O-3β-acetoxyandrost-5-ene-17β-acyl-p-bromobenzamidoxime

• 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: O-3β-acetoxyandrost-5-ene-17β-acyl-p-bromobenzamidoxime
• 英文别名: [(Z)-[amino-(4-bromophenyl)methylidene]amino] (3S,8S,9S,10R,13S,14S,17S)-3-acetyloxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
• 化学式: C₂₉H₃₇BrN₂O₄
• 分子量: 557.528
• InChiKey: ZHKNYAVCIUECEW-QQRWRABKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.98
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  O-3β-acetoxyandrost-5-ene-17β-acyl-p-bromobenzamidoxime 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到3β-acetoxy-17β-(5'-[3'-4"-bromophenyl]-1',2',4'-oxadiazolyl)androst-5-ene
  参考文献：
  名称：

  An efficient approach to novel 17-5′-(1′,2′,4′)-oxadiazolyl androstenes via the cyclodehydration of cytotoxic O-steroidacylamidoximes, and an evaluation of their inhibitory action on 17α-hydroxylase/C17,20-lyase

  摘要：

  Novel 17-exo-oxadiazoles in the androst-5-ene series were efficiently synthesized in a two-step sequence via the corresponding O-acylamidoxime intermediates (obtained from steroidal 17-carboxylic acids and amidoximes in the presence of coupling reagent), which then underwent tetrabutylammonium fluoride-induced cyclocondensation under mild reaction conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their inhibitory effect on rat testicular C-17,C-20-lyase and their antiproliferative action on four malignant human adherent cell lines (HeLa, MCF7, A2780 and A431). One of the oxadiazolyl derivatives proved to exert significant enzyme-inhibitory action (IC50 = 0.60 mu M), while some of the isolated O-acylated amidoxime intermediates displayed high cytotoxic activities on all examined cell lines, with IC50 values in the range 0.22-3.94 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.038
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 吡啶 、 溴 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 15.25h， 生成 O-3β-acetoxyandrost-5-ene-17β-acyl-p-bromobenzamidoxime
  参考文献：
  名称：

  An efficient approach to novel 17-5′-(1′,2′,4′)-oxadiazolyl androstenes via the cyclodehydration of cytotoxic O-steroidacylamidoximes, and an evaluation of their inhibitory action on 17α-hydroxylase/C17,20-lyase

  摘要：

  Novel 17-exo-oxadiazoles in the androst-5-ene series were efficiently synthesized in a two-step sequence via the corresponding O-acylamidoxime intermediates (obtained from steroidal 17-carboxylic acids and amidoximes in the presence of coupling reagent), which then underwent tetrabutylammonium fluoride-induced cyclocondensation under mild reaction conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their inhibitory effect on rat testicular C-17,C-20-lyase and their antiproliferative action on four malignant human adherent cell lines (HeLa, MCF7, A2780 and A431). One of the oxadiazolyl derivatives proved to exert significant enzyme-inhibitory action (IC50 = 0.60 mu M), while some of the isolated O-acylated amidoxime intermediates displayed high cytotoxic activities on all examined cell lines, with IC50 values in the range 0.22-3.94 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.038

文献信息

• An efficient approach to novel 17-5′-(1′,2′,4′)-oxadiazolyl androstenes via the cyclodehydration of cytotoxic O-steroidacylamidoximes, and an evaluation of their inhibitory action on 17α-hydroxylase/C17,20-lyase
  作者：Dóra Kovács、János Wölfling、Nikoletta Szabó、Mihály Szécsi、Ida Kovács、István Zupkó、Éva Frank

  DOI：10.1016/j.ejmech.2013.10.038

  日期：2013.12

  Novel 17-exo-oxadiazoles in the androst-5-ene series were efficiently synthesized in a two-step sequence via the corresponding O-acylamidoxime intermediates (obtained from steroidal 17-carboxylic acids and amidoximes in the presence of coupling reagent), which then underwent tetrabutylammonium fluoride-induced cyclocondensation under mild reaction conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their inhibitory effect on rat testicular C-17,C-20-lyase and their antiproliferative action on four malignant human adherent cell lines (HeLa, MCF7, A2780 and A431). One of the oxadiazolyl derivatives proved to exert significant enzyme-inhibitory action (IC50 = 0.60 mu M), while some of the isolated O-acylated amidoxime intermediates displayed high cytotoxic activities on all examined cell lines, with IC50 values in the range 0.22-3.94 mu M. (C) 2013 Elsevier Masson SAS. All rights reserved.