(20R)-21-O-pentanoyl-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} | 1239885-85-8

• 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-pentanoyl-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-pentanoyl-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)-3,17-dihydroxy-10,13-dimethyl-17-[(2R)-1-pentanoyloxypropan-2-yl]-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: 1239885-85-8
• 化学式: C₄₇H₆₈O₁₆
• 分子量: 889.047
• InChiKey: UJZCRWTXMSMCMB-LOXMYWLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  63
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 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-benzyloxy-6β-methoxy-20-methyl-3α,5α-cyclopregnane-16β,17α-diol 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 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0~50.0 ℃ 、5.0 MPa 条件下， 反应 37.5h， 生成 (20R)-21-O-pentanoyl-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

文献信息

• Synthesis and Biological Activity of 22-Deoxo-23-oxa Analogues of Saponin OSW-1
  作者：Jadwiga Maj、Jacek W. Morzycki、Lucie Rárová、Jana Oklešt'ková、Miroslav Strnad、Agnieszka Wojtkielewicz

  DOI：10.1021/jm101648h

  日期：2011.5.12

  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.