methyl 5-isopropyl-3-naphthalen-2-ylisoxazole-4-carboxylate | 933799-92-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 5-isopropyl-3-naphthalen-2-ylisoxazole-4-carboxylate
• CAS: 933799-92-9
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: WBRIOBNZKBVVKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-isopropyl-3-naphthalen-2-ylisoxazole-4-carboxylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以69%的产率得到5-isopropyl-3-naphthalen-2-ylisoxazole-4-methanol
  参考文献：
  名称：

  Design, synthesis, and evaluation of non-steroidal farnesoid X receptor (FXR) antagonist

  摘要：

  A series of substituted-isoxazole derivatives was prepared as candidate farnesoid X receptor (FXR) antagonists, based on our previously proposed ligand superfamily concept. Structure-activity relationship studies indicated that the shape and the structural bulkiness of the substituent at the 5-position of the isoxazole ring affected FXR-antagonistic activity. Compounds 15g (5-substituent: 2-naphthyl) and 15h (5-substituent: 4-biphenyl) were identified as potent antagonists with higher selectivity for FXR over progesterone receptor than the naturally occurring FXR antagonist GS. The 5-substituent is also a critical determinant of the characteristic corepressor recruitment profile of this class of FXR antagonists, though distinct mechanisms appear to be involved: 15h stabilizes the corepressor-nuclear receptor interaction, while 15g inhibits coactivator recruitment. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.046
• 作为产物：
  描述：

  2-naphthaldoxime 在 N-氯代丁二酰亚胺 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 methyl 5-isopropyl-3-naphthalen-2-ylisoxazole-4-carboxylate
  参考文献：
  名称：

  Design, synthesis, and evaluation of non-steroidal farnesoid X receptor (FXR) antagonist

  摘要：

  A series of substituted-isoxazole derivatives was prepared as candidate farnesoid X receptor (FXR) antagonists, based on our previously proposed ligand superfamily concept. Structure-activity relationship studies indicated that the shape and the structural bulkiness of the substituent at the 5-position of the isoxazole ring affected FXR-antagonistic activity. Compounds 15g (5-substituent: 2-naphthyl) and 15h (5-substituent: 4-biphenyl) were identified as potent antagonists with higher selectivity for FXR over progesterone receptor than the naturally occurring FXR antagonist GS. The 5-substituent is also a critical determinant of the characteristic corepressor recruitment profile of this class of FXR antagonists, though distinct mechanisms appear to be involved: 15h stabilizes the corepressor-nuclear receptor interaction, while 15g inhibits coactivator recruitment. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.046