(5'R)-17β-(1-acetyl-5-p-bromophenyl-3-pyrazolinyl)androst-5-en-3β-yl acetate | 1369424-23-6

• 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: (5'R)-17β-(1-acetyl-5-p-bromophenyl-3-pyrazolinyl)androst-5-en-3β-yl acetate
• CAS: 1369424-23-6
• 化学式: C₃₂H₄₁BrN₂O₃
• 分子量: 581.593
• InChiKey: QLBOQDXISYOTNT-GITRKTANSA-N

反应信息

• 作为反应物：
  描述：

  (5'R)-17β-(1-acetyl-5-p-bromophenyl-3-pyrazolinyl)androst-5-en-3β-yl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以73%的产率得到(5'R)-17β-(1-acetyl-5-p-bromophenyl-3-pyrazolinyl)androst-5-en-3β-ol
  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
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 8.0h， 以348 mg的产率得到(5'R)-17β-(1-acetyl-5-p-bromophenyl-3-pyrazolinyl)androst-5-en-3β-yl acetate
  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