9-benzyl-2-n-butoxyadenine | 83492-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-benzyl-2-n-butoxyadenine
• 英文别名: 9-benzyl-2-butoxyadenine；6-Amino-9-benzyl-2-butoxypurine；9-benzyl-2-butoxypurin-6-amine
• CAS: 83492-16-4
• 化学式: C₁₆H₁₉N₅O
• 分子量: 297.36
• InChiKey: JCVKJQUOQXIDAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 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：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-n-butoxyadenine 在 溴 、 sodium acetate 、 sodium hydroxide 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 19.0h， 生成 6-氨基-9-苄基-2-丁氧基-7H-嘌呤-8-酮
  参考文献：
  名称：

  轻松合成功能化的Toll样受体7激动剂。

  摘要：

  Toll样受体7激动剂的蛋白结合物已显示出引发强大的免疫反应。为了促进我们在这一领域的研究，我们小组已经开发出了许多保留免疫刺激活性的功能化衍生物的有效合成方法。

  DOI：

  10.1016/j.tetlet.2014.11.126
• 作为产物：
  描述：

  2-氯-6-氨基嘌呤 在 potassium carbonate 作用下， 以 二甲基亚砜 、 正丁醇 为溶剂， 反应 54.03h， 生成 9-benzyl-2-n-butoxyadenine
  参考文献：
  名称：

  轻松合成功能化的Toll样受体7激动剂。

  摘要：

  Toll样受体7激动剂的蛋白结合物已显示出引发强大的免疫反应。为了促进我们在这一领域的研究，我们小组已经开发出了许多保留免疫刺激活性的功能化衍生物的有效合成方法。

  DOI：

  10.1016/j.tetlet.2014.11.126

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。
• Synthesis and bronchodilating activity of 2,9-disubstituted adenine derivatives: BB-1502 (9-cyclohexy-2-n-propoxy-9H-adenine) and its analogs.
  作者：TAKAYUKI NAITO、SUSUMU NAKAGAWA、TAKAAKI OKITA、HARUHIRO YAMASHITA、TETSURO YAMASAKI、HIDEO KAMEI、KOZO TOMATSU、HIDEYO IMANISHI、HIROSHI KAWAGUCHI

  DOI：10.1248/cpb.30.2011

  日期：——

  A series of 2, 9-disubstituted adenine derivatives was prepared and evaluated for bronchodilating activity. 9-(2-Cyclohexenyl), 9-tetrahydropyranyl and 9-benzyl derivatives of 2, 6-dichloropurine were converted to the 2-chloroadenines. Subsequent nucleophilic substitution of the 2-chloro group with alkoxides, mercaptides and amines afforded the desired compounds. 9-Cyclohexyl derivatives were prepared by hydrogenation of the corresponding 9-cyclohexenyl compounds. Bronchodilating activities of the new adenine derivatives were evaluated in a number of biological systems. 9-(2-Cyclohexenyl)- and 9-cyclohexyladenines having an ethoxy, n-propoxy, n-butoxy or n-propylthio group at the 2-position showed potent bronchodilating activity. Reduced activity was observed with lower or higher alkoxy homologs and branched alkoxy congeners. 9-Cyclohexyl-2-n-propoxy-9H-adenine (designated as BB-1502) was selected for further studies in view of its high intrinsic activity and favorable pharmacological profile.

  一系列2,9-二取代的腺苷衍生物被制备并评估其支气管扩张活性。9-(2-环己烯基)、9-四氢吡喃基和9-苄基的2,6-二氯嘌呤衍生物被转化为2-氯腺嘌呤。随后用醇盐、硫醇盐和胺对2-氯基团进行亲核取代，得到目标化合物。通过还原相应的9-环己烯基化合物制备9-环己基衍生物。这些新的腺苷衍生物的支气管扩张活性在一系列生物系统中进行了评估。在2位具有乙氧基、正丙氧基、正丁氧基或正丙硫基的9-(2-环己烯基)-和9-环己基腺嘌呤显示出强效的支气管扩张活性。较低或较高的醇氧同系物以及支链醇氧类似物的活性降低。9-环己基-2-正丙氧基-9H-腺嘌呤（标记为BB-1502）因其高内在活性和良好的药理学特性被选中进行进一步研究。
• 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。
• Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers
  作者：Kosaku Hirota、Kazunori Kazaoka、Hironao Sajiki

  DOI：10.1016/s0968-0896(03)00234-7

  日期：2003.7

  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.
• US6329381B1
  申请人：——

  公开号：US6329381B1

  公开（公告）日：2001-12-11