3-(2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-propionic acid | 16076-06-5

• 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: 3-(2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-propionic acid
• 英文别名: 3-(2-oxo-1,2,3,4-tetrahydro-[7]quinolyl)-propionic acid；3-(2-Oxo-1,2,3,4-tetrahydro-[7]chinolyl)-propionsaeure；3-(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)propionic acid；3,4-Dihydro-carbostyril-(β-propionsaeure)-7；3-(2-oxo-3,4-dihydro-1H-quinolin-7-yl)propanoic acid
• CAS: 16076-06-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: KJCRQSOLDRREJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-propionic acid 在 硫酸 、 potassium nitrate 作用下， 生成 3-(6-nitro-2-oxo-1,2,3,4-tetrahydro-[7]quinolyl)-propionic acid
  参考文献：
  名称：

  线性和角苯并二吡啶VI（1，5-蒽唑啉和4，5-邻菲咯啉）。（42. MitteilungüberStickstoff-Heterocyclen）

  摘要：

  DOI：

  10.1002/hlca.19390220161
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 镍 、 乙酸乙酯 作用下， 生成 3-(2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-propionic acid
  参考文献：
  名称：

  线性和角苯并二吡啶VI（1，5-蒽唑啉和4，5-邻菲咯啉）。（42. MitteilungüberStickstoff-Heterocyclen）

  摘要：

  DOI：

  10.1002/hlca.19390220161

文献信息

• Benzazepine Compound
  申请人：KOSHIO Hiroyuki

  公开号：US20110269744A1

  公开（公告）日：2011-11-03

  [Problem] Provided is a compound which is useful as an agent for treating or preventing 5-HT 2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like. [Means for Solution] The present inventors have investigated compounds having a 5-HT 2C receptor agonist activity, which is promising as an active ingredient of a pharmaceutical composition for treating or preventing incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like, and have found that the benzazepine compounds of the present invention have an excellent 5-HT 2C receptor agonist activity, thereby completing the present invention. That is, the benzazepine compounds of the present invention have a 5-HT 2C receptor agonist activity and can be used as an agent for treating or preventing 5-HT 2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like.

  提供的是一种化合物，可用作治疗或预防与5-HT 2C 受体相关的疾病的药剂，特别是尿失禁，如压力性尿失禁、急迫性尿失禁、混合性尿失禁等，性功能障碍，如勃起功能障碍综合征等，肥胖等。 【解决方案】本发明者研究了具有5-HT 2C 受体激动剂活性的化合物，这种活性有望作为治疗或预防尿失禁，如压力性尿失禁、急迫性尿失禁、混合性尿失禁等，性功能障碍，如勃起功能障碍综合征等，肥胖等的药物组合物的有效成分。他们发现本发明的苯并环己酮类化合物具有出色的5-HT 2C 受体激动剂活性，从而完成了本发明。换句话说，本发明的苯并环己酮类化合物具有5-HT 2C 受体激动剂活性，可用作治疗或预防与5-HT 2C 受体相关的疾病的药剂，特别是尿失禁，如压力性尿失禁、急迫性尿失禁、混合性尿失禁等，性功能障碍，如勃起功能障碍综合征等，肥胖等。
• BENZAZEPINE COMPOUND
  申请人：Koshio Hiroyuki

  公开号：US20130012496A1

  公开（公告）日：2013-01-10

  Provided is a compound which is useful as an agent for treating or preventing 5-HT 2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like. The present inventors have investigated compounds having a 5-HT 2C receptor agonist activity and have found that the benzazepine compounds of the present invention have an excellent 5-HT 2C receptor agonist activity, thereby completing the present invention. That is, the benzazepine compounds of the present invention have a 5-HT 2C receptor agonist activity and can be used as an agent for treating or preventing 5-HT 2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like.

  提供了一种化合物，可用作治疗或预防5-HT2C受体相关疾病的药剂，特别是尿失禁，如压力性尿失禁，切勿性尿失禁，混合性尿失禁等，性功能障碍，如勃起功能障碍综合症等，肥胖症等。本发明人研究了具有5-HT2C受体激动剂活性的化合物，并发现本发明的苯并氮杂环化合物具有优异的5-HT2C受体激动剂活性，从而完成了本发明。也就是说，本发明的苯并氮杂环化合物具有5-HT2C受体激动剂活性，并可用作治疗或预防5-HT2C受体相关疾病的药剂，特别是尿失禁，如压力性尿失禁，切勿性尿失禁，混合性尿失禁等，性功能障碍，如勃起功能障碍综合症等，肥胖症等。
• Benzazepine compound
  申请人：Koshio Hiroyuki

  公开号：US09108977B2

  公开（公告）日：2015-08-18

  Provided is a compound which is useful as an agent for treating or preventing 5-HT2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like. The present inventors have investigated compounds having a 5-HT2C receptor agonist activity and have found that the benzazepine compounds of the present invention have an excellent 5-HT2C receptor agonist activity, thereby completing the present invention. That is, the benzazepine compounds of the present invention have a 5-HT2C receptor agonist activity and can be used as an agent for treating or preventing 5-HT2C receptor-related diseases, particularly incontinence such as stress urinary incontinence, urge urinary incontinence, mixed urinary incontinence, and the like, sexual dysfunction such as erectile dysfunction syndrome and the like, obesity, and the like.

  提供了一种化合物，可作为治疗或预防5-HT2C受体相关疾病的药物，特别是治疗失禁，如压力性尿失禁、急迫性尿失禁、混合性尿失禁等，性功能障碍，如勃起功能障碍综合征等，肥胖症等。本发明人研究了具有5-HT2C受体激动剂活性的化合物，并发现本发明的苯并氮杂环化合物具有优异的5-HT2C受体激动剂活性，从而完成了本发明。也就是说，本发明的苯并氮杂环化合物具有5-HT2C受体激动剂活性，可作为治疗或预防5-HT2C受体相关疾病的药物，特别是治疗失禁，如压力性尿失禁、急迫性尿失禁、混合性尿失禁等，性功能障碍，如勃起功能障碍综合征等，肥胖症等。
• 10.1002/ardp.202400279
  作者：Rathing, Friederike、Schepmann, Dirk、Wünsch, Bernhard

  DOI：10.1002/ardp.202400279

  日期：——

  synthesized in an eight-step sequence starting with terephthalaldehyde (5). Key steps pf the synthesis were the intramolecular Friedel–Crafts acylation of propionic acids 10 to yield the cyclopenta[g]quinolinediones 11 and the Mannich reaction of diketone 11a followed by conjugate addition at the α,β-unsaturated ketone 12a. Although the quinolones 13a, 15a, and 16a contain an H-bond donor group (secondary

  设计 4 型环戊 [g] 喹诺酮类药物的目的是用喹诺酮系统生物等位地替代有效的 GluN2B 配体（如 ifenprodil 和 Ro 25-6981）的苯酚，并限制环戊烷系统中氨基丙醇亚结构的构象灵活性。设计的配体以八步序列合成，从对苯二甲醛开始 （5）。合成的关键步骤是丙酸 10 的分子内 Friedel-Crafts 酰化反应，得到环戊[g]喹啉二酮 11，以及二酮 11a 的曼尼希反应，然后在 α，β-不饱和酮 12a 处添加共轭物。尽管喹诺酮类药物 13a、15a 和 16a 含有 H 键供体基团（次级内酰胺）作为 ifenprodil 和 Ro 25-6981，但它们仅显示出中等的 GluN2B 亲和力 （K > 410 nM）。然而，在喹诺酮类 N 原子处引入亲脂性取代基导致苄基和苄氧甲基衍生物顺式-13c （Ko = 36 nM） 和 13e （Ko = 27 nM） 的 GluN2B
• Teuber,H.-J.; Dietrich,M., Chemische Berichte, 1967, vol. 100, # 9, p. 2908 - 2917
  作者：Teuber,H.-J.、Dietrich,M.

  DOI：——

  日期：——