2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulononitrile | 410082-11-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulononitrile
• 英文别名: [(2S,3S,4R,5S)-3-azido-4-benzoyloxy-5-cyanooxolan-2-yl]methyl benzoate
• CAS: 410082-11-0
• 化学式: C₂₀H₁₆N₄O₅
• 分子量: 392.371
• InChiKey: SLIZGROUKUCLAS-MHORFTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulononitrile 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以58%的产率得到5-(3-azido-2,5-di-O-benzoyl-3-deoxy-β-D-xylofuranosyl)tetrazole
  参考文献：
  名称：

  Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties

  摘要：

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01126-7
• 作为产物：
  描述：

  2,5-anhydro-4,6-di-O-benzoyl-3-O-methanesulfonyl-D-glucose ethylene acetal 在 吡啶 、 盐酸 、 sodium azide 、 盐酸羟胺 、 sodium acetate 、 甲基磺酰氯 、 三氟乙酸 、 calcium carbonate 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 312.5h， 生成 2,5-anhydro-4-azido-3,6-di-O-benzoyl-4-deoxy-D-gulononitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties

  摘要：

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01126-7

文献信息

• Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties
  作者：Mirjana Popsavin、Ljilja Torović、Saša Spaić、Srdjan Stankov、Agneš Kapor、Zoran Tomić、Velimir Popsavin

  DOI：10.1016/s0040-4020(01)01126-7

  日期：2002.1

  3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2'-benzamido (15) and 3'-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.