(25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-D-glucopyranoside | 1333212-95-5

• 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-22-oxocholest-5-en-26-yl β-D-glucopyranoside
• 英文别名: [(3S,8S,9S,10R,13S,14S,16S,17R)-16-acetyloxy-10,13-dimethyl-17-[(2S,6R)-6-methyl-3-oxo-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1333212-95-5
• 化学式: C₃₇H₅₈O₁₁
• 分子量: 678.861
• InChiKey: XBOVAVCKDMGHHC-ZSWZTRMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  48
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  169
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  薯蓣皂素 在 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of the glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside: A selective anticancer agent in cervicouterine cell lines

  摘要：

  The synthesis and biological evaluation of the new cholestane glycoside (25R)-3 beta,16 beta-diacetoxy-22oxocholest-5-en-26-yl beta-D-glucopyranoside starting from diosgenin is described. This compound showed selective antiproliferative activity against CaSki, ViBo, and HeLa cervicouterine cancer cells. Its effect on the cell-cycle was determined. The cytotoxic effects of the title compound on cervicouterine cancer cell lines and human lymphocytes indicate that the main cell death process is not necrosis; hence it is not cytotoxic. The title compound induced apoptosis in cervicouterine cancer cells. Importantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of peripheral blood lymphocytes. The title compound showed selective antitumor activity and greater antiproliferative activity than its aglycon, and therefore serves as a promising lead candidate for further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.058

文献信息

• Synthesis and biological evaluation of the glycoside (25R)-3β,16β-diacetoxy-22-oxocholest-5-en-26-yl β-d-glucopyranoside: A selective anticancer agent in cervicouterine cell lines
  作者：María A. Fernández-Herrera、Hugo López-Muñoz、José M.V. Hernández-Vázquez、Moisés López-Dávila、Sankar Mohan、María L. Escobar-Sánchez、Luis Sánchez-Sánchez、B. Mario Pinto、Jesús Sandoval-Ramírez

  DOI：10.1016/j.ejmech.2011.05.058

  日期：2011.9

  The synthesis and biological evaluation of the new cholestane glycoside (25R)-3 beta,16 beta-diacetoxy-22oxocholest-5-en-26-yl beta-D-glucopyranoside starting from diosgenin is described. This compound showed selective antiproliferative activity against CaSki, ViBo, and HeLa cervicouterine cancer cells. Its effect on the cell-cycle was determined. The cytotoxic effects of the title compound on cervicouterine cancer cell lines and human lymphocytes indicate that the main cell death process is not necrosis; hence it is not cytotoxic. The title compound induced apoptosis in cervicouterine cancer cells. Importantly, the antiproliferative activity on tumor cells did not affect the proliferative potential of peripheral blood lymphocytes. The title compound showed selective antitumor activity and greater antiproliferative activity than its aglycon, and therefore serves as a promising lead candidate for further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.