3-(4-methylpiperazin-1-yl)-5-hydroxyquinoline | 1268264-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-(4-methylpiperazin-1-yl)-5-hydroxyquinoline
• 英文别名: 3-(4-Methylpiperazin-1-yl)quinolin-5-ol
• CAS: 1268264-40-9
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: JEQMQTBIOQZUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methylpiperazin-1-yl)-5-hydroxyquinoline 、 3-氰基苄基溴 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到5-(3-cyanobenzyloxy)-3-(4-methylpiperazin-1-yl)quinoline
  参考文献：
  名称：

  Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a Novel Anticancer Agent

  摘要：

  By use of an improved synthetic strategy, a series of 3,5-disubstituted and 3,5,7-trisubstituted quinolines were readily prepared. 3,5,7-Trisubstituted quinolines 21a-c, 211, and 27a-c were identified as the most potent c-Met inhibitors with IC50 of less than 1.0 nM. Compound 21b showed the most promising overall PK profile and has high potency and extraordinary selectivity to c-Met against c-Met family member Ron and 12 other tyrosine kinases. It produced constitutive inhibition of c-Met phosphorylation in c-Met dependent cell lines. At doses of 100 mg/kg, compound 21b showed statistically significant tumor growth inhibition (68-69%) in both NIH-3T3-TPR-Met and U-87 MG human gliobastoma xenograft models. These results clearly indicated that compound 21b is a potent and highly selective c-Met inhibitor. Its favorable in vitro and in vivo profiles warrant further investigation.

  DOI：

  10.1021/jm101340q
• 作为产物：
  描述：

  3-(4-methylpiperazine-1-yl)-5-aminoquinoline 在 硫酸 、 溶剂黄146 、 sodium nitrite 、 水 作用下， 以 水 为溶剂， 反应 0.58h， 以30%的产率得到3-(4-methylpiperazin-1-yl)-5-hydroxyquinoline
  参考文献：
  名称：

  Synthesis and c-Met Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-nitrobenzylamino)-7- (trifluoromethyl)quinoline as a Novel Anticancer Agent

  摘要：

  By use of an improved synthetic strategy, a series of 3,5-disubstituted and 3,5,7-trisubstituted quinolines were readily prepared. 3,5,7-Trisubstituted quinolines 21a-c, 211, and 27a-c were identified as the most potent c-Met inhibitors with IC50 of less than 1.0 nM. Compound 21b showed the most promising overall PK profile and has high potency and extraordinary selectivity to c-Met against c-Met family member Ron and 12 other tyrosine kinases. It produced constitutive inhibition of c-Met phosphorylation in c-Met dependent cell lines. At doses of 100 mg/kg, compound 21b showed statistically significant tumor growth inhibition (68-69%) in both NIH-3T3-TPR-Met and U-87 MG human gliobastoma xenograft models. These results clearly indicated that compound 21b is a potent and highly selective c-Met inhibitor. Its favorable in vitro and in vivo profiles warrant further investigation.

  DOI：

  10.1021/jm101340q