Acetic acid 2-(8-chlorosulfonyl-1,3-dioxo-4-phenyl-1,3-dihydro-pyrrolo[3,4-c]quinolin-2-yl)-ethyl ester | 854948-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Acetic acid 2-(8-chlorosulfonyl-1,3-dioxo-4-phenyl-1,3-dihydro-pyrrolo[3,4-c]quinolin-2-yl)-ethyl ester
• 英文别名: 2-(8-Chlorosulfonyl-1,3-dioxo-4-phenylpyrrolo[3,4-c]quinolin-2-yl)ethyl acetate
• CAS: 854948-76-8
• 化学式: C₂₁H₁₅ClN₂O₆S
• 分子量: 458.879
• InChiKey: HMAXWZMORYDKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-(8-chlorosulfonyl-1,3-dioxo-4-phenyl-1,3-dihydro-pyrrolo[3,4-c]quinolin-2-yl)-ethyl ester 、 吗啉 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 Acetic acid 2-[8-(morpholine-4-sulfonyl)-1,3-dioxo-4-phenyl-1,3-dihydro-pyrrolo[3,4-c]quinolin-2-yl]-ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-c]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors

  摘要：

  Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo-[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-Methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.

  DOI：

  10.1021/jm048987t
• 作为产物：
  描述：

  2-(2-Hydroxy-ethyl)-1,3-dioxo-4-phenyl-2,3-dihydro-1H-pyrrolo[3,4-c]quinoline-8-sulfonic acid; compound with pyridine 在 三氯氧磷 作用下， 以 环丁砜 为溶剂， 反应 2.5h， 生成 Acetic acid 2-(8-chlorosulfonyl-1,3-dioxo-4-phenyl-1,3-dihydro-pyrrolo[3,4-c]quinolin-2-yl)-ethyl ester
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-c]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors

  摘要：

  Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo-[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-Methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.

  DOI：

  10.1021/jm048987t