2-[6-Amino-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purin-8-yl]-propan-2-ol | 227763-94-2

• 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: 2-[6-Amino-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purin-8-yl]-propan-2-ol
• 英文别名: 2-[6-amino-3-[(3-cyclopentyloxy-4-methoxyphenyl)methyl]purin-8-yl]propan-2-ol
• CAS: 227763-94-2
• 化学式: C₂₁H₂₇N₅O₃
• 分子量: 397.477
• InChiKey: HTZYCNVPJINMRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  108.31
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[6-Amino-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purin-8-yl]-propan-2-ol 在 氨 、 potassium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.0h， 生成 4-{1-[6-Amino-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purin-8-yl]-1-methyl-ethoxymethyl}-benzamide
  参考文献：
  名称：

  8-Substituted Analogues of 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl- adenine: Highly Potent and Selective PDE4 Inhibitors

  摘要：

  3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-adenine V11294 (1) has been identified as a lead structure, which selectively inhibits human lung PDE4 (436 nM) and is also active in a number of in vitro and in vivo models of inflammation. Here we describe the synthesis and pharmacology of a series of highly potent 8-[(benzyloxy)methyl]-substituted analogues, with potencies in the range 10-300 nM. In addition, several compounds showed interesting PDE4 subtype specificities, for example, the 3-thienyl derivative 5v, which showed 6-10 nM potency at PDE4B, D3, and D5 and a 20- to 200-fold selectivity over A and D2, respectively.

  DOI：

  10.1021/jm030603w
• 作为产物：
  描述：

  2-(6-amino-9H-purin-8-yl)propan-2-ol 、 4-(氯甲基)-2-(环戊氧基)-1-甲氧基苯 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以31%的产率得到2-[6-Amino-3-(3-cyclopentyloxy-4-methoxy-benzyl)-3H-purin-8-yl]-propan-2-ol
  参考文献：
  名称：

  8-Substituted Analogues of 3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl- adenine: Highly Potent and Selective PDE4 Inhibitors

  摘要：

  3-(3-Cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-adenine V11294 (1) has been identified as a lead structure, which selectively inhibits human lung PDE4 (436 nM) and is also active in a number of in vitro and in vivo models of inflammation. Here we describe the synthesis and pharmacology of a series of highly potent 8-[(benzyloxy)methyl]-substituted analogues, with potencies in the range 10-300 nM. In addition, several compounds showed interesting PDE4 subtype specificities, for example, the 3-thienyl derivative 5v, which showed 6-10 nM potency at PDE4B, D3, and D5 and a 20- to 200-fold selectivity over A and D2, respectively.

  DOI：

  10.1021/jm030603w

文献信息

• EP1045849A4
  申请人：——

  公开号：EP1045849A4

  公开（公告）日：2001-10-31
• PURINE DERIVATIVES HAVING PHOSPHODIESTERASE IV INHIBITION ACTIVITY
  申请人：Euro-Celtique S.A.

  公开号：EP1045849B1

  公开（公告）日：2003-07-02
• US6228859B1
  申请人：——

  公开号：US6228859B1

  公开（公告）日：2001-05-08
• US6319928B1
  申请人：——

  公开号：US6319928B1

  公开（公告）日：2001-11-20
• US6413975B1
  申请人：——

  公开号：US6413975B1

  公开（公告）日：2002-07-02