phenyl 3-azido-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside | 611210-53-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: phenyl 3-azido-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside
• 英文别名: (2R,3S,4R)-4-azido-2-methyl-6-phenylsulfanyloxan-3-ol
• CAS: 611210-53-8
• 化学式: C₁₂H₁₅N₃O₂S
• 分子量: 265.336
• InChiKey: NIZARHBYDAKWFW-CJAZQULPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 3-azido-2,3,6-trideoxy-1-thio-D-arabinohexopyranoside 在 Lindlar's catalyst 咪唑 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 氢气 、 potassium carbonate 、 氟化氢吡啶 、 苯硫酚 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 43.75h， 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
• 作为产物：
  描述：

  methyl 3-azido-2,3,6-trideoxy-α-D-arabino-hexopyranoside 、 苯硫酚 在 三氟化硼乙醚 作用下， 反应 0.83h， 以99%的产率得到phenyl 3-azido-2,3,6-trideoxy-1-thio-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