N-(3-chlorophenyl)-(E)-β-styrenecarboxamide | 64741-15-7

• 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: N-(3-chlorophenyl)-(E)-β-styrenecarboxamide
• 英文别名: (2E)-N-(3-chlorophenyl)cinnamamide；(E)-N-(3-chlorophenyl)cinnamamide；trans-cinnamic acid-(3-chloro-anilide)；trans-Zimtsaeure-(3-chlor-anilid)；N-(3-Chlorophenyl)Cinnamamide；(E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide
• CAS: 64741-15-7
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: ZUKRPXSFAZWKHZ-MDZDMXLPSA-N

物化性质

• 沸点：
  456.4±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肉桂酸 在 氯化亚砜 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 N-(3-chlorophenyl)-(E)-β-styrenecarboxamide
  参考文献：
  名称：

  肉桂酸的酯，酰胺和取代衍生物：合成，抗菌活性和QSAR研究。

  摘要：

  合成了肉桂酸的一系列酯（I（ak）），取代的衍生物（II（ad））和酰胺（III（aq）），并将其作为抗菌剂和抗真菌剂进行了评估。属于系列I，II和III的所有衍生物均显示出与标准品相当的抗菌活性。化合物I（f）和II（c）被证明是最有效的化合物。利用多元线性回归分析进行定量构效关系（QSAR）研究，以发现化合物的不同计算理化参数与生物活性之间的相关性。肉桂酸衍生物I（ak），II（ad）和III（aq）的结构特征及其抗菌活性的定量模型表明，革兰氏阴性大肠杆菌和白色念珠菌（真菌）是最敏感的微生物。

  DOI：

  10.1016/j.ejmech.2004.06.013

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。
• Niestroj, Michael; Neumann, Wilhelm P.; Thies, Olaf, Chemische Berichte, 1994, vol. 127, # 6, p. 1131 - 1136
  作者：Niestroj, Michael、Neumann, Wilhelm P.、Thies, Olaf

  DOI：——

  日期：——
• Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors
  作者：Mao Zhang、Xiang Lu、Hong-Jia Zhang、Na Li、Yu Xiao、Hai-Liang Zhu、Yong-Hao Ye

  DOI：10.1007/s00044-012-0093-z

  日期：2013.2

  A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 mu M, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.
• Monoamine oxidase inhibition by selected anilide derivatives
  作者：Lesetja Legoabe、Johann Kruger、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.ejmech.2011.08.036

  日期：2011.10

  A series of anilide derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The most potent inhibitors among the derivatives that were initially evaluated were (2E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide (2c) and (2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide (2d) with IC50 values of 0.53 mu M and 0.45 mu M, respectively. These derivatives exhibited reversible and selective inhibition of MAO-B with binding affinities 37 fold higher for MAO-B than for MAO-A. Analysis of the possible binding interactions of these inhibitors with active site models of human MAO-A and B led to the design of phenolic and benzonitrile derivatives of 2c and 2d. Among these were (2E)-N-(3-chlorophenyl)-3-(4-hydroxyphenyl)prop-2-enamide (7c) and (2E)-N-(3-bromophenyl)-3-(4-hydroxyphenyl)prop-2-enamide (7d) which inhibited MAO-B selectively and reversibly with IC50 values of 0.032 mu M and 0.026 mu M, respectively. These inhibitors were at least 14 fold more potent than 2c and 2d. This study concludes that N,3-diphenylprop-2-enamide is a suitable scaffold for the design of selective MAO-B inhibitors and structural modifications to enhance the binding affinities of the inhibitors for the MAO-B active site include substitution with halogens on the N-phenyl ring and substitution with hydroxyl and nitrile functional groups on the para and meta positions, respectively, of the C3 phenyl ring. Possible binding modes of these structures within the MAO-B active site are proposed with the emphasis on the interactions of the inhibitor halogens and the hydroxyl and nitrile functional groups with active site residues and water molecules. (C) 2011 Elsevier Masson SAS. All rights reserved.
• The C/At is out of the bag: a gene for mental illness
  作者：M-L Wong

  DOI：10.1038/sj.tpj.6500003

  日期：2001.1.1