5-hydroxy-7-methoxy-3-(p-tolyl)quinolin-4(1H)-one | 1528669-25-1

• 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: 5-hydroxy-7-methoxy-3-(p-tolyl)quinolin-4(1H)-one
• 英文别名: 5-hydroxy-7-methoxy-3-(4-methylphenyl)-1H-quinolin-4-one
• CAS: 1528669-25-1
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: PUAPRPRXLKFBQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基苯基乙酸乙酯 在 cerium(III) chloride heptahydrate 、 sodium hydride 、 sodium iodide 作用下， 以 二苯醚 、 联苯 、 乙醚 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 32.0h， 生成 5-hydroxy-7-methoxy-3-(p-tolyl)quinolin-4(1H)-one
  参考文献：
  名称：

  Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones

  摘要：

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.047

文献信息

• Synthesis and anticancer evaluation of 3-substituted quinolin-4-ones and 2,3-dihydroquinolin-4-ones
  作者：Santosh Rajput、Christopher R. Gardner、Timothy W. Failes、Greg M. Arndt、David StC. Black、Naresh Kumar

  DOI：10.1016/j.bmc.2013.11.047

  日期：2014.1

  A series of 3-aryl-5,7-dimethoxyquinolin-4-ones 8 and 3-aryl-5,7-dimethoxy-2,3-dihydroquinolin-4-ones 13 were synthesized in good yields. Demethylation under a range of conditions afforded the corresponding 5-hydroxy and 5,7-dihydroxy derivatives. Biological evaluation against a range of cancer cells lines showed that the quinolin-4-one scaffold was more cytotoxic than the reduced 2,3-dihydroquinolin-4-one scaffold. The most active monohydroxy compound 15f demonstrated 85.9-99% reduction in cell viability against the cell lines tested. (C) 2013 Elsevier Ltd. All rights reserved.