| 1256497-90-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• CAS: 1256497-90-1
• 化学式: C₂₉H₄₂O₅
• 分子量: 470.649
• InChiKey: FEKFMSRTJINZSK-FTGJUWFPSA-N

反应信息

• 作为反应物：
  描述：

  在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 6.0h， 以80%的产率得到3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
  参考文献：
  名称：

  Stereochemical Survey of Digitoxin Monosaccharides

  摘要：

  A stereochemically diverse array of monosaccharide analogues of the trisaccharide-based cardiac glycoside natural product digitoxin has been synthesized using a de novo asymmetric approach. The analogues were tested for cytotoxicity against nonsmall cell human lung cancer cells (NCI-H460). The results were compared with digitoxin and its aglycone digitoxigenin. Three novel digitoxin monosaccharide analogues with beta-D-digitoxose, alpha-L-rhamnose, and alpha-L-amicetose sugar moieties showed excellent selectivity and activity. Further investigation revealed that digitoxin alpha-L-rhamnose and alpha-L-amicetose analogues displayed similar anti-proliferation effects but with at least 5-fold greater potency in apoptosis induction than digitoxin against NCI-H460. This study demonstrates the ability to improve the digitoxin anticancer activity by modification of the stereochemistry and substitution of the carbohydrate moiety of this known cardiac drug.

  DOI：

  10.1021/ml100219d
• 作为产物：
  描述：

  在 N-甲基吗啉 、 三苯基膦 、 偶氮二甲酸二乙酯 、 2-硝基苯磺酰肼 作用下， 反应 6.08h， 以98%的产率得到
  参考文献：
  名称：

  Stereochemical Survey of Digitoxin Monosaccharides

  摘要：

  A stereochemically diverse array of monosaccharide analogues of the trisaccharide-based cardiac glycoside natural product digitoxin has been synthesized using a de novo asymmetric approach. The analogues were tested for cytotoxicity against nonsmall cell human lung cancer cells (NCI-H460). The results were compared with digitoxin and its aglycone digitoxigenin. Three novel digitoxin monosaccharide analogues with beta-D-digitoxose, alpha-L-rhamnose, and alpha-L-amicetose sugar moieties showed excellent selectivity and activity. Further investigation revealed that digitoxin alpha-L-rhamnose and alpha-L-amicetose analogues displayed similar anti-proliferation effects but with at least 5-fold greater potency in apoptosis induction than digitoxin against NCI-H460. This study demonstrates the ability to improve the digitoxin anticancer activity by modification of the stereochemistry and substitution of the carbohydrate moiety of this known cardiac drug.

  DOI：

  10.1021/ml100219d