ethyl 3-{8-[6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinolinyl]amino}-propanoimidate

• 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: ethyl 3-{8-[6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinolinyl]amino}-propanoimidate
• 英文别名: 6-methoxy-8-[2-(ethoxycarboiminoyl)ethylamino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline；Ethyl 3-[[6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]amino]propanimidate
• 化学式: C₂₃H₂₄F₃N₃O₃
• 分子量: 447.457
• InChiKey: JBRYXBWUMOKFOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.5
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 3-{8-[6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinolinyl]amino}-propanoimidate 在 氨 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以57%的产率得到6-methoxy-8-[2-(amidinoylethyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline
  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
• 作为产物：
  描述：

  8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 在 盐酸 作用下， 以 苯 、 苯酚 为溶剂， 反应 120.0h， 生成 ethyl 3-{8-[6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinolinyl]amino}-propanoimidate
  参考文献：
  名称：

  WO2007/127930

  摘要：

  公开号：

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.
• WO2007/127930
  申请人：——

  公开号：——

  公开（公告）日：——