7α-allyl-3-oxoandrosta-1,4-dien-17β-ol | 1440522-08-6

• 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: 7α-allyl-3-oxoandrosta-1,4-dien-17β-ol
• 英文别名: (7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-7-prop-2-enyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 1440522-08-6
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: VCMZRFQODPCUAH-FZVWNVPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7α-allyl-3-oxoandrosta-1,4-dien-17β-ol 在 Jones reagent 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 以88%的产率得到7α-allylandrosta-1,4-diene-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
• 作为产物：
  描述：

  17β-hydroxy-7α-allyl-4-androsten-3-one 在 苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 34.0h， 以50%的产率得到7α-allyl-3-oxoandrosta-1,4-dien-17β-ol
  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

• 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.