3-amino-8-chloro-5,6-dihydro-6-methylbenzo[f]quinazolin-1(2H)-one | 139986-59-7

• 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: 3-amino-8-chloro-5,6-dihydro-6-methylbenzo[f]quinazolin-1(2H)-one
• 英文别名: 3-amino-8-chloro-6-methyl-5,6-dihydro-2H-benzo[f]quinazolin-1-one
• CAS: 139986-59-7
• 化学式: C₁₃H₁₂ClN₃O
• 分子量: 261.711
• InChiKey: LBWKYRAAEFPNRI-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-8-chloro-5,6-dihydro-6-methylbenzo[f]quinazolin-1(2H)-one 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 反应 2.5h， 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：

  对氯苯乙酸 在 三氯化铝 、 草酰氯 、 sodium ethanolate 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 28.25h， 生成 3-amino-8-chloro-5,6-dihydro-6-methylbenzo[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
• US5405851A
  申请人：——

  公开号：US5405851A

  公开（公告）日：1995-04-11
• US5661155A
  申请人：——

  公开号：US5661155A

  公开（公告）日：1997-08-26
• US6090941A
  申请人：——

  公开号：US6090941A

  公开（公告）日：2000-07-18
• US6762188B1
  申请人：——

  公开号：US6762188B1

  公开（公告）日：2004-07-13