methyl (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylate | 1226460-05-4

• 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: methyl (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylate
• 英文别名: (E)-methyl 3-[4-(2',2',2'-trifluoroethoxy)phenyl]prop-2-enoate；methyl (E)-3-[4-(2,2,2-trifluoroethoxy)phenyl]prop-2-enoate
• CAS: 1226460-05-4
• 化学式: C₁₂H₁₁F₃O₃
• 分子量: 260.213
• InChiKey: VFMRMOGRTKDDEO-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylate 在 水 、 potassium carbonate 、 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 甲醇 、 乙腈 为溶剂， 反应 27.0h， 生成 (E)-3-(4-(2',2',2'-trifluoroethoxy)styryl)-[ 1,2,4]triazolo[ 3,4-α]phthalazine
  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：

  4-香豆酸 在 硫酸 、 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 29.67h， 生成 methyl (E)-3-(4-(2,2,2-trifluoroethoxy)phenyl)acrylate
  参考文献：
  名称：

  [EN] NOVEL ANTI-FIBROTIC DRUGS
  [FR] NOUVEAUX MÉDICAMENTS ANTI-FIBROTIQUES

  摘要：

  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.

  公开号：

  WO2022258792A1

文献信息

• Synthesis and anticancer activity evaluation of 2(4-alkoxyphenyl)cyclopropyl hydrazides and triazolo phthalazines
  作者：Prithwiraj De、Michel Baltas、Delphine Lamoral-Theys、Céline Bruyère、Robert Kiss、Florence Bedos-Belval、Nathalie Saffon

  DOI：10.1016/j.bmc.2010.02.041

  日期：2010.4

  A series of new 2(4-alkoxyphenyl) cyclopropyl hydrazide-and triazolo-derivatives were synthesized starting from 4-hydroxycinnamic acid (1) in a clean, mild, efficient and straightforward synthetic protocol. These compounds consisting of different alkoxy substitution, phenylcyclopropyl backbone and different heterocyclic groups were evaluated for in vitro anticancer activity against 4 cell lines displaying certain levels of resistance to pro-apoptotic stimuli and 2 cell lines sensitive to pro-apoptotic compounds. Compounds 7f and 8e were most active and displaying moderate in vitro cytostatic effect through different mechanisms. Significantly, chemically modified derivatives could be obtained in order to develop novel types of compounds aiming to combat apoptosis-resistant cancers, for example, those cancers associated with dismal prognoses. (C) 2010 Elsevier Ltd. All rights reserved.
• [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.
• Design, Synthesis, and Biological Evaluation of New Cinnamic Derivatives as Antituberculosis Agents
  作者：Prithwiraj De、Georges Koumba Yoya、Patricia Constant、Florence Bedos-Belval、Hubert Duran、Nathalie Saffon、Mamadou Daffé、Michel Baltas

  DOI：10.1021/jm101510d

  日期：2011.3.10

  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.