7α-allylandrosta-1,4-diene-3,17-dione | 1440522-10-0

• 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-allylandrosta-1,4-diene-3,17-dione
• 英文别名: (7R,8R,9S,10R,13S,14S)-10,13-dimethyl-7-prop-2-enyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 1440522-10-0
• 化学式: C₂₂H₂₈O₂
• 分子量: 324.463
• InChiKey: HYFHLRQTEBVTMF-MTLIHHAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7α-allylandrosta-1,4-diene-3,17-dione 在 甲酸 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 193.0h， 以28%的产率得到7α-(2ξ,3ξ-epoxypropyl)androsta-1,4-diene-3,17-dione
  参考文献：
  名称：

  探索新的化学功能，以改善甾族化合物对芳香化酶的抑制作用。

  摘要：

  在这项工作中，已经发现了微粒体和乳腺癌细胞中新的有效的甾体芳香化酶抑制剂。3,4-（亚乙二氧基）androsta-3,5-dien-17-one（12）的合成是一种新的甾族化合物，其中含有杂环二恶烯稠合在A环中，导致发现了新的反应，提出了一种机制。建立了新的结构-活性关系。一些5β-类固醇（例如化合物4β，5β-环氧雄烷-17-一（9））显示出芳香化酶抑制活性，因为它们采用与芳香化酶天然底物雄烯二酮类似的A环构型。此外，还公开了增加平面度的新化学特征，特别是3α，4α-环丙烷环，如3α，4α-亚甲基-5α-雄烷-17-一（5）（IC50 =0.11μM）和Δ（9 -11）在C环中的双键，如androsta-4,9（11）-diene-3，17-二酮（13）（IC50 =0.25μM）。此外，诱导拟合对接（IFD）模拟和新陈代谢部位（SoM）预测有助于解释该酶中新的有效甾体芳香酶抑制剂的识别

  DOI：

  10.1016/j.bmc.2016.04.056
• 作为产物：
  描述：

  17β-hydroxy-7α-allyl-4-androsten-3-one 在 Jones reagent 、 苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 丙酮 、 甲苯 为溶剂， 反应 34.0h， 生成 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

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.
• Exploring new chemical functionalities to improve aromatase inhibition of steroids
  作者：Carla L. Varela、Cristina Amaral、Georgina Correia-da-Silva、Saul C. Costa、Rui A. Carvalho、Giosuè Costa、Stefano Alcaro、Natércia A.A. Teixeira、Elisiário J. Tavares-da-Silva、Fernanda M.F. Roleira

  DOI：10.1016/j.bmc.2016.04.056

  日期：2016.6

  In this work, new potent steroidal aromatase inhibitors both in microsomes and in breast cancer cells have been found. The synthesis of the 3,4-(ethylenedioxy)androsta-3,5-dien-17-one (12), a new steroid containing a heterocycle dioxene fused in the A-ring, led to the discovery of a new reaction for which a mechanism is proposed. New structure-activity relationships were established. Some 5β-steroids

  在这项工作中，已经发现了微粒体和乳腺癌细胞中新的有效的甾体芳香化酶抑制剂。3,4-（亚乙二氧基）androsta-3,5-dien-17-one（12）的合成是一种新的甾族化合物，其中含有杂环二恶烯稠合在A环中，导致发现了新的反应，提出了一种机制。建立了新的结构-活性关系。一些5β-类固醇（例如化合物4β，5β-环氧雄烷-17-一（9））显示出芳香化酶抑制活性，因为它们采用与芳香化酶天然底物雄烯二酮类似的A环构型。此外，还公开了增加平面度的新化学特征，特别是3α，4α-环丙烷环，如3α，4α-亚甲基-5α-雄烷-17-一（5）（IC50 =0.11μM）和Δ（9 -11）在C环中的双键，如androsta-4,9（11）-diene-3，17-二酮（13）（IC50 =0.25μM）。此外，诱导拟合对接（IFD）模拟和新陈代谢部位（SoM）预测有助于解释该酶中新的有效甾体芳香酶抑制剂的识别