(E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylic acid | 1268243-15-7

• 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-(2,2,2-trifluoroethoxy)phenyl)acrylic acid
• 英文别名: (E)-3-[4-(2',2',2'-trifluoroethoxy)phenyl]prop-2-enoic acid；(E)-3-[4-(2,2,2-trifluoroethoxy)phenyl]prop-2-enoic acid
• CAS: 1268243-15-7
• 化学式: C₁₁H₉F₃O₃
• mdl: MFCD11200567
• 分子量: 246.186
• InChiKey: XVPLDBHSEDUMPC-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.181
• 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：

  (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylic acid 、 盐酸肼屈嗪 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以66%的产率得到(2E,N',E)-3-[4-(2',2',2'-trifluoroethoxy)phenyl]-N'-[phthalazin-1-(2H)-ylidiene]acrylohydrazide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents

  摘要：

  Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H(37)Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.

  DOI：

  10.1021/jm101510d
• 作为产物：
  描述：

  methyl (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到(E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents

  摘要：

  Tuberculosis, HIV coinfection with TB, emergence of multidrug-resistant TB, and extensively drug-resistant TB are the major causes of death from infectious diseases worldwide. Because no new drug has been introduced in the last several decades, new classes of molecules as anti-TB drugs are urgently needed. Herein, we report the synthesis and structure-activity relationships of a series of thioester, amide, hydrazide, and triazolophthalazine derivatives of 4-alkoxy cinnamic acid. Many compounds exhibited submicromolar minimum inhibitory concentrations against Mycobacterium tuberculosis strain (H(37)Rv). Interestingly, compound 13e, a 4-isopentenyloxycinnamyl triazolophthalazine derivative, was found to be 100-1800 times more active than isoniazid (INH) when tested for its ability to inhibit the growth of INH-resistant M. tuberculosis strains. The results also revealed that 13e does not interfere with mycolic acid biosynthesis, thereby pointing to a different mode of action and representing an attractive lead compound for the development of new anti-TB agents.

  DOI：

  10.1021/jm101510d

文献信息

• [EN] NOVEL ANTI-FIBROTIC DRUGS<br/>[FR] NOUVEAUX MÉDICAMENTS ANTI-FIBROTIQUES
  申请人：[en]HELMHOLTZ ZENTRUM MÜNCHEN - DEUTSCHES FORSCHUNGSZENTRUM FÜR GESUNDHEIT UND UMWELT (GMBH)

  公开号：WO2022258792A1

  公开（公告）日：2022-12-15

  The present invention relates to new cinnamic add amides which may be used for treatment of fibrosis and neoplasia and to cinnamic acid amides for use in the treatment of fibrosis, neoplasia, arthrolithiasis, familiar mediterranean fever and pericarditis. Further, the invention relates to a pharmaceutical composition comprising said cinnamic acid amides and to a screening essay for identifying compounds suitable for the treatment of fibrosis.