methyl 4-ethoxyphenylglyoxylate | 80768-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-ethoxyphenylglyoxylate
• 英文别名: Methyl 4-ethoxybenzoylformate；methyl 2-(4-ethoxyphenyl)-2-oxoacetate
• CAS: 80768-36-1
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: PKRAEDHYHXDEBD-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C
• 沸点：
  317.6±25.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-ethoxyphenylglyoxylate 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 生成 methyl 2-(4-ethoxyphenyl)but-3-enoate
  参考文献：
  名称：

  Johnson, Wynona M. P.; Holan, George, Australian Journal of Chemistry, 1981, vol. 34, # 11, p. 2363 - 2368

  摘要：

  DOI：
• 作为产物：
  描述：

  草酸二甲酯 、 4-乙氧基苯乙酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 methyl 4-ethoxyphenylglyoxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of novel diaryl-1,5-diazoles derivatives bearing morpholine as potent dual COX-2/5-LOX inhibitors and antitumor agents

  摘要：

  In this paper, 41 hybrid compounds containing diaryl-1,5-diazole and morpholine structures acting as dual COX-2/5-LOX inhibitors have been designed, synthesized and biologically evaluated. Most of them showed potent antiproliferative activities and COX-2/5-LOX inhibitory in vitro. Among them, compound A33 displayed the most potency against cancer cell lines (IC50 = 6.43-10.97 mu M for F10, HeLa, A549 and MCF-7 cells), lower toxicity to non-cancer cells than celecoxib (A33: IC50 = 194.01 mu M vs. celecoxib: IC50 = 97.87 mu M for 293T cells), and excellent inhibitory activities on COX-2 (IC50 = 0.17 mu M) and 5-LOX (IC50 = 0.68 mu M). Meanwhile, the molecular modeling study was performed to position compound A33 into COX-2 and 5-LOX active sites to determine the probable binding models. Mechanistic studies demonstrated that compound A33 could block cell cycle in G2 phase and subsequently induced apoptosis of F10 cells. Furthermore, compound A33 could significantly inhibit tumor growth in F10-xenograft mouse model, and pharmacokinetic study of compound A33 indicated that it showed better stability in vivo. in general, compound A33 could be a promising candidate for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.03.008

文献信息

• JOHNSON, W. M. P.;HOLAN, G., AUSTRAL. J. CHEM., 1981, 34, N 11, 2363-2368
  作者：JOHNSON, W. M. P.、HOLAN, G.

  DOI：——

  日期：——
• Design, synthesis and evaluation of novel diaryl-1,5-diazoles derivatives bearing morpholine as potent dual COX-2/5-LOX inhibitors and antitumor agents
  作者：Zhang Li、Zhong-Chang Wang、Xin Li、Muhammad Abbas、Song-Yu Wu、Shen-Zhen Ren、Qi-Xing Liu、Yi Liu、Peng-Wen Chen、Yong-Tao Duan、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2019.03.008

  日期：2019.5

  In this paper, 41 hybrid compounds containing diaryl-1,5-diazole and morpholine structures acting as dual COX-2/5-LOX inhibitors have been designed, synthesized and biologically evaluated. Most of them showed potent antiproliferative activities and COX-2/5-LOX inhibitory in vitro. Among them, compound A33 displayed the most potency against cancer cell lines (IC50 = 6.43-10.97 mu M for F10, HeLa, A549 and MCF-7 cells), lower toxicity to non-cancer cells than celecoxib (A33: IC50 = 194.01 mu M vs. celecoxib: IC50 = 97.87 mu M for 293T cells), and excellent inhibitory activities on COX-2 (IC50 = 0.17 mu M) and 5-LOX (IC50 = 0.68 mu M). Meanwhile, the molecular modeling study was performed to position compound A33 into COX-2 and 5-LOX active sites to determine the probable binding models. Mechanistic studies demonstrated that compound A33 could block cell cycle in G2 phase and subsequently induced apoptosis of F10 cells. Furthermore, compound A33 could significantly inhibit tumor growth in F10-xenograft mouse model, and pharmacokinetic study of compound A33 indicated that it showed better stability in vivo. in general, compound A33 could be a promising candidate for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Johnson, Wynona M. P.; Holan, George, Australian Journal of Chemistry, 1981, vol. 34, # 11, p. 2363 - 2368
  作者：Johnson, Wynona M. P.、Holan, George

  DOI：——

  日期：——