2'-deoxy-4'-thioguanosine | 135656-33-6

• 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: 2'-deoxy-4'-thioguanosine
• 英文别名: 9-[2-deoxy-4-thio-β-D-ribofuranosyl]guanine；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl]-1H-purin-6-one；2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)thiolan-2-yl]-1H-purin-6-one
• CAS: 135656-33-6
• 化学式: C₁₀H₁₃N₅O₃S
• 分子量: 283.311
• InChiKey: XLVOEODWHRRGAV-KVQBGUIXSA-N

物化性质

• 熔点：
  259-262 °C(Solv: ethanol (64-17-5))
• 密度：
  2.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  9-Trimethylsilyl-2,6-dichlorpurin 在 sodium azide 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 四氯化锡 、 tin(ll) chloride 、 adenosine deaminase 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 2'-deoxy-4'-thioguanosine
  参考文献：
  名称：

  Synthesis and Biological Activity of 4′-Thio-2′-deoxy Purine Nucleosides

  摘要：

  Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9 alpha and 9 beta anomers as major products. These anomers were separated and converted to 2'-deoxy-4'-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their alpha-anomers.

  DOI：

  10.1080/15257779908041540

文献信息

• The Synthesis and Biological Activity of Certain 4'-Thionucleosides
  作者：John Secrist、William Parker、Kamal Tiwari、Lea Messini、Sue Shaddix、Lucy Rose、L. Lee Bennett、John Montgomery

  DOI：10.1080/15257779508012449

  日期：1995.5.1

  Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented.

  摘要介绍了几种类型的4'-硫代核苷作为潜在抗癌剂的合成和生物学活性。还介绍了有关4'-硫代胸苷的作用机理的详细研究。
• Regio- and Stereoselective Synthesis of 2′-Deoxy-4′-thioguanine Nucleosides: Evaluation of Anti-Hepatitis B Virus Activity and ­Cytotoxicity Leading to Improved Selectivity Index by 4′-C-Cyanation
  作者：Kazuhiro Haraguchi、Hiroki Kumamoto、Shuhei Imoto、Nobuyo Kuwata-Higashi、Hiroaki Mitsuya

  DOI：10.1055/s-0043-1763629

  日期：2024.4

  the α-anomer. By using a derivative obtained from 17, a practical chemical synthesis of 2′-deoxy-4′-thioguanosine was developed. 4′-α-C-Cyano-2′-deoxy-4′-thioguanosine was synthesized, starting from a 4-(acetoxymethyl)-2-deoxy-2-iodo-4-thioribofuranose derivative as a glycosyl donor. An evaluation of the anti-hepatitis B virus (HBV) activity and the cytotoxicity toward the host cell revealed that 4'

  已开发出嘌呤碱基的N 9 - 区域和 β-端基异构体选择性 4'-硫代糖苷化。2-脱氧-2-碘-4-呋喃硫代核糖基糖基供体与N- (6-氯-9H-嘌呤-2-基)-2-甲基丙酰胺之间的反应得到相应的2'-脱氧-4'-硫代嘌呤核苷的产率为 87%，其N 7 -区域异构体的产率为 6%，没有形成 α-端基异构体。通过使用从17获得的衍生物，开发了2'-脱氧-4'-硫鸟苷的实用化学合成方法。以4-(乙酰氧基甲基)-2-脱氧-2-碘-4-硫代呋喃核糖衍生物为糖基供体，合成了 4'-α-C-氰基-2'-脱氧-4'-硫代鸟苷。抗乙型肝炎病毒 (HBV) 活性和对宿主细胞的细胞毒性的评估表明，4'- C -cyano-2'-deoxy-4'-thioguanosine 的抗 HBV 活性比 2'-C-cyano-2'-deoxy-4'-thioguanosine 强约 100 倍。 '-脱氧-4'-硫鸟苷
• Cyclic di-nucleotide compounds as sting agonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10766919B2

  公开（公告）日：2020-09-08

  A class of polycyclic compounds of general formula (I), of general formula (I′), or of general formula (I″), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, and R8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类通式(I)、通式(I′)或通式(I″)的多环化合物，其中Base1、Base2、Y、Ya、Xa、Xa1、Xb、Xb1、Xc、Xc1、Xd、Xd1、R1、R1a、R2、本文定义的 R2a、R3、R4、R4a、R5、R6、R6a、R7、R7a、R8 和 R8a 可用作 I 型干扰素产生的诱导剂，特别是 STING 活性剂。还提供了合成和使用这些化合物的工艺。
• Cyclic di-nucleotide compounds as STING agonists
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10759825B2

  公开（公告）日：2020-09-01

  A class of polycyclic compounds of general formula (I), of general formula (I′), or of general formula (I″), wherein Base1, Base2, Y, Ya, Xa, Xa1, Xb, Xb1, Xc, Xc1, Xd, Xd1, R1, R1a, R2, R2a, R3, R4, R4a, R5, R6, R6a, R7, R7a, R8, and R8a are defined herein, that may be useful as inductors of type I interferon production, specifically as STING active agents, are provided. Also provided are processes for the synthesis and use of compounds.

  一类通式(I)、通式(I′)或通式(I″)的多环化合物，其中Base1、Base2、Y、Ya、Xa、Xa1、Xb、Xb1、Xc、Xc1、Xd、Xd1、R1、R1a、R2、本文定义的 R2a、R3、R4、R4a、R5、R6、R6a、R7、R7a、R8 和 R8a 可用作 I 型干扰素产生的诱导剂，特别是 STING 活性剂。还提供了合成和使用这些化合物的工艺。
• [EN] 2'-DEOXY-4'-THIORIBONUCLEOSIDES AS ANTIVIRAL AND ANTICANCER AGENTS
  申请人：SOUTHERN RESEARCH INSTITUTE

  公开号：WO1991004033A1

  公开（公告）日：1991-04-04

  (EN) 2'-Deoxy-4'-thio-ribonucleosides, intermediates in their production, and their use as antiviral and anticancer agents are disclosed.(FR) L'invention concerne des 2'-désoxy-4'-thio-ribonuclésides, des intermédiaires utilisés dans leur production, et leur utilisation en tant qu'agents antiviraux et anticancéreux.

  (EN) 2'-脱氧-4'-硫核苷酸，它们的中间产物以及作为抗病毒和抗癌药的用途得以披露。 (FR) L'invention concerne des 2'-désoxy-4'-thio-ribonuclésides, des intermédiaires utilisés dans leur production, et leur utilisation en tant qu'agents antiviraux et anticancéreux.