5-Chloro-3-(2-nitropropen-1-yl)indole | 835-49-4

• 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: 5-Chloro-3-(2-nitropropen-1-yl)indole
• 英文别名: 5-chloro-3-(2-nitroprop-1-enyl)-1H-indole
• CAS: 835-49-4
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: FRWWVBACCSQZRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Chloro-3-(2-nitropropen-1-yl)indole 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以94.9%的产率得到1-(5-氯-1H-吲哚-3-基)丙烷-2-胺
  参考文献：
  名称：

  ORGANIC COMPOUNDS

  摘要：

  这项发明涉及具有有趣药理特性的有机化合物。具体来说，这些化合物在治疗和/或预防由疟原虫、间日疟原虫、疟原虫、卵形疟原虫、克氏锥虫等引起的感染方面具有用途，以及像唐氏锥虫属的寄生虫，例如唐氏锥虫等。该发明还涉及含有这些化合物的药物组合物，以及它们的制备方法。

  公开号：

  US20090275560A1
• 作为产物：
  描述：

  5-氯吲哚 在 ammonium acetate 、 三氯氧磷 作用下， 反应 19.55h， 生成 5-Chloro-3-(2-nitropropen-1-yl)indole
  参考文献：
  名称：

  Alpha-ethyltryptamines as dual dopamine–serotonin releasers

  摘要：

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.062

文献信息

• 3-(Aminopropyl)indoles
  申请人：Clin Midy

  公开号：US03953442A1

  公开（公告）日：1976-04-27

  Pharmacologically valuable 3-(aminopropyl)-indoles have the general formula ##SPC1## In which R.sub.1 is phenyl, halophenyl, nitrophenyl, aminophenyl, loweralkoxyphenyl or pyridyl, R.sub.2 is hydrogen or methyl, R.sub.3 and R.sub.4 are each hydrogen or lower alkyl or taken together form a polymethylene group which may be interrupted by oxygen so that --NR.sub.3 R.sub.4 is a heteromonocycle having 5 or 6 nuclear atoms and R.sub.5 is hydrogen, fluorine, chlorine or methoxy. Especially interesting are those compounds in which at least one of R.sub.1 and R.sub.5 comprises a flourine atom and --NR.sub.3 R.sub.4 is pyrrolidino. The compounds are made by condensation of correspondingly substituted indolylacetones with amines HNR.sub.3 R.sub.4 in a reducing medium or, in certain cases, by reduction of correspondingly substituted indolylacetoximes with or without subsequent lower alkylation.

  具有药理学价值的3-(氨基丙基)-吲哚具有通用公式##SPC1## 其中R.sub.1是苯基、卤代苯基、硝基苯基、氨基苯基、低烷氧基苯基或吡啶基，R.sub.2是氢或甲基，R.sub.3和R.sub.4分别是氢或低烷基或一起形成可被氧中断的多亚甲基基团，以使--NR.sub.3 R.sub.4成为具有5或6个核原子的杂单环，R.sub.5是氢、氟、氯或甲氧基。特别有趣的是那些至少有一个R.sub.1和R.sub.5包含氟原子和--NR.sub.3 R.sub.4是吡咯烷基的化合物。这些化合物是通过对应取代的吲哚乙酮和胺HNR.sub.3 R.sub.4在还原介质中缩合制备的，或者在某些情况下，通过还原对应取代的吲哚乙酰肟并在有或没有随后的低烷基化反应下制备的。
• ORGANIC COMPOUNDS
  申请人：ANG Shi Hua

  公开号：US20090275560A1

  公开（公告）日：2009-11-05

  The invention relates to organic compounds which have interesting pharmaceutical properties. In particular, the compounds are useful in the treatment and/or prevention of infections such as those caused by Plasmodium falciparum, Plasmodium vivax, Plasmodium malariae, Plasmodium ovale, Trypanosoma cruzi and parasites of the Leishmania genus such as, for example, Leishmania donovani . The invention also relates to pharmaceutical compositions containing the compounds, as well as processes for their preparation.

  这项发明涉及具有有趣药理特性的有机化合物。具体来说，这些化合物在治疗和/或预防由疟原虫、间日疟原虫、疟原虫、卵形疟原虫、克氏锥虫等引起的感染方面具有用途，以及像唐氏锥虫属的寄生虫，例如唐氏锥虫等。该发明还涉及含有这些化合物的药物组合物，以及它们的制备方法。
• Alpha-ethyltryptamines as dual dopamine–serotonin releasers
  作者：Bruce E. Blough、Antonio Landavazo、John S. Partilla、Ann M. Decker、Kevin M. Page、Michael H. Baumann、Richard B. Rothman

  DOI：10.1016/j.bmcl.2014.07.062

  日期：2014.10

  The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were > 10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2A receptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2A receptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential. (C) 2014 Elsevier Ltd. All rights reserved.