2-(4-fluorobenzyl)isoquinoline-1,3,4(2H)-trione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(4-fluorobenzyl)isoquinoline-1,3,4(2H)-trione
• 英文别名: 2-(4-Fluoro-benzyl)isoquinoline-1,3,4-trione；2-[(4-fluorophenyl)methyl]isoquinoline-1,3,4-trione
• 化学式: C₁₆H₁₀FNO₃
• 分子量: 283.259
• InChiKey: XFTAXSAPJPVWNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异喹啉 、 对氟甲苯 在 叔丁基过氧化氢 、 碘 作用下， 以 水 为溶剂， 反应 24.0h， 以71%的产率得到2-(4-fluorobenzyl)isoquinoline-1,3,4(2H)-trione
  参考文献：
  名称：

  碘催化甲基芳烃对异喹啉的氧化性多个CH键官能化：异喹啉-1,3,4（2H）-三酮的有效合成

  摘要：

  通过连续的苄基sp3 CH碘化/ N-苄基化/酰胺化/双sp2 CH氧化顺序，开发了碘催化的甲基喹啉与异喹啉的多重CH键官能化反应。该反应利用未官能化的异喹啉和易于获得的甲基芳烃作为起始原料，在无金属的条件下进行，避免了多步实验操作，使其成为合成N-苄基异喹啉-1,3的有效方法，4-三酮。

  DOI：

  10.1039/c7ob01539a

文献信息

• Design, Synthesis, and Biological Evaluation of Isoquinoline-1,3,4-trione Derivatives as Potent Caspase-3 Inhibitors
  作者：Yi-Hua Chen、Ya-Hui Zhang、Hua-Jie Zhang、Da-Zhi Liu、Min Gu、Jing-Ya Li、Fang Wu、Xing-Zu Zhu、Jia Li、Fa-Jun Nan

  DOI：10.1021/jm050896o

  日期：2006.3.1

  A series of isoquinoline-1,3,4-trione derivatives were identified as novel and potent inhibitors of caspase-3 through structural modification of the original compound from high-throughput screening. Various analogues (2, 6, 9, 13, and 14) were synthesized and identified as caspase inhibitors, and the introduction of a 6-N-acyl group (compound 13) greatly improved their activity. Some of them showed low nanomolar potency against caspase-3 in vitro (for example, for 6k, IC50 = 40 nM) and significant protection against apoptosis in a model cell system. Additionally, compound Of demonstrated a dose-dependent decrease in infarct volume in the transient MCA occlusion stroke model. The present small-molecule caspase-3 inhibitor with novel structures different from structures of known caspase inhibitors revealed a new direction for therapeutic strategies directed against diseases involving abnormally up-regulated apoptosis.
• US7683073B2
  申请人：——

  公开号：US7683073B2

  公开（公告）日：2010-03-23
• Iodine-catalyzed oxidative multiple C–H bond functionalization of isoquinolines with methylarenes: an efficient synthesis of isoquinoline-1,3,4(2H)-triones
  作者：Di Zhu、Wen-Kun Luo、Luo Yang、Da-You Ma

  DOI：10.1039/c7ob01539a

  日期：——

  An iodine-catalyzed multiple C-H bonds functionalization of isoquinolines with methylarenes via successively benzylic sp3 C-H iodination/N-benzylation/amidation/double sp2 C-H oxidation sequence is developed. This reaction utilizes un-functionalized isoquinolines and readily available methylarenes as starting materials, proceeds under metal-free conditions, and avoids muti-step experimental operation

  通过连续的苄基sp3 CH碘化/ N-苄基化/酰胺化/双sp2 CH氧化顺序，开发了碘催化的甲基喹啉与异喹啉的多重CH键官能化反应。该反应利用未官能化的异喹啉和易于获得的甲基芳烃作为起始原料，在无金属的条件下进行，避免了多步实验操作，使其成为合成N-苄基异喹啉-1,3的有效方法，4-三酮。