3-Chloro-6-((3,5-dimethoxyphenoxy)methyl)-2-phenylquinoxaline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Chloro-6-((3,5-dimethoxyphenoxy)methyl)-2-phenylquinoxaline
• 英文别名: 3-chloro-6-[(3,5-dimethoxyphenoxy)methyl]-2-phenylquinoxaline
• 化学式: C₂₃H₁₉ClN₂O₃
• 分子量: 406.868
• InChiKey: CWNXINJPWCQNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,5-二甲氧基苯酚 、 6-Bromomethyl-3-chloro-2-phenyl-quinoxaline 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以72%的产率得到3-Chloro-6-((3,5-dimethoxyphenoxy)methyl)-2-phenylquinoxaline
  参考文献：
  名称：

  Quinoxaline chemistry Part 10. Quinoxaline 10-oxa-analogues of trimetrexate (TMQ ) and of 5,8-dideazafolic acid. Synthesis and evaluation of in vitro anticancer activity

  摘要：

  Among twenty-eight novel compounds (twenty-two 2,13-disubstituted-6-[(substituted-phenoxy)methyl-quinoxalines and six 4-[(2,3-disubstituted-quinoxalin-6-yl) methoxy]benzoylglutamates) only thirteen were selected at NCI for evaluation of their in vitro anticancer activity. The results have shown that compounds 3l,c,b,e and 4b were endowed with Significantly high values of percent tumor growth inhibition on several tumor cell lines at 10(-4) M, while compound 3t was characterized by a high selectivity, being still strongly inhibiting on three cell lines at 10(-5) M. Comparison of the presently observed activity with that of the previously described aza-analogues confirms that the effected isosteric substitution is highly valuable in some cases. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00003-2

文献信息

• Quinoxaline chemistry Part 10. Quinoxaline 10-oxa-analogues of trimetrexate (TMQ ) and of 5,8-dideazafolic acid. Synthesis and evaluation of in vitro anticancer activity
  作者：Gabriella Vitale、Paola Corona、Mario Loriga、Giuseppe Paglietti

  DOI：10.1016/s0014-827x(98)00003-2

  日期：1998.2

  Among twenty-eight novel compounds (twenty-two 2,13-disubstituted-6-[(substituted-phenoxy)methyl-quinoxalines and six 4-[(2,3-disubstituted-quinoxalin-6-yl) methoxy]benzoylglutamates) only thirteen were selected at NCI for evaluation of their in vitro anticancer activity. The results have shown that compounds 3l,c,b,e and 4b were endowed with Significantly high values of percent tumor growth inhibition on several tumor cell lines at 10(-4) M, while compound 3t was characterized by a high selectivity, being still strongly inhibiting on three cell lines at 10(-5) M. Comparison of the presently observed activity with that of the previously described aza-analogues confirms that the effected isosteric substitution is highly valuable in some cases. (C) 1998 Elsevier Science S.A. All rights reserved.