2,3,5-Tri-O-benzoyl-1-O-metyl-4-C-ethyl-beta-D-ribofuranose | 565450-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-Tri-O-benzoyl-1-O-metyl-4-C-ethyl-beta-D-ribofuranose
• 英文别名: [(2R,3S,4R,5R)-3,4-dibenzoyloxy-2-ethyl-5-methoxyoxolan-2-yl]methyl benzoate
• CAS: 565450-93-3
• 化学式: C₂₉H₂₈O₈
• 分子量: 504.537
• InChiKey: ZOIJLXBOFWTOPK-DZRFEFHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,3,5-Tri-O-benzoyl-1-O-metyl-4-C-ethyl-beta-D-ribofuranose 在 ammonium sulfate 、 硫酸 、 六甲基二硅氮烷 作用下， 以 溶剂黄146 、 间二甲苯 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins

  摘要：

  Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety of modified sugars for the ribofuranose was explored in our laboratories with expectation that certain sugar-modified toyocamycin analogues may be selectively cytotoxic to cancer cells. In this article, we report synthesis and cytotoxicity of 4'-C- and T-C-substituted toyocamycins, which were prepared via the condensations of 4-C- and 5-C-substituted ribofuranose derivatives 11, 12, 13, 20, 21, and 26 with the silylated form of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]py (27) and subsequent debromination and debenzoylation. When compared to the parent toyocamycin, all these analogues showed much lower cytotoxicity to human prostate cancer cells (HTB-81), mouse melanoma cancer cells (B16) as well as normal human fibroblasts. Compound le showed a significant cytotoxicity to the prostate cancer cells and a moderate selectivity. The results suggested that sugar modifications, especially those that may affect phosphorylation of nucleosides, could alter cytotoxicity profile significantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00221-2
• 作为产物：
  描述：

  ((3aS,6R,6aR)-6-甲氧基-2,2-二甲基四氢呋喃并[3,4-d][1,3]二氧杂环戊烯-4,4-二基)二甲醇 在 palladium on activated charcoal 、 N,N'-二环己基碳二亚胺 吡啶 、 氢气 、 sodium pentanolate 、 二甲基亚砜 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 乙醚 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 30.5h， 生成 2,3,5-Tri-O-benzoyl-1-O-metyl-4-C-ethyl-beta-D-ribofuranose
  参考文献：
  名称：

  Synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins

  摘要：

  Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety of modified sugars for the ribofuranose was explored in our laboratories with expectation that certain sugar-modified toyocamycin analogues may be selectively cytotoxic to cancer cells. In this article, we report synthesis and cytotoxicity of 4'-C- and T-C-substituted toyocamycins, which were prepared via the condensations of 4-C- and 5-C-substituted ribofuranose derivatives 11, 12, 13, 20, 21, and 26 with the silylated form of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]py (27) and subsequent debromination and debenzoylation. When compared to the parent toyocamycin, all these analogues showed much lower cytotoxicity to human prostate cancer cells (HTB-81), mouse melanoma cancer cells (B16) as well as normal human fibroblasts. Compound le showed a significant cytotoxicity to the prostate cancer cells and a moderate selectivity. The results suggested that sugar modifications, especially those that may affect phosphorylation of nucleosides, could alter cytotoxicity profile significantly. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00221-2

文献信息

• Sugar modified nucleosides as viral replication inhibitors
  申请人：Hong Zhi

  公开号：US20070032448A1

  公开（公告）日：2007-02-08

  Various 2′-modified nucleoside analogs and corresponding prodrugs are provided, and particularly contemplated methods of use include use as antiviral agents, and especially as antiviral agents against HCV.

  提供了各种2'-修饰核苷类似物及相应的前药，特别考虑使用的方法包括用作抗病毒剂，尤其是用作抗HCV的抗病毒剂。
• Synthesis and cytotoxicity of 4′-C- and 5′-C-substituted toyocamycins
  作者：Esmir Gunic、Jean-Luc Girardet、Zbigniew Pietrzkowski、Cathey Esler、Guangyi Wang

  DOI：10.1016/s0968-0896(00)00221-2

  日期：2001.1

  Toyocamycin and some analogues have shown potent antitumor activities; however, none of them could be used clinically primarily owing to their cytotoxicity to normal human cells. In order to overcome the weakness of these nucleoside analogues, substitution of a variety of modified sugars for the ribofuranose was explored in our laboratories with expectation that certain sugar-modified toyocamycin analogues may be selectively cytotoxic to cancer cells. In this article, we report synthesis and cytotoxicity of 4'-C- and T-C-substituted toyocamycins, which were prepared via the condensations of 4-C- and 5-C-substituted ribofuranose derivatives 11, 12, 13, 20, 21, and 26 with the silylated form of 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]py (27) and subsequent debromination and debenzoylation. When compared to the parent toyocamycin, all these analogues showed much lower cytotoxicity to human prostate cancer cells (HTB-81), mouse melanoma cancer cells (B16) as well as normal human fibroblasts. Compound le showed a significant cytotoxicity to the prostate cancer cells and a moderate selectivity. The results suggested that sugar modifications, especially those that may affect phosphorylation of nucleosides, could alter cytotoxicity profile significantly. (C) 2000 Elsevier Science Ltd. All rights reserved.