2-amino-9-benzyl-8-bromoadenine | 226908-04-9

• 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-amino-9-benzyl-8-bromoadenine
• 英文别名: 2,6-diamino-9-benzyl-8-bromopurine；9-benzyl-8-bromopurine-2,6-diamine
• CAS: 226908-04-9
• 化学式: C₁₂H₁₁BrN₆
• 分子量: 319.164
• InChiKey: SQMVMJQSXQSXEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-9-benzyl-8-bromoadenine 在 sodium hydroxide 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 9-Benzyl-N²-butyl-8-methoxy-9H-purine-2,6-diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers

  摘要：

  Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine (9) indicated the most potent activity with MEC of 0.001 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00234-7
• 作为产物：
  描述：

  2-氯-6-氨基嘌呤 在 氨 、 溴 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-amino-9-benzyl-8-bromoadenine
  参考文献：
  名称：

  Synthesis and structure–Activity relationships of 2-Amino-8-hydroxyadenines as orally active interferon inducing agents

  摘要：

  Recently, we have reported the 8-hydroxyadenine derivatives (2-4) as a novel class of interferon (IFN) inducing agents. In the present study, a series of 8-hydroxyadenines, which possess various amino moieties at the adenine C(2)-position, were synthesized and evaluated for their ability to induce endogenous IFN in comparison to the known active agent, Imiquimod. Among the compounds prepared, compound 9o possessing a 2-methoxyethylamino group at C(2)-position of adenine was found to exhibit potent IFN inducing activity in vivo. Compound 9o induced IFN from the dosage of 0.1 mg/kg, which was 30-fold potent than that of Imiquimod, and showed a good oral bioavailability (F = 81%) (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.032

文献信息

• Heterocyclic compounds
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：US06329381B1

  公开（公告）日：2001-12-11

  The present invention relates to a heterocyclic compound of the following general formula (I): wherein X is sulfur atom, oxygen atom or —NR3— (R3 may form a heterocyclic ring or a substituted heterocyclic ring with R1 via the nitrogen atom), R1 is alkyl group, substituted alkyl group, aryl group, substituted aryl group, heterocyclic group or substituted heterocyclic group, and R2 is hydrogen atom, halogen atom etc.; or its pharmaceutically acceptable salt and interferon inducers, antiviral agents, anticancer agents and therapeutic agents for immunologic diseases comprising the compound (I) or its pharmaceutically acceptable salt as active ingredients.

  本发明涉及以下通式（I）的杂环化合物：其中X是硫原子、氧原子或—NR3—（R3可能通过氮原子与R1形成杂环环或取代杂环环），R1是烷基、取代烷基、芳基、取代芳基、杂环基或取代杂环基，R2是氢原子、卤原子等；或其药学上可接受的盐和干扰素诱导剂、抗病毒剂、抗癌剂和免疫性疾病治疗剂，包括化合物（I）或其药学上可接受的盐作为活性成分。
• NOVEL HETEROCYCLIC COMPOUNDS
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1035123A1

  公开（公告）日：2000-09-13

  The present invention relates to a heterocyclic compound of the following general formula (I): wherein X is sulfur atom, oxygen atom or -NR3- (R3 may form a heterocyclic ring or a substituted heterocyclic ring with R1 via the nitrogen atom), R1 is alkyl group, substituted alkyl group, aryl group, substituted aryl group, heterocyclic group or substituted heterocyclic group, and R2 is hydrogen atom, halogen atom etc.; or its pharmaceutically acceptable salt and interferon inducers, antiviral agents, anticancer agents and therapeutic agents for immunologic diseases comprising the compound (I) or its pharmaceutically acceptable salt as active ingredients.

  本发明涉及以下通式(I)的杂环化合物： 其中 X 是硫原子、氧原子或-NR3-（R3 可通过氮原子与 R1 形成杂环或取代的杂环）、 R1 是烷基、取代的烷基、芳基、取代的芳基、杂环基或取代的杂环基，以及 R2 是氢原子、卤素原子等； 或其药学上可接受的盐，以及干扰素诱导剂、抗病毒剂、抗癌剂和以化合物（I）或其药学上可接受的盐为活性成分的免疫疾病治疗剂。
• Adenine derivatives as inhibitors of the casein kinase CK1delta enzyme
  作者：Andrea Spinaci、Catia Lambertucci、Cui Chang、Michela Buccioni、Gabriella Marucci、Eleonora Cescon、Stephanie Federico、Giampiero Spalluto、Diego Dal Ben、Rosaria Volpini

  DOI：10.1007/s00044-024-03202-6

  日期：2024.4

  adenine derivative library revealed that some compounds are able to inhibit the CK1δ enzyme isoform with IC50 in the low µM range. Molecular docking analyses were performed at a X-ray structure of the enzyme, leading to the rational design of novel di- and tri-substituted adenines that were synthesized and characterized. Biological evaluation demonstrated that the new compounds are endowed with moderate

  CK1δ 的过度表达与癌症和神经退行性疾病的发展有关，使得该蛋白的配体非常有希望用于治疗这些疾病的候选药物和/或用于其研究的药理学工具。对内部腺嘌呤衍生物库的筛选活动表明，一些化合物能够抑制 CK1δ 酶亚型，IC 50在低 µM 范围内。对酶的 X 射线结构进行分子对接分析，从而合理设计合成和表征的新型二取代和三取代腺嘌呤。生物学评价表明，新化合物具有中等的CK1δ抑制活性。特别是，在 40 µM 浓度下测试的2-氨基-9-苄基腺嘌呤 ( 12 ) 及其 8-溴衍生物14抑制酶，分别留下约 35% 和 42% 的残余活性。对接研究提供了对这些数据的解释，并为进一步开发这些化合物以获得更有效的 CK1δ 抑制剂提供了建议。
• 8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide
  作者：David Bliman、Mariell Pettersson、Mattias Bood、Morten Grøtli

  DOI：10.1016/j.tetlet.2014.03.084

  日期：2014.4

  2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified. (C) 2014 The Authors. Published by Elsevier Ltd.
• US6329381B1
  申请人：——

  公开号：US6329381B1

  公开（公告）日：2001-12-11