8-溴-9-丁基-9h-嘌呤-6-胺 | 202136-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 8-溴-9-丁基-9h-嘌呤-6-胺
• 英文名称: (8-bromo-9-butyl-9H-purin-6-yl)amine
• 英文别名: 8-bromo-9-butylpurin-6-amine
• CAS: 202136-43-4
• 化学式: C₉H₁₂BrN₅
• 分子量: 270.132
• InChiKey: FKNNQOCJLMQVAV-UHFFFAOYSA-N

物化性质

• 熔点：
  152-154 °C
• 沸点：
  446.5±48.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-溴-9-丁基-9h-嘌呤-6-胺 以63%的产率得到9-butyl-8-hydroxyadenine
  参考文献：
  名称：

  Type 2 helper T cell-selective immune response suppressors

  摘要：

  本发明涉及一种选择性抑制T细胞辅助型2型免疫应答的免疫应答调节剂、免疫调节剂和抗过敏剂，分别包括一种以通式(I)表示的嘌呤衍生物作为活性成分：其中R2是氢或烃基，在其中—CH2—不直接与嘌呤骨架结合的部分可能被CO、SO2、O或S取代，而未直接与嘌呤骨架结合的部分可能被N、C-卤或C—CN取代；R6是羟基、氨基或被一个或两个烃基取代的氨基；R8是羟基、巯基、酰氧基或烃基取代的氧羰氧基；以及R9是烃基，在其中—CH2—不直接与嘌呤骨架结合的部分可能被CO、SO2、O或S取代，而未直接与嘌呤骨架结合的部分可能被N、C-卤或C—CN取代；或其互变异构体或嘌呤衍生物或其互变异构体的盐。

  公开号：

  US06376501B1
• 作为产物：
  描述：

  9-丁基嘌呤-6-胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以41%的产率得到8-溴-9-丁基-9h-嘌呤-6-胺
  参考文献：
  名称：

  8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

  摘要：

  Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radioligand binding assays or functional cyclase experiments in respect to their interaction with all the four adenosine receptor subtypes. Results show that the presence of the bromine atom in 8-position of 9-substituted adenines promotes in general the interaction with the adenosine receptors, in particular at the A(2A) subtype. The present study also demonstrates that adenine derivatives could be a good starting point to obtain selective adenosine A(2B) receptor antagonists. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.030

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。
• Purine analogs having HSP90-inhibiting activity
  申请人：Conforma Therapeutics Corporation

  公开号：US07241890B2

  公开（公告）日：2007-07-10

  Novel purine compounds of Formula I. and tautomers, pharmaceutically acceptable salts, and prodrugs thereof, wherein X is S, S(O), or S(O)2; and O is selected from alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl, and heterocyclic, all optionally substituted, are described, as are pharmaceutical compositions comprising the same, complexes comprising the same, e.g., HSP90 complexes, and methods of using the same.

  本发明涉及一种新型嘌呤化合物I及其互变异构体、药学上可接受的盐和前药。其中，X为S、S(O)或S(O)2; O选自烷基、环烷基、芳基烷基、芳基、杂环芳基和杂环，均可选择性地被取代。同时，本发明还涉及含有该化合物的制药组合物、包括该化合物的复合物，如HSP90复合物，以及使用它们的方法。
• 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。
• TYPE 2 HELPER T CELL-SELECTIVE IMMUNE RESPONSE SUPPRESSORS
  申请人：Japan Energy Corporation

  公开号：EP1043021A1

  公开（公告）日：2000-10-11

  The present invention relates to a type 2 helper T cell-selective immune response inhibitor, an immune response regulator and an anti-allergic agent, individually comprising, as an active ingredient, a purine derivative represented by General Formula (I):    wherein R2 is hydrogen or a hydrocarbon group in which -CH2- not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C-H not directly bound to the purine skeleton may be substituted by N, C-halogen or C-CN; R6 is hydroxyl, amino or amino which is mono- or di-substituted by a hydrocarbon group(s); R8 is hydroxyl, mercapto, acyloxy or hydrocarbon group-substituting oxycarbonyloxy; and R9 is a hydrocarbon group in which -CH2- not directly bound to the purine skeleton may be substituted by CO, SO2, O or S, and C-H not directly bound to the purine skeleton may be substituted by N, C-halogen or C-CN; or its tautomer or a salt of the purine derivative or the tautomer.

  本发明涉及一种 2 型辅助性 T 细胞选择性免疫应答抑制剂、免疫应答调节剂和抗过敏剂，其活性成分分别包括通式 (I) 所代表的嘌呤衍生物： 其中 R2 是氢或烃基，其中与嘌呤骨架不直接结合的-CH2-可被 CO、SO2、O 或 S 取代，与嘌呤骨架不直接结合的 C-H 可被 N、C-卤素或 C-CN 取代； R6 是羟基、氨基或被烃基单取代或二取代的氨基； R8 是羟基、巯基、酰氧基或被烃基取代的氧羰氧基；以及 R9 是烃基，其中与嘌呤骨架不直接结合的- -可被 CO、SO2、O 或 S 取代，与嘌呤骨架不直接结合的 C-H 可被 N、C-卤素或 C-CN 取代； 或其同系物，或该嘌呤衍生物或其同系物的盐。
• Development of a Purine-Scaffold Novel Class of Hsp90 Binders that Inhibit the Proliferation of Cancer Cells and Induce the Degradation of Her2 Tyrosine Kinase
  作者：Gabriela Chiosis、Brian Lucas、Alexander Shtil、Henri Huezo、Neal Rosen

  DOI：10.1016/s0968-0896(02)00253-5

  日期：2002.11

  The first published synthesis and characterization of a purine-scaffold library of hsp90 inhibitors is presented. The purine-scaffold represents a platform for the creation of easily synthesizable and derivatizable soluble molecules that are amenable for oral administration. The most active compound of the series (71) exhibits binding to hsp90 comparable to the natural product derivative 17AAG that is now in Phase I clinical trial as a cancer therapeutic. 71 Induces the degradation of Her2 tyrosine kinase and arrests the MCF-7 breast cancer cell line at low micromolar concentrations (IC50 = 2 muM). (C) 2002 Elsevier Science Ltd. All rights reserved.