(4-Methoxy-3-methyl-1-benzofuran-2-yl)[3-(trifluoromethyl)phenyl]methanone | 1207969-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-Methoxy-3-methyl-1-benzofuran-2-yl)[3-(trifluoromethyl)phenyl]methanone
• 英文别名: (4-Methoxy-3-methyl-1-benzofuran-2-yl)-[3-(trifluoromethyl)phenyl]methanone；(4-methoxy-3-methyl-1-benzofuran-2-yl)-[3-(trifluoromethyl)phenyl]methanone
• CAS: 1207969-06-9
• 化学式: C₁₈H₁₃F₃O₃
• 分子量: 334.295
• InChiKey: UTECINJCNWQFFI-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C(Solvent: Methanol)
• 沸点：
  406.3±45.0 °C(predicted)
• 密度：
  1.294±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-Methoxy-3-methyl-1-benzofuran-2-yl)[3-(trifluoromethyl)phenyl]methanone 在 吡啶 、 四(三苯基膦)钯 、 三溴化硼 、 sodium carbonate 、 一水合肼 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 乙二醇 为溶剂， 反应 29.0h， 生成 3-{3-methyl-2-[3-(trifluoromethyl)benzyl]-1-benzofuran-4-yl}benzoic acid
  参考文献：
  名称：

  Discovery of the First Potent and Orally Available Agonist of the Orphan G-Protein-Coupled Receptor 52

  摘要：

  G-protein-coupled receptor 52 (GPR52) is an orphan Gs-coupled G-protein-coupled receptor. GPR52 inhibits dopamine D2 receptor signaling and activates dopamine D1/N-methyl-d-aspartate receptors via intracellular cAMP accumulation, and therefore, GPR52 agonists may have potential as a novel class of antipsychotics. A series of GPR52 agonists with a bicyclic core was designed to fix the conformation of the phenethyl ether moiety of compounds 2a and 2b. 3-[2-(3-Chloro-5-fluorobenzyl)-1-benzothiophen-7-yl]-N-(2-methoxyethyl)benzamide 7m showed potent activity (pEC50 = 7.53 ± 0.08) and good pharmacokinetic properties. Compound 7m significantly suppressed methamphetamine-induced hyperactivity in mice after oral administration of 3 mg/kg without disturbance of motor function.

  DOI：

  10.1021/jm5002919
• 作为产物：
  描述：

  间三氟甲基苯乙酮 在 potassium carbonate 、 copper(ll) bromide 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 32.0h， 生成 (4-Methoxy-3-methyl-1-benzofuran-2-yl)[3-(trifluoromethyl)phenyl]methanone
  参考文献：
  名称：

  Discovery of the First Potent and Orally Available Agonist of the Orphan G-Protein-Coupled Receptor 52

  摘要：

  G-protein-coupled receptor 52 (GPR52) is an orphan Gs-coupled G-protein-coupled receptor. GPR52 inhibits dopamine D2 receptor signaling and activates dopamine D1/N-methyl-d-aspartate receptors via intracellular cAMP accumulation, and therefore, GPR52 agonists may have potential as a novel class of antipsychotics. A series of GPR52 agonists with a bicyclic core was designed to fix the conformation of the phenethyl ether moiety of compounds 2a and 2b. 3-[2-(3-Chloro-5-fluorobenzyl)-1-benzothiophen-7-yl]-N-(2-methoxyethyl)benzamide 7m showed potent activity (pEC50 = 7.53 ± 0.08) and good pharmacokinetic properties. Compound 7m significantly suppressed methamphetamine-induced hyperactivity in mice after oral administration of 3 mg/kg without disturbance of motor function.

  DOI：

  10.1021/jm5002919

文献信息

• AMIDE COMPOUND
  申请人：Setoh Masaki

  公开号：US20100041891A1

  公开（公告）日：2010-02-18

  A compound having GPR52 agonist activity or a salt thereof is provided. The compound can be provided as a preventive/therapeutic agent for schizophrenia or the like. The compound is represented by the following formula: wherein A represents —CONR a — or —NR a CO—, R a represents a hydrogen atom or the like, B represents a hydrogen atom or the like, a ring Cy1 represents a six-membered aromatic ring which may have one or more substituents in addition to a group represented by -A-B, a ring Cy2 represents a six-membered ring which may be substituted with a halogen atom or the like, a ring Cy3 represents a five- or six-membered ring which may have one or more substituents; X represents C 1-2 alkylene or the like, m represents an integer of 0 to 2, and a ring Cy4 represents a six-membered aromatic ring which may have one or more substituents.

  提供具有GPR52激动剂活性或其盐的化合物。该化合物可作为预防/治疗精神分裂症等疾病的药物。该化合物由以下公式表示：其中A代表—CONRa—或—NRaCO—，Ra代表氢原子或类似物质，B代表氢原子或类似物质，环Cy1代表一个六元芳香环，除了由-A-B表示的基团外，可能有一个或多个取代基，环Cy2代表一个六元环，可能被卤素原子或类似物质取代，环Cy3代表一个有一个或多个取代基的五元或六元环；X代表C1-2烷基或类似物质，m代表0到2之间的整数，环Cy4代表一个六元芳香环，可能有一个或多个取代基。
• [EN] AMIDE COMPOUND<br/>[FR] COMPOSÉ AMIDE
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2010018874A1

  公开（公告）日：2010-02-18

  A compound having GPR52 agonist activity or a salt thereof is provided. The compound can be provided as a preventive / therapeutic agent for schizophrenia or the like. The compound is represented by the following formula (Ia): wherein A represents -CONR2- or -NR2CO-, R2 represents a hydrogen atom or the like, B represents a hydrogen atom or the like, a ring CyI represents a six-membered aromatic ring which may have one or more substituents in addition to a group represented by -A-B, a ring Cy2 represents a six-membered ring which may be substituted with a halogen atom or the like, a ring Cy3 represents a five- or six-membered ring which may have one or more substituents; X represents C1-2 alkylene or the like, m represents an integer of 0 to 2, and a ring Cy4 represents a six-membered aromatic ring which may have one or more substituents.
• Discovery of the First Potent and Orally Available Agonist of the Orphan G-Protein-Coupled Receptor 52
  作者：Masaki Setoh、Naoki Ishii、Mitsunori Kono、Yuhei Miyanohana、Eri Shiraishi、Toshiya Harasawa、Hiroyuki Ota、Tomoyuki Odani、Naoyuki Kanzaki、Kazunobu Aoyama、Teruki Hamada、Masakuni Kori

  DOI：10.1021/jm5002919

  日期：2014.6.26

  G-protein-coupled receptor 52 (GPR52) is an orphan Gs-coupled G-protein-coupled receptor. GPR52 inhibits dopamine D2 receptor signaling and activates dopamine D1/N-methyl-d-aspartate receptors via intracellular cAMP accumulation, and therefore, GPR52 agonists may have potential as a novel class of antipsychotics. A series of GPR52 agonists with a bicyclic core was designed to fix the conformation of the phenethyl ether moiety of compounds 2a and 2b. 3-[2-(3-Chloro-5-fluorobenzyl)-1-benzothiophen-7-yl]-N-(2-methoxyethyl)benzamide 7m showed potent activity (pEC50 = 7.53 ± 0.08) and good pharmacokinetic properties. Compound 7m significantly suppressed methamphetamine-induced hyperactivity in mice after oral administration of 3 mg/kg without disturbance of motor function.