3β-acetoxy-15β-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-androstan-17β-ol | 1360600-95-8

• 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-acetoxy-15β-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-androstan-17β-ol
• 英文别名: [(3S,5S,8R,9S,10S,13S,14S,15R,17S)-17-hydroxy-10,13-dimethyl-15-[4-(4-methylphenyl)triazol-1-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1360600-95-8
• 化学式: C₃₀H₄₁N₃O₃
• 分子量: 491.674
• InChiKey: QENUCBZPVLFPFP-OPWINVCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-15β-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-androstan-17β-ol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.33h， 以95%的产率得到3β-acetoxy-15β-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-androstan-17-one
  参考文献：
  名称：

  A facile ‘click’ approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro

  摘要：

  Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15 beta-azido-17 beta-hydroxy-5 alpha-androstan-3 beta-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15 beta-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15 beta-triazolyl-5 alpha-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.008
• 作为产物：
  描述：

  15β-azido-17β-hydroxy-5α-androstan-3β-yl acetate 、 4-甲苯基乙炔 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以75%的产率得到3β-acetoxy-15β-[4-(4-tolyl)-1H-1,2,3-triazol-1-yl]-5α-androstan-17β-ol
  参考文献：
  名称：

  A facile ‘click’ approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro

  摘要：

  Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15 beta-azido-17 beta-hydroxy-5 alpha-androstan-3 beta-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15 beta-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15 beta-triazolyl-5 alpha-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.008

文献信息

• A facile ‘click’ approach to novel 15β-triazolyl-5α-androstane derivatives, and an evaluation of their antiproliferative activities in vitro
  作者：Zalán Kádár、Judit Molnár、Gyula Schneider、István Zupkó、Éva Frank

  DOI：10.1016/j.bmc.2012.01.008

  日期：2012.2

  Intermolecular Cu(I)-catalyzed azide-alkyne cycloadditions of 15 beta-azido-17 beta-hydroxy-5 alpha-androstan-3 beta-yl acetate with different terminal alkynes under optimized reaction conditions were carried out to furnish 15 beta-triazolyl derivatives in good yields. Subsequent oxidation of the 'click' products with the Jones reagent afforded the corresponding 17-ketones. All the synthetized compounds were tested on three malignant human cell lines (HeLa, MCF7 and A431) in order to investigate their antiproliferative activities in vitro. Evidence of cell cycle blockade and apoptosis induction was obtained for the most effective five selected compounds by means of flow cytometry and microscopic techniques. The 15 beta-triazolyl-5 alpha-androstane framework may be considered an appropriate base for the design of steroidal antiproliferative agents. (C) 2012 Elsevier Ltd. All rights reserved.