2-(dimethylamino)quinolin-8-ol | 70125-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(dimethylamino)quinolin-8-ol
• CAS: 70125-18-7
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD00168933
• 分子量: 188.229
• InChiKey: LGPJCCZQFZBUON-UHFFFAOYSA-N

物化性质

• 沸点：
  365.7±27.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-6-(4-(三氟甲基)苯基)嘧啶 、 2-(dimethylamino)quinolin-8-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以23%的产率得到N,N-dimethyl-8-(6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)quinolin-2-ylamine
  参考文献：
  名称：

  Novel Vanilloid Receptor-1 Antagonists:  2. Structure−Activity Relationships of 4-Oxopyrimidines Leading to the Selection of a Clinical Candidate

  摘要：

  A series of novel 4-oxopyrimidine TRPV1 antagonists was evaluated in assays measuring the blockade of capsaicin or acid-induced influx of calcium into CHO cells expressing TRPV1. The investigation of the structure-activity relationships in the heterocyclic A-region revealed the optimum pharmacophoric elements required for activity in this series and resulted in the identification of subnanomolar TRPV1 antagonists. The most potent of these antagonists were thoroughly profiled in pharmacokinetic assays. Optimization of the heterocyclic A-region led to the design and synthesis of 23, a compound that potently blocked multiple modes of TRPV1 activation. Compound 23 was shown to be effective in a rodent "on-target" biochemical challenge model (capsaicin-induced flinch, ED50 = 0.33 mg/kg p.o.) and was antihyperalgesic in a model of inflammatory pain (CFA-induced thermal hyperalgesia, MED = 0.83 mg/kg, p.o.). Based on its in vivo efficacy and pharmacokinetic profile, compound 23 (N-{4-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide; AMG 517) was selected for further evaluation in human clinical trials.

  DOI：

  10.1021/jm070190p
• 作为产物：
  描述：

  2-phenoxy-8-methoxyquinoline 在 三溴化硼 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 2-(dimethylamino)quinolin-8-ol
  参考文献：
  名称：

  螯合辅助的2-芳氧基喹啉的脱芳氧基胺化胺：生物活性PRMT5抑制剂关键片段的新合成途径†

  摘要：

  通过铜催化剂已经完成了O-或N-螯合基团官能化的2-芳氧基喹啉的高度区域选择性的脱芳氧基胺化。底物的螯合官能团在指导C-2-选择性胺化过程中起着关键作用，该过程通过芳氧基的新型芳香亲核取代进行。该方法可方便地获得一类重要的功能化2-氨基喹啉（分离产率高达88％），并已成功地用于重要生物活性PRMT5抑制剂关键片段的合成。

  DOI：

  10.1039/c8ob00911b

文献信息

• [EN] 8-HYDROXY QUINOLINE DERIVATIVES<br/>[FR] DERIVES DE QUINOLINE 8-HYDROXY
  申请人：PRANA BIOTECHNOLOGY LTD

  公开号：WO2004007461A1

  公开（公告）日：2004-01-22

  The present invention relates to a method for the treatment, amelioration and/or prophylaxis of a neurological condition, in particular neurodegenerative disorders which comprises the administration of an effective amount of a compound of formula (I): to a subject in need thereof. The present invention also relates to a compound of formula (II) and processes for its preparation.

  本发明涉及一种用于治疗、改善和/或预防神经系统疾病，特别是神经退行性疾病的方法，包括向需要的受试者施用化合物(I)的有效量。本发明还涉及一种化合物(II)及其制备方法。
• 8-HYDROXY QUINOLINE DERIVATIVES
  申请人：PRANA BIOTECHNOLOGY LIMITED

  公开号：US20150094334A1

  公开（公告）日：2015-04-02

  The present invention describes a method for the treatment of a neurological condition in a subject which comprises administering to a subject in need thereof a therapeutically effect amount of a compound of the formula or pharmaceutically acceptable salts, hydrates, or solvates thereof.

  本发明描述了一种治疗受试者神经疾病的方法，包括向需要治疗的受试者施用公式中的化合物或其药学上可接受的盐、水合物或溶剂化物的治疗有效量。
• 8-Hydroxy quinoline derivatives
  申请人：Barnham Kevin Jeffrey

  公开号：US20080161353A1

  公开（公告）日：2008-07-03

  The present invention describes a method for the treatment of a neurological condition in a subject which comprises administering to a subject in need thereof a therapeutically effect amount of a compound of the formula or pharmaceutically acceptable salts, hydrates, or solvates thereof.

  本发明描述了一种治疗主体神经系统疾病的方法，该方法包括向需要治疗的主体中给予一定治疗效果的化合物，该化合物的化学式如下，或其药学上可接受的盐、水合物或溶剂化物。
• Method of treatment of age-related macular degeneration (AMD)
  申请人：Prana Biotechnology Ltd

  公开号：EP2514423A2

  公开（公告）日：2012-10-24

  The present invention relates generally to the field of treatment and prophylaxis of retinal degenerative diseases. More particularly, the present invention contemplates a method for preventing, reducing the risk of development of, or otherwise treating or ameliorating the symptoms of, age-related macular degeneration (AMD) or related retinal conditions in mammals and in particular humans. The present invention further provides therapeutic compositions enabling dose-dependent or dose-specific administration of agents useful in the treatment and prophylaxis of age-related macular degeneration or related retinal degenerative conditions.

  本发明一般涉及视网膜变性疾病的治疗和预防领域。更具体地说，本发明考虑了一种方法，用于预防、降低哺乳动物，尤其是人类的老年性黄斑变性（AMD）或相关视网膜疾病的发病风险，或以其他方式治疗或改善其症状。本发明进一步提供了治疗组合物，可根据剂量或剂量特异性给药，用于治疗和预防老年性黄斑变性或相关视网膜退行性病变。
• Small molecules for the modulation of MCL-1 and methods of modulating cell death, cell division, cell differentiation and methods of treating disorders
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US10000511B2

  公开（公告）日：2018-06-19

  This invention relates to compounds which selectively bind to the survival protein MCL-1 with high affinity and selectivity, pharmaceutical compositions containing such compounds and the use of those compounds or compositions for modulating MCL-1 activity and for treating hyperproliferative disorders, angiogenesis disorders, cell cycle regulation disorders, autophagy regulation disorders, inflammatory disorders, and/or infectious disorders and/or for enhancing cellular engraftment and/or wound repair, as a sole agent or in combination with other active ingredients.

  本发明涉及以高亲和力和选择性与存活蛋白 MCL-1 选择性结合的化合物、含有此类化合物的药物组合物，以及使用这些化合物或组合物调节 MCL-1 活性和治疗过度增殖性疾病、血管生成疾病、细胞周期调节疾病、自噬调节疾病、炎症性疾病和/或感染性疾病和/或增强细胞移植和/或伤口修复，可作为单独制剂或与其他活性成分组合使用。