2-(cyclopropylmethyl)-5-hydroxyisoindoline-1,3-dione | 1260225-27-1

• 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: 2-(cyclopropylmethyl)-5-hydroxyisoindoline-1,3-dione
• 英文别名: 2-(Cyclopropylmethyl)-5-hydroxyisoindole-1,3-dione
• CAS: 1260225-27-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: HEBYFZMQEIQEIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-(cyclopropylmethyl)-5-hydroxyisoindoline-1,3-dione 在 溶剂黄146 、 锌 作用下， 反应 0.08h， 以63%的产率得到2-(cyclopropylmethyl)-5-hydroxyisoindolin-1-one
  参考文献：
  名称：

  Design and Synthesis of an Orally Active Metabotropic Glutamate Receptor Subtype-2 (mGluR2) Positive Allosteric Modulator (PAM) That Decreases Cocaine Self-Administration in Rats

  摘要：

  The modification of 3'((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1 H-inden-5-yloxy)methyl)biphenyl 4-carboxylic acid (BINA, 1) by incorporating heteroatoms into the structure and replacing the cyclopentyl moiety led to the development of new mGluR2 positive allosteric modulators (PAMs) with optimized potency and superior druglike properties These analogues are more potent than 1 in vitro and are highly selective for mGluR2 vs other mGluR subtypes They have significantly improved pharmacokinetic (PK) properties, with excellent oral bioavailability and brain penetration The benzisothiazol-3-one derivative 14 decreased cocaine self-administration in rats, providing proof-of-concept for the use of mGluR2 PAMs for the treatment of cocaine dependence

  DOI：

  10.1021/jm1012165
• 作为产物：
  描述：

  4-羟基邻苯二甲酸 以 甲苯 为溶剂， 反应 12.0h， 生成 2-(cyclopropylmethyl)-5-hydroxyisoindoline-1,3-dione
  参考文献：
  名称：

  Design and Synthesis of an Orally Active Metabotropic Glutamate Receptor Subtype-2 (mGluR2) Positive Allosteric Modulator (PAM) That Decreases Cocaine Self-Administration in Rats

  摘要：

  The modification of 3'((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1 H-inden-5-yloxy)methyl)biphenyl 4-carboxylic acid (BINA, 1) by incorporating heteroatoms into the structure and replacing the cyclopentyl moiety led to the development of new mGluR2 positive allosteric modulators (PAMs) with optimized potency and superior druglike properties These analogues are more potent than 1 in vitro and are highly selective for mGluR2 vs other mGluR subtypes They have significantly improved pharmacokinetic (PK) properties, with excellent oral bioavailability and brain penetration The benzisothiazol-3-one derivative 14 decreased cocaine self-administration in rats, providing proof-of-concept for the use of mGluR2 PAMs for the treatment of cocaine dependence

  DOI：

  10.1021/jm1012165