17β-hydroxy-7α-allyl-4-androsten-3-one | 60533-52-0

• 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: 17β-hydroxy-7α-allyl-4-androsten-3-one
• 英文别名: 7α-Allyltestosteron；7α-allyl-3-oxoandrost-4-en-17β-ol；7α-allyl-4-androsten-17β-ol-3-one；7α-allyltestosterone；(7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-7-prop-2-enyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 60533-52-0
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: SEZGXBYRQLDVNO-FZVWNVPGSA-N

物化性质

• 沸点：
  461.6±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  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
• 作为产物：
  描述：

  17β-<(tert-butyldimethylsilyl)oxy>androsta-4,6-dien-3-one 在 四氯化钛 oxonium 作用下， 以 二氯甲烷 为溶剂， 生成 17β-hydroxy-7α-allyl-4-androsten-3-one
  参考文献：
  名称：

  立体定向合成von7α-烯丙基和7α-丙基甾体

  摘要：

  DOI：

  10.1016/s0040-4039(00)80344-5

文献信息

• Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity
  作者：Joyce F. Grunwell、Harvey D. Benson、J.O'Neal Johnston、Vladimir Petrow

  DOI：10.1016/0039-128x(76)90136-7

  日期：1976.6

  A series of 7alpha- and 7beta- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17beta-hydroxy-7alpha-methyl-5-androsten-3-one (2), 17beta-hydroxy-7alpha-methyl-5-estren-3-one acetate and 17beta-hydroxy-7alpha-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter anti-hormonal properties, and not with the androgenicity of these compounds.
• Synthesis and preliminary in vitro biological evaluation of 7α-testosterone–chlorambucil hybrid designed for the treatment of prostate cancer
  作者：Dominic Bastien、Rana Hanna、Valérie Leblanc、Éric Asselin、Gervais Bérubé

  DOI：10.1016/j.ejmech.2013.04.027

  日期：2013.6

  The synthesis of 7 alpha-testosterone-chlorambucil hybrid is reported. This compound is made from testosterone in a 6 step reaction sequence and with 23% overall yield. An alternative convergent reaction sequence yielded the same hybrid through a Grubbs metathesis reaction between chlorambucil allyl ester and 7 alpha-allyltestosterone with 35% overall yield. KIT assays showed that the hybrid is selective towards hormone-dependent prostate cancer cell line (LNCaP (AR+)) and shows similar activity than the parent drug, chlorambucil. Thus, the new hybrid shows promising potential for drug targeting of hormone-dependent prostate cancer through its capacity of delivering chlorambucil directly to the site of treatment. This could extend the use of chlorambucil to prostate cancer in the future. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 7α-Alkyltestosterone derivatives: Synthesis and activity as androgens and as aromatase inhibitors
  作者：Alan J. Solo、Claude Caroli、Michael V. Darby、Thomas McKay、W.David Slaunwhite、Peter Hebborn

  DOI：10.1016/0039-128x(82)90001-0

  日期：1982.12

  The 7 alpha-ethyl,propyl,butyl,3'-t-butoxypropyl,allyl,3'-hydroxypropyl 17-acetate, and 3'-chloropropyl 17-acetate derivatives of testosterone and the 7 alpha-3'-t-butoxypropyl, 3'-hydroxypropyl,3'-acetoxypropyl,3'-bromoacetoxypropyl, 3'-chloropropyl, and 2'-oxo-3'-bromopropyl derivatives of 4-androstene-3,17-dione were synthesized. The testosterone derivatives were found to lose androgenic and anabolic activity rapidly as the size of the group at the 7 position increased. Many of the compounds were tested as inhibitors of aromatase. The 17-keto compounds were more active than the corresponding alcohols and the enzyme was found to tolerate at least the bulk of a hydroxypropyl group at the C-7 alpha position.
• NICKISH, KLAUS;LAURENT, HENRY, TETRAHEDRON LETT., 29,(1988) N 13, 1533-1536
  作者：NICKISH, KLAUS、LAURENT, HENRY

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG VON 7$g(a)-PROPYLSTEROIDEN
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0262201B1

  公开（公告）日：1991-02-27