isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside | 1269649-14-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
• CAS: 1269649-14-0
• 化学式: C₄₃H₄₈O₁₄S
• 分子量: 820.912
• InChiKey: KKNSDUZTMRIJIX-ZGAFTXRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  58.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 isopropyl 2,3,4-tri-O-benzoyl-β-D-xylopyranosyl-(1->3)-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)]-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis

  摘要：

  To investigate the relationship of cytotoxicity and saponins with varied aglycones, based on the structure of indioside E 1, a natural derived anti-tumor active ingredient from Chinese medicinal plant Solanum indicum L., five novel saponins 2-6 bearing the same trisaccharide moiety together with 1 were efficiently synthesized via a transglycosylation strategy. MTT assay revealed the killing effects to tumor cells of the synthesized saponins are varied with the change of aglycones. Furthermore, time-lapse microscopy, LDH release, PI staining, and immunocytochemical investigations demonstrated that the cell death caused by neosaponin 2 was through oncotic necrosis involving plasma membrane perturbation and destruction of cytoskeleton. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.046
• 作为产物：
  描述：

  isopropyl 3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以92%的产率得到isopropyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-3-O-fluorenylmethoxycarbonyl-4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Efficient synthesis of trisaccharide saponins and their tumor cell killing effects through oncotic necrosis

  摘要：

  To investigate the relationship of cytotoxicity and saponins with varied aglycones, based on the structure of indioside E 1, a natural derived anti-tumor active ingredient from Chinese medicinal plant Solanum indicum L., five novel saponins 2-6 bearing the same trisaccharide moiety together with 1 were efficiently synthesized via a transglycosylation strategy. MTT assay revealed the killing effects to tumor cells of the synthesized saponins are varied with the change of aglycones. Furthermore, time-lapse microscopy, LDH release, PI staining, and immunocytochemical investigations demonstrated that the cell death caused by neosaponin 2 was through oncotic necrosis involving plasma membrane perturbation and destruction of cytoskeleton. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.046