(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol | 1571926-26-5

• 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: (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 1571926-26-5
• 化学式: C₂₇H₃₄N₂O₂
• 分子量: 418.579
• InChiKey: UVHKEFNFHYSYQK-QOGDKHJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3β-acetoxy-5-androstene-17β-carbaldehyde 在 碘苯二乙酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 9.17h， 生成 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(5-phenyl-1,3,4-oxadiazol-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  A facile access to novel steroidal 17-2′-(1′,3′,4′)-oxadiazoles, and an evaluation of their cytotoxic activities in vitro

  摘要：

  Novel types of 17-exo-heterocycles in the Delta(5) androstene series carrying an 1,3,4-oxadiazole moiety were efficiently synthesized via aldehyde N-acylhydrazone intermediates, obtained from the microwaveassisted condensation of 3 beta-hydroxy-or 3 beta-acetoxyandrost-5-ene-17 beta-carbaldehyde with different acylhydrazides. The subsequent phenyl iodonium diacetate-induced oxidative cyclization proceeded under mild conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their antiproliferative activities on four malignant adherent cell lines (HeLa, MCF7, A2780 and A431), and exhibited the highest potency against HeLa cells, some of them revealing action comparable to that of the reference agent cisplatin. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.069

文献信息

• A facile access to novel steroidal 17-2′-(1′,3′,4′)-oxadiazoles, and an evaluation of their cytotoxic activities in vitro
  作者：Dóra Kovács、Gergő Mótyán、János Wölfling、Ida Kovács、István Zupkó、Éva Frank

  DOI：10.1016/j.bmcl.2014.01.069

  日期：2014.3

  Novel types of 17-exo-heterocycles in the Delta(5) androstene series carrying an 1,3,4-oxadiazole moiety were efficiently synthesized via aldehyde N-acylhydrazone intermediates, obtained from the microwaveassisted condensation of 3 beta-hydroxy-or 3 beta-acetoxyandrost-5-ene-17 beta-carbaldehyde with different acylhydrazides. The subsequent phenyl iodonium diacetate-induced oxidative cyclization proceeded under mild conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their antiproliferative activities on four malignant adherent cell lines (HeLa, MCF7, A2780 and A431), and exhibited the highest potency against HeLa cells, some of them revealing action comparable to that of the reference agent cisplatin. (c) 2014 Elsevier Ltd. All rights reserved.