5-methoxy-3-(3-methoxy-benzyl)-3H-benzooxazol-2-one | 1208448-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-methoxy-3-(3-methoxy-benzyl)-3H-benzooxazol-2-one
• 英文别名: 5-methoxy-3-[(3-methoxyphenyl)methyl]-1,3-benzoxazol-2-one
• CAS: 1208448-81-0
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: JYLQBTRPLQHVPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-3-(3-methoxy-benzyl)-3H-benzooxazol-2-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 3-(3-hydroxybenzyl)-5-methoxybenzoxazol-2-one
  参考文献：
  名称：

  Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF)

  摘要：

  The cytokine MIF is involved in inflammation and cell proliferation via pathways initiated by its binding to the transmembrane receptor CD74. MIF also exhibits keto-enol tautomerase activity, believed to be vestigial in mammals. Starting from a 1 mu M hit from virtual screening, substituted benzoxazol-2-ones have been discovered as antagonists with IC50 values as low as 7.5 nM in a tautomerase assay and 80 nM in a MIF-CD74 binding assay. Additional studies for one of the potent inhibitors demonstrated that it is not a covalent inhibitor of MIF and that it attenuates MIF-dependent ERK1/2 phosphorylation in human synovial fibroblasts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.129
• 作为产物：
  描述：

  5-甲氧基-3H-苯并恶唑-2-酮 、 3-甲氧基溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-methoxy-3-(3-methoxy-benzyl)-3H-benzooxazol-2-one
  参考文献：
  名称：

  Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF)

  摘要：

  The cytokine MIF is involved in inflammation and cell proliferation via pathways initiated by its binding to the transmembrane receptor CD74. MIF also exhibits keto-enol tautomerase activity, believed to be vestigial in mammals. Starting from a 1 mu M hit from virtual screening, substituted benzoxazol-2-ones have been discovered as antagonists with IC50 values as low as 7.5 nM in a tautomerase assay and 80 nM in a MIF-CD74 binding assay. Additional studies for one of the potent inhibitors demonstrated that it is not a covalent inhibitor of MIF and that it attenuates MIF-dependent ERK1/2 phosphorylation in human synovial fibroblasts. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.129

文献信息

• MIF MODULATORS
  申请人：Jorgensen William L.

  公开号：US20120040974A1

  公开（公告）日：2012-02-16

  The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression.

  该发明提供了新型杂环化合物、制药组合物和治疗方法，可调节MIF表达水平并治疗与高或低MIF表达水平有关的疾病。
• MIF modulators
  申请人：YALE UNIVERSITY

  公开号：US10202343B2

  公开（公告）日：2019-02-12

  The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression.

  本发明提供了新型杂环化合物、药物组合物和治疗方法，可调节 MIF 的表达水平，治疗与 MIF 表达水平过高或过低有关的疾病。
• [EN] MIF MODULATORS<br/>[FR] MODULATEURS DE MIF
  申请人：UNIV YALE

  公开号：WO2010021693A3

  公开（公告）日：2010-07-01
• US9540322B2
  申请人：——

  公开号：US9540322B2

  公开（公告）日：2017-01-10
• US9643922B2
  申请人：——

  公开号：US9643922B2

  公开（公告）日：2017-05-09