6-甲氧基-8-[(2-呋喃基甲基)氨基]-4-甲基-5-(3-三氟甲基苯氧基)-喹啉 | 1041867-83-7

• 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
• 中文名称: 6-甲氧基-8-[(2-呋喃基甲基)氨基]-4-甲基-5-(3-三氟甲基苯氧基)-喹啉
• 英文名称: 6-methoxy-8-[(2-furanylmethyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)-quinoline
• 英文别名: 6-Methoxy-8-[(2-furanylmethyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline；N-(furan-2-ylmethyl)-6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-amine
• CAS: 1041867-83-7
• 化学式: C₂₃H₁₉F₃N₂O₃
• 分子量: 428.411
• InChiKey: NQWLDYQSVOCLKR-UHFFFAOYSA-N

物化性质

• 沸点：
  526.3±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO: 100mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  糠醛 、 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 、 meathnol 为溶剂， 反应 5.0h， 以52%的产率得到6-甲氧基-8-[(2-呋喃基甲基)氨基]-4-甲基-5-(3-三氟甲基苯氧基)-喹啉
  参考文献：
  名称：

  Synthesis and anti-breast cancer activities of substituted quinolines

  摘要：

  Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy) anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy) quinoline (14). The amino function of 8-amino-6-methoxy-4- methyl-5-(3-trifluoromethylphenyloxy) quinoline, prepared from 14, was connected to various side chains via alkylation with N( 3-iodopropyl) phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl) amino]-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline is 16 +/- 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.024

文献信息

• Synthesis and anti-breast cancer activities of substituted quinolines
  作者：Aibin Shi、Thu A. Nguyen、Srinivas K. Battina、Sandeep Rana、Dolores J. Takemoto、Peter K. Chiang、Duy H. Hua

  DOI：10.1016/j.bmcl.2008.04.024

  日期：2008.6

  Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy) anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy) quinoline (14). The amino function of 8-amino-6-methoxy-4- methyl-5-(3-trifluoromethylphenyloxy) quinoline, prepared from 14, was connected to various side chains via alkylation with N( 3-iodopropyl) phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl) amino]-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline is 16 +/- 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing. (C) 2008 Elsevier Ltd. All rights reserved.