6-<(4-carbomethoxyphenoxy)methyl>-3,4-dihydro-4-oxo-3-<(pivaloyloxy)methyl>quinazoline | 118895-92-4

• 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-<(4-carbomethoxyphenoxy)methyl>-3,4-dihydro-4-oxo-3-<(pivaloyloxy)methyl>quinazoline
• 英文别名: Methyl 4-[[3-(2,2-dimethylpropanoyloxymethyl)-4-oxoquinazolin-6-yl]methoxy]benzoate
• CAS: 118895-92-4
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: ZQTSIXQWVHVBDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-<(4-carbomethoxyphenoxy)methyl>-3,4-dihydro-4-oxo-3-<(pivaloyloxy)methyl>quinazoline 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以81%的产率得到6-<(4-carboxyphenoxy)methyl>-3,4-dihydro-4-oxo-quinazoline
  参考文献：
  名称：

  Comparison of the biological effects of selected 5,8-dideazafolate analogs with their 2-desamino counterparts

  摘要：

  Three new 5,8-dideaza analogues of folic acid devoid of an amino group at position 2 have been prepared by using synthetic routes patterned after earlier methodologies. They were 2-desamino-5,8-dideazaisofolic acid, 2b, 2-desamino-10-thia-5,8-dideazafolic acid, 2c, and 2-desamino-10-oxa-5,8-dideazafolic acid, 2d. These compounds were found to be 4-6-fold more cytoxic toward L1210 leukemia cells than their 2-NH2 counterparts and to be poor inhibitors of mammalian thymidylate synthase. However, they were only 1.5-3-fold less inhibitory toward dihydrofolate reductase than the analogous compounds containing a 2-NH2 group. The known thymidylate synthase inhibitors 2-desamino-10-propargyl-5,8-dideazafolic acid and 10-propargyl-5,8-dideazafolic acid were included in this study for purposes of comparison.

  DOI：

  10.1021/jm00124a019
• 作为产物：
  描述：

  <6-(bromomethyl)-4-oxo-3(4H)-quinazolinyl>methyl 2,2-dimethylpropanoate 、 对羟基苯甲酸甲酯 在 cesium bicarbonate 作用下， 生成 6-<(4-carbomethoxyphenoxy)methyl>-3,4-dihydro-4-oxo-3-<(pivaloyloxy)methyl>quinazoline
  参考文献：
  名称：

  Comparison of the biological effects of selected 5,8-dideazafolate analogs with their 2-desamino counterparts

  摘要：

  Three new 5,8-dideaza analogues of folic acid devoid of an amino group at position 2 have been prepared by using synthetic routes patterned after earlier methodologies. They were 2-desamino-5,8-dideazaisofolic acid, 2b, 2-desamino-10-thia-5,8-dideazafolic acid, 2c, and 2-desamino-10-oxa-5,8-dideazafolic acid, 2d. These compounds were found to be 4-6-fold more cytoxic toward L1210 leukemia cells than their 2-NH2 counterparts and to be poor inhibitors of mammalian thymidylate synthase. However, they were only 1.5-3-fold less inhibitory toward dihydrofolate reductase than the analogous compounds containing a 2-NH2 group. The known thymidylate synthase inhibitors 2-desamino-10-propargyl-5,8-dideazafolic acid and 10-propargyl-5,8-dideazafolic acid were included in this study for purposes of comparison.

  DOI：

  10.1021/jm00124a019

文献信息

• HYNES, JOHN B.;PATIL, SHIRISH A.;HAGAN, ROBERT L.;COLE, AIMEE;KOHLER, WIL+, J. MED. CHEM., 32,(1989) N, C. 852-856
  作者：HYNES, JOHN B.、PATIL, SHIRISH A.、HAGAN, ROBERT L.、COLE, AIMEE、KOHLER, WIL+

  DOI：——

  日期：——