1-(4,5-dihydro-3-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-hydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl)-5-(4-methoxyphenyl) pyrazol-1-yl)ethanone | 1369424-68-9

• 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: 1-(4,5-dihydro-3-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-hydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl)-5-(4-methoxyphenyl) pyrazol-1-yl)ethanone
• 英文别名: (5'S)-17β-(1-acetyl-5-p-methoxyphenyl-3-pyrazolinyl)androst-5-en-3β-ol；1-[(3S)-5-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1369424-68-9
• 化学式: C₃₁H₄₂N₂O₃
• 分子量: 490.686
• InChiKey: OKEYQEWFTPUQNX-GXSNQGPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (5'S)-17β-(1-acetyl-5-p-methoxyphenyl-3-pyrazolinyl)androst-5-en-3β-yl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到1-(4,5-dihydro-3-((10R,13S)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3-hydroxy-10,13-dimethyl-1H-cyclopenta[a]phenanthren-17-yl)-5-(4-methoxyphenyl) pyrazol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis of D-ring-substituted (5′R)- and (5′S)-17β-pyrazolinylandrostene epimers and comparison of their potential anticancer activities

  摘要：

  Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17 beta-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C-17,C-20-lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.02.001

文献信息

• Steroidal pyrazolines and pyrazoles as potential 5α-reductase inhibitors: Synthesis and biological evaluation
  作者：Abid H. Banday、Shameem A. Shameem、Salika Jeelani

  DOI：10.1016/j.steroids.2014.09.004

  日期：2014.12

  Taking pregnenolone as the starting material, two series of pyrazolinyl and pyrazolyl pregnenolones were synthesized through different routes. The synthesis of the analogs of both series is multistep and proceeds in good overall yields. While the key step in the synthesis of pyrazolinyl pregnenolones is the heterocyclization of benzylidine derivatives (3) in presence of hydrazine hydrate, it is the

  以孕烯醇酮为起始原料，通过不同途径合成了两个系列的吡唑啉基和吡唑基孕烯醇酮。两个系列的类似物的合成是多步的，并且以良好的总产率进行。吡唑啉基孕烯醇酮合成的关键步骤是在水合肼存在下苄基衍生物（3）的杂环化反应，但它是3β-羟基-21-羟甲基亚甲基pregn-5-en-3β-ol-20-的缩合反应（ 5）与苯肼合成吡唑基衍生物。测试了两个系列的化合物的5α-还原酶抑制活性。在筛选出具有5α-还原酶抑制活性的所有化合物中，发现化合物4b，4c和6b的活性最高。