4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin9(4H)-one | 75185-00-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin9(4H)-one
• 英文别名: 4-[(4-Chlorophenyl)methyl]-1,2,6-trimethyl-6,7-dihydroimidazo[1,2-a]purin-9-one
• CAS: 75185-00-1
• 化学式: C₁₇H₁₈ClN₅O
• 分子量: 343.816
• InChiKey: CQLZAYNZUHTVKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-amino-8-[(4-chlorophenyl)methyl]-2-methyl-6-nitroso-2,3-dihydroimidazo[1,2-a]pyrimidin-5-one 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin9(4H)-one
  参考文献：
  名称：

  Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones

  摘要：

  The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat.

  DOI：

  10.1021/jm00185a008

文献信息

• TEMPLE D. L. JR.; YEVICH J. P.; GATT J. D.; OWENS D.; HANNING C.; COVINGT+, J. MED. CHEM., 1980, 23, NO 11, 1188-1198
  作者：TEMPLE D. L. JR.、 YEVICH J. P.、 GATT J. D.、 OWENS D.、 HANNING C.、 COVINGT+

  DOI：——

  日期：——
• US4298734A
  申请人：——

  公开号：US4298734A

  公开（公告）日：1981-11-03
• US4366156A
  申请人：——

  公开号：US4366156A

  公开（公告）日：1982-12-28
• Substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones
  作者：D. L. Temple、J. P. Yevich、J. D. Catt、D. Owens、C. Hanning、R. R. Covington、R. J. Seidehamel、K. W. Dungan

  DOI：10.1021/jm00185a008

  日期：1980.11

  The synthesis of a series of substituted 6,7-dihydroimidazo[1,2-a]purin-9(4H)-ones is described. Several members of the series exhibit enhanced antiallergic and bronchodilator activity and reduced side effects as compared to theophylline. Structure-activity relationships and metabolic considerations are discussed for the series. Analogues substituted with a 4-(4-chlorobenzyl) moiety, such as 33 and 40, shown an optimal balance of antiallergic and bronchodilator activity and are of particular interest. Compound 33 is significantly more potent than theophylline against both metacholine- and antigen-induced bronchospasms, does not affect spontaneous motor activity, and shows minimal cardiovascular effects in the rat.