6-Nitro-1-(3-pyrrolidin-1-ylpropyl)indole | 915037-82-0

• 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
• 英文名称: 6-Nitro-1-(3-pyrrolidin-1-ylpropyl)indole
• CAS: 915037-82-0
• 化学式: C₁₅H₁₉N₃O₂
• 分子量: 273.335
• InChiKey: SOCHCCMOHGODMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Nitro-1-(3-pyrrolidin-1-ylpropyl)indole 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 生成 C₁₅H₂₁N₃
  参考文献：
  名称：

  1,6-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,6-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). By varying the basic amine side chain at the 1-position of the indole ring, several potent and selective inhibitors of human neuronal NOS were identified. In general compounds with bulkier side chains displayed increased selectivity for nNOS over eNOS and iNOS isoforms. One of the compounds, (R)-8 was shown to reduce tactile hyperesthesia (allodynia) after oral administration (30 mg/kg) in an in vivo rat model of dural inflammation relevant to migraine pain. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.042
• 作为产物：
  描述：

  6-硝基吲哚 在 sodium hydride 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 6-Nitro-1-(3-pyrrolidin-1-ylpropyl)indole
  参考文献：
  名称：

  1,6-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,6-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase (NOS). By varying the basic amine side chain at the 1-position of the indole ring, several potent and selective inhibitors of human neuronal NOS were identified. In general compounds with bulkier side chains displayed increased selectivity for nNOS over eNOS and iNOS isoforms. One of the compounds, (R)-8 was shown to reduce tactile hyperesthesia (allodynia) after oral administration (30 mg/kg) in an in vivo rat model of dural inflammation relevant to migraine pain. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.042

文献信息

• SUBSTITUTED INDOLE COMPOUNDS HAVING NOS INHIBITORY ACTIVITY
  申请人：Maddaford Shawn

  公开号：US20080249302A1

  公开（公告）日：2008-10-09

  The present invention features inhibitors of nitric oxide synthase (NOS), particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, morphine/opioid induced tolerance and hyperalgesia.

  本发明涉及一种一氧化氮合酶（NOS）抑制剂，特别是那些选择性地抑制神经元一氧化氮合酶（nNOS）而不是其他NOS亚型。本发明的NOS抑制剂，单独或与其他药理活性剂联合使用，可用于治疗或预防诸如中风、再灌注损伤、神经退行性疾病、头部创伤、CABG、偏头痛（有和无先兆）、伴有痛觉过敏的偏头痛、中枢后中风疼痛（CPSP）、神经病性疼痛、吗啡/阿片类药物引起的耐受和高敏感性等疾病。
• US7375219B2
  申请人：——

  公开号：US7375219B2

  公开（公告）日：2008-05-20
• US7951940B2
  申请人：——

  公开号：US7951940B2

  公开（公告）日：2011-05-31
• US8586620B2
  申请人：——

  公开号：US8586620B2

  公开（公告）日：2013-11-19
• [EN] SUBSTITUTED INDOLE COMPOUNDS HAVING NOS INHIBITORY ACTIVITY<br/>[FR] COMPOSÉS INDOLE SUBSTITUÉS DÉPOURVUS D'ACTIVITÉ INHIBITRICE
  申请人：NEURAXON INC

  公开号：WO2007063418A2

  公开（公告）日：2007-06-07

  [EN] The present invention features inhibitors of nitric oxide synthase (NOS)5 particularly those that selectively inhibit neuronal nitric oxide synthase (nNOS) in preference to other NOS isoforms. The NOS inhibitors of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing conditions such as, for example, stroke, reperfusion injury, neurodegeneration, head trauma, CABG, migraine headache with and without aura, migraine with allodynia, central post-stroke pain (CPSP), neuropathic pain, morphine/opioid induced tolerance and hyperalgesia.
  [FR] La présente invention concerne des inhibiteurs de synthase d'oxyde nitrique (NOS), notamment ceux qui inhibent sélectivement la synthase d'oxyde nitrique (nNOS) préférablement à d'autres isoformes de NOS. Les inhibiteurs de NOS de l'invention, seuls ou en combinaison avec d'autres agents pharmaceutiquement actifs, peuvent être utilisés pour traiter ou prévenir des affections telles que, par exemple, l'accident cérébrovasculaire, la lésion de reperfusion, la neurodégénérescence, le traumatisme crânien, le pontage aortocoronarien, les maux de tête migraineux avec et sans aura, la migraine avec allodynie, la douleur centrale post-AVC, la douleur neuropathique, la tolérance induite par morphine/opioïde et l'hyperalgésie.