(R)-1,2,7-Tribenzyl-5-cyclopropyl-7,8-dihydro-1H,5H-imidazo[2,1-b]purin-4-one | 851707-03-4

• 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: (R)-1,2,7-Tribenzyl-5-cyclopropyl-7,8-dihydro-1H,5H-imidazo[2,1-b]purin-4-one
• 英文别名: (7R)-1,2,7-tribenzyl-5-cyclopropyl-7,8-dihydroimidazo[2,1-b]purin-4-one
• CAS: 851707-03-4
• 化学式: C₃₁H₂₉N₅O
• 分子量: 487.604
• InChiKey: XNSZVGJFUJDTMW-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1,2,7-Tribenzyl-5-cyclopropyl-7,8-dihydro-1H,5H-imidazo[2,1-b]purin-4-one 在 palladium dihydroxide 、 甲酸铵 作用下， 以 甲醇 为溶剂， 生成 (7R)-2,7-dibenzyl-5-cyclopropyl-7,8-dihydro-3H-imidazo[2,1-b]purin-4-one
  参考文献：
  名称：

  Optimization of purine based PDE1/PDE5 inhibitors to a potent and selective PDE5 inhibitor for the treatment of male ED

  摘要：

  In search of a PDE5 inhibitor for erectile dysfunction, an SAR was developed from a PDE1/PDE5 purine series of leads, which had modest PDE5 potency and poor isozyme selectivity. A compound (41) with PDE5 inhibition and in vivo activity similar to sildenafil was discovered from this effort. In addition, purine 41 demonstrated superior overall PDE isozyme selectivity when compared to the approved PDE5 inhibitors sildenafil, vardenafil, and tadalafil, which may result in a more favorable side-effect profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.083
• 作为产物：
  描述：

  Ethyl 5-amino-1,2-dibenzylimidazole-4-carboxylate 在 sodium methylate 、 甲基磺酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 甲苯 为溶剂， 生成 (R)-1,2,7-Tribenzyl-5-cyclopropyl-7,8-dihydro-1H,5H-imidazo[2,1-b]purin-4-one
  参考文献：
  名称：

  Optimization of purine based PDE1/PDE5 inhibitors to a potent and selective PDE5 inhibitor for the treatment of male ED

  摘要：

  In search of a PDE5 inhibitor for erectile dysfunction, an SAR was developed from a PDE1/PDE5 purine series of leads, which had modest PDE5 potency and poor isozyme selectivity. A compound (41) with PDE5 inhibition and in vivo activity similar to sildenafil was discovered from this effort. In addition, purine 41 demonstrated superior overall PDE isozyme selectivity when compared to the approved PDE5 inhibitors sildenafil, vardenafil, and tadalafil, which may result in a more favorable side-effect profile. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.083

文献信息

• Optimization of purine based PDE1/PDE5 inhibitors to a potent and selective PDE5 inhibitor for the treatment of male ED
  作者：Craig D. Boyle、Ruo Xu、Theodros Asberom、Samuel Chackalamannil、John W. Clader、William J. Greenlee、Henry Guzik、Yuequing Hu、Zhiyong Hu、Claire M. Lankin、Dmitri A. Pissarnitski、Andrew W. Stamford、Yuguang Wang、Jeffrey Skell、Stanley Kurowski、Subbarao Vemulapalli、Jairam Palamanda、Madhu Chintala、Ping Wu、Joyce Myers、Peng Wang

  DOI：10.1016/j.bmcl.2005.02.083

  日期：2005.5

  In search of a PDE5 inhibitor for erectile dysfunction, an SAR was developed from a PDE1/PDE5 purine series of leads, which had modest PDE5 potency and poor isozyme selectivity. A compound (41) with PDE5 inhibition and in vivo activity similar to sildenafil was discovered from this effort. In addition, purine 41 demonstrated superior overall PDE isozyme selectivity when compared to the approved PDE5 inhibitors sildenafil, vardenafil, and tadalafil, which may result in a more favorable side-effect profile. (c) 2005 Elsevier Ltd. All rights reserved.