4-(1-Methylpiperidin-4-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-amine | 823191-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-(1-Methylpiperidin-4-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-amine
• 英文别名: 4-(1-methylpiperidin-4-yl)-2,3-dihydro-1,4-benzoxazin-6-amine
• CAS: 823191-53-3
• 化学式: C₁₄H₂₁N₃O
• 分子量: 247.34
• InChiKey: UMTIFVVEOWDQRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氟苯甲酰氯 、 4-(1-Methylpiperidin-4-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-amine 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到4-Fluoro-N-[4-(1-methyl-piperidin-4-yl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-benzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT1F receptor agonists

  摘要：

  Several fused bicyclic systems have been investigated to serve as the core structure of potent and selective 5-HT1F receptor agonists. Replacement of the indole nucleus in 2 with indazole and 'inverted' indazole provided more potent and selective 5-HT1F receptor ligands. Indoline and 1,2-benzisoxazole systems also provided potent 5-HT1F receptor agonists, and the 5-HT1A receptor selectivity of the indoline- and 1,2-benzisoxazole-based 5-HT1F receptor agonists could be improved with modification of the benzoyl moiety of the benzamides. Through these studies, we found that the inherent geometries of the templates, not the nature of hybridization of the linking atom, were important for the 5-HT1F receptor recognition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.079
• 作为产物：
  描述：

  6-硝基-3,4-二氢-2H-1,4-苯并噁嗪 在 palladium on activated charcoal 氢气 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-(1-Methylpiperidin-4-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-amine
  参考文献：
  名称：

  Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT1F receptor agonists

  摘要：

  Several fused bicyclic systems have been investigated to serve as the core structure of potent and selective 5-HT1F receptor agonists. Replacement of the indole nucleus in 2 with indazole and 'inverted' indazole provided more potent and selective 5-HT1F receptor ligands. Indoline and 1,2-benzisoxazole systems also provided potent 5-HT1F receptor agonists, and the 5-HT1A receptor selectivity of the indoline- and 1,2-benzisoxazole-based 5-HT1F receptor agonists could be improved with modification of the benzoyl moiety of the benzamides. Through these studies, we found that the inherent geometries of the templates, not the nature of hybridization of the linking atom, were important for the 5-HT1F receptor recognition. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.079

文献信息

• Design, synthesis and evaluation of bicyclic benzamides as novel 5-HT1F receptor agonists
  作者：Deyi Zhang、Dan Kohlman、Joseph Krushinski、Sidney Liang、Bai-Ping Ying、John E. Reilly、Sean R. Dinn、David B. Wainscott、Suzanne Nutter、Wendy Gough、David L.G. Nelson、John M. Schaus、Yao-Chang Xu

  DOI：10.1016/j.bmcl.2004.09.079

  日期：2004.12

  Several fused bicyclic systems have been investigated to serve as the core structure of potent and selective 5-HT1F receptor agonists. Replacement of the indole nucleus in 2 with indazole and 'inverted' indazole provided more potent and selective 5-HT1F receptor ligands. Indoline and 1,2-benzisoxazole systems also provided potent 5-HT1F receptor agonists, and the 5-HT1A receptor selectivity of the indoline- and 1,2-benzisoxazole-based 5-HT1F receptor agonists could be improved with modification of the benzoyl moiety of the benzamides. Through these studies, we found that the inherent geometries of the templates, not the nature of hybridization of the linking atom, were important for the 5-HT1F receptor recognition. (C) 2004 Elsevier Ltd. All rights reserved.