1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenyl-3-isoquinolinecarboxylic acid | 152818-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenyl-3-isoquinolinecarboxylic acid
• 英文别名: 2,6,7-trimethyl-4-phenyl-1 (2H)-isoquinolinone-3-carboxylic acid；2,6,7-Trimethyl-4-phenyl-1(2H)-isoquinolinone-3-carboxylic acid；4-phenyl-2,6,7-trimethyl-1(2H)-isoquinolinone-3-carboxylic acid；2,6,7-Trimethyl-1-oxo-4-phenylisoquinoline-3-carboxylic acid
• CAS: 152818-34-3
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: BIPPDQBIBCJHPJ-UHFFFAOYSA-N

物化性质

• 沸点：
  488.7±45.0 °C(predicted)
• 密度：
  1.269±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenyl-3-isoquinolinecarboxylic acid 生成 4-(2-fluorophenyl)-6,7-dimethylisocoumarin-3-carboxylic acid
  参考文献：
  名称：

  Condensed heterocyclic compounds, their production and use

  摘要：

  代表性化合物如6-氯-N-(2,6-二乙氧基苯基)-4-(2-甲基苯基-2-氧代-2H-1-苯并吡喃-3-基)乙酰胺，其化学式为：##STR1## 或其盐类。该化合物具有优异的抑制ACAT（酰基辅酶A胆固醇酰基转移酶）活性、降低血液胆固醇水平以及抑制速激肽受体的作用。本发明还涉及该化合物的制备方法及其应用。

  公开号：

  US05482967A1
• 作为产物：
  描述：

  2-benzoyl-4,5-dimethylbenzoic acid 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 反应 69.0h， 生成 1,2-dihydro-2,6,7-trimethyl-1-oxo-4-phenyl-3-isoquinolinecarboxylic acid
  参考文献：
  名称：

  Novel, Potent, and Orally Active Substance P Antagonists: Synthesis and Antagonist Activity of N-Benzylcarboxamide Derivatives of Pyrido[3,4-b]pyridine

  摘要：

  A series of 4-phenylisoquinolone derivatives were synthesized and evaluated for NK1 (substance P) antagonist activity. Highly potent antagonists, 4-phenyl-3-isoquinolone-N-benzylcarboxamides (11), were discovered from the structure-activity relationship studies on the isoquinolone-urea lead la. Optimization of the activity in this series resulted in the development of 5-phenyl-6-pyrido[3,4-b]pyridine-N-benzylcarboxamides (30) which are highly potent orally active NK1 antagonists. Among the compounds synthesized, N-[3,5-bis(trifluoromethyl)benzyl]7,8-dihydro-N, 7-dimethyl-8-oxo-5-(substituted phenyl)6-pyrido[3,4-b]pyridinecarboxamides (30a,f,g) showed excellent antagonist activities with IC50 values (in vitro inhibition of [I-125]- BH-SP binding in human IM-9 cells) of 0.21-0.34 nM and ED(50) values (in vivo inhibition of capsaicin-induced plasma extravasation in guinea-pig trachea, iv) of 0.017-0.030 mg/kg. These compounds exhibited significantly potent activity upon oral administration with ED(50) values of 0.068-0.17 mg/kg. Conformational studies on 30g indicated that the two stable conformers of 30g are quite similar to those of CP-99,994.

  DOI：

  10.1021/jm00016a014

文献信息

• Tachykinin receptor antagonists, isoquinolones and their production
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0566069A1

  公开（公告）日：1993-10-20

  Novel composition represented by the formula: wherein ring A and ring B each means a benzene ring which may be substituted; R means a hydrogen atom or an alkyl group which may be substituted; R¹ means a hydrogen atom or an alkyl group which may be substituted; R² means a hydrocarbon group which may be substituted or a heterocyclic group which may be substituted, or R¹ and R², taken together with the adjacent nitrogen atom, jointly form a ring which may be substituted, or a pharmaceutically acceptable salt thereof which is a useful tachykinin receptor antagonist.

  由式表示的新型组合物： 其中环 A 和环 B 各指一个可被取代的苯环；R 指一个氢原子或一个可被取代的烷基；R¹ 指一个氢原子或一个可被取代的烷基；R² 指一个可被取代的烃基或一个可被取代的杂环基，或 R¹ 和 R² 与相邻的氮原子共同形成一个可被取代的环，或其药学上可接受的盐，是一种有用的速激肽受体拮抗剂。
• US5482967A
  申请人：——

  公开号：US5482967A

  公开（公告）日：1996-01-09
• US5523305A
  申请人：——

  公开号：US5523305A

  公开（公告）日：1996-06-04
• US5700810A
  申请人：——

  公开号：US5700810A

  公开（公告）日：1997-12-23