(E)-4-(6-iodo-2-(4-nitrostyryl)-4-oxoquinazolin-3(4H)-yl)benzoic acid | 1237744-39-6

• 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: (E)-4-(6-iodo-2-(4-nitrostyryl)-4-oxoquinazolin-3(4H)-yl)benzoic acid
• 英文别名: 4-[6-iodo-2-[(E)-2-(4-nitrophenyl)ethenyl]-4-oxoquinazolin-3-yl]benzoic acid
• CAS: 1237744-39-6
• 化学式: C₂₃H₁₄IN₃O₅
• 分子量: 539.286
• InChiKey: MILASULEORRJGF-KGVSQERTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(6-iodo-2-methyl-4-oxoquinazolin-3(4H)-yl)benzoic acid 、 对硝基苯甲醛 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以66%的产率得到(E)-4-(6-iodo-2-(4-nitrostyryl)-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

• Subunit Selective NMDA Receptor Antagonists For The Treatment Of Neurological Conditions
  申请人：Traynelis Stephen F.

  公开号：US20110319416A1

  公开（公告）日：2011-12-29

  Provided are compounds, pharmaceutical compositions and methods of treating or preventing disorders associated with NMDA receptor activity, including schizophrenia, Parkinson's disease, cognitive disorders, depression, neuropathic pain, stroke, traumatic brain injury, epilepsy, and related neurologic events or neurodegeneration. Compounds of the general Formulas A-E, and pharmaceutically acceptable salts, esters, prodrugs or derivatives thereof are disclosed.
• [EN] SUBUNIT SELECTIVE NMDA RECEPTOR ANTAGONISTS FOR THE TREATMENT OF NEUROLOGICAL CONDITIONS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR NMDA, SÉLECTIFS POUR DES SOUS-UNITÉS, ET DESTINÉS AU TRAITEMENT D'ÉTATS NEUROLOGIQUES
  申请人：UNIV EMORY

  公开号：WO2010088408A2

  公开（公告）日：2010-08-05

  Provided are compounds, pharmaceutical compositions and methods of treating or preventing disorders associated with NMDA receptor activity, including schizophrenia, Parkinson's disease, cognitive disorders, depression, neuropathic pain, stroke, traumatic brain injury, epilepsy, and related neurologic events or neurodegeneration. Compounds of the general Formulas A-E, and pharmaceutically acceptable salts, esters, prodrugs or derivatives thereof are disclosed.
• 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.