7α-allylandrost-4-ene-3,17-dione | 137107-57-4

• 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: 7α-allylandrost-4-ene-3,17-dione
• 英文别名: 7α-allyl-4-androsten-3,17-dione；(7R,8R,9S,10R,13S,14S)-10,13-dimethyl-7-prop-2-enyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 137107-57-4
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: IORXLLVTTVDESX-MTLIHHAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  17β-hydroxy-7α-allyl-4-androsten-3-one 在 Jones reagent 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 以73%的产率得到7α-allylandrost-4-ene-3,17-dione
  参考文献：
  名称：

  Design, synthesis and biochemical studies of new 7α-allylandrostanes as aromatase inhibitors

  摘要：

  Two series of derivatives of 7 alpha-allylandrostenedione, namely its 3-deoxo and 1-ene analogs, were designed and synthesised and their biochemical activity towards aromatase evaluated. In each of these series, the C-17 carbonyl group was further replaced by the hydroxyl and acetoxyl groups. The attained data pointed out that the absence of the C-3 carbonyl group led to a slightly decrease in the inhibitory activity and the introduction of an additional double bond in C-1 revealed to be a very beneficial structural change in the studied compounds (compound 12, IC50 = 0.47 mu M, K-i = 45.00 nM). Furthermore, the relevance of the C-17 carbonyl group in the D-ring as a structural feature required to achieve maximum aromatase inhibitory activity is also observed for this set of derivatives. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2013.02.016

文献信息

• US5227375A
  申请人：——

  公开号：US5227375A

  公开（公告）日：1993-07-13
• [EN] AROMATASE INHIBITORS
  申请人：——

  公开号：WO1991012206A2

  公开（公告）日：1991-08-22

  [FR] De nouveaux inhibiteurs de l'aromatase sont utiles dans des préparations thérapeutiques de traitement de maladies provoquées par l'oestrogène. Ces composés sont des dérivés spécifiques d'androstanedione et d'androstènedione substitué en position alpha ayant un effet fortement inhibiteur de l'aromatase. L'invention concerne la synthèse de ces composés et des compositions pharmaceutiques les contenant.
• Design, synthesis and biochemical studies of new 7α-allylandrostanes as aromatase inhibitors
  作者：Carla L. Varela、Cristina Amaral、Georgina Correia-da-Silva、Rui A. Carvalho、Natércia A. Teixeira、Saul C. Costa、Fernanda M.F. Roleira、Elisiário J. Tavares-da-Silva

  DOI：10.1016/j.steroids.2013.02.016

  日期：2013.7

  Two series of derivatives of 7 alpha-allylandrostenedione, namely its 3-deoxo and 1-ene analogs, were designed and synthesised and their biochemical activity towards aromatase evaluated. In each of these series, the C-17 carbonyl group was further replaced by the hydroxyl and acetoxyl groups. The attained data pointed out that the absence of the C-3 carbonyl group led to a slightly decrease in the inhibitory activity and the introduction of an additional double bond in C-1 revealed to be a very beneficial structural change in the studied compounds (compound 12, IC50 = 0.47 mu M, K-i = 45.00 nM). Furthermore, the relevance of the C-17 carbonyl group in the D-ring as a structural feature required to achieve maximum aromatase inhibitory activity is also observed for this set of derivatives. (C) 2013 Elsevier Inc. All rights reserved.