N-(4-nitro-3-trifluoromethyl-phenyl)-3-ferrocenylmethoxy-2-hydroxy-2-methyl-propanamide | 1283675-88-6

• 英文名称: N-(4-nitro-3-trifluoromethyl-phenyl)-3-ferrocenylmethoxy-2-hydroxy-2-methyl-propanamide
• CAS: 1283675-88-6
• 化学式: C₂₂H₂₁F₃FeN₂O₅
• 分子量: 506.261
• InChiKey: YVHQTAMFQRXKMF-GGMCWBHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
  None

反应信息

• 作为产物：
  描述：

  二茂铁甲醇 、 2-甲基-N-[4-硝基-3-(三氟甲基)苯基]环氧乙烷-2-甲酰胺 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以31%的产率得到N-(4-nitro-3-trifluoromethyl-phenyl)-3-ferrocenylmethoxy-2-hydroxy-2-methyl-propanamide
  参考文献：
  名称：

  Synthesis and biological activity of ferrocenyl derivatives of the non-steroidal antiandrogens flutamide and bicalutamide

  摘要：

  A series of ferrocenyl derivatives of the two non steroidal antiandrogens flutamide and bicalutamide have been prepared. Ferrocenyl bicalutamide complexes were initially synthesized in their racemic forms, and subsequently prepared as pure (R) and (S) enantiomers, and their structure was determined by X-ray crystallography. Most of the complexes retain a modest affinity for the androgen receptor and show an antiproliferative effect on both hormone-dependent (LNCaP) and -independent (PC-3) prostate cancer cells. Ferrocenyl derivatives of bicalutamide are the most cytotoxic (IC50 values on PC-3 around 15 mu M); however, they are less potent than the ferrocenyl derivatives of ethynyltestosterone or nilutamide (IC50 around 5 mu M). (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.10.051