[(1S,3R,5S,7R,9S,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-yl]methyl acetate | 676541-62-1

• 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
• 英文名称: [(1S,3R,5S,7R,9S,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-yl]methyl acetate
• CAS: 676541-62-1
• 化学式: C₃₃H₄₅NO₉S
• 分子量: 631.788
• InChiKey: CJWSTEOSEITQRD-YVDLPNPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸三甲基硅酯 、 [(1S,3R,5S,7R,9S,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-yl]methyl acetate 在 吡啶 作用下， 反应 3.5h， 以30%的产率得到[(1S,3R,5S,7R,9S,10S,12R,14R,15S,18R,19R,22S,23R)-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-10,22-bis(trimethylsilyloxy)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-yl]methyl acetate
  参考文献：
  名称：

  Identification of a Novel Cardenolide (2‘ ‘-Oxovoruscharin) from Calotropis procera and the Hemisynthesis of Novel Derivatives Displaying Potent in Vitro Antitumor Activities and High in Vivo Tolerance:  Structure−Activity Relationship Analyses

  摘要：

  Analysis of the methanolic extract of Calotropis procera root barks enabled the identification of a novel cardenolide (2"-oxovoruscharin) to be made. Of the 27 compounds that we hemisynthesized, one (23) exhibited a very interesting profile with respect to its hemisynthetic chemical yield, its in vitro antitumor activity, its in vitro inhibitory influence on the Na+/K+-ATPase activity, and its in vivo tolerance. Compound 23 displayed in vitro antitumor activity on a panel of 57 human cancer cell lines similar to taxol, and higher than SN-38 (the active metabolite of irinotecan), two of the most potent drugs used in hospitals to combat cancer.

  DOI：

  10.1021/jm049405a
• 作为产物：
  描述：

  uscharin 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 [(1S,3R,5S,7R,9S,10R,12R,14R,15S,18R,19R,22S,23R)-10,22-dihydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)spiro[4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-9,2'-5H-1,3-thiazole]-14-yl]methyl acetate
  参考文献：
  名称：

  Identification of a Novel Cardenolide (2‘ ‘-Oxovoruscharin) from Calotropis procera and the Hemisynthesis of Novel Derivatives Displaying Potent in Vitro Antitumor Activities and High in Vivo Tolerance:  Structure−Activity Relationship Analyses

  摘要：

  Analysis of the methanolic extract of Calotropis procera root barks enabled the identification of a novel cardenolide (2"-oxovoruscharin) to be made. Of the 27 compounds that we hemisynthesized, one (23) exhibited a very interesting profile with respect to its hemisynthetic chemical yield, its in vitro antitumor activity, its in vitro inhibitory influence on the Na+/K+-ATPase activity, and its in vivo tolerance. Compound 23 displayed in vitro antitumor activity on a panel of 57 human cancer cell lines similar to taxol, and higher than SN-38 (the active metabolite of irinotecan), two of the most potent drugs used in hospitals to combat cancer.

  DOI：

  10.1021/jm049405a