4-amino-7-(2-C-methyl-β-D-ribofuranosyl)imidazo[2,1-f][1,2,4]triazine | 1192264-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-7-(2-C-methyl-β-D-ribofuranosyl)imidazo[2,1-f][1,2,4]triazine
• 英文别名: (2S,3R,4R,5R)-2-(4-aminoimidazo[2,1-f][1,2,4]triazin-7-yl)-5-(hydroxymethyl)-3-methyl-tetrahydrofuran-3,4-diol；(2S,3R,4R,5R)-2-(4-aminoimidazo[2,1-f][1,2,4]triazin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol
• CAS: 1192264-58-6
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: XROGSIFMSJECNU-HGIWHZBTSA-N

物化性质

• 密度：
  1.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-7-(2-C-methyl-β-D-ribofuranosyl)imidazo[2,1-f][1,2,4]triazine 在 磷酸三甲酯 、 三氯氧磷 作用下， 生成 [(2R,3R,4R,5S)-5-(4-aminoimidazo[2,1-f][1,2,4]triazin-7-yl)-3,4-dihydroxy-4-methyloxolan-2-yl]methyl dihydrogen phosphate
  参考文献：
  名称：

  [EN] CARBA-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  [FR] ANALOGUES DE CARBA-NUCLÉOSIDE POUR UN TRAITEMENT ANTIVIRAL

  摘要：

  提供的是式I核苷酸磷酸酯和其前药，包括咪唑[1,5-f][1,2.4]三唑基、咪唑[1,2,4]三唑基和[1,2,4]三唑[4,3-f][1,2,4]三唑基。所提供的化合物、组合物和方法对于治疗黄病毒科病毒感染，特别是丙型肝炎感染，具有益处。其中X1或X2独立地为C-R10或N，且至少其中之一为N。

  公开号：

  WO2009132123A1
• 作为产物：
  描述：

  2-C-甲基-D-核糖酸-1,4-内酯 在 水 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 122.41h， 生成 4-amino-7-(2-C-methyl-β-D-ribofuranosyl)imidazo[2,1-f][1,2,4]triazine
  参考文献：
  名称：

  5’-脱氧-5’-异丙基取代氨基核苷类化合物、 其制备方法和用途

  摘要：

  本发明公开了通式7所示的5’‑脱氧‑5’‑异丙基取代氨基核苷类化合物，该类化合物7的制备方法，以及该类化合物7作为中间体在制备5’‑脱氧‑5’‑多取代氨基核苷类化合物1中的应用。

  公开号：

  CN109748944B

文献信息

• Synthesis and characterization of 2′-C-Me branched C-nucleosides as HCV polymerase inhibitors
  作者：Aesop Cho、Lijun Zhang、Jie Xu、Darius Babusis、Thomas Butler、Rick Lee、Oliver L. Saunders、Ting Wang、Jay Parrish、Jason Perry、Joy Y. Feng、Adrian S. Ray、Choung U. Kim

  DOI：10.1016/j.bmcl.2012.04.065

  日期：2012.6

  A series of 2′-C-methyl branched purine and pyrimidine C-nucleosides were prepared. Their anti-HCV activity and pharmacological properties were profiled, and compared with known 2′-C-Me N-nucleoside counterparts. In particular, 2′-C-Me 4-aza-7,9-dideazaadenosine C-nucleoside (2) was found to have potent and selective anti-HCV activity in vitro as well as a favorable pharmacokinetic profile and in vivo

  制备了一系列2'- C-甲基支链嘌呤和嘧啶C-核苷。对它们的抗 HCV 活性和药理特性进行了分析，并与已知的 2'- C- Me N-核苷对应物进行了比较。特别是，发现 2' - C -Me 4-aza-7,9-dideazaadenosine C -nucleoside ( 2)在体外具有有效和选择性的抗 HCV 活性以及良好的药代动力学特征和体内潜力效力优于相应的N-核苷。
• Discovery and Synthesis of C-Nucleosides as Potential New Anti-HCV Agents
  作者：Alistair G. Draffan、Barbara Frey、Brett Pool、Carlie Gannon、Edward M. Tyndall、Michael Lilly、Paula Francom、Richard Hufton、Rosliana Halim、Saba Jahangiri、Silas Bond、Van T. T. Nguyen、Tyrone P. Jeynes、Veronika Wirth、Angela Luttick、Danielle Tilmanis、Jesse D. Thomas、Melinda Pryor、Kate Porter、Craig J. Morton、Bo Lin、Jianmin Duan、George Kukolj、Bruno Simoneau、Ginette McKercher、Lisette Lagacé、Ma’an Amad、Richard C. Bethell、Simon P. Tucker

  DOI：10.1021/ml500077j

  日期：2014.6.12

  Nucleoside analogues have long been recognized as prospects for the discovery of direct acting antivirals (DAM) to treat hepatitis C virus because they have generally exhibited cross-genotype activity and a high barrier to resistance. C-Nucleosides have the potential for improved metabolism and pharmacokinetic properties over their N-nucleoside counterparts due to the presence of a strong carbon carbon glycosidic bond and a non-natural heterocyclic base. Three 2'CMe-C-adenosine analogues and two 2'CMe-guanosine analogues were synthesized and evaluated for their these analogues were found to inhibit the NS5B polymerase, and pharmacokinetic properties demonstrating the potential of this drug anti-HCV efficacy. The nucleotide triphosphates of four of adenosine analogue 1 was discovered to have excellent class.
• CARBA-NUCLEOSIDE ANALOGS FOR ANTIVIRAL TREATMENT
  申请人：Gilead Sciences, Inc.

  公开号：EP2280973B1

  公开（公告）日：2012-11-28
• US8012941B2
  申请人：——

  公开号：US8012941B2

  公开（公告）日：2011-09-06
• [EN] ANTIVIRAL NUCLEOSIDE ANALOGS<br/>[FR] ANALOGUES NUCLÉOSIDIQUES ANTIVIRAUX
  申请人：BIOCRYST PHARM INC

  公开号：WO2010036407A2

  公开（公告）日：2010-04-01

  The invention provides compounds as described herein, as well as pharmaceutical compositions comprising the compounds, and synthetic methods and intermediates that are useful for preparing the compounds. The compounds are useful as anti-viral agents and/or as anti-cancer agents.