(E)-N-(2-acetamidoethyl)-3-{4-[(E)-3,7-dimethylocta-2,6-dienyloxy]phenyl}acrylamide | 1119760-73-4

• 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: (E)-N-(2-acetamidoethyl)-3-{4-[(E)-3,7-dimethylocta-2,6-dienyloxy]phenyl}acrylamide
• 英文别名: (E)-N-(2-acetamidoethyl)-3-{4-[(E)-3,7-dimethylocta-2,6-dienyloxy]-phenyl}prop-2-enamide；(E)-N-(2-acetamidoethyl)-3-[4-[(2E)-3,7-dimethylocta-2,6-dienoxy]phenyl]prop-2-enamide
• CAS: 1119760-73-4
• 化学式: C₂₃H₃₂N₂O₃
• 分子量: 384.519
• InChiKey: WCUQVIWENGYYLR-NIEGGPFSSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  649.4±55.0 °C(predicted)
• 密度：
  1.045±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (E)-4-(geranyloxy)cinnamate 在 4-二甲氨基吡啶 、 水 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (E)-N-(2-acetamidoethyl)-3-{4-[(E)-3,7-dimethylocta-2,6-dienyloxy]phenyl}acrylamide
  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

• Synthesis and evaluation of a novel series of pseudo-cinnamic derivatives as antituberculosis agents
  作者：Georges Koumba Yoya、Florence Bedos-Belval、Patricia Constant、Hubert Duran、Mamadou Daffé、Michel Baltas

  DOI：10.1016/j.bmcl.2008.11.082

  日期：2009.1

  In an effort to develop potent new antituberculous drugs effective against Mycobacterium tuberculosis, we have prepared series of cinnamic derivatives (thioesters and amides) with 4-hydroxy and 4-alkoxy groups and investigated the in vitro activities of these compounds. Among them some displayed a good in vitro antibacterial activity, such as (E)-N-(2-acetamidoethyl)-3-4-[(E)-3,7-dimethylocta-2,6-dienyloxy]phenyl} acrylamide 4b that showed a minimum inhibitory concentration of 0.1 mu g/mL (0.26 mu M) against M. tuberculosis H37Rv. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.