5-bromo-2-(2-fluorophenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one | 1354035-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 5-bromo-2-(2-fluorophenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one
• 英文别名: 5-bromo-2-(2-fluorophenyl)-1H-benzo[e]isoindol-3-one
• CAS: 1354035-55-4
• 化学式: C₁₈H₁₁BrFNO
• 分子量: 356.194
• InChiKey: MAMDTUPPAUPFFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-2-(2-fluorophenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三乙酰氧基硼氢化钠 、 臭氧 、 三环己基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 15.58h， 生成 1-{[2-(2-fluorophenyl)-3-oxo-2,3-dihydro-1H-benzo[e]isoindol-5-yl]methyl}-4-pyridin-2-ylpiperidine-4-carbonitrile
  参考文献：
  名称：

  Discovery of Naphthyl-Fused 5-Membered Lactams as a New Class of M₁ Positive Allosteric Modulators

  摘要：

  Selective activation of the M-1 muscarinic receptor via positive allosteric modulation represents an original approach to treat the cognitive decline in patients with Alzheimer's disease. A series of naphthyl-fused 5-membered lactams were identified as a new class of M-1 positive allosteric modulators and were found to possess good potency and in vivo efficacy.

  DOI：

  10.1021/ml500055h
• 作为产物：
  描述：

  甲基-1-羟基-2-萘甲酸盐 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 溴 、 溶剂黄146 、 lithium chloride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 5-bromo-2-(2-fluorophenyl)-1,2-dihydro-3H-benzo[e]isoindol-3-one
  参考文献：
  名称：

  Discovery of Naphthyl-Fused 5-Membered Lactams as a New Class of M₁ Positive Allosteric Modulators

  摘要：

  Selective activation of the M-1 muscarinic receptor via positive allosteric modulation represents an original approach to treat the cognitive decline in patients with Alzheimer's disease. A series of naphthyl-fused 5-membered lactams were identified as a new class of M-1 positive allosteric modulators and were found to possess good potency and in vivo efficacy.

  DOI：

  10.1021/ml500055h

文献信息

• Isoindolone M1 receptor positive allosteric modulators
  申请人：Beshore Douglas C.

  公开号：US08697690B2

  公开（公告）日：2014-04-15

  The present invention is directed to isoindolone compounds of formula (I) which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及式(I)的异吲哚酮化合物，它们是M1受体正向变构调节剂，并且在治疗M1受体参与的疾病，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍方面有用。本发明还涉及包含该化合物的制药组合物，以及在治疗M1受体介导的疾病中使用该化合物和组合物的用途。
• ISOINDOLONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS
  申请人：Beshore Douglas C.

  公开号：US20130109686A1

  公开（公告）日：2013-05-02

  The present invention is directed to isoindolone compounds of formula (I) which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.

  本发明涉及式(I)的异吲哚酮化合物，其为M1受体阳性变构调节剂，并且在治疗涉及M1受体的疾病中具有用途，如阿尔茨海默病、精神分裂症、疼痛或睡眠障碍。本发明还涉及包含该化合物的制药组合物，以及在治疗由M1受体介导的疾病中使用该化合物和组合物的方法。
• US8697690B2
  申请人：——

  公开号：US8697690B2

  公开（公告）日：2014-04-15
• [EN] ISOINDOLONE M1 RECEPTOR POSITIVE ALLOSTERIC MODULATORS<br/>[FR] MODULATEURS ALLOSTÉRIQUES POSITIFS DU RÉCEPTEUR M1 DE L'ISOINDOLONE
  申请人：MERCK SHARP & DOHME

  公开号：WO2012003147A1

  公开（公告）日：2012-01-05

  The present invention is directed to isoindolone compounds of formula (I) which are M1 receptor positive allosteric modulators and that are useful in the treatment of diseases in which the M1 receptor is involved, such as Alzheimer's disease, schizophrenia, pain or sleep disorders. The invention is also directed to pharmaceutical compositions comprising the compounds, and to the use of the compounds and compositions in the treatment of diseases mediated by the M1 receptor.
• Discovery of Naphthyl-Fused 5-Membered Lactams as a New Class of M₁ Positive Allosteric Modulators
  作者：Zhi-Qiang Yang、Youheng Shu、Lei Ma、Marion Wittmann、William J. Ray、Matthew A. Seager、Kenneth A. Koeplinger、Charles D. Thompson、George D. Hartman、Mark T. Bilodeau、Scott D. Kuduk

  DOI：10.1021/ml500055h

  日期：2014.5.8

  Selective activation of the M-1 muscarinic receptor via positive allosteric modulation represents an original approach to treat the cognitive decline in patients with Alzheimer's disease. A series of naphthyl-fused 5-membered lactams were identified as a new class of M-1 positive allosteric modulators and were found to possess good potency and in vivo efficacy.