4-(3-(5-Nitro-1H-indol-1-yl)propyl)morpholine | 954386-88-0

• 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: 4-(3-(5-Nitro-1H-indol-1-yl)propyl)morpholine
• 英文别名: 4-[3-(5-nitroindol-1-yl)propyl]morpholine
• CAS: 954386-88-0
• 化学式: C₁₅H₁₉N₃O₃
• 分子量: 289.334
• InChiKey: YZEHZRTVJKNEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 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：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-(5-Nitro-1H-indol-1-yl)propyl)morpholine 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 生成 N-(1-(3-morpholinopropyl)-1H-indol-5-yl)thiophene-2-carboximidamide
  参考文献：
  名称：

  1,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase. A variety of flexible and restricted basic amine side chain substitutions was explored at the 1-position of the indole ring, while keeping the amidine group fixed at the 5-position. Compounds having N-(1-(2-(1-methylpyrrolidin-2-yl) ethyl)- (12, (R)-12, (S)-12 and 13) and N-(1-(1-methylazepan-4-yl)-side chains (14, 15, (-)-15 and (+)-15) showed increased inhibitory activity for the human nNOS isoform and selectivity over eNOS and iNOS isoforms. The most potent compound of the series for human nNOS (IC(50) = 0.02 mu M) (S)-12 showed very good selectivity over the eNOS (eNOS/nNOS = 96-fold) and iNOS (iNOS/nNOS = 850-fold) isoforms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.022
• 作为产物：
  描述：

  5-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 4-(3-(5-Nitro-1H-indol-1-yl)propyl)morpholine
  参考文献：
  名称：

  1,5-Disubstituted indole derivatives as selective human neuronal nitric oxide synthase inhibitors

  摘要：

  A series of 1,5-disubstituted indole derivatives was designed, synthesized and evaluated as inhibitors of human nitric oxide synthase. A variety of flexible and restricted basic amine side chain substitutions was explored at the 1-position of the indole ring, while keeping the amidine group fixed at the 5-position. Compounds having N-(1-(2-(1-methylpyrrolidin-2-yl) ethyl)- (12, (R)-12, (S)-12 and 13) and N-(1-(1-methylazepan-4-yl)-side chains (14, 15, (-)-15 and (+)-15) showed increased inhibitory activity for the human nNOS isoform and selectivity over eNOS and iNOS isoforms. The most potent compound of the series for human nNOS (IC(50) = 0.02 mu M) (S)-12 showed very good selectivity over the eNOS (eNOS/nNOS = 96-fold) and iNOS (iNOS/nNOS = 850-fold) isoforms. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.022

文献信息

• 1,5 And 3,6- substituted indole compounds having NOS inhibitory activity
  申请人：Maddaford Shawn

  公开号：US20070254940A1

  公开（公告）日：2007-11-01

  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, or chronic pain.

  本发明涉及一种一氧化氮合酶（NOS）的抑制剂，特别是那些选择性地抑制神经一氧化氮合酶（nNOS）而不是其他NOS同工酶。本发明的NOS抑制剂，单独或与其他药用活性剂联合使用，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、冠状动脉搭桥手术（CABG）、有或无先兆的偏头痛、伴有触痛的偏头痛、中枢性中风后疼痛（CPSP）、神经病性疼痛或慢性疼痛等病症。
• 1,5 and 3,6-substituted indole compounds having NOS inhibitory activity
  申请人：NeurAxon, Inc.

  公开号：US07989447B2

  公开（公告）日：2011-08-02

  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, or chronic pain.

  本发明涉及一种一氧化氮合酶（NOS）抑制剂，特别是那些能够选择性地抑制神经型一氧化氮合酶（nNOS）而不影响其他NOS同工酶。本发明的NOS抑制剂可以单独或与其他药物活性剂联合使用，用于治疗或预防中风、再灌注损伤、神经退行性疾病、头部创伤、冠状动脉搭桥术（CABG）、带和不带先兆的偏头痛、带有痛觉过敏的偏头痛、中枢后中风痛（CPSP）、神经性疼痛或慢性疼痛等症状。
• Synthesis, Molecular Docking and ADME Prediction of 1H-indole/5- substituted Indole Derivatives as Potential Antioxidant and Anti- Inflammatory Agents
  作者：Rajesh Kumar Singh、Archana Kumari

  DOI：10.2174/1573406418666220812152950

  日期：2023.2

  OBJECTIVE The goal of this study was to synthesize N-substituted indole derivatives with different heterocyclic moieties through propyl linker with the aim of getting highly potent anti-inflammatory and antioxidant agents. METHODS Synthesized compounds were analyzed by analytical techniques such as IR, 1H NMR, 13C NMR spectra, and mass spectrometry. Molecular docking and ADME calculation were employed

  背景技术炎症是一种保护性的生物过程，但在极端条件下，它会变得对身体非常可怕。抗氧化剂和抗炎剂治疗相似的疾病状况，因为炎症和氧化应激通常遵循相似的致病途径。目的本研究的目的是通过丙基连接体合成具有不同杂环基团的N-取代吲哚衍生物，以获得高效的抗炎和抗氧化药物。方法 通过红外、1H NMR、13C NMR 光谱和质谱等分析技术对合成的化合物进行分析。对合成化合物采用分子对接和 ADME 计算，分别估计它们的 COX-2 酶抑制和药物样特性。通过 DPPH 测定和还原力测定评估抗氧化活性。使用吲哚美辛作为标准药物，评估了所选衍生物在急性（角叉菜胶诱导的爪水肿法）和慢性水平（福尔马林诱导的炎症法）下的抗炎活性。结果 此处合成了十二种吲哚衍生物（11a-c、12a-c、13a-c 和 14a-c）。其中，化合物 12c 被发现是最好的 COX-2 酶抑制剂，因为它显示出良好的相互作用能。在 ADME
• 1,5 AND 3,6- SUBSTITUTED INDOLE COMPOUNDS HAVING NOS INHIBITORY ACTIVITY
  申请人：Neuraxon Inc.

  公开号：EP2010527B1

  公开（公告）日：2013-08-14
• US7989447B2
  申请人：——

  公开号：US7989447B2

  公开（公告）日：2011-08-02