4-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid | 477552-43-5

• 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: 4-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid
• 英文别名: 4-(6-iodo-2-methyl-4-oxoquinazolin-3-yl)benzoic acid
• CAS: 477552-43-5
• 化学式: C₁₆H₁₁IN₂O₃
• 分子量: 406.179
• InChiKey: BXARHESJLHDIFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-吡啶甲醛 、 4-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以58%的产率得到(E)-4-(6-iodo-4-oxo-2-(2-(pyridin-3-yl)vinyl)quinazolin-3(4H)-yl)benzoic acid
  参考文献：
  名称：

  Quinazolin-4-one Derivatives: A Novel Class of Noncompetitive NR2C/D Subunit-Selective N-Methyl-d-aspartate Receptor Antagonists

  摘要：

  We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl]-6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.

  DOI：

  10.1021/jm100027p
• 作为产物：
  描述：

  6-iodo-2-methylbenzo[d][1,3]oxazin-4-one 、 对氨基苯甲酸 在 溶剂黄146 作用下， 以45%的产率得到4-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid
  参考文献：
  名称：

  Quinazolin-4-one Derivatives: A Novel Class of Noncompetitive NR2C/D Subunit-Selective N-Methyl-d-aspartate Receptor Antagonists

  摘要：

  We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl]-6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.

  DOI：

  10.1021/jm100027p

文献信息

• Quinazolin-4-one Derivatives: A Novel Class of Noncompetitive NR2C/D Subunit-Selective <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptor Antagonists
  作者：Cara A. Mosley、Timothy M. Acker、Kasper B. Hansen、Praseeda Mullasseril、Karen T. Andersen、Phuong Le、Kimberly M. Vellano、Hans Bräuner-Osborne、Dennis C. Liotta、Stephen F. Traynelis

  DOI：10.1021/jm100027p

  日期：2010.8.12

  We describe a new class of subunit-selective antagonists of N-methyl D-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl]-6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.