N-tert-butyl-1-(3-methoxy-4-phenylmethoxyphenyl)methanimine oxide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-tert-butyl-1-(3-methoxy-4-phenylmethoxyphenyl)methanimine oxide
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: XXPBRYXWOHKPJN-MOSHPQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-苄氧基-3-甲氧基苯甲醛 、 N-叔丁基羟胺盐酸盐 在 sodium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以66%的产率得到N-tert-butyl-1-(3-methoxy-4-phenylmethoxyphenyl)methanimine oxide
  参考文献：
  名称：

  α-Phenyl-N-tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia/reperfusion

  摘要：

  Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamster cheek pouch' assay were studied and 1, as well as 4a, 4b, and 7 (derived from piperonal, O-benzyl vanillin, and furfural, respectively), showed to be more active than shark cartilage or a-tocopherol. No correlation was found between the protective effect of these nitrones and their log P (partition coefficient) or their capacity to trap OH and CH3 radicals. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.033

文献信息

• Alpha-aryl-N-alkylnitrones and pharmaceutical compositions containing the same
  申请人：Kelleher A. Judith

  公开号：US20050124691A1

  公开（公告）日：2005-06-09

  Disclosed are novel α-aryl-N-alkylnitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for preventing and/or treating neurodegenerative, autoimmune and inflammatory conditions in mammals and as analytical reagents for detecting free radicals.

  本发明涉及一种新型的α-芳基-N-烷基亚硝基化合物和含有这种化合物的药物组合物。所述组合物可用作治疗哺乳动物神经退行性、自身免疫和炎症疾病的治疗剂，并可用作检测自由基的分析试剂。
• N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters
  作者：Ayres G. Dias、Carlos E.V. Santos、Fatima Z.G.A. Cyrino、Eliete Bouskela、Paulo R.R. Costa

  DOI：10.1016/j.bmc.2009.04.004

  日期：2009.6

  N-Alquil nitrones 1c and 3-6 were prepared from aromatic aldehydes and N-tert-butylhydroxylamine or N-methylhydroxylamine in good yields and soft conditions. Their protective effect against microvascular damages caused by ischemia/reperfusion in 'hamster cheek pouch' assay was investigated and compare with that observed for nitrones 1a,b and 2, previously studied. Nitrones 3b, 4b and 4c were the most active ones in inhibiting macromolecular permeability increase induced by ischemia/reperfusion when administered by gavage and intravenous, while 3a and 4a were active only after intravenous administration. N-tert-butylhydroxylamine and Nt-methylhydroxylamine, products of the hydrolysis of these nitrones, were weakly active when administered by gavage or intravenous. Nitrone (4a) was the most potent in inhibiting macromolecular permeability increase induced by histamine. In this case, N-tert-butylhydroxylamine was as active as 4a. The lypophylicity in nitrones, specially in N-methyl nitrones, play an important role on the protective action when compounds were administered by gavage. (C) 2009 Published by Elsevier Ltd.
• $g(a)-ARYL-$i(N)-ALKYLNITRONES AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME
  申请人：Renovis, Inc.

  公开号：EP1025079B1

  公开（公告）日：2005-02-02
• US6046232A
  申请人：——

  公开号：US6046232A

  公开（公告）日：2000-04-04
• US6433008B1
  申请人：——

  公开号：US6433008B1

  公开（公告）日：2002-08-13