3β-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)-pregn-5-en-20-one

• 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'',3'',4'',6''-tetra-O-benzoyl-β-D-glucopyranosyl)-16α-(2',5'-dimethoxyphenyl)-pregn-5-en-20-one
• 英文别名: [(2R,3R,4S,5R,6R)-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]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₆₃H₆₆O₁₃
• 分子量: 1031.21
• InChiKey: YETQBFYIXNAIMB-CHDJMEMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  76
• 可旋转键数：
  19
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3β-O-(2'',3'',4'',6''-tetra-O-benzoyl-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82%的产率得到1-[(3S,8S,9S,10R,13S,14S,16R,17S)-16-(2,5-dimethoxyphenyl)-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
  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-妊娠双烯醇酮 在 咪唑 、 3 A molecular sieve 、 四丁基氟化铵 、 碘 、 silver trifluoromethanesulfonate 、 magnesium 、 1,2-二溴乙烷 、 烯丙基三甲基硅烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 66.0h， 生成 3β-O-(2'',3'',4'',6''-tetra-O-benzoyl-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

文献信息

• A Lactosylated Steroid Contributes in Vivo Therapeutic Benefits in Experimental Models of Mouse Lymphoma and Human Glioblastoma
  作者：Laurent Ingrassia、Prosper Nshimyumukiza、Janique Dewelle、Florence Lefranc、Lise Wlodarczak、Stéphanie Thomas、Gwenaël Dielie、Christelle Chiron、Chantal Zedde、Pierre Tisnès、Rob van Soest、Jean-Claude Braekman、Francis Darro、Robert Kiss

  DOI：10.1021/jm050971v

  日期：2006.3.1

  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.