(2S,4S)-(+)-4-O-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexapyranosyl)-2-fluoroacetyl-2,4,5,12-tetrahydroxy-1,2,3,4-tetrahydro-6,11-naphthacenedione | 116710-05-5

• 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: (2S,4S)-(+)-4-O-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexapyranosyl)-2-fluoroacetyl-2,4,5,12-tetrahydroxy-1,2,3,4-tetrahydro-6,11-naphthacenedione
• 英文别名: 3'-N-trifluoroacetyl-14-fluoro-4-demethoxydaunorubicin；2,2,2-trifluoro-N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-(2-fluoroacetyl)-3,5,12-trihydroxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]acetamide
• CAS: 116710-05-5
• 化学式: C₂₈H₂₅F₄NO₁₀
• 分子量: 611.501
• InChiKey: AUQPCNNNLXLTNI-WEGFOYQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  43.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  179.69
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,4S)-(+)-4-O-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexapyranosyl)-2-fluoroacetyl-2,4,5,12-tetrahydroxy-1,2,3,4-tetrahydro-6,11-naphthacenedione 生成 (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-(2-fluoroacetyl)-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
  参考文献：
  名称：

  TEHRADZIMA, AIURO;MATSUDA, FUYUXIKO;MATSUMOTO, MITSUERI

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,4S)-(+)-2-fluoroacetyl-2,4,5,11-tetrahydroxy-1,2,3,4-tetrahydro-6,11-naphthcenedione 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 5.83h， 生成 (2S,4S)-(+)-4-O-(2,3,6-trideoxy-3-trifluoroacetamido-α-L-lyxo-hexapyranosyl)-2-fluoroacetyl-2,4,5,12-tetrahydroxy-1,2,3,4-tetrahydro-6,11-naphthacenedione
  参考文献：
  名称：

  Efficient synthesis and antitumor activity of novel 14-fluoroanthracyclines

  摘要：

  DOI：

  10.1016/s0040-4039(00)96527-4

文献信息

• 14-Fluoroanthracyclines. Novel syntheses and antitumor activity.
  作者：TERUYO MATSUMOTO、MASAKO OHSAKI、KAORU YAMADA、FUYUHIKO MATSUDA、SHIRO TERASHIMA

  DOI：10.1248/cpb.36.3793

  日期：——

  The 14-fluoroanthracyclines (5-10) carrying L-daunosamine, D-2-deoxyribose, or L-2-deoxyfucose as their glycosidic sugar moieties, were synthesized starting from (-)-7-deoxy-4-demethoxydaunomycinone ((R)-11a) or (-)-7-deoxydaunomycinone ((R)-11b). As key steps, the synthetic route features a novel fluorination reaction in which tetrabutylammonium fluoride is employed in the presence of a half equivalent of p-toluenesulfonic acid, and the previously explored glycosidation reaction in which trimethylsilyl trifluoromethanesulfonate is utilized as an activating reagent. In P388 in vivo tests, 5, 6, 9, and 10 exhibited prominent cytotoxicity comparable with that of adriamycin (1). Notable antitumor activity was also observed for 6 and 9 in P388 in vivo tests.

  以(-)-7-脱氧-4-去甲氧基大芸霉素酮((R)-11a)或(-)-7-脱氧大芸霉素酮((R)-11b)为出发点，合成了以L-脱氨基糖、D-2-脱氧核糖或L-2-脱氧岩藻糖为糖苷键的14-氟蒽环类化合物(5-10)。作为关键步骤，该合成路线采用了新颖的氟化反应，即在对甲苯磺酸的半当量存在下使用四丁基氟化铵，以及之前探索过的糖苷化反应，即使用三甲基硅基三氟甲磺酸盐作为活化试剂。在 P388 体内试验中，5、6、9 和 10 表现出与阿霉素（1）相当的显著细胞毒性。在 P388 体内试验中，还观察到 6 和 9 具有显著的抗肿瘤活性。
• MATSUMOTO, TERUYO;OHSAKI, MASAKO;YAMADA, KAORU;MATSUDA, FUYUHIKO;TERASHIM+, CHEM. AND PHARM. BULL., 36,(1988) N 10, C. 3793-3804
  作者：MATSUMOTO, TERUYO、OHSAKI, MASAKO、YAMADA, KAORU、MATSUDA, FUYUHIKO、TERASHIM+

  DOI：——

  日期：——