2-[3-(3,4-dihydroxyphenyl)acryloylamino]-3-(4-hydroxyphenyl)propionic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[3-(3,4-dihydroxyphenyl)acryloylamino]-3-(4-hydroxyphenyl)propionic acid methyl ester
• 英文别名: Methyl 2-[3-(3,4-dihydroxyphenyl)prop-2-enoylamino]-3-(4-hydroxyphenyl)propanoate
• 化学式: C₁₉H₁₉NO₆
• 分子量: 357.363
• InChiKey: WCKQISDLXKTVDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[3-(3,4-dihydroxyphenyl)acryloylamino]-3-(4-hydroxyphenyl)propionic acid methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 N-[3',4'-Dihydroxy-(E)-cinnamoyl]-L-tyrosine
  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：

  2-氨基-3-(4-羟基苯基)丙酸甲酯 、 咖啡酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 以34%的产率得到2-[3-(3,4-dihydroxyphenyl)acryloylamino]-3-(4-hydroxyphenyl)propionic acid methyl ester
  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

• Derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition
  申请人：——

  公开号：US20040082664A1

  公开（公告）日：2004-04-29

  The present invention relates to derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition, more particularly the compounds of the present invention specifically inhibit the activation of T lymphocyte by src homology region 2(SH2) domain of T lymphocyte (lck), so that they can be used for the treatment, prevention and/or diagnosis of graft rejection, autoimmune diseases, inflammatory diseases, etc.

  本发明涉及羟基苯基衍生物、其制备方法及其药物组合物，更具体地，本发明的化合物特异性地抑制T淋巴细胞的src同源区域2（SH2）结构域（lck），从而可用于移植排斥、自身免疫性疾病、炎症性疾病等的治疗、预防和/或诊断。
• DERIVATIVES OF HYDROXYPHENYL, A METHOD FOR PREPARING THEREOF AND THEIR PHARMACEUTICAL COMPOSITION
  申请人：Mogam Biotechnology Research Institute

  公开号：EP1499585A1

  公开（公告）日：2005-01-26
• [EN] DERIVATIVES OF HYDROXYPHENYL, A METHOD FOR PREPARING THEREOF AND THEIR PHARMACEUTICAL COMPOSITION<br/>[FR] DERIVES D'HYDROXYPHENYLE, LEUR METHODE DE PREPARATION ET LEUR COMPOSITION PHARMACEUTIQUE
  申请人：MOGAM BIOTECH RES INST

  公开号：WO2003089405A1

  公开（公告）日：2003-10-30

  The present invention relates to derivatives of hydroxyphenyl, a method for preparing thereof and their pharmaceutical composition, more particularly the compounds of the present invention specifically inhibit the activation of T lymphocyte by src homology region 2(SH2) domain of T lymphocyte (lck), so that they can be used for the treatment, prevention and/or diagnosis of graft rejection, autoimmune diseases, inflammatory diseases, etc.
• [EN] PHARMACEUTICAL COMPOSITION COMPRISING HYDROXYLPHENYL DERIVATIVES OF ROSMARINIC ACID FOR ANTICANCER<br/>[FR] COMPOSITION PHARMACEUTIQUE COMPORTANT DES DERIVES D'HYDROXYPHENYLE DE L'ACIDE ROSMARINIQUE POUR LE TRAITEMENT CONTRE LE CANCER
  申请人：MOGAM BIOTECH RES INST

  公开号：WO2005072723A1

  公开（公告）日：2005-08-11

  The present invention relates to a pharmaceutical composition for anticancer containing hydroxylphenyl derivatives of rosmarinic acid as an effective ingredient. Hydroxylphenyl derivatives of rosmarinic acid of the present invention strongly induce apoptosis of T-cell derived leukemia cells and even B-cell derived leukemia cells expressing Lck abnormally. However, they do not elicit apoptosis of other cell lines originated from B-cells and monocytes, which usually do not express Lck. While hydroxylphenyl derivatives of rosmarinic acid of the present invention do not induce apoptosis of peripheral blood mononuclear cells from healthy donors, they induce apoptosis of peripheral blood mononuclear cells from leukemia patients. When hydroxyl groups in the phenyl rings of rosmarininc acid are eliminated or masked, the apoptotic activity is removed, indicating that hydroxyl groups of phenyl rings located in both ends of rosmarinic acid are indispensable for apoptosis. Hydroxylphenyl derivatives of rosmarinic acid of the present invention induce apoptosis of cancer cells but not normal cells, so that they can be effectively used for preventing and treating cancers.
• 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.