3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide | 340258-61-9

• 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: 3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide
• 英文别名: (2E)-N,3-bis(4-methoxyphenyl)acrylamide；(E)-N,3-bis(4-methoxyphenyl)acrylamide；4-methoxy-cinnamic acid p-anisidide；4-Methoxy-zimtsaeure-p-anisidid；(E)-N,3-bis(4-methoxyphenyl)prop-2-enamide
• CAS: 340258-61-9
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: YCSMIPXQNWXSAJ-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide 在 乙酰胺 、 磷酸 、 phosphorus pentoxide 、 potassium carbonate 、 三氯氧磷 作用下， 反应 2.0h， 生成 6-甲氧基-2-氨基喹啉
  参考文献：
  名称：

  Identification and Specificity Studies of Small-Molecule Ligands for SH3 Protein Domains

  摘要：

  The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with K-d = 125 muM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2-aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.

  DOI：

  10.1021/jm049533z
• 作为产物：
  描述：

  甲氧苯胺 在 吡啶 、 盐酸胍 、 溶剂黄146 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 35.33h， 生成 3-(4-methoxyphenyl)-N-(4-methoxyphenyl)prop-(2E)-enamide
  参考文献：
  名称：

  avenanthramides类似物的替代方法及其抗自由基活性

  摘要：

  摘要本文致力于通过丙二酸单苯胺与芳香醛的缩合合成芳基丙二酸单苯胺和肉桂酰基苯胺。提出的合成路线应用简单，便宜且可商购的芳族醛和胺，因此克服了涉及羟基肉桂酸衍生物的传统方案。此外，提出了一种温和有效的吡啶介导的芳基丙二酸丙二酸单苯胺中C sp 2处羧基的羧基脱羧，从而导致肉桂酰基苯胺。通过X射线分析另外批准了所获得的选定的亚芳基衍生物的结构。研究了合成化合物的抗自由基性能（2,2-二苯基-1-吡咯肼基和丙氧基测试）和结构-活性关系。 图形概要

  DOI：

  10.1007/s00706-018-2288-6

文献信息

• Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
  作者：Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.201500010

  日期：2015.4

  synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation

  在2,3-二氯-5存在下，以仲醇、Cu(ClO4)2·6H2O为催化剂，以叠氮化三甲基甲硅烷(TMSN3)为氮源，探索了一种温和、简便的酰胺合成方法。 ,6-二氰基对苯醌 (DDQ) 在环境温度下。该方法已成功地适用于直接从其相应的醇制备叠氮化物，并在 ω-卤代叠氮化物的形成和烯丙醇在苄醇部分存在下的叠氮化中提供出色的化学选择性。此外，该策略为合成可作为 β-氨基酸前体的叠氮化物提供了机会。
• Substituted Hantzsch Esters as Versatile Radical Reservoirs in Photoredox Reactions
  作者：Fangjun Gu、Wenhao Huang、Xu Liu、Wenxin Chen、Xu Cheng

  DOI：10.1002/adsc.201701348

  日期：2018.3.1

  Substituted Hantzsch esters can act as radical reservoirs in photoredox reactions, steadily releasing a carbon radical and a hydrogen atom radical in the absence of an additional electron acceptor. We propose that radical release by substituted Hantzsch esters occurs via a mechanism involving an internal redox cycle. Cinnamidecinnamides, styrenes, α,β‐unsaturated acids, and diarylethenes could be alkylated

  取代的Hantzsch酯可在光氧化还原反应中充当自由基储存库，在不存在其他电子受体的情况下稳定释放碳自由基和氢原子自由基。我们建议，通过涉及内部氧化还原循环的机制，发生由取代的汉茨（Hantschsch）酯释放的自由基。肉桂酰胺，苯乙烯，α，β-不饱和酸和二芳烃可以用这些试剂平稳地烷基化。
• 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。