9-butyl-8-(3-methoxy-phenylsulfanyl)adenine | 521308-36-1

• 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-(3-methoxy-phenylsulfanyl)adenine
• 英文别名: 9-Butyl-8-(3-methoxy-phenylsulfanyl)-9H-purin-6-ylamine；9-butyl-8-(3-methoxyphenyl)sulfanylpurin-6-amine
• CAS: 521308-36-1
• 化学式: C₁₆H₁₉N₅OS
• 分子量: 329.426
• InChiKey: FGVWJELBOMNOGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  561.2±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)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-butyl-8-(3-methoxy-phenylsulfanyl)adenine 在 aluminum oxide 、 Oxone 、 偶氮二甲酸二叔丁酯 、 水 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 4.0h， 生成 [9-Butyl-8-(3-methoxyphenyl)sulfinylpurin-6-yl]imino-triphenyl-lambda5-phosphane
  参考文献：
  名称：

  Synthesis of 8-arylsulfoxyl/sulfonyl adenines

  摘要：

  We report a method for the synthesis of 9-N-alkyl-8-arylsulfoxyl adenines and 9-N-alkyl-8-arylsulfonyl adenines. The approach starts with a tandem one-pot reaction that by using Mitsunobu conditions converts 8-arylsulfanyl adenines to the corresponding iminophosphorane protected 9-N-alkyl-8-arylsulfanyl adenines. These compounds were further subjected to selective OXONE(R)/alumina mediated oxidation followed by deprotection of the amine leading to the desired sulfoxides and sulfones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.009
• 作为产物：
  描述：

  8-溴腺嘌呤 在 偶氮二甲酸二叔丁酯 、 potassium carbonate 、 三苯基膦 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.5h， 生成 9-butyl-8-(3-methoxy-phenylsulfanyl)adenine
  参考文献：
  名称：

  Evaluation of 8-Arylsulfanyl, 8-Arylsulfoxyl, and 8-Arylsulfonyl Adenine Derivatives as Inhibitors of the Heat Shock Protein 90

  摘要：

  Hsp90 is a chaperone protein with important roles in maintaining transformation and in elevating the survival and growth potential of cancer cells. Currently there is an increasing interest in developing inhibitors of this protein as anticancer therapeutics. One of such inhibitors, the purine-scaffold class, has been reported to be potent and selective against Hsp90 both in vitro and in vivo models of cancer. Here, a series of 8-arylsulfanyl, -sulfoxyl, and -sulfonyl adenine members of the purine class was synthesized and evaluated as inhibitors of the chaperone. The structure-activity relationship and selectivity for tumor Hsp90 of compounds within the series is presented. Our results suggest that 8-arylsulfanyl adenine derivatives are good inhibitors of chaperone activity, whereas oxidation of the sulfides to sulfoxides or sulfones leads to compounds of decreased activity. The study identifies derivative 11v as the most potent Hsp90 inhibitor of the purine-scaffold series published to date (EC50 = 30 nM), and also as the compound of this class with highest selectivity for tumor vs normal cell Hsp90 (700 to 3000-fold). Most rewardingly, this work has allowed for the identification of Hsp90 inhibitors with selective affinities for Hsp90-client protein complexes, derivatives that may represent useful pharmacological tools in dissecting Hsp90-regulated processes.

  DOI：

  10.1021/jm049012b

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。
• PURINE ANALOGS HAVING HSP90-INHIBITING ACTIVITY
  申请人：Conforma Therapeutic Corporation

  公开号：EP1440072A2

  公开（公告）日：2004-07-28
• EP1440072A4
  申请人：——

  公开号：EP1440072A4

  公开（公告）日：2005-02-02