(20R)-21-O-heptanoyl-20-methylpregn-5-ene-3β,16β,17α,21-tetraol 16-O-{2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-α-L-arabinopyranoside} | 1239885-87-0

• 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: (20R)-21-O-heptanoyl-20-methylpregn-5-ene-3β,16β,17α,21-tetraol 16-O-{2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-α-L-arabinopyranoside}
• 英文别名: (20R)-21-O-heptanoyl-20-methylpregn-5-ene-3β,16β,17α,21-tetraol 16-O-{2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl-(1→3)-2'-O-acetyl-α-L-arabinopyranoside}；[(2S,3R,4S,5R)-2-[(2S,3R,4S,5S)-3-acetyloxy-2-[[(3S,8R,9S,10R,13S,14S,16S,17S)-17-[(2R)-1-heptanoyloxypropan-2-yl]-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-16-yl]oxy]-5-hydroxyoxan-4-yl]oxy-4,5-dihydroxyoxan-3-yl] 4-methoxybenzoate
• CAS: 1239885-87-0
• 化学式: C₄₉H₇₂O₁₆
• 分子量: 917.101
• InChiKey: XTHAHKMSWVMJBF-QLUTUFGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  65
• 可旋转键数：
  19
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  226
• 氢给体数：
  5
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  (20R)-21-O-heptanoyl-20-methyl-6β-methoxy-3α,5α-cyclopregnan-16β,17α,21-triol 16-O-{2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranoside} 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以92%的产率得到(20R)-21-O-heptanoyl-20-methylpregn-5-ene-3β,16β,17α,21-tetraol 16-O-{2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-α-L-arabinopyranoside}
  参考文献：
  名称：

  Synthesis and Biological Activity of 22-Deoxo-23-oxa Analogues of Saponin OSW-1

  摘要：

  Analogues of the potent cytotoxic saponin OSW-1 were prepared from the readily available steroidal 16 beta,17 alpha,22-triol. The new 22-deoxo-23-oxa analogues of OSW-1 were screened against eight cancer cell lines and normal human fibroblasts. The analogues proved to be slightly less active than OSW-1 but also less toxic to normal cells. They induce concentration- and time-dependent apoptosis of mammalian cancer cells with caspase-3 activation.

  DOI：

  10.1021/jm101648h