1-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]-4-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-β-D-arabinopyranosid-3-ylmethyl]benzene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]-4-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-β-D-arabinopyranosid-3-ylmethyl]benzene
• 英文别名: 2-[(2R,4R,5S,6R)-5-hydroxy-4-[[4-[[[(2R,3S,4R,6S)-3-hydroxy-2-methyl-6-[2-(quinoxaline-2-carbonyloxy)ethoxy]oxan-4-yl]amino]methyl]phenyl]methylamino]-6-methyloxan-2-yl]oxyethyl quinoxaline-2-carboxylate
• 化学式: C₄₂H₄₈N₆O₁₀
• 分子量: 796.877
• InChiKey: FUKOBRXDLDIKLU-LJYFLFAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  58
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  206
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  2-喹喔啉甲酰氯 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， 生成 1-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-α-D-arabino-hexopyranosid-3-ylmethyl]-4-[2-(2-quinoxaloyloxy)ethyl 3-amino-2,3,6-trideoxy-β-D-arabinopyranosid-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

文献信息

• Molecular design, chemical synthesis and biological evaluation of quinoxaline–carbohydrate hybrids as novel and selective photo-induced DNA cleaving and cytotoxic agents
  作者：Kazunobu Toshima、Tomonori Kimura、Ryusuke Takano、Tomohiro Ozawa、Akiko Ariga、Yutaka Shima、Kazuo Umezawa、Shuichi Matsumura

  DOI：10.1016/s0040-4020(03)00820-2

  日期：2003.8

  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.