3-benzyloxy-4-(2-chlorophenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-benzyloxy-4-(2-chlorophenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole
• 英文别名: Methyl 4-[4-(2-chlorophenyl)-3-phenylmethoxy-1,2-oxazol-5-yl]piperidine-1-carboxylate
• 化学式: C₂₃H₂₃ClN₂O₄
• 分子量: 426.9
• InChiKey: AHPQQYHTRILYIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-4-(2-chlorophenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以76%的产率得到4-(2-chlorophenyl)-5-(4-piperidinyl)-3-isoxazolol hydrobromide
  参考文献：
  名称：

  4-Aryl-5-(4-Piperidyl)-3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Structure−Activity Relationships

  摘要：

  A series of 4-aryl-5-(4-piperidyl)-3-isoxazolol GABA(A) antagonists have been synthesized and pharmacologically characterized. The meta-phenyl-substituted compounds 9k and 9m and the para-phenoxy-substituted compound 9l all display high affinities (K-i = 10-70 nM) and antagonist potencies in the low nanomolar range (K-i = 9-10 nM). These potencies are significantly higher than those of previously reported 4-PIOL antagonists and considerably higher than that of the standard GABA(A) antagonist SR 95531.

  DOI：

  10.1021/jm070038n
• 作为产物：
  描述：

  2-氯苯基硼酸 、 3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以78%的产率得到3-benzyloxy-4-(2-chlorophenyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole
  参考文献：
  名称：

  4-Aryl-5-(4-Piperidyl)-3-Isoxazolol GABA_A Antagonists:  Synthesis, Pharmacology, and Structure−Activity Relationships

  摘要：

  A series of 4-aryl-5-(4-piperidyl)-3-isoxazolol GABA(A) antagonists have been synthesized and pharmacologically characterized. The meta-phenyl-substituted compounds 9k and 9m and the para-phenoxy-substituted compound 9l all display high affinities (K-i = 10-70 nM) and antagonist potencies in the low nanomolar range (K-i = 9-10 nM). These potencies are significantly higher than those of previously reported 4-PIOL antagonists and considerably higher than that of the standard GABA(A) antagonist SR 95531.

  DOI：

  10.1021/jm070038n