4'-O-hydroxy-6'-O-benzylidene triacetate plumieride | 760188-18-9

• 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: 4'-O-hydroxy-6'-O-benzylidene triacetate plumieride
• 英文别名: methyl (1S,4aS,7R,7aS)-4'-[(1S)-1-acetyloxyethyl]-1-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
• CAS: 760188-18-9
• 化学式: C₃₄H₃₈O₁₅
• 分子量: 686.667
• InChiKey: HSDRWVCMSGAZLX-PDWGQDRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  189
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  4'-O-hydroxy-6'-O-benzylidene triacetate plumieride 在 molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 methyl (1S,4aS,7R,7aS)-1-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4'-[(1S)-1-hydroxyethyl]-5'-oxospiro[4a,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-furan]-4-carboxylate
  参考文献：
  名称：

  Structural Modifications of Plumieride Isolated from Plumeria bicolor and the Effect of These Modifications on in Vitro Anticancer Activity

  摘要：

  Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). For investigating the effect of substituents on cytotoxic activity it was modified into a series of compounds. Replacing the methyl ester functionality of plumieride with alkyl amides of variable carbon units improved the cytotoxic activity, and a correlation between overall lipophilicity and cytotoxic activity was observed. In plumieride, the glucose moiety was converted into a di- and trisaccharide by following the protection and deprotection approach, and the resulting compounds produced enhanced cytotoxicity. However, these compounds were found to be less effective than plumeiride containing a dodecyl (12 carbon units) amide group. Among all of the derivatives, the naturally occurring plumieride showed the least cytotoxicity (50% cell kill = 49.5 mug/mL), and the dodecyl amide analogue of plumieridepentaacetate produced the best efficacy (50% cell kill = 11.8 mug/mL). The di- and trisaccharide analogues were found to be slightly less effective than the dodecyl derivative (50% cell kill = 15-17 mug/mL). The in vitro cytotoxicity of the plumieride analogues was determined in radiation-induced fibrosarcoma (RIF) tumor cells.

  DOI：

  10.1021/jo0491408
• 作为产物：
  描述：

  (4aR,6S,7R,8S,8aR)-6-(((1S,4aS,7R,7aS)-4'-((S)-1-acetoxyethyl)-4-(methoxycarbonyl)-5'-oxo-4a,7a-dihydro-1H,5'H-spiro[cyclopenta[c]pyran-7,2'-furan]-1-yl)oxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl diacetate 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以78.6%的产率得到4'-O-hydroxy-6'-O-benzylidene triacetate plumieride
  参考文献：
  名称：

  Structural Modifications of Plumieride Isolated from Plumeria bicolor and the Effect of These Modifications on in Vitro Anticancer Activity

  摘要：

  Plumieride was isolated as one of the major components from the biologically active methanolic extract of the bark of Plumeria bicolor (family Apocynaceae). For investigating the effect of substituents on cytotoxic activity it was modified into a series of compounds. Replacing the methyl ester functionality of plumieride with alkyl amides of variable carbon units improved the cytotoxic activity, and a correlation between overall lipophilicity and cytotoxic activity was observed. In plumieride, the glucose moiety was converted into a di- and trisaccharide by following the protection and deprotection approach, and the resulting compounds produced enhanced cytotoxicity. However, these compounds were found to be less effective than plumeiride containing a dodecyl (12 carbon units) amide group. Among all of the derivatives, the naturally occurring plumieride showed the least cytotoxicity (50% cell kill = 49.5 mug/mL), and the dodecyl amide analogue of plumieridepentaacetate produced the best efficacy (50% cell kill = 11.8 mug/mL). The di- and trisaccharide analogues were found to be slightly less effective than the dodecyl derivative (50% cell kill = 15-17 mug/mL). The in vitro cytotoxicity of the plumieride analogues was determined in radiation-induced fibrosarcoma (RIF) tumor cells.

  DOI：

  10.1021/jo0491408