(20R)-21-O-benzoyl-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} | 1239885-80-3

• 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-benzoyl-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-benzoyl-20-methylpregn-5-ene-3β,16β,17α,21-tetraol 16-O-{2-O-(4-methoxybenzoyl)-β-D-xylopyranosylo-(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-benzoyloxypropan-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: 1239885-80-3
• 化学式: C₄₉H₆₄O₁₆
• 分子量: 909.038
• InChiKey: BCDIEMIGOYNHFR-QSCSDMBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  65
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.65
• 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-benzoyl-6β-methoxy-20-methyl-3α,5α-cyclopregnane-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 水 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以88%的产率得到(20R)-21-O-benzoyl-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：

  Novel Saponin Compounds, Methods of Preparation Thereof, Use Thereof and Pharmaceutical Compositions

  摘要：

  本发明涉及式II的新型皂苷化合物，其中MBz表示p-甲氧基苯甲酰基，R选自包括C6-10芳基，C6-10芳基-C1-4烷基，C1-18酰基，C3-18烯基，C6-10芳基-C（O）-，C6-10芳基-C1-4烷基-C（O）-的群，其中每个基均可选择性地被取代。这些化合物具有选择性细胞毒活性，可用于治疗增生性疾病。本发明还涉及制备这些新化合物的方法以及含有这些化合物的制药组合物。

  公开号：

  US20110311652A1

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.
• Novel Saponin Compounds, Methods of Preparation Thereof, Use Thereof and Pharmaceutical Compositions
  申请人：Morzycki Jacek Witold

  公开号：US20110311652A1

  公开（公告）日：2011-12-22

  This invention relates to novel saponin compounds of formula II wherein MBz denotes p-methoxybenzoyl, and R is selected from the group comprising C 6-10 aryl, C 6-10 aryl-C 1-4 alkyl-, C 1-18 alkanoyl, C 3-18 alkenyl, C 6-10 aryl-C(O)—, C 6-10 aryl-C 1-4 alkyl-C(O)—, wherein each of the groups can optionally be substituted. These compounds possess a selective cytostatic activity, useful, e.g., in the treatment of proliferative diseases. The invention further relates to methods of preparation of the novel compounds and to a pharmaceutical composition containing these compounds.

  本发明涉及式II的新型皂苷化合物，其中MBz表示p-甲氧基苯甲酰基，R选自包括C6-10芳基，C6-10芳基-C1-4烷基，C1-18酰基，C3-18烯基，C6-10芳基-C（O）-，C6-10芳基-C1-4烷基-C（O）-的群，其中每个基均可选择性地被取代。这些化合物具有选择性细胞毒活性，可用于治疗增生性疾病。本发明还涉及制备这些新化合物的方法以及含有这些化合物的制药组合物。