2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one | 176257-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one
• 英文别名: (1R,2S,10S,13S,14R)-7-(4-fluorophenyl)-10,14-dimethyl-6,7,9-triazapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-4(8),5,18-trien-17-one
• CAS: 176257-17-3
• 化学式: C₂₆H₃₀FN₃O
• 分子量: 419.542
• InChiKey: QEJWRLCGYDGCGI-FEVZJFHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 2'-p-fluorophenyl-17a-aza-4α,5α-oxido-D-homo-5-androstano[17,16-c]pyrazol-3-one 、 2'-p-fluorophenyl-17a-aza-4β,5β-oxido-D-homo-5-androstano[17,16-c]pyrazol-3-one
  参考文献：
  名称：

  Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles

  摘要：

  Cholesterol, testosterone acetate and dehydroepiandrosterone acetate were used as starting materials for the preparation of azasteroidal [3,2-c]- and [17,16-c]pyrazole derivatives. In case of the 4-aza androstane series, a mixture of 5 alpha/5 beta epimers 8 was obtained, which were separated by chemical methods. The compounds 4, 5, 10, 12, 13, 15, 16 and 18-22 were screened for antiinflammatory activity using the carrageenan rat paw oedema model. Oxirane 22 was found to be around ten times more potent than hydrocortisone. Evaluation of compounds 14, 18 and 19 for their antineoplastic activity was also carried out at the National Cancer Institute, Bethesda, MD, USA, using standard procedures.

  DOI：

  10.1016/0223-5234(96)89140-9
• 作为产物：
  描述：

  Acetic acid (2S,4aR,4bS,6aS,11aS,11bR)-8-(4-fluoro-phenyl)-4a,6a-dimethyl-2,3,4,4a,4b,5,6,6a,7,8,11,11a,11b,12-tetradecahydro-1H-7,8,9-triaza-cyclopenta[b]chrysen-2-yl ester 在 氢氧化钾 、 aluminum isopropoxide 作用下， 以 环己酮 、 甲苯 为溶剂， 反应 4.75h， 生成 2'-(p-fluorophenyl)-17a-aza-2'H-pyrazolo[4',3':16,17]-D-homoandrost-4-en-3-one
  参考文献：
  名称：

  Synthesis and biological activity of azasteroidal [3,2-c]- and [17,16-c]pyrazoles

  摘要：

  Cholesterol, testosterone acetate and dehydroepiandrosterone acetate were used as starting materials for the preparation of azasteroidal [3,2-c]- and [17,16-c]pyrazole derivatives. In case of the 4-aza androstane series, a mixture of 5 alpha/5 beta epimers 8 was obtained, which were separated by chemical methods. The compounds 4, 5, 10, 12, 13, 15, 16 and 18-22 were screened for antiinflammatory activity using the carrageenan rat paw oedema model. Oxirane 22 was found to be around ten times more potent than hydrocortisone. Evaluation of compounds 14, 18 and 19 for their antineoplastic activity was also carried out at the National Cancer Institute, Bethesda, MD, USA, using standard procedures.

  DOI：

  10.1016/0223-5234(96)89140-9

文献信息

• An aza-steroidal [17,16-<i>c</i>]pyrazole derivative: 2′-(<i>p</i>-fluorophenyl)-17a-aza-2′<i>H</i>-pyrazolo[4′,3′:16,17]-<i>D</i>-homoandrost-4-en-3-one
  作者：S. Thamotharan、V. Parthasarathi、Ranju Gupta、D. P. Jindal、Anthony Linden

  DOI：10.1107/s0108270103029159

  日期：2004.2.15

  crystallographically independent molecules, the core skeletons of which have the same absolute configuration and almost identical conformations, except for differences in the orientation of the p-fluorophenyl ring. The tetrahydropyridine ring adopts a half-chair conformation, while the cyclohexenone ring has a slightly distorted envelope conformation. The cyclohexane rings have chair conformations, sometimes

  标题化合物C（26）H（30）FN（3）O的不对称单元包含两个晶体学独立的分子，其核心骨架具有相同的绝对构型和几乎相同的构型，除了对氟苯基环。四氢吡啶环采用半椅构象，而环己烯酮环则具有略微扭曲的包膜构象。环己烷环具有椅子构象，有时会稍微变形。观察到分子间NH.O，NH.N和CH.F相互作用以及分子内CH.N相互作用。