4-[(4-Chlorophenyl)Methyl]-6,7-Dihydro-9-Imino-3H,4H-Imidazo[1,2-a]Purine | 75199-29-0

• 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-9-Imino-3H,4H-Imidazo[1,2-a]Purine
• 英文别名: 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1H-imidazo[1,2-a]purin-9-imine
• CAS: 75199-29-0
• 化学式: C₁₄H₁₃ClN₆
• 分子量: 300.75
• InChiKey: MFUSRNVIDOJLCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-amino-8-<(4-chlorophenyl)methyl>-6-(formylamino)-2,3-dihydroimidazo<1,2-a>pyrimidin-5(8H)-one 在 sodium hydroxide 、 tetraphosphorus decasulfide 、 氨 、 乙酸酐 、 原甲酸三乙酯 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 26.0h， 生成 4-[(4-Chlorophenyl)Methyl]-6,7-Dihydro-9-Imino-3H,4H-Imidazo[1,2-a]Purine
  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

• 6,7-dihydro-3H-imidazo[1,2-a]-purine-9(4H)-ones
  申请人：Mead Johnson & Company

  公开号：US04642345A1

  公开（公告）日：1987-02-10

  Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-one.

  咪唑嘧啶酮和其他含有额外融合咪唑或三唑环的二氮杂杂环嘧啶酮具有支气管扩张剂、介质释放抑制剂、磷酸二酯酶抑制剂和周围血管扩张剂的用途。它们口服有效，可用于哮喘的预防和治疗。首选化合物是4-[(4-氯苯基)甲基]-6,7-二氢-3H-咪唑[1,2-a]-嘌呤-9(4H)-酮。
• 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：——
• US4366156A
  申请人：——

  公开号：US4366156A

  公开（公告）日：1982-12-28
• US4404380A
  申请人：——

  公开号：US4404380A

  公开（公告）日：1983-09-13
• US4489078A
  申请人：——

  公开号：US4489078A

  公开（公告）日：1984-12-18