2'-C-甲基-6-S-甲基-6-硫代-肌苷 | 172722-76-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: 2'-C-甲基-6-S-甲基-6-硫代-肌苷
• 英文名称: 9-(2-C-methyl-β-D-ribofuranosyl)-6-thiomethyl purine
• 英文别名: 9-(2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine；(2R,3R,4R,5R)-5-(hydroxymethyl)-3-methyl-2-(6-methylsulfanylpurin-9-yl)oxolane-3,4-diol
• CAS: 172722-76-8
• 化学式: C₁₂H₁₆N₄O₄S
• 分子量: 312.349
• InChiKey: ANEIGUBXMDWQAE-YUTYNTIBSA-N

物化性质

• 沸点：
  614.6±65.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-C-甲基-6-S-甲基-6-硫代-肌苷 、 4-甲氧基三苯基氯甲烷 在 吡啶 作用下， 反应 48.0h， 以74%的产率得到9-(5'-O-(p-anisyldiphenylmethyl)-2'-C-methyl-β-D-ribofuranosyl)-6-(methylsulfanyl)purine
  参考文献：
  名称：

  [EN] NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  [FR] DERIVES NUCLEOSIDIQUES DESTINES AU TRAITEMENT DE L'INFECTION PAR LE VIRUS DE L'HEPATITE C

  摘要：

  公开号：

  WO2003093290A3
• 作为产物：
  描述：

  1,3,5-三苯甲酰基-D-呋喃核糖 在 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 氨 、 四氯化钛 、 四氯化锡 、 magnesium sulfate 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2'-C-甲基-6-S-甲基-6-硫代-肌苷
  参考文献：
  名称：

  A concise synthesis of 2′-c-methylribonucleosides

  摘要：

  2'-C-Methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-alpha-D-ribose with good overall yields.

  DOI：

  10.1016/0040-4039(95)01635-u

文献信息

• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：Genelabs Technologies, Inc.

  公开号：US20040147464A1

  公开（公告）日：2004-07-29

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本文揭示了用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：Roberts Christopher Don

  公开号：US20080249060A1

  公开（公告）日：2008-10-09

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• Synthesis of 9-(2-β-C-methyl-β-d-ribofuranosyl)-6-substituted purine derivatives as inhibitors of HCV RNA replication
  作者：Yili Ding、Jean-Luc Girardet、Zhi Hong、Vicky C.H. Lai、Haoyun An、Yung-hyo Koh、Stephanie Z. Shaw、Weidong Zhong

  DOI：10.1016/j.bmcl.2004.11.020

  日期：2005.2

  A series of 9-(2'-beta-C-methyl-p-D-ribofuranosyl)-6-substituted purine derivatives were synthesized as potential inhibitors of HCV RNA replication. Their inhibitory activities in a cell based HCV replicon assay were reported. A prodrug approach was used to further improve the potency of these compounds by increasing the intracellular levels of 5'-monophosphate metabolites. These nucleotide prodrugs showed much improved inhibitory activities of HCV RNA replication. (C) 2004 Elsevier Ltd. All rights reserved.
• A Short, Flexible Route toward 2‘-<i>C</i>-Branched Ribonucleosides
  作者：Rogers E. Harry-O'kuru、Jennifer M. Smith、Michael S. Wolfe

  DOI：10.1021/jo961893+

  日期：1997.3.1

  A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-0-benzoyl-alpha-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC drop CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the beta-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.
• 2′-<i>C</i>-Alkylribonucleosides: Design, Synthesis, and Conformation
  作者：Rogers E. Harry-O'kuru、Emily A. Kryjak、Michael S. Wolfe

  DOI：10.1080/07328319708006205

  日期：1997.7

  Certain 2'-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed.