6-(2-Amino-ethoxy)-4H-benzo[1,4]oxazin-3-one | 845887-34-5

• 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: 6-(2-Amino-ethoxy)-4H-benzo[1,4]oxazin-3-one
• 英文别名: 6-(2-aminoethoxy)-4H-1,4-benzoxazin-3-one
• CAS: 845887-34-5
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: JFSIEFIFSVCUNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-bromopropyloxy)indole 、 6-(2-Amino-ethoxy)-4H-benzo[1,4]oxazin-3-one 在 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以20%的产率得到6-{2-[3-(1H-Indol-4-yloxy)-propylamino]-ethoxy}-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity

  摘要：

  Starting from a high throughput screening hit, a series of 3,4-dihydro-2H-benzoxazinones has been identified with both high affinity for the 5-HT1A receptor and potent 5-HT reuptake inhibitory activity. The 5-(2-methyl)quinolinyloxy derivative combined high 5-HT1A/1B/1D receptor affinities with low intrinsic activity and potent inhibition of the 5-HT reuptake site (pK(i) 8.2). This compound also had good oral bioavailability and brain penetration in the rat. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.030
• 作为产物：
  描述：

  4-羟基-3-硝基苯基苯甲酸酯 在 palladium on activated charcoal 、 三丁基膦 、 sodium methylate 、 potassium carbonate 、 三氟乙酸 、 1,1'-azodicarbonyl-dipiperidine 、 环己烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 45.0h， 生成 6-(2-Amino-ethoxy)-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity

  摘要：

  Starting from a high throughput screening hit, a series of 3,4-dihydro-2H-benzoxazinones has been identified with both high affinity for the 5-HT1A receptor and potent 5-HT reuptake inhibitory activity. The 5-(2-methyl)quinolinyloxy derivative combined high 5-HT1A/1B/1D receptor affinities with low intrinsic activity and potent inhibition of the 5-HT reuptake site (pK(i) 8.2). This compound also had good oral bioavailability and brain penetration in the rat. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.030

文献信息

• 3,4-Dihydro-2H-benzoxazinones are 5-HT1A receptor antagonists with potent 5-HT reuptake inhibitory activity
  作者：Peter J. Atkinson、Steven M. Bromidge、Mark S. Duxon、Laramie M. Gaster、Michael S. Hadley、Beverley Hammond、Christopher N. Johnson、Derek N. Middlemiss、Stephanie E. North、Gary W. Price、Harshad K. Rami、Graham J. Riley、Claire M. Scott、Tracey E. Shaw、Kathryn R. Starr、Geoffrey Stemp、Kevin M. Thewlis、David R. Thomas、Mervyn Thompson、Antonio K.K. Vong、Jeannette M. Watson

  DOI：10.1016/j.bmcl.2004.11.030

  日期：2005.2

  Starting from a high throughput screening hit, a series of 3,4-dihydro-2H-benzoxazinones has been identified with both high affinity for the 5-HT1A receptor and potent 5-HT reuptake inhibitory activity. The 5-(2-methyl)quinolinyloxy derivative combined high 5-HT1A/1B/1D receptor affinities with low intrinsic activity and potent inhibition of the 5-HT reuptake site (pK(i) 8.2). This compound also had good oral bioavailability and brain penetration in the rat. (C) 2004 Elsevier Ltd. All rights reserved.