N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide | 206351-43-1

• 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: N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide
• 英文别名: (1S,3aS,3bS,9aR,9bS,11aS)-9a,11a-dimethyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-7-oxo-1,2,3,3a,3b,4,6,8,9,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS: 206351-43-1
• 化学式: C₂₆H₃₀F₃N₃O₄
• 分子量: 505.537
• InChiKey: WIIDVNHUUXSJMZ-IVFONSFGSA-N

物化性质

• 沸点：
  694.5±55.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide 在 甲酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以76.25%的产率得到N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-aza-5α-androstane-17β-carboxamide
  参考文献：
  名称：

  Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

  摘要：

  An N-aryl-3-oxo-4-aza-5 alpha-androst-1-ene-17 beta-carboxamide and three N-aryl or alkyl substituted 17 alpha-hydroxy-3-oxo-4-aza-5 alpha -androstane-17 beta-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17 beta-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.

  DOI：

  10.3987/com-97-s(n)35
• 作为产物：
  描述：

  孕烯醇酮 在 吡啶 、 氢氧化钾 、 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 ammonium acetate 、 碘 、 aluminum isopropoxide 、 sodium carbonate 作用下， 以 甲醇 、 环己酮 、 溶剂黄146 、 甲苯 、 叔丁醇 为溶剂， 反应 27.5h， 生成 N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-17β-carboxamide
  参考文献：
  名称：

  Anti-AIDS agents. Part 36: 1 17-carboxylated steroids as potential anti-HIV agents

  摘要：

  In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 microM and 300, respectively.

  DOI：

  10.1016/s0968-0896(99)00169-8

文献信息

• Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes
  作者：Peng Xia、Zheng-yu Yang、Yi Xia、Hao-bing Zhang、Ke-hua Zhang、Xun Sun、Ying Chen、Yun-qing Zheng

  DOI：10.3987/com-97-s(n)35

  日期：——

  An N-aryl-3-oxo-4-aza-5 alpha-androst-1-ene-17 beta-carboxamide and three N-aryl or alkyl substituted 17 alpha-hydroxy-3-oxo-4-aza-5 alpha -androstane-17 beta-carboxamides were synthesized as antiandrogen candidates from 3-oxoandrost-4-ene-17 beta-carboxylic acid and androst-4-ene-3,17-dione respectively. The chemo- and stereoselective reduction of 3-oxo-4-aza-5-ene intermediates with formic acid and their tautomerism in a solution of chloroform and methanol were described.
• Anti-AIDS agents. Part 36: 1 17-carboxylated steroids as potential anti-HIV agents
  作者：Peng Xia、Zheng-Yu Yang、Yi Xia、Yun-Qing Zheng、L.Mark Cosentino、Kuo-Hsiung Lee

  DOI：10.1016/s0968-0896(99)00169-8

  日期：1999.9

  In our search for novel anti-HIV agents, seven 17-carboxylated steroid derivatives were synthesized and evaluated as potential anti-HIV agents. Compound 13 exhibited potent anti-HIV activity in acutely infected H9 lymphocytes with EC50 and therapeutic index values of 0.8 microM and 300, respectively.