3-(3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionic acid | 1187947-07-4

• 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-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionic acid
• 英文别名: 3-[3-[3-(3-Fluoro-4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]-1,2,4-oxadiazol-5-yl]propanoic acid
• CAS: 1187947-07-4
• 化学式: C₁₅H₁₄FN₃O₅
• 分子量: 335.292
• InChiKey: JSNHKQSIZKMVAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionic acid 在 氯化亚砜 作用下， 生成
  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：

  丁二酸酐 、 3-(3-fluoro-4-methoxyphenyl)-N'-hydroxy-4,5-dihydroisoxazole-5-carboximidamide 以 吡啶 为溶剂， 反应 8.0h， 以64%的产率得到3-(3-(3-(3-fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)-1,2,4-oxadiazol-5-yl)propionic acid
  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

文献信息

• Novel derivatives of ISO-1 as potent inhibitors of MIF biological function
  作者：Sarala Balachandran、Atish Rodge、Pradip K. Gadekar、Vitthal N. Yadav、Divya Kamath、Anshu Chetrapal-Kunwar、Pooja Bhatt、Shaila Srinivasan、Somesh Sharma、Ram A. Vishwakarma、Nilesh M. Dagia

  DOI：10.1016/j.bmcl.2009.06.052

  日期：2009.8

  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.