7-trifluoromethyl-3-hydroxy-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione | 1394058-40-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 7-trifluoromethyl-3-hydroxy-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione
• 英文别名: 1-[3-hydroxy-2,4-dioxo-7-(trifluoromethyl)-1H-quinazolin-6-yl]pyrrole-3-carbaldehyde
• CAS: 1394058-40-2
• 化学式: C₁₄H₈F₃N₃O₄
• 分子量: 339.23
• InChiKey: KKQGHPQTBLEIJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-trifluoromethyl-3-hydroxy-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione 在 potassium permanganate 、 sodium hydrogensulfite 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.5h， 以75%的产率得到7-trifluoromethyl-3-hydroxy-6-(3-carboxypyrrol-1-yl)-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  3-Hydroxy-1H-quinazoline-2,4-dione derivatives as new antagonists at ionotropic glutamate receptors: Molecular modeling and pharmacological studies

  摘要：

  Based on our 3-hydroxy-7-chloroquinazoline-2,4-dione derivatives, previously reported as antagonists at ionotropic glutamate receptors, we synthesized new 3-hydroxyquinazoline-2,4-diones bearing a trifluoromethyl group at the 7-position and different groups at position 6. Glycine/NMDA, AMPA and kainate receptor binding data showed that the 7-trifluoromethyl residue increased AMPA and kainate receptor affinity and selectivity, with respect to the 7-chlorine atom. Among the probed 6-substituents, the 6-(1,2,4-triazol-4-yl) group (compound 8) was the most advantageous for AMPA receptor affinity and selectivity. Derivative 8 demonstrated to be effective in decreasing neuronal damage produced by oxygen and glucose deprivation in organotypic rat hippocampal slices and also showed anticonvulsant effects in pentylenetetrazole-induced convulsions. The previously reported kainate receptor antagonist 6-(2-carboxybenzoyl)-amino-7-chloro-3-hydroxyquinazoline-2,4-dione 3 prevented the failure of neurotransmission induced by oxygen and glucose deprivation in the CA1 region of rat hippocampal slices. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.036
• 作为产物：
  描述：

  2,5-二甲氧基-3-四氢呋喃缩醛 在 溶剂黄146 作用下， 反应 0.5h， 以83%的产率得到7-trifluoromethyl-3-hydroxy-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  3-Hydroxy-1H-quinazoline-2,4-dione derivatives as new antagonists at ionotropic glutamate receptors: Molecular modeling and pharmacological studies

  摘要：

  Based on our 3-hydroxy-7-chloroquinazoline-2,4-dione derivatives, previously reported as antagonists at ionotropic glutamate receptors, we synthesized new 3-hydroxyquinazoline-2,4-diones bearing a trifluoromethyl group at the 7-position and different groups at position 6. Glycine/NMDA, AMPA and kainate receptor binding data showed that the 7-trifluoromethyl residue increased AMPA and kainate receptor affinity and selectivity, with respect to the 7-chlorine atom. Among the probed 6-substituents, the 6-(1,2,4-triazol-4-yl) group (compound 8) was the most advantageous for AMPA receptor affinity and selectivity. Derivative 8 demonstrated to be effective in decreasing neuronal damage produced by oxygen and glucose deprivation in organotypic rat hippocampal slices and also showed anticonvulsant effects in pentylenetetrazole-induced convulsions. The previously reported kainate receptor antagonist 6-(2-carboxybenzoyl)-amino-7-chloro-3-hydroxyquinazoline-2,4-dione 3 prevented the failure of neurotransmission induced by oxygen and glucose deprivation in the CA1 region of rat hippocampal slices. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.036

文献信息

• 3-Hydroxy-1H-quinazoline-2,4-dione derivatives as new antagonists at ionotropic glutamate receptors: Molecular modeling and pharmacological studies
  作者：Vittoria Colotta、Ombretta Lenzi、Daniela Catarzi、Flavia Varano、Lucia Squarcialupi、Chiara Costagli、Alessandro Galli、Carla Ghelardini、Anna Maria Pugliese、Giovanna Maraula、Elisabetta Coppi、Domenico E. Pellegrini-Giampietro、Felicita Pedata、Davide Sabbadin、Stefano Moro

  DOI：10.1016/j.ejmech.2012.05.036

  日期：2012.8

  Based on our 3-hydroxy-7-chloroquinazoline-2,4-dione derivatives, previously reported as antagonists at ionotropic glutamate receptors, we synthesized new 3-hydroxyquinazoline-2,4-diones bearing a trifluoromethyl group at the 7-position and different groups at position 6. Glycine/NMDA, AMPA and kainate receptor binding data showed that the 7-trifluoromethyl residue increased AMPA and kainate receptor affinity and selectivity, with respect to the 7-chlorine atom. Among the probed 6-substituents, the 6-(1,2,4-triazol-4-yl) group (compound 8) was the most advantageous for AMPA receptor affinity and selectivity. Derivative 8 demonstrated to be effective in decreasing neuronal damage produced by oxygen and glucose deprivation in organotypic rat hippocampal slices and also showed anticonvulsant effects in pentylenetetrazole-induced convulsions. The previously reported kainate receptor antagonist 6-(2-carboxybenzoyl)-amino-7-chloro-3-hydroxyquinazoline-2,4-dione 3 prevented the failure of neurotransmission induced by oxygen and glucose deprivation in the CA1 region of rat hippocampal slices. (C) 2012 Elsevier Masson SAS. All rights reserved.