17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid | 206351-42-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid
• 英文别名: 3-[(3S,3aS,5aS,6R,9aS,9bS)-3a,6-dimethyl-3-[[4-nitro-3-(trifluoromethyl)phenyl]carbamoyl]-7-oxo-1,2,3,4,5,5a,8,9,9a,9b-decahydrocyclopenta[a]naphthalen-6-yl]propanoic acid
• CAS: 206351-42-0
• 化学式: C₂₆H₃₁F₃N₂O₆
• 分子量: 524.537
• InChiKey: XICFADNRSXYKAE-IVFONSFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  126.61
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid 在 氨 作用下， 以 乙二醇 为溶剂， 以62.94%的产率得到N-(3'-trifluoromethyl-4'-nitrophenyl)-3-oxo-4-azaandrost-5-ene-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：

  3-氧代-雄甾-4-烯-17beta-羧酸 在 potassium permanganate 、 sodium periodate 、 氯化亚砜 、 sodium carbonate 作用下， 以 吡啶 、 水 、 甲苯 、 叔丁醇 为溶剂， 反应 4.0h， 生成 17β-[N-(3'-trifluoromethyl-4'-nitrophenyl)aminocarbonyl]-5-oxo-A-nor-3,5-secoandrostan-3-oic acid
  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

文献信息

• 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.