1,4-bis[2-(2-quinoxaloyloxy)ethyl 3-amino-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]benzene | 611210-63-0

• 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 3-amino-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]benzene
• CAS: 611210-63-0
• 化学式: C₅₄H₇₆N₆O₁₀Si₂
• 分子量: 1025.4
• InChiKey: WCRSVKCEGLAZKB-UEHHEPSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.29
• 重原子数：
  72.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  183.6
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  1,4-bis[2-(2-quinoxaloyloxy)ethyl 3-amino-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]benzene 在 氟化氢吡啶 作用下， 以 吡啶 为溶剂， 反应 16.0h， 以89%的产率得到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：

  2-tert-butyldimethylsilyloxyethyl 4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-3-N-p-nitrobenzenesulfonylamino-α-D-arabino-hexopyranoside 在 potassium carbonate 、 氟化氢吡啶 、 苯硫酚 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.33h， 生成 1,4-bis[2-(2-quinoxaloyloxy)ethyl 3-amino-4-O-tert-butyldimethylsilyl-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