3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbonitrile | 1187946-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbonitrile
• CAS: 1187946-87-7
• 化学式: C₁₁H₉FN₂O₂
• 分子量: 220.203
• InChiKey: BJLFSWSFGJXGKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbonitrile 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、413.69 kPa 条件下， 反应 2.0h， 以63.82%的产率得到(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)methanamine hydrochloride
  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-fluoro-N-hydroxy-4-methoxybenzimidoyl chloride 、 丙烯腈 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazole-5-carbonitrile
  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