9-butyl-8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine | 521308-37-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 9-butyl-8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine
• 英文别名: 9-butyl-8-[(2,5-dimethoxyphenyl)sulfanyl]-9H-purin-6-amine；9-butyl-8-(2,5-dimethoxyphenyl)sulfanylpurin-6-amine
• CAS: 521308-37-2
• 化学式: C₁₇H₂₁N₅O₂S
• 分子量: 359.452
• InChiKey: FPMBLCHVDGURBC-UHFFFAOYSA-N

物化性质

• 沸点：
  589.3±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-butyl-8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine 在 sodium nitrite 作用下， 以 溶剂黄146 、 水 为溶剂， 反应 20.17h， 以79%的产率得到8-(2,5-dimethoxyphenylthio)-9-butyl-1H-purin-6(9H)-one
  参考文献：
  名称：

  [EN] NEW COMPOUNDS AS HSP90 INHIBITORS
  [FR] NOUVEAUX COMPOSÉS INHIBITEURS DE LA HSP90

  摘要：

  该发明提供了式（I）的新化合物，其中：a、b、c或d成员中的一个是氮原子，其余成员是碳原子；R3是从以下组成的基团中选择的：-S-R14和-CH2-R15。式（I）的化合物对于治疗由热休克蛋白90（Hsp 90）介导的疾病是有用的。

  公开号：

  WO2009007399A1
• 作为产物：
  描述：

  8-溴腺嘌呤 在 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 9-butyl-8-(2,5-dimethoxy-phenylsulfanyl)-9H-purin-6-ylamine
  参考文献：
  名称：

  Orally Active Purine-Based Inhibitors of the Heat Shock Protein 90

  摘要：

  Orally active Hsp90 inhibitors are of interest as potential chemotherapeutic agents. Recently, fully synthetic 8-benzyladenines and 8-sulfanyladenines such as 4 were disclosed as Hsp90 inhibitors, but these compounds are not water soluble and consequently have unacceptably low oral bioavailabilities. We now report that water-solubility can be achieved by inserting an amino functionality in the N(9) side chain. This results in compounds that are potent, soluble in aqueous media, and orally bioavailable. In an HER-2 degradation assay, the highest potency was achieved with the neopentylamine 42 (HER-2 IC50 = 90 nM). In a murine tumor xenograft model (using the gastric cancer cell line N87), the H3PO4 salts of the amines 38, 39, and 42 induced tumor growth inhibition when administered orally at 200 mg/kg/day. The amines 38, 39, and 42 are the first Hsp90 inhibitors shown to inhibit tumor growth upon oral dosage.

  DOI：

  10.1021/jm0503087

文献信息

• Purine analogs having hsp90-inhibiting activity
  申请人：Kasibhatla Rao Srinivas

  公开号：US20050049263A1

  公开（公告）日：2005-03-03

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same.

  本发明描述了新型嘌呤化合物及其互变异构体以及其药学上可接受的盐，以及包含它们的制药组合物、包含它们的复合物（例如HSP90复合物）和使用它们的方法。
• Orally Active Purine-Based Inhibitors of Heat Shock Protein 90
  申请人：Kasibhatla R. Srinivas

  公开号：US20070129334A1

  公开（公告）日：2007-06-07

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same. Methods of using the novel purine compounds of the invention, and tautomers and pharmaceutically acceptable salts thereof, include their use in inhibiting heat shock protein 90's (HSP90's) to thereby treat or prevent HSP90-dependent diseases, e.g., proliferative disorders such as breast cancer.

  本发明描述了新型嘌呤化合物及其互变异构体和药学上可接受的盐，以及包含它们的制药组合物、包含它们的复合物（例如HSP90复合物）和使用它们的方法。使用本发明的新型嘌呤化合物、互变异构体和药学上可接受的盐的方法包括在抑制热休克蛋白90（HSP90）中使用它们，从而治疗或预防HSP90依赖性疾病，例如增生性疾病如乳腺癌。
• Purine analogs having HSP90-inhibiting activity
  申请人：Kasibhatla Srinivas Rao

  公开号：US20080125446A1

  公开（公告）日：2008-05-29

  Novel purine compounds and tautomers and pharmaceutically acceptable salts thereof are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same.

  本发明涉及新型嘌呤化合物及其互变异构体和药学上可接受的盐，还涉及包含它们的药物组合物、包含它们的复合物，例如HSP90复合物，以及使用它们的方法。
• COMPOUNDS AS HSP90 INHIBITORS
  申请人：Pedemonte Marc Martinell

  公开号：US20100240656A1

  公开（公告）日：2010-09-23

  The invention provides novel compounds of formula (I) wherein: one of the a, b, c or d members is a nitrogen atom and the remaining members are carbon atoms; and R 3 is a radical selected from the group consisting of: —S—R 14 and —CH 2 —R 15 . The compounds of formula (I) are useful for treating diseases mediated by a heat shock protein 90 (Hsp 90).

  本发明提供了公式（I）的新化合物，其中：a、b、c或d成员中的一个是氮原子，其余成员是碳原子；R3是从以下组中选择的基团：—S—R14和—CH2—R15。公式（I）的化合物可用于治疗由热休克蛋白90（Hsp90）介导的疾病。
• PURINE ANALOGS HAVING HSP90-INHIBITING ACTIVITY
  申请人：Conforma Therapeutic Corporation

  公开号：EP1440072A2

  公开（公告）日：2004-07-28