3-hexyl-3-hydroxyisoindolin-1-one | 1356832-82-0

• 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-hexyl-3-hydroxyisoindolin-1-one
• 英文别名: 3-hexyl-3-hydroxy-2H-isoindol-1-one
• CAS: 1356832-82-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SQCZZQTWTAUSOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hexyl-3-hydroxyisoindolin-1-one 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 3-hexyl-2,3-dihydro-1H-isoindol-1-one
  参考文献：
  名称：

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones

  摘要：

  使用手性磷酸作为催化剂和 Hantzsch 酯作为氢源开发了外消旋叔醇（3-取代的 3-羟基异吲哚啉-1-酮）的不对称氢解，其 ee 高达 95%。这种不对称转移氢化的反应过程可以直接通过酰亚胺离子中间体发生。

  DOI：

  10.1039/c2cc16832d
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 alkaline earth salt of/the/ methylsulfuric acid 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-hexyl-3-hydroxyisoindolin-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

• Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones
  作者：Mu-Wang Chen、Qing-An Chen、Ying Duan、Zhi-Shi Ye、Yong-Gui Zhou

  DOI：10.1039/c2cc16832d

  日期：——

  Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones, was developed using chiral phosphoric acid as catalyst and a Hantzsch ester as the hydrogen source with up to 95% ee. The reaction process of this asymmetric transfer hydrogenation may occur directly through the acyliminium ion intermediate.

  使用手性磷酸作为催化剂和 Hantzsch 酯作为氢源开发了外消旋叔醇（3-取代的 3-羟基异吲哚啉-1-酮）的不对称氢解，其 ee 高达 95%。这种不对称转移氢化的反应过程可以直接通过酰亚胺离子中间体发生。
• 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.