3-Nitro-N-(1,3,4-trioxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-benzamide | 807335-41-7

• 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: 3-Nitro-N-(1,3,4-trioxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-benzamide
• 英文别名: 3-nitro-N-(1,3,4-trioxo-1,2,3,4-tetrahydroisoquinolin-5-yl)benzamide；3-nitro-N-(1,3,4-trioxoisoquinolin-5-yl)benzamide
• CAS: 807335-41-7
• 化学式: C₁₆H₉N₃O₆
• 分子量: 339.264
• InChiKey: MUHRCQVERAKWFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氨基-1(2H)-异喹啉酮 在 吡啶 、 盐酸 、 potassium dichromate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 3-Nitro-N-(1,3,4-trioxo-1,2,3,4-tetrahydro-isoquinolin-5-yl)-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Isoquinoline-1,3,4-trione Derivatives as Potent Caspase-3 Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm050896o

文献信息

• US7683073B2
  申请人：——

  公开号：US7683073B2

  公开（公告）日：2010-03-23
• 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.