(E)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)-3-(4-hydroxy-3-methoxyphenyl)-N-phenylacrylamide | 1451263-15-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)-3-(4-hydroxy-3-methoxyphenyl)-N-phenylacrylamide
• 英文别名: coumaroyl(3-OMe)-DL-N(Ph)Phg-NHtBu；(E)-N-[2-(tert-butylamino)-2-oxo-1-phenylethyl]-3-(4-hydroxy-3-methoxyphenyl)-N-phenylprop-2-enamide
• CAS: 1451263-15-2
• 化学式: C₂₈H₃₀N₂O₄
• 分子量: 458.557
• InChiKey: CCDQZNYXALGGJX-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  阿魏酸 、 异氰酸叔丁酯 、 苯甲醛 、 苯胺 以 甲醇 为溶剂， 反应 25.0h， 以51%的产率得到(E)-N-(2-(tert-butylamino)-2-oxo-1-phenylethyl)-3-(4-hydroxy-3-methoxyphenyl)-N-phenylacrylamide
  参考文献：
  名称：

  Ugi Multicomponent Reaction Product: The Inhibitive Effect on DNA Oxidation Depends upon the Isocyanide Moiety

  摘要：

  The hydroxyl-substituted benzoic acid (as phenyl group A in the product), aniline (as phenyl group B in the product), benzaldehyde (as phenyl group C in the product), and four isocyanides are employed to synthesize bis-amide via an Ugi four-component reaction. The effects of the obtained 20 bis-amides on quenching radicals and inhibiting DNA oxidation are estimated. It is found that the antioxidant effectiveness of bis-amide generated by hydroxyl groups is markedly influenced by the structural feature derived from isocyanide. The phenolic hydroxyl group attaching to phenyl group A plays a major role in scavenging radicals, and the radical-scavenging property is reinforced by the structural moiety introduced from ferrocenylmethyl isocyanide. The same conclusion is also obtained when bis-amides are used to inhibit DNA oxidation. It is still found that the ferrocenylmethyl moiety enhances the antioxidant effect of hydroxyl group at phenyl group A in protecting DNA against the oxidation. Moreover, when the bis-amide is prepared by the same isocyanide, e.g. ethyl isocyanoacetate, it is found that the hydroxyl group at phenyl group C plays the major role in inhibiting DNA oxidation, followed by the hydroxyl groups attaching to phenyl groups B and A.

  DOI：

  10.1021/jo401426n

文献信息

• Ugi Multicomponent Reaction Product: The Inhibitive Effect on DNA Oxidation Depends upon the Isocyanide Moiety
  作者：Rui Wang、Zai-Qun Liu

  DOI：10.1021/jo401426n

  日期：2013.9.6

  The hydroxyl-substituted benzoic acid (as phenyl group A in the product), aniline (as phenyl group B in the product), benzaldehyde (as phenyl group C in the product), and four isocyanides are employed to synthesize bis-amide via an Ugi four-component reaction. The effects of the obtained 20 bis-amides on quenching radicals and inhibiting DNA oxidation are estimated. It is found that the antioxidant effectiveness of bis-amide generated by hydroxyl groups is markedly influenced by the structural feature derived from isocyanide. The phenolic hydroxyl group attaching to phenyl group A plays a major role in scavenging radicals, and the radical-scavenging property is reinforced by the structural moiety introduced from ferrocenylmethyl isocyanide. The same conclusion is also obtained when bis-amides are used to inhibit DNA oxidation. It is still found that the ferrocenylmethyl moiety enhances the antioxidant effect of hydroxyl group at phenyl group A in protecting DNA against the oxidation. Moreover, when the bis-amide is prepared by the same isocyanide, e.g. ethyl isocyanoacetate, it is found that the hydroxyl group at phenyl group C plays the major role in inhibiting DNA oxidation, followed by the hydroxyl groups attaching to phenyl groups B and A.