N-cyclohexyl-3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propanamide | 1187947-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-cyclohexyl-3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propanamide
• 英文别名: N-cyclohexyl-3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazole-5-yl)-1,2,4-oxadiazol-5-yl)propanamide；N-cyclohexyl-3-[3-[3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-1,2,4-oxadiazol-5-yl]propanamide
• CAS: 1187947-16-5
• 化学式: C₂₀H₂₃FN₄O₄
• 分子量: 402.425
• InChiKey: QEZDZADMWFLFMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  N-cyclohexyl-3-(3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propanamide 在 三氟二甲基硫醚络合物 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到N-cyclohexyl-3-(3-(3-(3-fluoro-4-hydroxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propanamide
  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