3-butyl-3-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one | 4770-21-2

• 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: 3-butyl-3-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one
• 英文别名: 3-n-Butyl-2-methyl-3-hydroxy-phthalimidin；2-Methyl-3-butyl-3-hydroxy-phthalimidin；3-Butyl-3-hydroxy-2-methylisoindolin-1-one；3-butyl-3-hydroxy-2-methylisoindol-1-one
• CAS: 4770-21-2
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: LQIOZXVYMYPLFN-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  384.3±42.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-butyl-3-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (±)-3-n-butyl-2-methyl-2,3-dihydro-1H-isoindol-1-one
  参考文献：
  名称：

  Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent

  摘要：

  To develop novel anti-ischemic stroke agents with better therapeutic efficacy and bioavailability, we designed and synthesized a series of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones compounds (3a-i) derivatives, one of which (3d) exhibited the strongest inhibitory activity for the adenosine diphosphate-induced and arachidonic acid-induced platelet aggregation. This activity is superior to that of 3-n-butylphthalide and comparable with aspirin and edaravone. Meanwhile, 3d not only exhibited a potent activity in scavenging free radicals and improving the survival of HT22 cells against the reactive oxygen species-mediated cytotoxicity in vitro but also significantly attenuated the ischemia/reperfusion-induced oxidative stress in ischemic rat brains. Results from transient middle cerebral artery occlusion and permanent middle cerebral artery occlusion model, indicated that 3d could significantly reduce infarct size, improve neurobehavioral deficits, and prominently decrease attenuation of cerebral damage. Most importantly, 3d possessed a very high absolute bioavailability and was rapidly distributed in brain tissue to keep high plasma drug concentration for the treatment of ischemic strokes. In conclusion, our findings suggest that 3-alkyl-2,3-dihydro-1H-isoindol-1-ones, a novel series of compounds, might be candidate drugs for the treatment of acute ischemic strokes, and 3d may be a promising therapeutic agent for the primary and secondary prevention of ischemic stroke.

  DOI：

  10.2147/dddt.s84731
• 作为产物：
  描述：

  N-甲基邻苯二甲酰亚胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-butyl-3-hydroxy-2-methyl-2,3-dihydro-isoindol-1-one
  参考文献：
  名称：

  Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent

  摘要：

  To develop novel anti-ischemic stroke agents with better therapeutic efficacy and bioavailability, we designed and synthesized a series of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones compounds (3a-i) derivatives, one of which (3d) exhibited the strongest inhibitory activity for the adenosine diphosphate-induced and arachidonic acid-induced platelet aggregation. This activity is superior to that of 3-n-butylphthalide and comparable with aspirin and edaravone. Meanwhile, 3d not only exhibited a potent activity in scavenging free radicals and improving the survival of HT22 cells against the reactive oxygen species-mediated cytotoxicity in vitro but also significantly attenuated the ischemia/reperfusion-induced oxidative stress in ischemic rat brains. Results from transient middle cerebral artery occlusion and permanent middle cerebral artery occlusion model, indicated that 3d could significantly reduce infarct size, improve neurobehavioral deficits, and prominently decrease attenuation of cerebral damage. Most importantly, 3d possessed a very high absolute bioavailability and was rapidly distributed in brain tissue to keep high plasma drug concentration for the treatment of ischemic strokes. In conclusion, our findings suggest that 3-alkyl-2,3-dihydro-1H-isoindol-1-ones, a novel series of compounds, might be candidate drugs for the treatment of acute ischemic strokes, and 3d may be a promising therapeutic agent for the primary and secondary prevention of ischemic stroke.

  DOI：

  10.2147/dddt.s84731

文献信息

• Samarium diiodide-mediated intermolecular coupling of organic halides with cyclic imides
  作者：Sorin Farcas、Jean-Louis Namy

  DOI：10.1016/s0040-4039(00)02148-1

  日期：2001.1

  SmI2-mediated couplings between a variety of organic halides and cyclic imides have been performed giving either hydroxylactams from N-methylsuccinimide and N-methylphthalimide or delta -ketoamides from N-methylglutarimide. In the latter case, ring opening occurs during hydrolysis. Couplings of imides with alkyl halides require a catalytic amount of NiI2. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent
  作者：Chunshun Zhao、Zujian Lan、Xiaoyu Xu、Xuefei Zhang、Ming Lei、Wenkai Xu、Jin Li、Zengrong Liang

  DOI：10.2147/dddt.s84731

  日期：——

  To develop novel anti-ischemic stroke agents with better therapeutic efficacy and bioavailability, we designed and synthesized a series of 3-alkyl-2,3-dihydro-1H-isoindol-1-ones compounds (3a-i) derivatives, one of which (3d) exhibited the strongest inhibitory activity for the adenosine diphosphate-induced and arachidonic acid-induced platelet aggregation. This activity is superior to that of 3-n-butylphthalide and comparable with aspirin and edaravone. Meanwhile, 3d not only exhibited a potent activity in scavenging free radicals and improving the survival of HT22 cells against the reactive oxygen species-mediated cytotoxicity in vitro but also significantly attenuated the ischemia/reperfusion-induced oxidative stress in ischemic rat brains. Results from transient middle cerebral artery occlusion and permanent middle cerebral artery occlusion model, indicated that 3d could significantly reduce infarct size, improve neurobehavioral deficits, and prominently decrease attenuation of cerebral damage. Most importantly, 3d possessed a very high absolute bioavailability and was rapidly distributed in brain tissue to keep high plasma drug concentration for the treatment of ischemic strokes. In conclusion, our findings suggest that 3-alkyl-2,3-dihydro-1H-isoindol-1-ones, a novel series of compounds, might be candidate drugs for the treatment of acute ischemic strokes, and 3d may be a promising therapeutic agent for the primary and secondary prevention of ischemic stroke.