5-(2,3-dimethoxyphenyl)-3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazole | 1187947-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,3-dimethoxyphenyl)-3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazole
• 英文别名: 5-(2,3-Dimethoxyphenyl)-3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol；5-(2,3-dimethoxyphenyl)-3-[3-(3-fluoro-4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-1,2,4-oxadiazole
• CAS: 1187947-29-0
• 化学式: C₂₀H₁₈FN₃O₅
• 分子量: 399.378
• InChiKey: JIMSLYLACPDQDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.2
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(2,3-dimethoxyphenyl)-3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazole 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)benzene-1,2-diol
  参考文献：
  名称：

  Novel derivatives of ISO-1 as potent inhibitors of MIF biological function

  摘要：

  A series of novel 1,2,4-oxadiazole, phthalimide, amide and other derivatives of ISO-1 were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds inhibited MIF enzymatic activity at levels better than ISO-1. Of note, compounds 7, 22, 23, 24, 25 and 27 inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells and, more importantly, inhibited the MIF-induced production of interleukin-6 (IL-6) and/or interleukin-1b (IL-1b) significantly better than ISO-1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.052
• 作为产物：
  描述：

  3-(3-fluoro-4-methoxyphenyl)-N'-hydroxy-4,5-dihydroisoxazole-5-carboximidamide 、 2,3-二甲氧基苯甲酸 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到5-(2,3-dimethoxyphenyl)-3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Novel derivatives of ISO-1 as potent inhibitors of MIF biological function

  摘要：

  A series of novel 1,2,4-oxadiazole, phthalimide, amide and other derivatives of ISO-1 were synthesized and probed for inhibition of macrophage migration inhibitory factor (MIF) activity. Several compounds inhibited MIF enzymatic activity at levels better than ISO-1. Of note, compounds 7, 22, 23, 24, 25 and 27 inhibited the spontaneous secretion/release/recognition of MIF from freshly isolated human peripheral blood mononuclear cells and, more importantly, inhibited the MIF-induced production of interleukin-6 (IL-6) and/or interleukin-1b (IL-1b) significantly better than ISO-1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.052