6-(4-(N-(t-butyloxycarbonyl)piperidinyl)methyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one | 420787-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6-(4-(N-(t-butyloxycarbonyl)piperidinyl)methyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one
• CAS: 420787-11-7
• 化学式: C₁₉H₂₅FN₂O₄
• 分子量: 364.417
• InChiKey: PTAURELYRHSLBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(4-(N-(t-butyloxycarbonyl)piperidinyl)methyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one 在 N-ethyl-diisopropylethylamine 、 三氟乙酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 6-[[1-[2-(7-chloro-2-methylquinolin-5-yl)oxyethyl]piperidin-4-yl]methyl]-8-fluoro-4H-1,4-benzoxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031
• 作为产物：
  描述：

  3-氟-4-甲氧基苯甲醛 在 palladium on activated charcoal sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 氢气 、 硝酸 、 溶剂黄146 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(4-(N-(t-butyloxycarbonyl)piperidinyl)methyl)-8-fluoro-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031

文献信息

• [EN] BENZOXAZINONE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE BENZOXAZINONE, PREPARATION ET UTILISATION ASSOCIEES
  申请人：GLAXO GROUP LTD

  公开号：WO2004099196A1

  公开（公告）日：2004-11-18

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, wherein R1 is hydrogen or C1-6alkyl; and R2 is fluoro or chloro. Methods of preparation and uses thereof in treatment of CNS disorders, such as depression or anxiety, are also disclosed.

  公式（I）的化合物及其药用盐已被披露，其中R1是氢或C1-6烷基；R2是氟或氯。还披露了其制备方法以及在治疗中枢神经系统疾病，如抑郁症或焦虑症中的用途。
• Studies on a series of potent, orally bioavailable, 5-HT1 receptor ligands
  作者：Simon E. Ward、Christopher N. Johnson、Peter J. Lovell、Claire M. Scott、Paul W. Smith、Geoffrey Stemp、Kevin M. Thewlis、Antonio K. Vong、Jeannette M. Watson

  DOI：10.1016/j.bmcl.2007.06.078

  日期：2007.9

  A series of 5-(piperidinylethyloxy)quinoline 5-HT1 receptor ligands have been studied by elaboration of the series of dual 5-HT1-SSRIs reported previously. These new compounds display a different pharmacological profile with potent affinity across the 5-HT1A, 5-HT1B and 5-HT1D receptors and selectivity against the serotonin transporter. Furthermore, they have improved pharmacokinetic profiles and CNS penetration. (c) 2007 Elsevier Ltd. All rights reserved.