9,10-anhydro-N-(trifluoroacetyl)adriamycin | 68168-15-0

• 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: 9,10-anhydro-N-(trifluoroacetyl)adriamycin
• 英文别名: N-(trifluoroacetyl)-9,10-anhydroadriamycin
• CAS: 68168-15-0
• 化学式: C₂₉H₂₆F₃NO₁₁
• 分子量: 621.521
• InChiKey: VVXNQBMEQSJBOS-DYOIPSMXSA-N

物化性质

• 沸点：
  834.8±65.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  44.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  188.92
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  9,10-anhydro-N-(trifluoroacetyl)adriamycin 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 9,10-anhydroadriamycin 14-O-(p-anisyldiphenylmethyl)
  参考文献：
  名称：

  阿霉素类似物。9,10-脱水柔红霉素，9,10-脱水阿霉素和一些相关化合物的制备。

  摘要：

  从柔红霉素，阿霉素和N-（三氟乙酰基）阿霉素14-开始制备标题化合物以及9,10-脱水-N-（三氟乙酰基）阿霉素14-戊酸酯（9,10-脱水-AD 32）。戊酸（公元32年）。另外，通过适当的烯烃的催化氢化获得9-脱氧柔红霉素和9-脱氧-AD 32。所有产品在抑制培养物中CCRF-CEM（人类淋巴细胞白血病）细胞生长方面的活性均明显低于母体药物。结果表明，在蒽环霉素9位的母体化合物中发现，叔醇功能对于促进这些药物的生物活性表达非常重要。

  DOI：

  10.1021/jm00346a027
• 作为产物：
  描述：

  阿霉素 、 三氟乙酸酐 在 吡啶 作用下， 反应 0.5h， 以39%的产率得到9,10-anhydro-N-(trifluoroacetyl)adriamycin
  参考文献：
  名称：

  Adriamycin analogs. Preparation and biological evaluation of some N-perfluoroacyl analogs of daunorubicin, adriamycin, and N-(trifluoroacetyl)adriamycin 14-valerate and their 9,10-anhydro derivatives

  摘要：

  The experimental and clinical antitumor activity, as well as the low toxicity, of N-(trifluoroacetyl)adriamycin 14-valerate (AD 32), a non-DNA binding anthracycline analogue, has led us to prepare and evaluate several N-perfluoroacyl analogues of daunorubicin, adriamycin, and N-(trifluoroacetyl)adriamycin 14-valerate. Target compounds were prepared by reaction of the appropriate perfluoroacyl anhydride with daunorubicin in chloroform-ether, with adriamycin in cold pyridine, and with adriamycin 14-valerate in ethyl acetate. In connection with this work, it was found that reaction of perfluoroacyl anhydrides with N-acylated or N-unsubstituted anthracyclines in pyridine at room temperature afforded with ease and in good yield the corresponding 9,10-anhydro-N-acylated derivatives. A number of products showed good to highly significant antitumor activity in vivo against the murine P388 leukemia system. However, the lack of in vivo antitumor activity of the pentafluoropropionyl and heptafluorobutyryl analogues of N-(trifluoroacetyl)adriamycin 14-valerate is noteworthy. The results continue to show that non-DNA binding anthracycline analogues can exhibit in vivo antitumor activity. Loss of the anthracycline 9-carbinol function by dehydration leads to reduction of biological activity as compared to the parent compound.

  DOI：

  10.1021/jm00344a019