2-Propoxybenzoyl isocyanate | 82251-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Propoxybenzoyl isocyanate
• 英文别名: 2-propoxybenzoyl isocyanate
• CAS: 82251-02-3
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: KXQSJWQJIJOBRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Propoxybenzoyl isocyanate 、 (1S,5R)-8-Methyl-8-azabicyclo[3.2.1]octan-3-amine 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 1-((1R,3R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-3-(2-propoxy-benzoyl)-urea
  参考文献：
  名称：

  Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas

  摘要：

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.

  DOI：

  10.1021/jm00087a003
• 作为产物：
  描述：

  草酰氯 、 2-丙氧基-苯甲酰胺 以 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 2-Propoxybenzoyl isocyanate
  参考文献：
  名称：

  Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas

  摘要：

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.

  DOI：

  10.1021/jm00087a003

文献信息

• Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
  申请人：HOECHST AKTIENGESELLSCHAFT

  公开号：EP0047496A1

  公开（公告）日：1982-03-17

  Sulfonylharnstoffe der Formel worin R1, R2, R3, X und Y die angegebenen Bedeutungen haben, sowie deren physiologisch verträglichen Salze, ihre Verwendung bei der Behandlung des Diabetes und pharmazeutische Präparate auf Basis dieser Verbindungen.

  式中 R1、R2、R3、X 和 Y 具有上述含义的磺脲类化合物及其生理耐受盐、它们在治疗糖尿病中的用途以及基于这些化合物的药物制剂。
• Novel antagonists of the 5-HT3 receptor. Synthesis and structure-activity relationships of (2-alkoxybenzoyl)ureas
  作者：Gerald Bradley、Terence J. Ward、Janet C. White、James Coleman、Ann Taylor、Keith F. Rhodes

  DOI：10.1021/jm00087a003

  日期：1992.5

  A series of benzoylureas derived from bicycle amines were prepared and evaluated for 5-HT3 antagonist activity on the rat isolated vagus nerve. From among these compounds, those analogues which were ortho substituted by an alkoxy group on the benzoyl function were shown to be potent 5-HT3 antagonists with similar or greater potency than the standard agent ondansetron. NMR and X-ray crystallography studies showed these o-alkoxy compounds to exist as a planar, hydrogen-bonded, tricyclic ring system. In molecular modeling studies on endo-N-[[(8-methyl-8-azabicyclo [3.2.1]octan-3-yl)amino]carbonyl]-2-(cyclopropylmethoxy)benzamide (30) the central hydrogen-bonded ring was able to mimic an aromatic ring present in previously reported 5-HT3 antagonists.