3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide | 406727-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide
• 英文别名: (2R)-N-[2-(3,4-dihydroxyphenyl)ethyl]-2-[3-(3,4-dihydroxyphenyl)prop-2-enoylamino]-3-tritylsulfanylpropanamide
• CAS: 406727-56-8
• 化学式: C₃₉H₃₆N₂O₆S
• 分子量: 660.791
• InChiKey: VRUBQYSGMNTYMV-YTTGMZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  164
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-mercaptoethyl}acrylamide
  参考文献：
  名称：

  Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

  摘要：

  Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.018
• 作为产物：
  描述：

  S-三苯甲基-L-半胱氨酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.5h， 生成 3-(3,4-dihydroxyphenyl)-N-{1-[2-(3,4-dihydroxyphenyl)ethylcarbamoyl]-2-(tritylsulfanyl)ethyl}acrylamide
  参考文献：
  名称：

  Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities

  摘要：

  Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.018

文献信息

• Novel molecular combination deriving from natural aminoacids and polyphenols: Design, synthesis and free-radical scavenging activities
  作者：Vertuani Silvia、Anna Baldisserotto、Emanuela Scalambra、Gemma Malisardi、Elisa Durini、Stefano Manfredini

  DOI：10.1016/j.ejmech.2012.02.018

  日期：2012.4

  Following the recent output of scientific publications in the matter of synergic activity between different antioxidants, we have undertaken the present study with the aim to synthesize new molecules with radical-scavengers activity based on the conjugation of bioactive portions (i.e. phenols, cysteine, methionine or tyrosine), characterized by different structures and mechanisms of action, to promote the simultaneous quenching of different radical species in the site of the oxidative damage. In this context, derivatives of phenolic acid, aminoacids and dopamine have been also prepared. The newly synthesized compounds were evaluated in vitro applying specific and complementary antioxidant test such as DPPH assay and ORAC test As emerged from the evaluation, prerequisites for the activity of the synthesized molecules were: i) the maintenance of at least two hydroxylic groups on the aromatic moiety of phenolic portion, ii) the presence of a spacer between the aromatic moiety and the carbonilic group. (C) 2012 Elsevier Masson SAS. All rights reserved.