3β-O-(α-D-mannopyranosyl)-(1->3)-[(α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl-lup-20(29)-ene | 1030385-80-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3β-O-(α-D-mannopyranosyl)-(1->3)-[(α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl-lup-20(29)-ene
• 英文别名: (2S,3S,4S,5S,6R)-2-[[(2R,3R,4S,5S,6S)-6-[[(1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl]oxy]-3,5-dihydroxy-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1030385-80-8
• 化学式: C₄₈H₈₀O₁₆
• 分子量: 913.154
• InChiKey: XDIIUXNCMRCNDE-AGXAZWHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  64
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  258
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3β-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1->3)-[(2,3,4,6-tera-O-benzoyl-α-D-mannopyranosyl)-(1->6)]-2,4-di-O-acetyl-α-D-mannopyranosyl-lup-20(29)-ene 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到3β-O-(α-D-mannopyranosyl)-(1->3)-[(α-D-mannopyranosyl)-(1->6)]-α-D-mannopyranosyl-lup-20(29)-ene
  参考文献：
  名称：

  [EN] SACCHARIDE LUPANE DERIVATIVES, THEIR USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE DERIVATIVES
  [FR] DÉRIVÉS DE SACCHARIDE LUPANE, LEUR UTILISATION ET COMPOSITIONS PHARMACEUTIQUES CONTENANT CES DÉRIVÉS

  摘要：

  本发明涉及一般式(I)的糖苷鲁潘衍生物，其中R表示从氢，羟基，氨基，巯基，烷氧基，烷基和糖基组成的群体中独立选择的取代基，R'表示从氢，羟基，烷基，羧基，酰基和糖基组成的群体中独立选择的取代基，其中至少一个R和R'含有糖基。本发明的另一个目的是将这些化合物用作药物和生长调节剂。本发明还包括含有上述衍生物的制药组合物。

  公开号：

  WO2009094958A1

文献信息

• Synthesis of lupane-type saponins bearing mannosyl and 3,6-branched trimannosyl residues and their evaluation as anticancer agents
  作者：Piotr Cmoch、Zbigniew Pakulski、Jana Swaczynová、Miroslav Strnad

  DOI：10.1016/j.carres.2008.02.011

  日期：2008.5

  The saponins modified with mono- or trimannosyl residues can provide a convenient means of delivering drugs to certain human cells via interactions with mannose receptors. In the study reported therein, we developed a convenient approach for the synthesis of 3-O-mannoside and branched trimannoside derivatives of the saponin lupeol and of C-28 acyl esters of 3-O-acetylbetulinic acid bearing the same mannosyl entities. Lupeol and 3-O-acetyl-betulinic acid were mannosylated with tetra-O-benzoyl-or tetra-O-acetyl-alpha-D-mannopyranosyl trichloroacetimidates. De-esterification followed by regioselective dimannosylation of the unprotected monosaccharide derivatives with 2 equiv of tetra-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate selectively yielded O-3,O-6-linked trimannosides. The cytotoxic activity of selected lupane-type saponins (derivatives of lupeol, betulinic acid, and betulin) toward normal human fibroblasts and various cancer cell lines was also compared. (c) 2008 Elsevier Ltd. All rights reserved.