hecogenyl 3,6-di-O-pivaloyl-β-D-glucopyranoside | 1373440-77-7

• 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: hecogenyl 3,6-di-O-pivaloyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4-(2,2-dimethylpropanoyloxy)-3,5-dihydroxy-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethyl-10-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1373440-77-7
• 化学式: C₄₃H₆₈O₁₁
• 分子量: 761.006
• InChiKey: WIHRVAAKJZJGCV-NQYLYJFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  hecogenyl 3,6-di-O-pivaloyl-β-D-glucopyranoside 、 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到hecogenyl 2,4-di-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-3,6-di-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  New insights into the structure–cytotoxicity relationship of spirostan saponins and related glycosides

  摘要：

  A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5 alpha-hydroxy-laxogenyl beta-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated beta-D-glucosides of 5 alpha-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.026
• 作为产物：
  描述：

  海柯吉宁 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 hecogenyl 3,6-di-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  New insights into the structure–cytotoxicity relationship of spirostan saponins and related glycosides

  摘要：

  A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5 alpha-hydroxy-laxogenyl beta-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated beta-D-glucosides of 5 alpha-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.026

文献信息

• New insights into the structure–cytotoxicity relationship of spirostan saponins and related glycosides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Sara Estévez、María Teresa Marrero、Francisco Estévez、Jaime Bermejo、Daniel G. Rivera

  DOI：10.1016/j.bmc.2012.02.026

  日期：2012.4

  A variety of spirostan saponins and related glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). A linear glycosylation strategy allowed for accessing a variety of functionalization patterns at both the spirostanic and the saccharide moieties, which provides new information regarding the structure-cytotoxicity relationship of this family of steroidal glycosides. Intriguing results were achieved with respect to hecogenyl and 5 alpha-hydroxy-laxogenyl beta-chacotriosides, turning out to be the former very cytotoxic and the latter no cytotoxic at all. Importantly, the partially pivaloylated beta-D-glucosides of 5 alpha-hydroxy-laxogenin were the most potent cytotoxic compounds among all tested glycosides. This comprises the first report on acylated spirostanyl glucosides displaying significant cytotoxicity, and therefore, it opens up new opportunities toward the development of saponin analogues as anticancer agents. (C) 2012 Elsevier Ltd. All rights reserved.