3β-O-(2-deoxy-2-acetamido-3,4,6-triacetyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)pregn-5-en-20-one | 881910-32-3

• 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: 3β-O-(2-deoxy-2-acetamido-3,4,6-triacetyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)pregn-5-en-20-one
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-6-[[(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-16-(2,5-dimethoxyphenyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 881910-32-3
• 化学式: C₄₃H₅₉NO₁₂
• 分子量: 781.941
• InChiKey: QPWRTLIJMMQPJU-JLFLLZGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  56
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3β-O-(2-deoxy-2-acetamido-3,4,6-triacetyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)pregn-5-en-20-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到N-[(2R,3R,4R,5S,6R)-2-[[(3S,8S,9S,10R,13S,14S,16R,17S)-17-acetyl-16-(2,5-dimethoxyphenyl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
  参考文献：
  名称：

  A Lactosylated Steroid Contributes in Vivo Therapeutic Benefits in Experimental Models of Mouse Lymphoma and Human Glioblastoma

  摘要：

  Various mono- and disaccharides were grafted onto a steroid backbone. Whereas in vitro these glycosylated steroids had no cytotoxic effects on six different human cancer cell lines, several of the glycosylated steroids under study did significantly modify the levels of in vitro migration of the human U373 glioblastoma, the A549 non-small-cell-lung cancer (NSCLC), and the PC-3 prostate cancer cells, with more pronounced effects in the case of a monosubstituted beta-L-fucopyranosyl-steroid (19), a monosubstituted beta-D-isomaltosyl-steroid (22), and a monosubstituted beta-D-lactosyl-steroid (24). These three compounds significantly increased the survival of conventional mice grafted subcutaneously with the P388 lymphoma, a lymphoma that metastasizes toward the liver. In vivo, the monosubstituted beta-D-lactosyl-steroid (24) also increased the antitumor effectiveness of cisplatin, a cytotoxic pro-apoptotic drug, in the case of the P388 lymphoma model. This compound also increased the survival of immunodeficient mice into whose brains human U373 glioblastoma cells had been orthotopically grafted.

  DOI：

  10.1021/jm050971v
• 作为产物：
  描述：

  16-脱氢孕烯醇酮乙酸酯 在 咪唑 、 calcium sulfate 、 四丁基氟化铵 、 碘 、 氰化汞 、 potassium carbonate 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 3β-O-(2-deoxy-2-acetamido-3,4,6-triacetyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)pregn-5-en-20-one
  参考文献：
  名称：

  A Lactosylated Steroid Contributes in Vivo Therapeutic Benefits in Experimental Models of Mouse Lymphoma and Human Glioblastoma

  摘要：

  Various mono- and disaccharides were grafted onto a steroid backbone. Whereas in vitro these glycosylated steroids had no cytotoxic effects on six different human cancer cell lines, several of the glycosylated steroids under study did significantly modify the levels of in vitro migration of the human U373 glioblastoma, the A549 non-small-cell-lung cancer (NSCLC), and the PC-3 prostate cancer cells, with more pronounced effects in the case of a monosubstituted beta-L-fucopyranosyl-steroid (19), a monosubstituted beta-D-isomaltosyl-steroid (22), and a monosubstituted beta-D-lactosyl-steroid (24). These three compounds significantly increased the survival of conventional mice grafted subcutaneously with the P388 lymphoma, a lymphoma that metastasizes toward the liver. In vivo, the monosubstituted beta-D-lactosyl-steroid (24) also increased the antitumor effectiveness of cisplatin, a cytotoxic pro-apoptotic drug, in the case of the P388 lymphoma model. This compound also increased the survival of immunodeficient mice into whose brains human U373 glioblastoma cells had been orthotopically grafted.

  DOI：

  10.1021/jm050971v