N-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)-9H-purin-6-yl)benzamide | 159981-08-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: N-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)-9H-purin-6-yl)benzamide
• 英文别名: N-Benzoyl-4'-thioadenosine；N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)thiolan-2-yl]purin-6-yl]benzamide
• CAS: 159981-08-5
• 化学式: C₁₇H₁₇N₅O₄S
• 分子量: 387.419
• InChiKey: NZMQTSLCENJVBH-CNEMSGBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  159
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)-9H-purin-6-yl)benzamide 在 吡啶 、 咪唑 、 叔丁基二甲基氯硅烷 作用下， 反应 22.0h， 生成 N-(9-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tert-butyldimethylsilyl)oxy)-4-hydroxytetrahydrothiophen-2-yl)-9H-purine-6-yl)benzamide
  参考文献：
  名称：

  环状二核苷酸化合物、其制备方法和应用

  摘要：

  本发明公开了环状二核苷酸化合物、其制备方法和应用，具体涉及一种式(I)所示的化合物，其药学上可接受的盐，其制备方法以及其在制备用于治疗和/或预防与激活STING蛋白相关的疾病的药物中的应用或作为疫苗佐剂的应用。所述与激活STING蛋白相关的疾病包括病毒感染，细菌感染，癌症，免疫系统相关疾病等。

  公开号：

  CN109694397B
• 作为产物：
  描述：

  ((3aS,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl)methanol 在 吡啶 、 三甲基氯硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.5h， 生成 N-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)-9H-purin-6-yl)benzamide
  参考文献：
  名称：

  [EN] CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS
  [FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES UTILISÉS COMME AGONISTES STING

  摘要：

  一类具有通用公式（I）的多环化合物的类别，其中Base1，Base2，Y，Za，Xa，Xa1，Xb，Xb1，Xc，Xc1，Xd，Xd1，R1，R1a，R2，R2a，R3，R4，R4a，R5，R6，R6a，R7，R7a，R8，R8a和R9按本说明书中定义，可能对作为I型干扰素产生的诱导剂特别有用，具体作为STING激活剂。还提供了合成和使用化合物的过程。

  公开号：

  WO2019125974A1

文献信息

• 4'-Thio-β-D-oligoribonucleotides: Nuclease Resistance and Hydrogen Bonding Properties
  作者：C. Leydier、L. Bellon、J. -L. Barascut、J. -L. Imbach

  DOI：10.1080/15257779508012526

  日期：1995.5.1

  The syntheses and the study of nuclease resistance and hydrogen bonding of modified oligoribonucleotides, i.e. 4'-thio-beta-D-oligoribonucleotides (4'-S-RNA), are reported.
• 4′-Thio-RNA: Synthesis, Base Pairing Properties and Interaction with Dimerization Initiation Site of HIV-1
  作者：David Dukhan、Florence De Valette、Roland Marquet、Bernard Ehresmann、Chantal Ehresmann、François Morvan、Jean-Louis Barascut、Jean-Louis Imbach

  DOI：10.1080/07328319908044740

  日期：1999.6

  In the present paper, we describe the synthesis of a modified 9-mer oligonucleotide, 4'-S-r(UGUGCACCU) containing for the first time 4'-thio-guanosine units. This modified 9-mer was found to inhibit in vitro genomic RNA dimerization as well as the wild type RNA.
• Investigations toward the selection of fully-modified 4′-thioRNA aptamers: Optimization of in vitro transcription steps in the presence of 4′-thioNTPs
  作者：Noriaki Minakawa、Mioko Sanji、Yuka Kato、Akira Matsuda

  DOI：10.1016/j.bmc.2008.09.048

  日期：2008.11

  We describe herein a method for isolating fully-modified 4 '-thioRNA aptamers against human alpha-thrombin using the SELEX protocol. In order to isolate the desired aptamers, in vitro transcription was examined in the presence of four kinds of 4 '-thioribonucleoside triphosphates (4 '-thioNTPs) in an effort to afford the fully-modified 4 '-thioRNA. The transcription efficiency of the 4 '-thioNTPs was first compared with that of the nucleoside 5 '-(alpha-thio)triphosphates (alpha SNTPs) and found to be less effective than that of the aSNTPs, especially when GTP and/or ATP were substituted for 4 '-thioGTP and/or 4 '-thioATP. Further attempts to improve its efficiency, including the use of a mutant RNA polymerase instead of the wild type, various additives, and 4 '-thioNTP concentrations were unsuccessful. Accordingly, the transcription was performed in the presence of 4 '-thioNTPs together with the natural GTP and ATP at the appropriate concentrations. Although this attempt furnished a highly-modified 4 '-thioRNA, but not a fully-modified 4 '-thioRNA, we eventually succeeded in isolating the fully-modified 4 '-thioRNA aptamers by SELEX using optimized transcription conditions, followed by post-modification of the resulting aptamers. (C) 2008 Elsevier Ltd. All rights reserved.
• CYCLIC DI-NUCLEOTIDE COMPOUNDS AS STING AGONISTS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：EP3727401A1

  公开（公告）日：2020-10-28