1-(4-Benzhydryl-piperazin-1-yl)-3-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-propan-2-ol | 125346-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-Benzhydryl-piperazin-1-yl)-3-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-propan-2-ol
• 英文别名: 1-(4-Benzhydrylpiperazin-1-yl)-3-[9-(oxan-2-yl)purin-6-yl]oxypropan-2-ol
• CAS: 125346-11-4
• 化学式: C₃₀H₃₆N₆O₃
• 分子量: 528.654
• InChiKey: NQHBITGSRALMRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(4-Benzhydryl-piperazin-1-yl)-3-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-propan-2-ol 在 溶剂黄146 作用下， 反应 18.0h， 以79%的产率得到6-[3-[4-(Diphenylmethyl)piperazin-1-yl]-2-hydroxypropoxy]-purine
  参考文献：
  名称：

  Synthesis and structure-activity relationship of 6-substituted purine derivatives as novel selective positive inotropes

  摘要：

  A series of purine derivatives was prepared and examined for selective inotropic activity in vitro and in vivo. Thioether-linked derivatives were superior to their oxygen and nitrogen isosteres. Substitution of electron-withdrawing groups on the benzhydryl moiety of these agents increased potency. The best compound of the study, 17 (carsatrin), was examined further and demonstrated selective oral activity as a positive inotrope. These compounds are presumed to act by affecting the kinetics of the cardiac sodium channel by analogy to the prototypic agent DPI 201106 (1). Their high selectivity for increasing contractile force and dP/dt without affecting blood pressure or heart rate is consistent with this mechanism. Carsatrin (17) was selected as a potential development candidate.

  DOI：

  10.1021/jm00102a001
• 作为产物：
  描述：

  6-氯嘌呤 在 氢氧化钾 、 18-冠醚-6 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 3.5h， 生成 1-(4-Benzhydryl-piperazin-1-yl)-3-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-propan-2-ol
  参考文献：
  名称：

  Synthesis and structure-activity relationship of 6-substituted purine derivatives as novel selective positive inotropes

  摘要：

  A series of purine derivatives was prepared and examined for selective inotropic activity in vitro and in vivo. Thioether-linked derivatives were superior to their oxygen and nitrogen isosteres. Substitution of electron-withdrawing groups on the benzhydryl moiety of these agents increased potency. The best compound of the study, 17 (carsatrin), was examined further and demonstrated selective oral activity as a positive inotrope. These compounds are presumed to act by affecting the kinetics of the cardiac sodium channel by analogy to the prototypic agent DPI 201106 (1). Their high selectivity for increasing contractile force and dP/dt without affecting blood pressure or heart rate is consistent with this mechanism. Carsatrin (17) was selected as a potential development candidate.

  DOI：

  10.1021/jm00102a001

文献信息

• Synthesis and structure-activity relationship of 6-substituted purine derivatives as novel selective positive inotropes
  作者：Jeffery B. Press、Robert Falotico、Zoltan G. Hajos、Rebecca Anne Sawyers、Ramesh M. Kanojia、Louella Williams、Barbara Haertlein、Jack A. Kauffman、Constance Lakas-Weiss、Joseph J. Salata

  DOI：10.1021/jm00102a001

  日期：1992.11

  A series of purine derivatives was prepared and examined for selective inotropic activity in vitro and in vivo. Thioether-linked derivatives were superior to their oxygen and nitrogen isosteres. Substitution of electron-withdrawing groups on the benzhydryl moiety of these agents increased potency. The best compound of the study, 17 (carsatrin), was examined further and demonstrated selective oral activity as a positive inotrope. These compounds are presumed to act by affecting the kinetics of the cardiac sodium channel by analogy to the prototypic agent DPI 201106 (1). Their high selectivity for increasing contractile force and dP/dt without affecting blood pressure or heart rate is consistent with this mechanism. Carsatrin (17) was selected as a potential development candidate.