2-(2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-α-D-ribofuranosyl)acetonitrile | 872201-78-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-α-D-ribofuranosyl)acetonitrile
• 英文别名: 2-[(3aS,4R,6R,6aR)-2,2,3a-trimethyl-6-(trityloxymethyl)-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-yl]acetonitrile
• CAS: 872201-78-0
• 化学式: C₃₀H₃₁NO₄
• 分子量: 469.58
• InChiKey: QUBSVIVVNQZDLX-GKWDUZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-α-D-ribofuranosyl)acetonitrile 、 Bredereck 试剂 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.5h， 生成 (2E)-3,6-anhydro-2-deoxy-2-C-[(N,N-dimethylamino)methylidene]-4,5-O-isopropylidene-4-C-methyl-7-O-(triphenylmethyl)-D-allo-and D-altro-septononitrile
  参考文献：
  名称：

  [EN] C-PURINE NUCLEOSIDE ANALOGS AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYMERASE
  [FR] ANALOGUES NUCLEOSIDIQUES DE C-PURINE, SERVANT D'INHIBITEURS D'ARN-POLYMERASE VIRALE ARN-DEPENDANTE

  摘要：

  公开号：

  WO2005123087A3
• 作为产物：
  描述：

  (3aR,6R,6aR)-2,2,3a-trimethyl-4-prop-2-enoxy-6-(trityloxymethyl)-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxole 、 氰甲基磷酸二乙酯 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 4.17h， 生成 2-(2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-β-D-ribofuranosyl)acetonitrile 、 2-(2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-α-D-ribofuranosyl)acetonitrile
  参考文献：
  名称：

  [EN] C-PURINE NUCLEOSIDE ANALOGS AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYMERASE
  [FR] ANALOGUES NUCLEOSIDIQUES DE C-PURINE, SERVANT D'INHIBITEURS D'ARN-POLYMERASE VIRALE ARN-DEPENDANTE

  摘要：

  公开号：

  WO2005123087A3

文献信息

• Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2′-C-methyladenosine
  作者：Gabor Butora、David B. Olsen、Steven S. Carroll、Daniel R. McMasters、Christoph Schmitt、Joseph F. Leone、Mark Stahlhut、Christine Burlein、Malcolm MacCoss

  DOI：10.1016/j.bmc.2007.05.020

  日期：2007.8

  As a part of an ongoing medicinal chemistry effort to identify inhibitors of the Hepatitis C Virus RNA replication, we report here the synthesis and biological evaluation of 9-deaza- and 7,9-dideaza-7-oxa-2'-C-methyladenosine. The parent 2'-C-methyladenosine shows excellent intracellular inhibitory activity but poor pharmacokinetic profile. Replacement of the nucleoside-defining 9-N of 2'-C-methyladenosine with a carbon atom was designed to yield metabolically more stable C-nucleosides. Modifications at position 7 were designed to exploit the importance of the hydrogen bond accepting properties of this heteroatom in modulating the adenosine deaminase (ADA) mediated 6-N deamination. 7-Oxa-7,9-dideaza-2'-C-methyladenosine was found to be a moderately active inhibitor of intracellular HCV RNA replication, whereas 9-deaza- 2'-C-methyladenosine showed only weak activity despite excellent overlap of both of the synthesized target compounds with T-C-methyladenosine's three dimensional structure. Position 7 of the nucleobase proved to be an effective handle for modulating ADA-mediated degradation, with the rate of degradation correlating with the hydrogen-bonding properties at this position. (c) 2007 Elsevier Ltd. All rights reserved.
• C-Purine Nucleoside Analogs As Inhibitors Of Rna-Dependent Rna Viral Polymerase
  申请人：Butora Gabor

  公开号：US20080021047A1

  公开（公告）日：2008-01-24

  The present invention provides C-purine nucleoside analogs and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such C-nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the C-nucleoside compounds of the present invention.
• US7534767B2
  申请人：——

  公开号：US7534767B2

  公开（公告）日：2009-05-19
• [EN] C-PURINE NUCLEOSIDE ANALOGS AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYMERASE<br/>[FR] ANALOGUES NUCLEOSIDIQUES DE C-PURINE, SERVANT D'INHIBITEURS D'ARN-POLYMERASE VIRALE ARN-DEPENDANTE
  申请人：MERCK & CO INC

  公开号：WO2005123087A3

  公开（公告）日：2006-07-13