ethyl 6-(benzyloxy)-4-hydroxy-7-methoxyquinoline-3-carboxylate | 1092581-26-4

• 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 6-(benzyloxy)-4-hydroxy-7-methoxyquinoline-3-carboxylate
• CAS: 1092581-26-4
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: AMPFAXQDTDYPNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.88
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-(benzyloxy)-4-hydroxy-7-methoxyquinoline-3-carboxylate 在 三氯氧磷 作用下， 反应 3.0h， 以16%的产率得到ethyl 6-(benzyloxy)-4-chloro-7-methoxyquinoline-3-carboxylate
  参考文献：
  名称：

  Potent and Selective Inhibitors of MTH1 Probe Its Role in Cancer Cell Survival

  摘要：

  Recent literature has claimed that inhibition of the enzyme MTH1 can eradicate cancer. MTH1 is one of the "housekeeping" enzymes that are responsible for hydrolyzing damaged nucleotides in cells and thus prevent them from being incorporated into DNA. We have developed orthogonal and chemically distinct tool compounds to those published in the literature to allow us to test the hypothesis that inhibition of MTH1 has wide applicability in the treatment of cancer. Here we present the work that led to the discovery of three structurally different series of MTH1 inhibitors with excellent potency, selectivity, and proven target engagement in cells. None of these compounds elicited the reported cellular phenotype, and additional siRNA and CRISPR experiments further support these observations. Critically, the difference between the responses of our highly selective inhibitors and published tool compounds suggests that the effect reported for the latter may be due to off-target cytotoxic effects. As a result, we conclude that the role of MTH1 in carcinogenesis and utility of its inhibition is yet to be established.

  DOI：

  10.1021/acs.jmedchem.5b01760

文献信息

• Synthesis and Anticoccidial Activities of Quinoline Carboxylate Derivatives with Methyl (E)-2-(3-methoxy)acrylate Moiety
  作者：Yuan Liu、Ya-Biao Weng、Zhao-Bing Chen、Yu-Liang Wang

  DOI：10.14233/ajchem.2013.14806

  日期：——

  A series of novel quinoline carboxylate derivatives with methyl (E)-2-(3-methoxy) acrylate group were designed and synthesized as anticoccidial medicines. The structures were confirmed by 1H NMR, IR and HR-MS spectra. The biological activities were primarily evaluated according to the anticoccidial index method. The results indicated that these compounds (7c, 7d, 7e, 7g) exhibited anticoccidial activities against Eimeria tenella. In particular, the anticoccidial index of 6-decyloxy-7-ethoxy-4-6-[2-(2-methoxy-1-methoxycarbonyl-vinyl)phenoxy]pyrimidin-4-yloxy}-quinoline-3-carboxylic acid ethyl ester (7e) was 168.7, which indicated that the compound has a good anticoccidial activity.

  设计并合成了一系列具有甲基(E)-2-(3-甲氧基)丙烯酸酯基团的新型喹啉羧酸衍生物作为抗球虫药物。通过1H NMR、IR和HR-MS光谱确认了其结构。根据抗球虫指数方法初步评估了生物活性。结果表明，这些化合物（7c、7d、7e、7g）对柔嫩艾美耳球虫具有抗球虫活性。特别是，6-癸氧基-7-乙氧基-4-6-[2-(2-甲氧基-1-甲氧羰基-乙烯基)苯氧基]嘧啶-4-氧基}-喹啉-3-羧酸乙酯（7e）的抗球虫指数为168.7，表明该化合物具有良好的抗球虫活性。