3-methyl-6-(2-propen-1-yl)-4H-[1,2,3]triazolo[5,1-c][1,4]benzoxazine | 876921-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methyl-6-(2-propen-1-yl)-4H-[1,2,3]triazolo[5,1-c][1,4]benzoxazine
• 英文别名: 3-Methyl-6-(2-propen-1-yl)-4H-[1,2,3]triazolo[5,1-c][1,4]-benzoxazine；3-methyl-6-prop-2-enyl-4H-triazolo[5,1-c][1,4]benzoxazine
• CAS: 876921-60-7
• 化学式: C₁₃H₁₃N₃O
• 分子量: 227.266
• InChiKey: IMWPGNVKYPMIEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-6-(2-propen-1-yl)-4H-[1,2,3]triazolo[5,1-c][1,4]benzoxazine 在 四氧化锇 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Design and Synthesis of Novel Tricyclic Benzoxazines as Potent 5-HT_1A/B/D Receptor Antagonists Leading to the Discovery of 6-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}-4H-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide (GSK588045)

  摘要：

  Bioisoteric replacement of the metabolically labile N-methyl amide group of a series of benzoxazinones with small heterocyclic rings has led to novel series of fused tricyclic benzoxazines which are potent 5-HT1A/B/D receptor antagonists with and without concomitant human serotonin transporter (hSerT) activity. Optimizing against multiple parameters in parallel identified 6-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}-4H-imidazo[5,1-c][1,4]benzoxazine-3-carboxamide (GSK588045) as a potent 5-HT1A/B/D receptor antagonist with a high degree of selectivity over human ether-a-go-go related gene (hERG) potassium channels, favorable pharmacokinetics, and excellent activity in vivo in rodent pharmacodynamic (PD) models. On the basis of its outstanding overall profile, this compound was progressed as a clinical candidate with the ultimate aim to assess its potential as a faster acting antidepressant/anxiolytic with reduced side-effect burden.

  DOI：

  10.1021/jm100482n
• 作为产物：
  描述：

  1-azido-2-(2-butyn-1-yloxy)-3-(2-propen-1-yl)benzene 在 silica gel 、 cyclohexane, ethyl acetate 作用下， 以 甲苯 为溶剂， 反应 2.5h， 以to afford the title compound (183 mg, 82%)的产率得到3-methyl-6-(2-propen-1-yl)-4H-[1,2,3]triazolo[5,1-c][1,4]benzoxazine
  参考文献：
  名称：

  FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS

  摘要：

  式(I)中的化合物，其中R1、R2、X、A、Y、B、Z1、Q、p、r和s在规范中定义，用于治疗精神疾病、抑郁症、焦虑症和性功能障碍等疾病。

  公开号：

  US20120022056A1

文献信息

• [EN] FUSED TRICYCLIC DERIVATIVES FOR THE TREATMENT OF PSYCHOTIC DISORDERS<br/>[FR] DERIVES TRICYCLIQUES ACCOLES POUR LE TRAITEMENT DE TROUBLES PSYCHOTIQUES
  申请人：GLAXO GROUP LTD

  公开号：WO2006024517A1

  公开（公告）日：2006-03-09

  Compounds of formula (I) wherein R1, R2, X, A, Y, B, Z1, Q, p, r and s are defined in the specification for treating inter alia psychotic disorders, depressive disorders, anxiety disorders and sexual dysfunctions.

  式中R1、R2、X、A、Y、B、Z1、Q、p、r和s在说明书中定义的用于治疗精神疾病、抑郁障碍、焦虑障碍和性功能障碍的(I)式化合物。