3-acetoxy-7-chloro-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione | 913974-10-4

• 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: 3-acetoxy-7-chloro-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione
• 英文别名: [7-chloro-6-(3-formylpyrrol-1-yl)-2,4-dioxo-1H-quinazolin-3-yl] acetate
• CAS: 913974-10-4
• 化学式: C₁₅H₁₀ClN₃O₅
• 分子量: 347.714
• InChiKey: WIBIROKYSUBCIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-acetoxy-7-chloro-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以48%的产率得到3-acetoxy-7-chloro-6-(3-carboxypyrrol-1-yl)-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  Structural Investigation of the 7-Chloro-3-hydroxy-1H-quinazoline-2,4-dione Scaffold to Obtain AMPA and Kainate Receptor Selective Antagonists. Synthesis, Pharmacological, and Molecular Modeling Studies

  摘要：

  In this paper, the study of new 7-chloro-3-hydroxy-1H-quinazoline-2,4-dione derivatives, designed as AMPA and kainate (KA) receptor antagonists, is reported. Some derivatives bear different carboxy-containing alkyl chains on the 3-hydroxy group, while various heterocyclic rings or amide moieties are present at the 6-position of other compounds. Binding data at Gly/NMDA, AMPA, and high-affinity KA receptors showed that the presence of the free 3-hydroxy group is of paramount importance for a good affinity at all three investigated receptors, while introduction of some 6-heterocyclic moieties yielded AMPA-selective antagonists. The most significant result was the finding of the 6-(2-carboxybenzoylamino)-3-hydroxy-1H-quinazolin-2,4dione 12, which possesses good affinity for high-affinity and low-affinity KA receptors (K-i = 0.62 mu M and 1.6 mu M, respectively), as well as good selectivity. To rationalize the trend of affinities of the reported derivatives, an intensive molecular modeling study was carried out by docking compounds to models of the Gly/NMDA, AMPA, and KA receptors.

  DOI：

  10.1021/jm0604880
• 作为产物：
  描述：

  2,5-二甲氧基-3-四氢呋喃缩醛 、 6-amino-7-chloro-3-acetoxyquinazoline-2,4-dione 在 溶剂黄146 作用下， 反应 0.5h， 以70%的产率得到3-acetoxy-7-chloro-6-(3-formylpyrrol-1-yl)-1H-quinazoline-2,4-dione
  参考文献：
  名称：

  Structural Investigation of the 7-Chloro-3-hydroxy-1H-quinazoline-2,4-dione Scaffold to Obtain AMPA and Kainate Receptor Selective Antagonists. Synthesis, Pharmacological, and Molecular Modeling Studies

  摘要：

  In this paper, the study of new 7-chloro-3-hydroxy-1H-quinazoline-2,4-dione derivatives, designed as AMPA and kainate (KA) receptor antagonists, is reported. Some derivatives bear different carboxy-containing alkyl chains on the 3-hydroxy group, while various heterocyclic rings or amide moieties are present at the 6-position of other compounds. Binding data at Gly/NMDA, AMPA, and high-affinity KA receptors showed that the presence of the free 3-hydroxy group is of paramount importance for a good affinity at all three investigated receptors, while introduction of some 6-heterocyclic moieties yielded AMPA-selective antagonists. The most significant result was the finding of the 6-(2-carboxybenzoylamino)-3-hydroxy-1H-quinazolin-2,4dione 12, which possesses good affinity for high-affinity and low-affinity KA receptors (K-i = 0.62 mu M and 1.6 mu M, respectively), as well as good selectivity. To rationalize the trend of affinities of the reported derivatives, an intensive molecular modeling study was carried out by docking compounds to models of the Gly/NMDA, AMPA, and KA receptors.

  DOI：

  10.1021/jm0604880