Methyl 4-((2,3-dimethoxy-6-quinoxalinyl)methoxy)benzoate | 206564-62-7

• 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: Methyl 4-((2,3-dimethoxy-6-quinoxalinyl)methoxy)benzoate
• 英文别名: methyl 4-[(2,3-dimethoxyquinoxalin-6-yl)methoxy]benzoate
• CAS: 206564-62-7
• 化学式: C₁₉H₁₈N₂O₅
• 分子量: 354.362
• InChiKey: MIOROHOHEQJBBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 4-((2,3-dimethoxy-6-quinoxalinyl)methoxy)benzoate 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以67%的产率得到4-((2,3-Dimethoxy-6-quinoxalinyl)methoxy)benzoic acid
  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
• 作为产物：
  描述：

  对羟基苯甲酸甲酯 、 6-溴甲基-2,3-二甲氧基-喹噁啉 在 cesium bicarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以92%的产率得到Methyl 4-((2,3-dimethoxy-6-quinoxalinyl)methoxy)benzoate
  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