乙基-2-(羟基(2-(三氟甲基)苯基)甲基)丙烯酸酯 | 1019388-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙基-2-(羟基(2-(三氟甲基)苯基)甲基)丙烯酸酯
• 英文名称: ethyl 2-(hydroxy(2-(trifluoromethyl)phenyl)methyl)acrylate
• 英文别名: ethyl-2-(hydroxyl(2-(trifluoromethyl)phenyl)methyl)acrylate；ethyl 3-hydroxy-2-methylene-3-(2-trifluoromethylphenyl)propionate；Ethyl 2-[hydroxy-[2-(trifluoromethyl)phenyl]methyl]prop-2-enoate
• CAS: 1019388-47-6
• 化学式: C₁₃H₁₃F₃O₃
• 分子量: 274.24
• InChiKey: HDUMFQCPJOBRQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙基-2-(羟基(2-(三氟甲基)苯基)甲基)丙烯酸酯 在 4-二甲氨基吡啶 、 三乙胺 、 β-isocupreidine 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 ethyl (R)-2-((2-oxopyridin-1(2H)-yl)(2-(trifluoromethyl)phenyl)methyl)acrylate
  参考文献：
  名称：

  双功能路易斯碱催化 2-羟基吡啶的不对称 N-烯丙基烷基化

  摘要：

  记录了手性路易斯碱催化的 2-羟基吡啶和 MBH 碳酸酯的对映选择性N-烯丙基烷基化，提供了一种方便地获得N-烷基化 2-吡啶酮的途径，其 ee 高达 99%，产率高达 99%。实验和计算研究表明，手性路易斯碱催化剂与 2-羟基吡啶之间的强氢键相互作用对该反应的反应性、化学选择性和对映选择性起着至关重要的作用。

  DOI：

  10.1021/acs.orglett.2c03207
• 作为产物：
  描述：

  2-三氟甲基苯甲醇 、 丙烯酸乙酯 在 硫酰氟 、 potassium carbonate 、 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以87%的产率得到乙基-2-(羟基(2-(三氟甲基)苯基)甲基)丙烯酸酯
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel arylpropionic esters for the treatment of acute kidney injury

  摘要：

  Acute kidney injury (AKI) is associated with a strong inflammatory response, and inhibiting the response effectively prevents or ameliorates AKI. A series of novel arylpropionic esters were designed, synthesized and evaluated their biological activity in LPS-stimulated RAW264.7 cells. Novel arylpropionic esters bearing multi-functional groups showed significant anti-inflammatory activity, in which, compound 13b exhibited the most potent activity through dose-dependent inhibiting the production of nitric oxide (NO, IC₅₀ = 3.52 μM), TNF-α and IL-6 (84.1% and 33.6%, respectively), as well as suppressing the expression of iNOS, COX-2 and TLR4 proteins. In C57BL/6 mice with cisplatin-induced AKI, compound 13b improved kidney function, inhibited inflammatory development, and reduced pathological damage of kidney tissues. In brief, this arylpropionic ester scaffold may be developed as anti-inflammatory agents.

  DOI：

  10.1016/j.bioorg.2020.104455

文献信息

• INDOLIZINONE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20140296530A1

  公开（公告）日：2014-10-02

  The present invention provides compounds of general formula A useful as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula A can be employed as therapeutics in human and veterinary medicine, where they can be used, for example, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases.

  本发明提供了一般式A的化合物，作为潜在的磷酸二酯酶3（PDE3）抑制剂，并提供了其制备方法。一般式A的衍生物可用作人类和兽医药学中的治疗剂，例如可用于治疗和预防以下疾病：心力衰竭、扩张型心肌病、血小板抑制剂、癌症和阻塞性肺部疾病。
• PYRIDOPYRIMIDINE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20140221651A1

  公开（公告）日：2014-08-07

  The present invention provides compounds of formula 1 as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula 1 can be employed as therapeutics in human and veterinary medicine, where they can be used, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases. Where in X=H, alkyl, aryl, heteroaryl Y=H, alkyl, aryl, heteroaryl R=substituted phenyl A=H, alkyl, alkoxy, halo, dihalo B=H, alkyl, alkoxy, halo, dihalo C=H, alkyl, alkoxy, halo, dihalo

  本发明提供了公式1的化合物作为潜在的磷酸二酯酶3（PDE3）抑制剂，并提供了其制备方法。公式1的衍生物可以作为人类和兽医药学中的治疗药物使用，用于治疗和预防以下疾病：心力衰竭、扩张型心肌病、血小板抑制剂、癌症和阻塞性肺部疾病。其中，X=H、烷基、芳基、杂环芳基；Y=H、烷基、芳基、杂环芳基；R=取代苯基；A=H、烷基、烷氧基、卤素、二卤代基；B=H、烷基、烷氧基、卤素、二卤代基；C=H、烷基、烷氧基、卤素、二卤代基。
• PROCESS FOR PREPARATION OF INDOLIZINE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTRASE 3 (PDE3) INHIBITORS
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20160159792A1

  公开（公告）日：2016-06-09

  The present invention provides compounds of general formula 1 useful as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula 1 can be employed as therapeutics in human and veterinary medicine, where they can be used, for example, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases.
• US9242982B2
  申请人：——

  公开号：US9242982B2

  公开（公告）日：2016-01-26
• US9249139B2
  申请人：——

  公开号：US9249139B2

  公开（公告）日：2016-02-02