2-methyl-6-(morpholin-4-ylsulfonyl)-3,4-quinolinedicarboxylic acid | 753482-38-1

• 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-methyl-6-(morpholin-4-ylsulfonyl)-3,4-quinolinedicarboxylic acid
• 英文别名: 2-methyl-6-(morpholine-4-sulfonyl)-3,4-quinolinedicarboxylic acid；2-Methyl-6-morpholin-4-ylsulfonylquinoline-3,4-dicarboxylic acid
• CAS: 753482-38-1
• 化学式: C₁₆H₁₆N₂O₇S
• 分子量: 380.378
• InChiKey: JNCJUPNCQZTWPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(morpholin-4-ylsulfonyl)-3,4-quinolinedicarboxylic acid 在 吡啶 、 乙酸酐 作用下， 反应 3.0h， 生成 4-methyl-8-(morpholin-4-ylsulfonyl)-furo[3,4-c]quinoline-1,3-dione
  参考文献：
  名称：

  1,3-Dioxo-4-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]quinolines as potent caspase-3 inhibitors

  摘要：

  Synthesis, biological evaluation and structure-activity relationships for a series of novel nonpeptide small molecule inhibitors of caspase-3 are described. Among the studied compounds, 8-sulfamide derivatives of 1,3-dioxo-4-methyl-2,3-dihydro-1H-pyr-rolo [3,4-c]quinolines have been identified as potent inhibitors of caspases-3. The most active compound within this series (8f) inhibited caspase-3 with IC50 = 4 nM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.027
• 作为产物：
  描述：

  5-(4-吗啉磺酰基)-1H-吲哚-2,3-二酮 、 乙酰乙酸乙酯 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 12.0h， 以68%的产率得到2-methyl-6-(morpholin-4-ylsulfonyl)-3,4-quinolinedicarboxylic acid
  参考文献：
  名称：

  Pyrrolo[3,4-c]quinoline-1,3-diones as potent caspase-3 inhibitors. Synthesis and SAR of 2-substituted 4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-diones

  摘要：

  Synthesis, biological evaluation and structure-activity relationships for a series of 2-substituted 4-methyl-8-(morpholine-4-sulfonyl)-1,3dioxo-2,3-dihydro-1H-pyffolo[3,4-c]quinolines are described. These compounds represent a new chemotype of nonpeptide small molecule inhibitors of caspase-3. Among the studied compounds, several potent inhibitors with IC50 in the range of 3-10 nM have been identified. The most active compound within this series, 7{49} and 7{58}, inhibited caspase-3 with IC50 = 3 nM. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.011

文献信息

• 1,3-Dioxo-4-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]quinolines as potent caspase-3 inhibitors
  作者：Dmitri V. Kravchenko、Vladimir V. Kysil、Alexey P. Ilyn、Sergey E. Tkachenko、Sergey Maliarchouk、Ilya M. Okun、Alexandre V. Ivachtchenko

  DOI：10.1016/j.bmcl.2005.02.027

  日期：2005.4

  Synthesis, biological evaluation and structure-activity relationships for a series of novel nonpeptide small molecule inhibitors of caspase-3 are described. Among the studied compounds, 8-sulfamide derivatives of 1,3-dioxo-4-methyl-2,3-dihydro-1H-pyr-rolo [3,4-c]quinolines have been identified as potent inhibitors of caspases-3. The most active compound within this series (8f) inhibited caspase-3 with IC50 = 4 nM. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.
• Pyrrolo[3,4-c]quinoline-1,3-diones as potent caspase-3 inhibitors. Synthesis and SAR of 2-substituted 4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-diones
  作者：Dmitri V. Kravchenko、Volodymyr M. Kysil、Sergey E. Tkachenko、Sergey Maliarchouk、Ilya M. Okun、Alexandre V. Ivachtchenko

  DOI：10.1016/j.ejmech.2005.07.011

  日期：2005.12

  Synthesis, biological evaluation and structure-activity relationships for a series of 2-substituted 4-methyl-8-(morpholine-4-sulfonyl)-1,3dioxo-2,3-dihydro-1H-pyffolo[3,4-c]quinolines are described. These compounds represent a new chemotype of nonpeptide small molecule inhibitors of caspase-3. Among the studied compounds, several potent inhibitors with IC50 in the range of 3-10 nM have been identified. The most active compound within this series, 749} and 758}, inhibited caspase-3 with IC50 = 3 nM. (c) 2005 Elsevier SAS. All rights reserved.