O^2',O^3',O^5'-tris-trimethylsilyl-N⁴-benzoylcytidine | 118684-37-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: O^2',O^3',O^5'-tris-trimethylsilyl-N⁴-benzoylcytidine
• 英文别名: persilylated N-benzoylcytidine；N-[1-[(2R,3R,4R,5R)-3,4-bis(trimethylsilyloxy)-5-(trimethylsilyloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 118684-37-0
• 化学式: C₂₅H₄₁N₃O₆Si₃
• 分子量: 563.874
• InChiKey: IIIHUSKOGDICAV-VDEHWKIFSA-N

物化性质

• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  98.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O^2',O^3',O^5'-tris-trimethylsilyl-N⁴-benzoylcytidine 在 水 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以100%的产率得到苯甲酰胞苷
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200
• 作为产物：
  描述：

  胞苷 在 吡啶 作用下， 反应 4.5h， 生成 O^2',O^3',O^5'-tris-trimethylsilyl-N⁴-benzoylcytidine
  参考文献：
  名称：

  An Improved Transient Method for the Synthesis ofN-Benzoylated Nucleosides

  摘要：

  The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCI) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.

  DOI：

  10.1081/scc-120017200

文献信息

• Design, synthesis, and antiviral properties of 4′-substituted ribonucleosides as inhibitors of hepatitis C virus replication: The discovery of R1479
  作者：David B. Smith、Joseph A. Martin、Klaus Klumpp、Stewart J. Baker、Peter A. Blomgren、Rene Devos、Caroline Granycome、Julie Hang、Christopher J. Hobbs、Wen-Rong Jiang、Carl Laxton、Sophie Le Pogam、Vincent Leveque、Han Ma、Graham Maile、John H. Merrett、Arkadius Pichota、Keshab Sarma、Mark Smith、Steven Swallow、Julian Symons、David Vesey、Isabel Najera、Nick Cammack

  DOI：10.1016/j.bmcl.2007.02.004

  日期：2007.5

  A series of 4'-substituted ribonucleoside derivatives has been prepared and evaluated for inhibition of hepatitis C virus (HCV) RNA replication in cell culture. The most potent and non-cytotoxic derivative was compound 28 (4'-azidocytidine, R1479) with an IC(50) of 1.28 microM in the HCV replicon system. The triphosphate of compound 28 was prepared and shown to be an inhibitor of RNA synthesis mediated

  制备了一系列的4'-取代核糖核苷衍生物，并评估了其在细胞培养中对丙型肝炎病毒（HCV）RNA复制的抑制作用。最有效和无细胞毒性的衍生物是化合物28（4'-叠氮基吡啶，R1479），在HCV复制子系统中的IC（50）为1.28 microM。制备了化合物28的三磷酸酯，并显示出它是由NS5B（IC（50）= 320 nM）介导的RNA合成抑制剂，NS5B是HCV编码的RNA聚合酶。有关类似物的数据已被用来对这一系列核苷的活性产生一些初步的要求。