3-amino-8-nitro-2H-benzo[f]quinazolin-1-one | 142933-67-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-8-nitro-2H-benzo[f]quinazolin-1-one
• CAS: 142933-67-3
• 化学式: C₁₂H₈N₄O₃
• 分子量: 256.221
• InChiKey: NJTYHQFCCDYKAQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-8-nitro-2H-benzo[f]quinazolin-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 185.0 ℃ 、293.03 kPa 条件下， 反应 4.5h， 生成
  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
• 作为产物：
  描述：

  苯并[F]喹唑啉-1-(2H)-酮,3-氨基- 生成 3-amino-5,6-dihydro-8-nitrobenzo[f]quinazolin-1(2H)-one 、 3-amino-8-nitro-2H-benzo[f]quinazolin-1-one 、 3-Amino-7-nitro-2H-benzo[f]quinazolin-1-one
  参考文献：
  名称：

  Pharmaceutically active benzoquinazoline compounds

  摘要：

  公开号：

  EP1199307B1

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.