3-(1-Methyl-piperidin-4-yl)-benzo[d]isoxazol-5-ylamine | 823191-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 3-(1-Methyl-piperidin-4-yl)-benzo[d]isoxazol-5-ylamine
• 英文别名: 3-(1-Methylpiperidin-4-yl)-1,2-benzoxazol-5-amine；3-(1-methylpiperidin-4-yl)-1,2-benzoxazol-5-amine
• CAS: 823191-42-0
• 化学式: C₁₃H₁₇N₃O
• 分子量: 231.297
• InChiKey: PSAXQIGFMPMQOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.3
• 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 、 3-(1-Methyl-piperidin-4-yl)-benzo[d]isoxazol-5-ylamine 以 1,4-二氧六环 为溶剂， 以50%的产率得到4-Fluoro-N-[3-(1-methyl-piperidin-4-yl)-benzo[d]isoxazol-5-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：

  N-甲氧基-N,1-二甲基哌啶-4-羧酰胺 在 吡啶 、 2,2,6,6-四甲基哌啶 、 盐酸 、 sodium hydroxide 、 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 盐酸羟胺 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 生成 3-(1-Methyl-piperidin-4-yl)-benzo[d]isoxazol-5-ylamine
  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.