6-Methoxy-4-(3-(N,N-dimethylamino)propylamino)-5,8-quinazolinedione | 120075-57-2

• 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-Methoxy-4-(3-(N,N-dimethylamino)propylamino)-5,8-quinazolinedione
• 英文别名: 4-[3-(dimethylamino)propylamino]-6-methoxyquinazoline-5,8-dione
• CAS: 120075-57-2
• 化学式: C₁₄H₁₈N₄O₃
• 分子量: 290.322
• InChiKey: XMEQVWNXYMYXAB-UHFFFAOYSA-N

物化性质

• 熔点：
  152 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  520.6±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙烯亚胺 、 6-Methoxy-4-(3-(N,N-dimethylamino)propylamino)-5,8-quinazolinedione 反应 4.5h， 以35%的产率得到6,7-二(氮丙啶-1-基)-4-(3-二甲基氨基丙基氨基)喹唑啉-5,8-二酮
  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：

  N-(6-methoxy-5-phenylmethoxyquinazolin-4-yl)-N',N'-dimethylpropane-1,3-diamine 在 palladium on activated charcoal potassium dihydrogenphosphate 、 potassium nitrososulfonate 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 6-Methoxy-4-(3-(N,N-dimethylamino)propylamino)-5,8-quinazolinedione
  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：——
• 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
  作者：Sylviane Giorgi-Renault、Jean Renault、Patricia Gebel-Servolles、Michel Baron、Claude Paoletti、Suzanne Cros、Marie Christine Bissery、Francois Lavelle、Ghanem Atassi

  DOI：10.1021/jm00105a007

  日期：1991.1

  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.