2,3-O-isopropylidene-1-hydroxy-2-C-methyl-5-O-trityl-D-ribofuranose | 943638-31-1

• 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: 2,3-O-isopropylidene-1-hydroxy-2-C-methyl-5-O-trityl-D-ribofuranose
• 英文别名: 2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-D-ribofuranose；2,3-O-isopropylidene-2-C-methyl-5-O-(triphenylmethyl)-D-ribofuranose；(3aR,6R,6aR)-2,2,3a-trimethyl-6-(trityloxymethyl)-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 943638-31-1
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: AKRVEOHLIMNAMF-OVHROIHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-O-isopropylidene-1-hydroxy-2-C-methyl-5-O-trityl-D-ribofuranose 在 四氯化碳 、 4 A molecular sieve 、 sodium hydride 、 三氟乙酸 、 三(二甲胺基)膦 作用下， 以 乙醚 为溶剂， 生成 4-氨基-7-(2-C-甲基-beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-5-甲腈
  参考文献：
  名称：

  Murai, Yasushi; Shiroto, Hironori; Ishizaki, Tatsuya, Heterocycles, 1992, vol. 33, # 1, p. 391 - 404

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl 2-C-methyl-2,3-O-(1-methylethylidene)-5-O-trityl-α-D-ribofuranoside 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 二异丁基氢化铝 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以73%的产率得到2,3-O-isopropylidene-1-hydroxy-2-C-methyl-5-O-trityl-D-ribofuranose
  参考文献：
  名称：

  Synthesis and HCV inhibitory properties of 9-deaza- and 7,9-dideaza-7-oxa-2′-C-methyladenosine

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.05.020

文献信息

• Novel Tricyclic Nucleosides or Nucleotides as Therapeutic Agents
  申请人：Cook Phillip Dan

  公开号：US20080200423A1

  公开（公告）日：2008-08-21

  Nucelosides and nucleotides containing a tricyclic base portion thereof are useful for treating infectious diseases and proliferative disorders, such as viral infections or cancer respectively.

  含有三环碱基部分的核苷和核苷酸可用于治疗感染性疾病和增生性疾病，例如病毒感染或癌症。
• NOVEL TRICYCLIC NUCLEOSIDES OR NUCLEOTIDES AS THERAPEUTIC AGENTS
  申请人：Cook Dan Phillip

  公开号：US20070135363A1

  公开（公告）日：2007-06-14

  Nucleosides and nucleotides containing a tricyclic base portion thereof are useful for treating infectious diseases and proliferative disorders, such as viral infections or cancer respectively.

  含有三环碱基部分的核苷和核苷酸可用于治疗感染性疾病和增殖性疾病，如病毒感染或癌症。
• [EN] NOVEL TRICYCLIC NUCLEOSIDES OR NUCLEOTIDES AS THERAPEUTIC AGENTS<br/>[FR] NOUVEAU NUCLEOSIDES OU NUCLEOTIDES TRICYCLIQUES UTILLISES COMME AGENTS THERAPEUTIQUES
  申请人：BIOTA INC

  公开号：WO2005021568A3

  公开（公告）日：2005-04-21
• [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
• 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.