(25R)-C-homo-12a-oxa-12-oxo-5α-spirostan-3β-yl 3,6-di-O-pivaloyl-β-D-glucopyranoside | 1391747-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (25R)-C-homo-12a-oxa-12-oxo-5α-spirostan-3β-yl 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,8S,9S,13S,14S,17S,19S)-5',7,9,14-tetramethyl-11-oxospiro[5,10-dioxapentacyclo[11.8.0.02,9.04,8.014,19]henicosane-6,2'-oxane]-17-yl]oxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1391747-46-8
• 化学式: C₄₃H₆₈O₁₂
• 分子量: 777.006
• InChiKey: DUTPMZIFMHDLOG-MGPBMJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  55
• 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：
  156
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (25R)-C-homo-12a-oxa-12-oxo-5α-spirostan-3β-yl 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， 生成
  参考文献：
  名称：

  Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides

  摘要：

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.018
• 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 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 121.0h， 生成 (25R)-C-homo-12a-oxa-12-oxo-5α-spirostan-3β-yl 3,6-di-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides

  摘要：

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.018

文献信息

• Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Sara Estévez、María Teresa Marrero、Francisco Estévez、Daniel G. Rivera

  DOI：10.1016/j.bmc.2012.05.018

  日期：2012.7

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.