[(S)-3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid | 899433-52-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(S)-3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid
• 英文别名: (S)-2-(3-(3-Fluoro-4-methoxyphenyl)-4,5-dihydroisoxazol-5-yl)acetic acid；2-[(5S)-3-(3-fluoro-4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
• CAS: 899433-52-4
• 化学式: C₁₂H₁₂FNO₄
• 分子量: 253.23
• InChiKey: FZRGTNVZONMQRB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(S)-3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 [(S)-3-(3-Fluoro-4-hydroxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid
  参考文献：
  名称：

  Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity

  摘要：

  Based on the scaffold of (S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester (ISO-1), an inhibitor of the proinflammatory cytokine MIF, two critical modifications and chiral resolution have significantly improved the potency of the inhibition. Compound (R)-17 is 20-fold more potent than ISO-1 and inhibits MIF tautomerase activity with an IC50 of 550 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.038
• 作为产物：
  描述：

  [3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid 生成 [(R)-3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid 、 [(S)-3-(3-Fluoro-4-methoxy-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid
  参考文献：
  名称：

  Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity

  摘要：

  Based on the scaffold of (S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester (ISO-1), an inhibitor of the proinflammatory cytokine MIF, two critical modifications and chiral resolution have significantly improved the potency of the inhibition. Compound (R)-17 is 20-fold more potent than ISO-1 and inhibits MIF tautomerase activity with an IC50 of 550 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.038

文献信息

• Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity
  作者：Kai Fan Cheng、Yousef Al-Abed

  DOI：10.1016/j.bmcl.2006.04.038

  日期：2006.7

  Based on the scaffold of (S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester (ISO-1), an inhibitor of the proinflammatory cytokine MIF, two critical modifications and chiral resolution have significantly improved the potency of the inhibition. Compound (R)-17 is 20-fold more potent than ISO-1 and inhibits MIF tautomerase activity with an IC50 of 550 nM. (c) 2006 Elsevier Ltd. All rights reserved.