5-iodo-2'-C-methyluridine | 1203461-96-4

• 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: 5-iodo-2'-C-methyluridine
• 英文别名: 1-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyltetrahydrofuran-2-yl)-5-iodopyrimidine-2,4(1H,3H)-dione；1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-yl]-5-iodopyrimidine-2,4-dione
• CAS: 1203461-96-4
• 化学式: C₁₀H₁₃IN₂O₆
• 分子量: 384.128
• InChiKey: DUXPOYGBBRNGIT-LTNPLRIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-iodo-2'-C-methyluridine 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  NMR-based conformational analysis of 2′,6-disubstituted uridines and antiviral evaluation of new phosphoramidate prodrugs

  摘要：

  Six novel phosphoramidate prodrugs of uridine analogues, with structural modifications introduced at the 6- and 2',6-positions, have been prepared and evaluated for selective antiviral activity against hepatitis C virus, as well as other positive-stranded RNA viruses. An analysis of the conformational properties of the parent nucleosides was carried out using two-dimensional NMR spectroscopy based experiments, highlighting a 3'-endo (North) sugar puckering preference and syn orientation. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.07.003
• 作为产物：
  描述：

  tri-O-benzoyl-5-iodo-2'-C-methyluridine 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以90%的产率得到5-iodo-2'-C-methyluridine
  参考文献：
  名称：

  Synthesis and Antiviral Evaluation of 2′-C-Methyl Analogues of 5-Alkynyl- and 6-Alkylfurano- and Pyrrolo[2,3-d]Pyrimidine Ribonucleosides

  摘要：

  A series of novel 2'-C-methylribonucleosides, involving 5-iodo and 5-alkynyl uridine analogues as well as related bicyclic furano- and pyrrolo[2,3-d]pyrimidinone compounds, has been synthesized and evaluated for their inhibitory effect on replication of the hepatitis C virus (HCV). The new nucleoside analogues did not show meaningful anti-HCV activity.

  DOI：

  10.1080/15257770903128870

文献信息

• [EN] CYTIDINE LIBRARIES AND COMPOUNDS SYNTHESIZED BY SOLID-PHASE COMBINATORIAL STRATEGIES<br/>[FR] BIBLIOTHEQUES A CYTIDINE ET COMPOSES DE CES BIBLIOTHEQUES DONT LA SYNTHESE REPOSE SUR DES STRATEGIES COMBINATOIRES EN PHASE SOLIDE
  申请人：RIBAPHARM INC

  公开号：WO2003051896A1

  公开（公告）日：2003-06-26

  Substituted cytidine nucleoside analog libraries and compounds in such libraries are prepared in a combinatorial library approach. Particularly preferred heterocyclic bases in such compounds and libraries include amino acid substituted cytidine nucleosides, 2'-O-substituted cytidine nucleosides, and N-substituted cytidine nucleosides, all of which may be useful in the treatment of various conditions, particularly viral infections and neoplastic diseases.