(25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside | 1257244-62-4

• 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: (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• CAS: 1257244-62-4
• 化学式: C₆₅H₈₂O₁₂
• 分子量: 1055.36
• InChiKey: BSRKPIPTZFLFSE-HMEOUNCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.63
• 重原子数：
  77.0
• 可旋转键数：
  23.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以95%的产率得到(25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the steroidal glycoside (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-d-glucopyranoside and its anti-cancer properties on cervicouterine HeLa, CaSki, and ViBo cells

  摘要：

  The synthesis of the new glycoside (25R)-3 beta,16 beta-diacetoxy-12,22-dioxo-5 alpha-cholestan-26-yl beta-D-glucopyranoside starting from hecogenin is described. This compound showed anti-cancer activity against cervicouterine cancer cells HeLa. CaSki and ViBo in the micromolar range. Its effect on cell proliferation, cell cycle and cell death is also described. The cytotoxic effect of the title compound on HeLa, CaSki and ViBo cells and human lymphocytes was evaluated through the LDH released in the culture supernatant, indicating that the main cell death process is not necrosis; the null effect on lymphocytes implies that it is not cytotoxic. The ability of this novel glycoside to induce apoptosis was investigated; several apoptosis events like chromatin condensation, formation of apoptotic bodies, as well as the increase in the expression of active caspase-3 and the fragmentation of DNA confirmed that the compound induced apoptosis in cervicouterine cancer cells. Significantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of normal fibroblasts from cervix and peripheral blood lymphocytes. The glycoside showed selective antitumor activity and greater antiproliferative activity than its aglycon; it therefore serves as a promising lead candidate for further optimization. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.051
• 作为产物：
  描述：

  (25R)-26-hydroxy-12,22-dioxo-5α-cholestan-3β,16β-diyl diacetate 、 2,3,4,6-tetra-O-benzyl-D-glucopyranose 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 1.0h， 以93%的产率得到(25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of the steroidal glycoside (25R)-3β,16β-diacetoxy-12,22-dioxo-5α-cholestan-26-yl β-d-glucopyranoside and its anti-cancer properties on cervicouterine HeLa, CaSki, and ViBo cells

  摘要：

  The synthesis of the new glycoside (25R)-3 beta,16 beta-diacetoxy-12,22-dioxo-5 alpha-cholestan-26-yl beta-D-glucopyranoside starting from hecogenin is described. This compound showed anti-cancer activity against cervicouterine cancer cells HeLa. CaSki and ViBo in the micromolar range. Its effect on cell proliferation, cell cycle and cell death is also described. The cytotoxic effect of the title compound on HeLa, CaSki and ViBo cells and human lymphocytes was evaluated through the LDH released in the culture supernatant, indicating that the main cell death process is not necrosis; the null effect on lymphocytes implies that it is not cytotoxic. The ability of this novel glycoside to induce apoptosis was investigated; several apoptosis events like chromatin condensation, formation of apoptotic bodies, as well as the increase in the expression of active caspase-3 and the fragmentation of DNA confirmed that the compound induced apoptosis in cervicouterine cancer cells. Significantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of normal fibroblasts from cervix and peripheral blood lymphocytes. The glycoside showed selective antitumor activity and greater antiproliferative activity than its aglycon; it therefore serves as a promising lead candidate for further optimization. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.051