(E)-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)acrylic acid

• 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)-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)acrylic acid
• 英文别名: 3-[4-(diethoxy-phosphoryl)-difluoro-methyl]-cinnamic acid；(E)-3-[4-[diethoxyphosphoryl(difluoro)methyl]phenyl]prop-2-enoic acid
• 化学式: C₁₄H₁₇F₂O₅P
• 分子量: 334.257
• InChiKey: TWGUXYYGZVUYIO-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)acrylic acid 在 草酰氯 、 三甲基溴硅烷 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 4-nitrophenyl (E)-3-(4-((bis(2-(butyrylthio)ethoxy)phosphoryl)difluoromethyl)phenyl)acrylate
  参考文献：
  名称：

  [EN] STAT MODULATORS AND USES THEREOF
  [FR] MODULATEURS DE STAT ET LEURS UTILISATIONS

  摘要：

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with STAT3 and/or STAT6.

  公开号：

  WO2023133336A1
• 作为产物：
  描述：

  tert-butyl (E)-3-(4-(diethoxyphosphoryldifluoromethyl)phenyl)prop-2-enoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (E)-3-(4-((diethoxyphosphoryl)difluoromethyl)phenyl)acrylic acid
  参考文献：
  名称：

  Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3

  摘要：

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.

  DOI：

  10.1021/ol9012662

文献信息

• Tyrosine phosphatase scafold synthesis
  申请人：——

  公开号：US20040225146A1

  公开（公告）日：2004-11-11

  Disclosed are 4-(difluoromethylene)phosphonate cinnamic acid derivatives as a molecular scaffold for the preparation of protein tyrosine phosphatase inhibitors. The invention also relates to a process for the combinatorial preparation of protein tyrosine phospatase inhibitors possessing a 4-(difluoromethylene)phosphonate cinnamic acid/ester molecular scaffold.

  本发明涉及4-(二氟甲基)磷酸肉桂酸衍生物作为制备蛋白酪氨酸磷酸酶抑制剂的分子支架。本发明还涉及一种制备具有4-(二氟甲基)磷酸肉桂酸/酯分子支架的蛋白酪氨酸磷酸酶抑制剂的组合制备过程。
• Synthesis of Phosphatase-Stable, Cell-Permeable Peptidomimetic Prodrugs That Target the SH2 Domain of Stat3
  作者：Pijus K. Mandal、Warren S.-L. Liao、John S. McMurray

  DOI：10.1021/ol9012662

  日期：2009.8.6

  The synthesis of prodrugs targeted to the SH2 domain of Stat3 is reported. Using a convergent strategy, the pivaloyloxymethyl phosphonodiester of pentachlorophenyl 4-phosphonodifluoromethylcinnamate, a phosphotyrosine surrogate, was synthesized and used to acylate peptidomimetic fragments that were prepared on solid supports. Two prodrugs described here inhibited the phosphorylation of Stat3 in breast tumor cells.
• [EN] STAT MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS DE STAT ET LEURS UTILISATIONS
  申请人：[en]RECLUDIX PHARMA, INC.

  公开号：WO2023133336A1

  公开（公告）日：2023-07-13

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with STAT3 and/or STAT6.