2-(4-Methoxyphenoxy)quinoline-3-carbaldehyde | 1039878-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-Methoxyphenoxy)quinoline-3-carbaldehyde
• CAS: 1039878-99-3
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: JHZWDCOKCOTDOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 、 2-(4-Methoxyphenoxy)quinoline-3-carbaldehyde 在 nickel(II) nitrate hexahydrate 作用下， 以 乙醇 为溶剂， 以90%的产率得到(E)-N'-((2-(4-methoxyphenoxy)quinolin-3-yl)methylene)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide
  参考文献：
  名称：

  Schiff’s base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors

  摘要：

  New Schiff's base derivatives 5a-j have been synthesized by reaction between 2-phenoxyquinoline-3-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 4 in presence of nickel(II) nitrate as a catalyst in ethanol under reflux in good yield (78-92%). All compounds were tested for anticancer and inhibition of EGFR. Of the compounds studied, majority of the compounds showed effective antiproliferation and inhibition of EGFR and HER-2 activities. Compound 5h showed most effective inhibition (IC50 = 0.12 +/- 0.05 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = -58.3691 kcal/mol). The binding was stabilized by two hydrogen bonds, two pi-cation and one pi-sigma interactions. Compound 5d showed most effective inhibition (IC50 = 0.37 +/- 0.04 mu M). (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.041
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 、 4-甲氧基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 2-(4-Methoxyphenoxy)quinoline-3-carbaldehyde
  参考文献：
  名称：

  微波辅助合成含2-芳氧基喹啉的新型4 H-色烯衍生物及其抗菌活性评估

  摘要：

  通过2-芳氧基喹啉-3-甲醛3a - 1，丙二腈4和化合物（环己二酮，二mid酮）5a - b的反应，在微波辐射下合成了一系列带有2-芳氧基喹啉核的4 H-色烯衍生物6a - x系列。在NaOH作为碱性催化剂存在下。所有化合物均针对三种革兰氏阳性菌（肺炎链球菌，破伤风梭菌，枯草芽孢杆菌），三种革兰氏阴性菌（鼠伤寒沙门氏菌，霍乱弧菌，大肠杆菌和两种真菌（烟曲霉，白色念珠菌）采用肉汤微量稀释MIC（最小抑制浓度）方法。通过对抗菌药物筛选的研究，发现与标准药物相比，大多数化合物对破伤风梭菌和枯草芽孢杆菌以及白色念珠菌具有活性。

  DOI：

  10.1007/s00044-012-0381-7

文献信息

• Microwave-assisted synthesis of novel 4H-chromene derivatives bearing 2-aryloxyquinoline and their antimicrobial activity assessment
  作者：Chetan B. Sangani、Nimesh M. Shah、Manish P. Patel、Ranjan G. Patel

  DOI：10.1007/s00044-012-0381-7

  日期：2013.8

  A new series of 4H-chromene derivatives 6a–x bearing 2-aryloxyquinoline nucleus have been synthesized under microwave irradiation by reaction of 2-aryloxyquinoline-3-carbaldehyde 3a–l, malononitrile 4, and compounds (Cyclohexanedione, Dimidone) 5a–b in the presence of NaOH as the basic catalyst. All the compounds were screened against three Gram-positive bacteria (Streptococcus pneumoniae, Clostridium

  通过2-芳氧基喹啉-3-甲醛3a - 1，丙二腈4和化合物（环己二酮，二mid酮）5a - b的反应，在微波辐射下合成了一系列带有2-芳氧基喹啉核的4 H-色烯衍生物6a - x系列。在NaOH作为碱性催化剂存在下。所有化合物均针对三种革兰氏阳性菌（肺炎链球菌，破伤风梭菌，枯草芽孢杆菌），三种革兰氏阴性菌（鼠伤寒沙门氏菌，霍乱弧菌，大肠杆菌和两种真菌（烟曲霉，白色念珠菌）采用肉汤微量稀释MIC（最小抑制浓度）方法。通过对抗菌药物筛选的研究，发现与标准药物相比，大多数化合物对破伤风梭菌和枯草芽孢杆菌以及白色念珠菌具有活性。
• Schiff’s base derivatives bearing nitroimidazole and quinoline nuclei: New class of anticancer agents and potential EGFR tyrosine kinase inhibitors
  作者：Jigar A. Makawana、Chetan B. Sangani、Lin Lin、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.02.041

  日期：2014.4

  New Schiff's base derivatives 5a-j have been synthesized by reaction between 2-phenoxyquinoline-3-carbaldehydes 3a-j and 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 4 in presence of nickel(II) nitrate as a catalyst in ethanol under reflux in good yield (78-92%). All compounds were tested for anticancer and inhibition of EGFR. Of the compounds studied, majority of the compounds showed effective antiproliferation and inhibition of EGFR and HER-2 activities. Compound 5h showed most effective inhibition (IC50 = 0.12 +/- 0.05 mu M) by binding in to the active pocket of EGFR receptor with minimum binding energy (Delta G(b) = -58.3691 kcal/mol). The binding was stabilized by two hydrogen bonds, two pi-cation and one pi-sigma interactions. Compound 5d showed most effective inhibition (IC50 = 0.37 +/- 0.04 mu M). (c) 2014 Elsevier Ltd. All rights reserved.