methyl N-(diphenylmethylene)-D-3-hydroxytyrosine | 618460-98-3

• 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: methyl N-(diphenylmethylene)-D-3-hydroxytyrosine
• 英文别名: methyl (2R)-2-(benzhydrylideneamino)-3-(3,4-dihydroxyphenyl)propanoate
• CAS: 618460-98-3
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: BGHIZSAIOSLWQQ-LJQANCHMSA-N

物化性质

• 沸点：
  542.3±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl N-(diphenylmethylene)-D-3-hydroxytyrosine 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.83h， 生成 methyl N-methyl-N(diphenylmethyl)-D-3-hydroxytyrosine
  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：

  3-羟基-D-酪氨酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 methyl N-(diphenylmethylene)-D-3-hydroxytyrosine
  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。
• JP2005/522523
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.