(1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-5-[4-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one | 1325214-27-4

• 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: (1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-5-[4-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
• CAS: 1325214-27-4
• 化学式: C₃₇H₅₃N₃O₁₂
• 分子量: 731.841
• InChiKey: WBIFIADSINUJHA-AKFBYIOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  226
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[1-[(1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-5-yl]triazol-4-yl]methoxy]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (1S,2R,5S,6S,7R,9R,11S,12S,15R,16S)-6-hydroxy-15-[(1S)-1-[(2R)-5-(hydroxymethyl)-4-methyl-6-oxo-2,3-dihydropyran-2-yl]ethyl]-2,16-dimethyl-5-[4-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]triazol-1-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-3-one
  参考文献：
  名称：

  Ring A structural modified derivatives of withaferin A and the evaluation of their cytotoxic potential

  摘要：

  Regio-/stereoselective Michael addition to ring A of withaferin-A was performed using an optimized reaction procedure to synthesise a library of 2,3-dihydro,3-beta-substituted withaferin-A derivatives. The analogues thus obtained were evaluated for in vitro cytotoxicity against various human cancer cell lines. 3-Azido analogue exhibited 35-fold increase (IC(50) = 0.02-1.9 mu M) in cytotoxicity against almost the entire cell lines tested when compared to the parent molecule. However, further modifications of 3-azido analogue with various alkynes under Husigen's cycloaddition conditions generated a variety of triazole derivatives with reduced cytotoxicity. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.05.012