1,4-bis[2-(2-quinoxaloyloxy)ethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-ylmethyl]benzene | 611210-62-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-bis[2-(2-quinoxaloyloxy)ethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-ylmethyl]benzene
• CAS: 611210-62-9
• 化学式: C₆₆H₈₂N₈O₁₈S₂Si₂
• 分子量: 1395.72
• InChiKey: DZGZKFQUARDWJU-NIMZRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.31
• 重原子数：
  96.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  320.58
• 氢给体数：
  0.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  1,4-bis[2-(2-quinoxaloyloxy)ethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-ylmethyl]benzene 在 potassium carbonate 、 氟化氢吡啶 、 苯硫酚 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 1,4-bis[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]benzene
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2
• 作为产物：
  描述：

  (2R,3S,4R)-4-Azido-6-(2-hydroxy-ethoxy)-2-methyl-tetrahydro-pyran-3-ol 在 Lindlar's catalyst 咪唑 、 2,6-二甲基吡啶 、 氢气 、 potassium carbonate 、 氟化氢吡啶 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.5h， 生成 1,4-bis[2-(2-quinoxaloyloxy)ethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranosid-3-ylmethyl]benzene
  参考文献：
  名称：

  Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents

  摘要：

  The quinoxaline moiety in antitumor quinoxaline antibiotics cleaved double stranded DNA at the 5' side guanine of the 5'-GG-3' site upon irradiation with UV light with a long wavelength and without any additive. The quinoxaline-carbohydrate hybrid system was very effective for the DNA cleavage. Furthermore, the quinoxaline-carbohydrate hybrids exhibited strong and selective cytotoxicity against cancer cells with photoirradiation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00820-2