(E)-N-(3,4-dimethoxyphenyl)-3,4-dimethoxycinnamamide

• 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-(3,4-dimethoxyphenyl)-3,4-dimethoxycinnamamide
• 英文别名: (E)-N,3-bis(3,4-dimethoxyphenyl)prop-2-enamide
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: OLATZDOEOPQUNF-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二甲氧基肉酸酸 、 3,4-二甲氧基苯胺 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 18.0h， 以31%的产率得到(E)-N-(3,4-dimethoxyphenyl)-3,4-dimethoxycinnamamide
  参考文献：
  名称：

  Restraining the flexibility of the central linker in terameprocol results in constrained analogs with improved growth inhibitory activity

  摘要：

  The semi-synthetic lignan terameprocol inhibits the transcription of several inflammatory and oncogenic genes and has been evaluated for its anti-cancer properties. Here we investigated the effect of restricting the flexibility of the carbon linker connecting the terminal rings of terameprocol on its growth inhibitory activity. Conformational restriction was explored by introducing unsaturation, inserting polar entities with limited flexibility and cyclization of the connecting linker. Twenty three compounds were synthesized and evaluated on a panel of malignant human cells. The most promising compounds were those with non-polar linkers, as seen in butadiene 1a and the cyclized benzylideneindane analog 7. Both compounds were more potent than terameprocol on pancreatic BxPC-3 cells with GI(50) values of 3.4 and 8.1 mu M, respectively. Selected isomers of 1a (E,E) and 7 (Z) adopted low energy bent conformations that mimicked the low energy conformer of terameprocol. It is tempting to propose that conformational similarity to terameprocol may have contributed to their good activity. The scaffolds of 1a and 7 should be further investigated for their anticancer potential. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.014

文献信息

• THERAPEUTIC COMPOSITIONS COMPRISING A COMBINATION OF A HARMINE AND ISOVANILLIN COMPONENT
  申请人：Ions Pharmaceutical S.À R.L.

  公开号：EP3275465A1

  公开（公告）日：2018-01-31

  Human therapeutic treatment compositions comprise the combination of at least one harmine component, and at least one isovanillin component, wherein the components of the composition are different. The compositions are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物由至少一种禾本科成分和至少一种异香兰素成分组合而成，其中组合物的成分各不相同。这些组合物可有效治疗人类疾病，尤其是人类癌症。
• Therapeutic compositions containing harmine and isovanillin components, and methods of use thereof
  申请人：Ankh Life Sciences Limited

  公开号：US10471049B2

  公开（公告）日：2019-11-12

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。这些制剂可有效治疗人类疾病，尤其是人类癌症。
• Human therapeutic agents
  申请人：Ankh Life Sciences Limited

  公开号：US10744124B2

  公开（公告）日：2020-08-18

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.

  人类治疗组合物包含姜黄素成分、禾本科成分和异香兰素成分中的至少两种，最好是三种成分的组合。这些制剂可有效治疗人类疾病，尤其是人类癌症。
• HUMAN THERAPEUTIC AGENTS
  申请人：Ankh Life Sciences Limited

  公开号：EP3188721B1

  公开（公告）日：2019-06-12
• THERAPEUTIC COMPOSITIONS CONTAINING HARMINE AND ISOVANILLIN COMPONENTS, AND METHODS OF USE THEREOF
  申请人：Ions Pharmaceutical S.à r.l.

  公开号：US20170042866A1

  公开（公告）日：2017-02-16

  Human therapeutic treatment compositions comprise at least two of a curcumin component, a harmine component, and an isovanillin component, and preferably all three in combination. The agents are effective for the treatment of human conditions, especially human cancers.