3-methoxy-17α-[3'-(4"-nitro)phenylisoxazol-5'-yl]-estra-1,3,5(10),16-tetraene | 1399860-82-2

• 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: 3-methoxy-17α-[3'-(4"-nitro)phenylisoxazol-5'-yl]-estra-1,3,5(10),16-tetraene
• 英文别名: 5-[(8S,9S,13S,14S)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]-3-(4-nitrophenyl)-1,2-oxazole
• CAS: 1399860-82-2
• 化学式: C₂₈H₂₈N₂O₄
• 分子量: 456.541
• InChiKey: JIJQXINNGMNHBA-DFIMXKNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯甲醛肟 在 吡啶 、 N-氯代丁二酰亚胺 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 三苯基膦 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 28.0h， 生成 3-methoxy-17α-[3'-(4"-nitro)phenylisoxazol-5'-yl]-estra-1,3,5(10),16-tetraene
  参考文献：
  名称：

  Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series

  摘要：

  Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17 alpha-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Delta(16.17) exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780). (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.05.003

文献信息

• Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series
  作者：Dóra Kovács、Zalán Kádár、Gergő Mótyán、Gyula Schneider、János Wölfling、István Zupkó、Éva Frank

  DOI：10.1016/j.steroids.2012.05.003

  日期：2012.9

  Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17 alpha-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Delta(16.17) exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780). (C) 2012 Elsevier Inc. All rights reserved.