7-[4-O-(2,3,6-trideoxy-3-amino-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-4-demethoxyadriamycinone hydrochloride

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 蒽环类药物
• 英文名称: 7-[4-O-(2,3,6-trideoxy-3-amino-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-4-demethoxyadriamycinone hydrochloride
• 英文别名: (7S,9S)-7-[(2R,4S,5S,6S)-5-[(2S,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• 化学式: C₃₂H₃₇NO₁₃*ClH
• 分子量: 680.106
• InChiKey: BSRQHWFOFMAZRL-PWPFGEIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  236
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  7-[4-O-(3-amino-2,3,6-trideoxy-3-N,4-O-di-allyloxycarbonyl-α-L-arabino-hexopyranosyl)-2,6-dideoxy-3-O-allyloxycarbonyl-α-L-lyxo-hexopyranosyl]-14-acetoxy-4-demethoxyadriamycinone 在 四(三苯基膦)钯 N,N-二甲基三甲基硅胺 、 三甲基硅乙酸酯 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 7-[4-O-(2,3,6-trideoxy-3-amino-α-L-arabino-hexopyranosyl)-2,6-dideoxy-α-L-lyxo-hexopyranosyl]-4-demethoxyadriamycinone hydrochloride
  参考文献：
  名称：

  Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity

  摘要：

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00411-4

文献信息

• Novel anthracycline oligosaccharides: influence of chemical modifications of the carbohydrate moiety on biological activity
  作者：A Cipollone、M Berettoni、M Bigioni、M Binaschi、C Cermele、E Monteagudo、L Olivieri、D Palomba、F Animati、C Goso、C.A Maggi

  DOI：10.1016/s0968-0896(01)00411-4

  日期：2002.5

  Several observations highlight the importance of the carbohydrate moiety for the biological activity of antitumoural anthracyclines. Here is reported the synthesis, cytotoxicity and topoisomerase II-mediated DNA cleavage intensity of the new oligosaccharide anthracyclines 1-4 modified in the sugar residue. Evaluation of cytotoxic potency on different cell lines, resulted in quite similar values among the different analogues. On the other hand, topoisomerase II-mediated DNA breaks level was different for the various compounds. and was not related to cytotoxicity, thus supporting previous observations reported for some monosaccharide anthracyclines modified in the carbohydrate portion. (C) 2002 Elsevier Science Ltd. All rights reserved.