咯啉基吡咯嗪的衍生物或其代谢物来缓解、预防和治疗焦虑、抑郁和性功能障碍的方法。一种首选实施例的化学式如下：