2-(2-Hydroxy-ethyl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione | 745046-21-3

• 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-(2-Hydroxy-ethyl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione
• 英文别名: 2-(2-Hydroxyethyl)-4-methyl-8-morpholin-4-ylsulfonylpyrrolo[3,4-c]quinoline-1,3-dione
• CAS: 745046-21-3
• 化学式: C₁₈H₁₉N₃O₆S
• 分子量: 405.431
• InChiKey: GDVWOQNDCVTYCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2-Hydroxy-ethyl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione 在 乙酸酐 、 zinc(II) chloride 作用下， 反应 70.5h， 生成 Acetic acid 2-{8-(morpholine-4-sulfonyl)-1,3-dioxo-4-[(E)-2-(4-trifluoromethyl-phenyl)-vinyl]-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-methyl-6-(morpholin-4-ylsulfonyl)-3,4-quinolinedicarboxylic acid 在 吡啶 、 乙酸酐 作用下， 反应 3.5h， 生成 2-(2-Hydroxy-ethyl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione
  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

• 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.
• [EN] QUINOLINE-CARBOXYLIC ACIDS AND THE DERIVATIVES THEREOF, A FOCUSED LIBRARY<br/>[FR] ACIDES QUINOLINE-CARBOXYLIQUES ET LEURS DERIVES ET BIBLIOTHEQUE FOCALISEE
  申请人：CHEMICAL DIVERSITY RES INST LT

  公开号：WO2004078731A1

  公开（公告）日：2004-09-16

  The invention relates to compounds, substituted guinoline-carboxylic acids and the derivatives thereof of general formula (1, 2, 3), the pharmaceutically acceptable salts thereof, N-oxides or hydrates and methods for the production thereof, a focused library, pharmaceutical compounds and the use thereof. Said compounds are embodied in the form of Caspase enzyme inhibitors and usefully used for curing various diseases associated to an increased apoptosis activity.
• 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.