(Z)-ethyl 3-((3,5-dimethoxyphenyl)amino)-2-(4-methoxyphenyl)acrylate | 190774-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-ethyl 3-((3,5-dimethoxyphenyl)amino)-2-(4-methoxyphenyl)acrylate
• 英文别名: ethyl (Z)-3-(3,5-dimethoxyanilino)-2-(4-methoxyphenyl)prop-2-enoate
• CAS: 190774-07-3
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: KGYKRRBYPAOVTJ-UYRXBGFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-((3,5-dimethoxyphenyl)amino)-2-(4-methoxyphenyl)acrylate 以 二苯醚 、 联苯 为溶剂， 以58%的产率得到5,7-dimethoxy-3-(4-methoxyphenyl)-1H-quinolin-4-one
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047
• 作为产物：
  描述：

  对甲氧基苯乙酸乙酯 在 sodium hydride 作用下， 以 乙醚 、 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 生成 (Z)-ethyl 3-((3,5-dimethoxyphenyl)amino)-2-(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047

文献信息

• Croisy, Martine; Huel, Christiane; Bisagni, Emile, Heterocycles, 1997, vol. 45, # 4, p. 683 - 690
  作者：Croisy, Martine、Huel, Christiane、Bisagni, Emile

  DOI：——

  日期：——
• Synthesis, structure, and structure–activity relationship analysis of enamines as potential antibacterials
  作者：Zhu-Ping Xiao、Jia-Yu Xue、Shu-Hua Tan、Huan-Qiu Li、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2007.03.060

  日期：2007.6

  Twenty-four enamines were synthesized and reported for the first time. Their chemical structures were confirmed by means of H-1 NMR, ESI mass spectra, and elemental analyses, and four of them were determined by single crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis ATCC 6633, Escherichia coli ATCC 35218, Pseudomonas fluorescens ATCC 13525, and Staphylococcus aureus ATCC 6538) and antifungal (Aspergillus niger ATCC 16404, Candida albicans ATCC 10231, and Trichophyton rubrum ATCC 10218) activities by MTT method. Compounds (E)-ethyl 3-(4-hydroxyphenylamino)-2-(4-methoxyphenyl)acrylate (9b), (E)-ethyl 3-(3,5-difluorophenylamino)-2-(4-chlorophenyl)acrylate (11b), (E)-ethyl 3(3,5-dichlorophenylamino)-2-(4-chlorophenyl)acrylate (12b), and (E)-ethyl 3-(4-methylphenylamino)-2-(4-chlorophenyl)acrylate (15b) showed considerable antibacterial activities against S. aureus ATCC 6538 with MICs of 3.8, 1.9, 1.1, and 0.9 mu g/mL, respectively. Structure-activity relationship (SAR) analysis disclosed, generally, an E-isomer exhibited higher antibacterial activity than the corresponding Z-isomer. An electron-withdrawing group on A-ring led to some decrease in activity, while on B-ring, a similar substitution provided higher activity.
• Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones
  作者：Santosh Rajput、Christopher R. Gardner、Timothy W. Failes、Greg M. Arndt、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.11.047

  日期：2014.1

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.