5-(2-ethoxy-ethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one | 858269-42-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-(2-ethoxy-ethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
• 英文别名: 5-(2-ethoxyethyl)-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one；5-(2-ethoxy-ethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one；5-(2-Aethoxy-aethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-on
• CAS: 858269-42-8
• 化学式: C₉H₁₄N₂O₂S
• 分子量: 214.288
• InChiKey: JCLBDLGXNRUDIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  57.88
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-ethoxy-ethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 在 lead(IV) acetate 、 盐酸 、 溶剂黄146 作用下， 生成 5-(2-chloro-ethyl)-6-methyl-3H-pyrimidin-4-one; hydrochloride
  参考文献：
  名称：

  A GENERAL SYNTHESIS FOR 2,3-DISUBSTITUTED AND 2,3,6-TRISUBSTITUTED 5-HYDROXYPYRAZINES

  摘要：

  DOI：

  10.1021/jo01198a003
• 作为产物：
  描述：

  ethyl 2-acetyl-4-ethoxybutanoate 、 硫脲 在 sodium ethanolate 作用下， 生成 5-(2-ethoxy-ethyl)-6-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
  参考文献：
  名称：

  A GENERAL SYNTHESIS FOR 2,3-DISUBSTITUTED AND 2,3,6-TRISUBSTITUTED 5-HYDROXYPYRAZINES

  摘要：

  DOI：

  10.1021/jo01198a003

文献信息

• Revised Pharmacophore Model for 5-HT_2A Receptor Antagonists Derived from the Atypical Antipsychotic Agent Risperidone
  作者：Urjita H. Shah、Supriya A. Gaitonde、José L. Moreno、Richard A. Glennon、Małgorzata Dukat、Javier González-Maeso

  DOI：10.1021/acschemneuro.8b00637

  日期：2019.5.15

  Pharmacophore models for 5-HT2A receptor antagonists consist of two aromatic/hydrophobic regions at a given distance from a basic amine. We have previously shown that both aromatic/hydrophobic moieties are unnecessary for binding or antagonist action. Here, we deconstructed the 5-HT2A receptor antagonist/serotonin-dopamine antipsychotic agent risperidone into smaller structural segments that were tested for 5-HT2A receptor affinity and function. We show, again, that the entire risperidone structure is unnecessary for retention of affinity or antagonist action. Replacement of the 6-fluoro-3-(4-piperidinyl)-1,2-benz[d]-isoxazole moiety by isosteric tryptamines resulted in retention of affinity and antagonist action. Additionally, 3-(4-piperidinyl)-1,2-benz[d]isoxazole (10), which represents less than half the structural features of risperidone, retains both affinity and antagonist actions. 5-HT2A receptor homology modeling/docking studies suggest that 10 binds in a manner similar to risperidone and that there is a large cavity to accept various N-4-substituted. analogues of 10 such as risperidone and related agents. Alterations of this "extended" moiety improve receptor binding and functional potency. We propose a new risperidone-based pharmacophore for 5-HT2A receptor antagonist action.