3-amino-5,6-dihydro-7-methoxybenzo[f]quinazolin-1(2H)-one

• 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: 3-amino-5,6-dihydro-7-methoxybenzo[f]quinazolin-1(2H)-one
• 英文别名: 3-amino-7-methoxy-5,6-dihydro-2H-benzo[f]quinazolin-1-one
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: OVKSGLNKYZSABF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  盐酸胍 、 methyl 3,4-dihydro-2-hydroxy-5-methoxynaphthalenecarboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 21.5h， 生成 3-amino-5,6-dihydro-7-methoxybenzo[f]quinazolin-1(2H)-one
  参考文献：
  名称：

  Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

  摘要：

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.

  DOI：

  10.1021/jm00068a004

文献信息

• Pharmaceutically active benzoquinazoline compounds
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP1199307B1

  公开（公告）日：2004-02-25
• Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones
  作者：William Pendergast、Jay V. Johnson、Scott H. Dickerson、Inderjit K. Dev、David S. Duch、Robert Ferone、William R. Hall、Joan Humphreys、Joseph M. Kelly、David C. Wilson

  DOI：10.1021/jm00068a004

  日期：1993.8

  The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo-[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 muM.