3-(3,4-dihydroxy-phenyl)-(R)-2-{[3-trans-(3,4-dihydroxy-phenyl)-acryloyl]-methyl-amino}-propionic acid | 618460-71-2

• 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: 3-(3,4-dihydroxy-phenyl)-(R)-2-{[3-trans-(3,4-dihydroxy-phenyl)-acryloyl]-methyl-amino}-propionic acid
• 英文别名: coumaroyl(3-OH)-D-N(Me)Tyr(3-OH)-OH；(2R)-3-(3,4-dihydroxyphenyl)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-methylamino]propanoic acid
• CAS: 618460-71-2
• 化学式: C₁₉H₁₉NO₇
• 分子量: 373.362
• InChiKey: NYBCBJWJETYPQN-WXJAXGNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  139
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-(3,4-dihydroxy-phenyl)-(R)-2-{[3-trans-(3,4-dihydroxy-phenyl)-acryloyl]-methyl-amino}-propionic acid 在 氯化亚砜 作用下， 生成 3-(3,4-dihydroxy-phenyl)-(R)-2-{[3-trans-(3,4-dihydroxy-phenyl)-acryloyl]-methyl-amino}-propionic acid methyl ester
  参考文献：
  名称：

  Design and synthesis of small chemical inhibitors containing different scaffolds for lck SH2 domain

  摘要：

  On the basis of the structure of (R)-rosmarinic acid, a series of small chemical compounds with a different scaffold was synthesized as inhibitors for lck SH2 domain. From ELISA results, most of all chemical compounds showed a similar or a little lower binding activity for lck SH2 domain compared to the lead compound, (R)-rosmarinic acid. It was characterized that the backbone rigidity between two catechol substructures was required for the full activity and acid substructure of the lead compound was important for the activity. We successfully identified novel lead compounds that did not contain phosphotyrosine moiety and might have an improved bioavailability as inhibitor for lck SH2 domain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00735-2
• 作为产物：
  描述：

  在 四丁基氟化铵 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 3-(3,4-dihydroxy-phenyl)-(R)-2-{[3-trans-(3,4-dihydroxy-phenyl)-acryloyl]-methyl-amino}-propionic acid
  参考文献：
  名称：

  Design and synthesis of small chemical inhibitors containing different scaffolds for lck SH2 domain

  摘要：

  On the basis of the structure of (R)-rosmarinic acid, a series of small chemical compounds with a different scaffold was synthesized as inhibitors for lck SH2 domain. From ELISA results, most of all chemical compounds showed a similar or a little lower binding activity for lck SH2 domain compared to the lead compound, (R)-rosmarinic acid. It was characterized that the backbone rigidity between two catechol substructures was required for the full activity and acid substructure of the lead compound was important for the activity. We successfully identified novel lead compounds that did not contain phosphotyrosine moiety and might have an improved bioavailability as inhibitor for lck SH2 domain. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00735-2

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.
• Design and synthesis of small chemical inhibitors containing different scaffolds for lck SH2 domain
  作者：See-Hyoung Park、Sun-Hee Kang、Sang-Hyeong Lim、Hyun-Sik Oh、Keun-Hyeung Lee

  DOI：10.1016/s0960-894x(03)00735-2

  日期：2003.10

  On the basis of the structure of (R)-rosmarinic acid, a series of small chemical compounds with a different scaffold was synthesized as inhibitors for lck SH2 domain. From ELISA results, most of all chemical compounds showed a similar or a little lower binding activity for lck SH2 domain compared to the lead compound, (R)-rosmarinic acid. It was characterized that the backbone rigidity between two catechol substructures was required for the full activity and acid substructure of the lead compound was important for the activity. We successfully identified novel lead compounds that did not contain phosphotyrosine moiety and might have an improved bioavailability as inhibitor for lck SH2 domain. (C) 2003 Elsevier Ltd. All rights reserved.