2-phenyl-6-sulfoquinoline-3,4-dicarboxylic acid | 753480-90-9

• 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: 2-phenyl-6-sulfoquinoline-3,4-dicarboxylic acid
• CAS: 753480-90-9
• 化学式: C₁₇H₁₁NO₇S
• 分子量: 373.343
• InChiKey: JAYIDQXZWKZJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-phenyl-6-sulfoquinoline-3,4-dicarboxylic acid 在 乙酸酐 、 三氯氧磷 作用下， 以 环丁砜 为溶剂， 反应 4.0h， 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
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 、 5-isatinsulfonic acid sodium salt 在 lithium hydroxide 作用下， 反应 12.0h， 生成 2-phenyl-6-sulfoquinoline-3,4-dicarboxylic acid
  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

文献信息

• Synthesis and Structure−Activity Relationship of 4-Substituted 2-(2-Acetyloxyethyl)-8-(morpholine- 4-sulfonyl)pyrrolo[3,4-<i>c</i>]quinoline- 1,3-diones as Potent Caspase-3 Inhibitors
  作者：Dmitri V. Kravchenko、Yulia A. Kuzovkova、Volodymyr M. Kysil、Sergey E. Tkachenko、Sergey Maliarchouk、Ilya M. Okun、Konstantin V. Balakin、Alexandre V. Ivachtchenko

  DOI：10.1021/jm048987t

  日期：2005.6.1

  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.