[2-(2-quinoxaloyloxy)ethyl] 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside | 611210-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-(2-quinoxaloyloxy)ethyl] 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
• CAS: 611210-54-9
• 化学式: C₂₅H₃₉N₃O₅Si
• 分子量: 489.687
• InChiKey: HBAWFQVDZHCGLN-OCYFJXFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  83.01
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  [2-(2-quinoxaloyloxy)ethyl] 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside 在 氟化氢吡啶 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以79%的产率得到[2-(2-quinoxaloyloxy)ethyl] 3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
  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：

  phenyl 3-azido-4-O-tert-butyldimethylsilyl-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 28.0h， 生成 [2-(2-quinoxaloyloxy)ethyl] 4-O-tert-butyldimethylsilyl-3-(N,N-dimethylamino)-2,3,6-trideoxy-α-D-arabinohexopyranoside
  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