4-benzylamino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-benzylamino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• 英文别名: 4-(benzylamino)-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile；4-(benzylamino)-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• 化学式: C₁₉H₁₉N₅O₄
• 分子量: 381.391
• InChiKey: JFDLRQPFOKGQDM-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氨基-5-氰基-7-(beta-d-呋喃核糖)吡咯并[2,3-d]嘧啶 在 吡啶 、 水 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 34.0h， 生成 4-benzylamino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents

  摘要：

  Several Toyocamycin (4) analogues were examined for their ability to inhibit HCV RNA in a replicon assay. Among the compounds examined 4-methylthio (18) and 5-carboxamide oxime derivatives (23 and 27) of Toyocamycin were found to have good activity and selectivity. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2006.07.003

文献信息

• [EN] DEAZAPURINE NUCLEOSIDE LIBRARIES AND COMPOUNDS<br/>[FR] BANQUES DE DEAZAPURINE NUCLEOSIDES ET COMPOSES
  申请人：RIBAPHARM INC

  公开号：WO2003051899A1

  公开（公告）日：2003-06-26

  Deazapurine nucleoside analog libraries are prepared in a combinatorial library approach. Particularly preferred compounds and libraries include various 7-deazapurines, 9-deazapurines, and 7-deaza-8-azaguanosine as heterocyclic bases, and it is generally preferred that such nucleosides include a ribofuranose as the sugar moiety. It is further contemplated that compounds generated using contemplated libraries may be useful in the treatment of various conditions, particularly viral infections and neoplastic diseases.
• Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents
  作者：Chamakura V.N.S. Varaprasad、Kanda S. Ramasamy、Jean-Luc Girardet、Esmir Gunic、Vicky Lai、Weidong Zhong、Haoyun An、Zhi Hong

  DOI：10.1016/j.bioorg.2006.07.003

  日期：2007.2

  Several Toyocamycin (4) analogues were examined for their ability to inhibit HCV RNA in a replicon assay. Among the compounds examined 4-methylthio (18) and 5-carboxamide oxime derivatives (23 and 27) of Toyocamycin were found to have good activity and selectivity. (c) 2006 Elsevier Inc. All rights reserved.