6-Bromomethyl-3-chloro-2-phenyl-quinoxaline | 206561-60-6

• 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: 6-Bromomethyl-3-chloro-2-phenyl-quinoxaline
• 英文别名: 6-(Bromomethyl)-3-chloro-2-phenylquinoxaline
• CAS: 206561-60-6
• 化学式: C₁₅H₁₀BrClN₂
• 分子量: 333.615
• InChiKey: XNNAVIMUESUBPW-UHFFFAOYSA-N

物化性质

• 沸点：
  426.3±40.0 °C(Predicted)
• 密度：
  1.539±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Bromomethyl-3-chloro-2-phenyl-quinoxaline 在 sodium hydroxide 、 cesium bicarbonate 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 4-(3-Ethoxy-2-phenyl-quinoxalin-6-ylmethoxy)-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：

  2-chloro-7-methyl-2-phenylquinoxaline 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 以58%的产率得到6-Bromomethyl-3-chloro-2-phenyl-quinoxaline
  参考文献：
  名称：

  Quinoxaline chemistry Part 9. Quinoxaline analogues of trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) and its precursors. Synthesis and evaluation of in vitro anticancer activity

  摘要：

  Eighteen quinoxalines bearing a methyleneanilino or methyleneaminobenzoylglutamate group on position 6 of the ring and various lipophilic substituents on positions 2 and 3 were prepared in order to discover if their structural analogy with both trimetrexate (TMQ) and 10-propargyl-5,8-dideazafolic acid (CB 3717) might display in vitro anticancer activity. Among these, 12 compounds were selected at the National Cancer Institute, Bethesda, MD, USA; they exhibited moderate (4b,d,i,l,m and 8) to strong (4f,h and 5a,e) cell-growth inhibition at a concentration of 10(-4) M. Interesting selectivities were also recorded between 10(-8) and 10(-6) M. These analogues proved to be less potent inihibitors of tumor cells than other classical and non-classical antifolate analogues previously described by us. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00002-0