8-甲氧基-5H-嘌呤-6-胺 | 28128-32-7

• 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-甲氧基-5H-嘌呤-6-胺
• 英文名称: 8-methoxyadenine
• 英文别名: 8-methoxy-9H-purin-6-amine；8-methoxy-7H-purin-6-amine
• CAS: 28128-32-7
• 化学式: C₆H₇N₅O
• 分子量: 165.154
• InChiKey: IGPPMJCXDBTGHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  89.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  8-甲氧基-5H-嘌呤-6-胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 9-(3-(4-ethylpiperazin-1-yl)propyl)-8-methoxy-9H-purin-6-amine
  参考文献：
  名称：

  A Chemical Switch for Transforming a Purine Agonist for Toll-like Receptor 7 to a Clinically Relevant Antagonist

  摘要：

  Toll-like receptor 7 (TLR7) is an established therapeutic target in myriad autoimmune disorders, but no TLR7 antagonist is available for clinical use to date. Herein, we report a purine scaffold TLR7 antagonist, first-of-its-kind to our knowledge, which was developed by rationally dissecting the structural requirements for TLR7-targeted activity for a purine scaffold. Specifically, we identified a singular chemical switch at C-2 that could make a potent purine scaffold TLR7 agonist to lose agonism and acquire antagonist activity, which could further be potentiated by the introduction of an additional basic center at C-6. We ended up developing a clinically relevant TLR7 antagonist with favorable pharmacokinetics and 70.8% oral bioavailability in mice. Moreover, the TLR7 antagonists depicted excellent selectivity against TLR8. To further validate the in vivo applicability of this novel TLR7 antagonist, we demonstrated its excellent efficacy in preventing TLR7-induced pathology in a preclinical murine model of psoriasis.

  DOI：

  10.1021/acs.jmedchem.0c00011
• 作为产物：
  描述：

  3-Benzyl-8-methoxy-3H-purin-6-ylamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 50.0 ℃ 、101.32 kPa 条件下， 反应 3.0h， 以91%的产率得到8-甲氧基-5H-嘌呤-6-胺
  参考文献：
  名称：

  Purines. LXXIV. Syntheses and Rearrangements of 8-Oxoadenines Monomethylated at the N6-, 1-, and 3-Positions.

  摘要：

  用沸腾的 2 N 盐酸处理 48 小时后，N6-甲基-8-氧代腺嘌呤核苷（1）、1-甲基-8-氧代腺嘌呤核苷（5）和 7-甲基-8-氧代腺嘌呤核苷（8）发生糖苷水解，但速度比相应的 8-未取代化合物慢得多，生成的缩醛（2、6 和 9）的产率为 45%-63%。在这些条件下，N6-甲基-8-氧代腺嘌呤（2）重新排列为 9-甲基-8-氧代腺嘌呤（3）（收率 8%），这可能是通过咪唑环的裂变和再封闭实现的。3- 甲基-8-羟基腺嘌呤（7）也发生了明显的甲基迁移，在类似条件下，用盐酸处理后可得到 1-甲基-8-氧代腺嘌呤（6），产率为 9%。

  DOI：

  10.1248/cpb.44.2318

文献信息

• Microelectronic device for electrochemical detection
  申请人：University of North Carolina at Chapel Hill et al.

  公开号：EP1193315A1

  公开（公告）日：2002-04-03

  A microelectronic device for electrochemical detection. The microelectronic device is suitable for detecting a member of a binding part, in particular a nucleic acid. The microelectronic device comprises a microelectronic substrate, a conductive electrode arranged on the substrate and a first member of a specific binding part immobilized on the substrate adjacent the conductive electrode. The conductive electrode may be a conductive oxidation-reduction detection electrode.

  一种用于电化学检测的微电子装置。该微电子装置适用于检测结合部位的成员，特别是核酸。该微电子装置包括一个微电子基板、一个布置在基板上的导电电极和一个固定在基板上与导电电极相邻的特定结合部位的第一个成员。导电电极可以是导电氧化还原检测电极。
• Short oligonucleotides as vaccine adjuvants and therapeutic agents
  申请人：SPRING BANK PHARMACEUTICALS, INC.

  公开号：US10391166B2

  公开（公告）日：2019-08-27

  The invention provides a method of treating a microbial infection in a subject and a method of improving an immune system response in a subject against a disease, condition, infection, or virus thereof, by administering an effective amount of a nucleoside, short oligonucleotide compound or an analog thereof, or a pharmaceutically acceptable salt, racemate, enantiomer, diastereomer, geometric isomer, or tautomer thereof. In addition, the invention provides methods for treating or preventing a viral infection, bacterial infection, parasitic infection, or fungal infection in a subject (such as, a human). The compounds of the invention include, for example, di-, and trinucleotide compounds as provided herein. The compounds of the invention are useful for different therapeutic applications including, such as, prophylactics and therapeutics. The invention also provides design and synthesis of a compound that is useful for various therapeutic applications as mentioned herein.

  本发明提供了一种治疗受试者微生物感染的方法，以及一种通过施用有效量的核苷、短寡核苷酸化合物或其类似物，或其药学上可接受的盐、外消旋体、对映体、非对映异构体、几何异构体或同系物，改善受试者免疫系统对疾病、病症、感染或病毒的反应的方法。此外，本发明还提供了治疗或预防受试者（如人类）病毒感染、细菌感染、寄生虫感染或真菌感染的方法。本发明的化合物包括例如本文提供的二核苷酸和三核苷酸化合物。本发明的化合物可用于不同的治疗应用，包括预防和治疗等。本发明还提供了一种化合物的设计和合成方法，该化合物可用于本文提及的各种治疗应用。
• Electrochemical detection of nucleic acid hybridization
  申请人：——

  公开号：US20020106683A1

  公开（公告）日：2002-08-08

  A method of detecting a nucleic acid (e.g., DNA, RNA) that contains at least one preselected base (e.g., adenine, guanine, 6-mercaptoguanine, 8-oxo-guanine, and 8-oxo-adenine) comprises (a) reacting the nucleic acid with a transition metal complex capable of oxidizing the preselected base in an oxidation-reduction reaction; (b) detecting the oxidation-reduction reaction; and (c) determining the presence or absence of the nucleic acid from the detected oxidation-reduction reaction at the preselected base. The method may be used in a variety of applications, including DNA sequencing, diagnostic assays, and quantitative analysis.

  一种检测含有至少一种预选碱基（如腺嘌呤、鸟嘌呤、6-巯基鸟嘌呤、8-氧代鸟嘌呤和 8-氧代腺嘌呤）的核酸（如 DNA、RNA）的方法包括：(a) 使核酸与过渡金属络合物反应、腺嘌呤、鸟嘌呤、6-巯基鸟嘌呤、8-氧代鸟嘌呤和 8-氧代腺嘌呤）的核酸的检测方法包括：(a) 使核酸与能在氧化还原反应中氧化预选碱基的过渡金属复合物反应；(b) 检测氧化还原反应；(c) 根据检测到的预选碱基的氧化还原反应确定核酸的存在与否。该方法可用于多种应用，包括 DNA 测序、诊断检测和定量分析。
• Methods for the electrochemical detection of target compounds
  申请人：Thorp Holden H.

  公开号：US20050123937A1

  公开（公告）日：2005-06-09

  The present invention concerns methods for the detection of a target nucleic acid sequence in a sample.

  本发明涉及检测样品中目标核酸序列的方法。
• Potential Purine Antagonists. XV. Preparation of Some 6,8-Disubstituted Purines¹
  作者：Roland K. Robins

  DOI：10.1021/ja01557a051

  日期：1958.12