5-(benzyloxy)-4-<(8-hydroxy-3,6-dioxaoctyl)oxy>-6-methoxyquinazoline | 130436-82-7

• 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: 5-(benzyloxy)-4-<(8-hydroxy-3,6-dioxaoctyl)oxy>-6-methoxyquinazoline
• 英文别名: 2-[2-[2-(6-methoxy-5-phenylmethoxyquinazolin-4-yl)oxyethoxy]ethoxy]ethanol
• CAS: 130436-82-7
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: WUZCNWGGRSDMOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  30.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92.16
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-4-<(8-hydroxy-3,6-dioxaoctyl)oxy>-6-methoxyquinazoline 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 以97%的产率得到4-{2-[2-(2-Hydroxy-ethoxy)-ethoxy]-ethoxy}-6-methoxy-quinazolin-5-ol
  参考文献：
  名称：

  Heterocyclic quinones. XVII. A new in vivo active antineoplastic drug: 6,7-bis(1-aziridinyl)-4-[[3-(N,N-dimethylamino)propyl]amino]-5,8-quinazolinedione

  摘要：

  A series of heterocyclic quinones 6-substituted and 6,7-disubstituted 4-(alkylamino)-5,8-quinazolinediones, have been synthesized in order to evaluate their in vitro cytotoxicity on L1210 leukemia cells. Among 14 derivatives that have been prepared and studied for the structure-activity relationship, the most potent cytotoxic compound on L1210 leukemia cells was the 6,7-bis(1-aziridinyl)-4-[[3-(N,N-dimethylamino)propyl]amino]-5,8-quinazolinedione (24). This compound has been tested with the use of a cell-image processor on MCF-7 human mammary and HBL human melanoma cell lines. The results show that compound 24 influences cell proliferation and blocks both cells lines in the S phase. In vivo antineoplastic activity of compound 24 has been demonstrated on a broad spectrum of murine experimental models, but it was found highly toxic and produced long-delayed deaths.

  DOI：

  10.1021/jm00105a007
• 作为产物：
  描述：

  5-(benzyloxy)-4-chloro-6-methoxyquinazoline 、 三乙二醇 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以82%的产率得到5-(benzyloxy)-4-<(8-hydroxy-3,6-dioxaoctyl)oxy>-6-methoxyquinazoline
  参考文献：
  名称：

  Heterocyclic quinones. XVII. A new in vivo active antineoplastic drug: 6,7-bis(1-aziridinyl)-4-[[3-(N,N-dimethylamino)propyl]amino]-5,8-quinazolinedione

  摘要：

  A series of heterocyclic quinones 6-substituted and 6,7-disubstituted 4-(alkylamino)-5,8-quinazolinediones, have been synthesized in order to evaluate their in vitro cytotoxicity on L1210 leukemia cells. Among 14 derivatives that have been prepared and studied for the structure-activity relationship, the most potent cytotoxic compound on L1210 leukemia cells was the 6,7-bis(1-aziridinyl)-4-[[3-(N,N-dimethylamino)propyl]amino]-5,8-quinazolinedione (24). This compound has been tested with the use of a cell-image processor on MCF-7 human mammary and HBL human melanoma cell lines. The results show that compound 24 influences cell proliferation and blocks both cells lines in the S phase. In vivo antineoplastic activity of compound 24 has been demonstrated on a broad spectrum of murine experimental models, but it was found highly toxic and produced long-delayed deaths.

  DOI：

  10.1021/jm00105a007

文献信息

• GIORGI-RENAULT, SYLVIANE;RENAULT, JEAN;CEBEL-SERVOLLES, PATRICIA;BARON, M+, J. MED. CHEM., 34,(1991) N, C. 38-46
  作者：GIORGI-RENAULT, SYLVIANE、RENAULT, JEAN、CEBEL-SERVOLLES, PATRICIA、BARON, M+

  DOI：——

  日期：——