17-beta-羟基-5alpha-雄甾-1-烯-3-酮乙酸盐 | 64-82-4

• 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
• 中文名称: 17-beta-羟基-5alpha-雄甾-1-烯-3-酮乙酸盐
• 英文名称: (5α,17β)-3-oxoandrost-1-en-17-yl acetate
• 英文别名: 17β-acetoxy-5α-androst-1-en-3-one；3-oxo-5α-androst-1-en-17β-yl acetate；17β-Acetoxy-5α-androst-1-en-3-on；17-beta-Hydroxy-5alpha-androst-1-en-3-one acetate；[(5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 64-82-4
• 化学式: C₂₁H₃₀O₃
• 分子量: 330.467
• InChiKey: NKZLRJOJLCHNQR-NGFSFWIMSA-N

物化性质

• 溶解度：
  溶于二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17-beta-羟基-5alpha-雄甾-1-烯-3-酮乙酸盐 在 chromium(VI) oxide 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 1-雄烯二酮
  参考文献：
  名称：

  An efficient synthesis of 5α-androst-1-ene-3,17-dione

  摘要：

  S alpha-Androst-1-ene-3,17-dione (5) as a prodrug of 1-testosterone (4) was prepared in four steps from 17 beta-Acetoxy-S alpha-androstan-3-one (stanolone acetate) (1) in high yield. Thus, stanolone acetate (1) was brominated in the presence of hydrogen chloride in acetic acid to give 17 beta-acetoxy-2-bromo-5 alpha-androstan-3-one (2), which underwent dehydrobromination using lithium carbonate as base with lithium bromide as an additive to give 17 beta-acetoxy-5 alpha-androst-l-en-3-one (3) in almost quantitative yield with 97% of purity. Compound (3) was hydrolyzed with sodium hydroxide to give 17 beta-hydroxy-5 alpha-androst-1-en-3-one (4,1-testosterone), which was oxidized with chromium trioxide to afford 5 alpha-androst-1-ene-3,17-dione (5). The overall yield of 5 was 78.2% with purity of 99%. In this method, the formation of 4-ene was diminished when 1-ene was introduced, and its mechanism was also discussed. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.09.008
• 作为产物：
  描述：

  (10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基)乙酸酯 在 盐酸 、 溴 、 lithium carbonate 、 lithium bromide 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 17-beta-羟基-5alpha-雄甾-1-烯-3-酮乙酸盐
  参考文献：
  名称：

  An efficient synthesis of 5α-androst-1-ene-3,17-dione

  摘要：

  S alpha-Androst-1-ene-3,17-dione (5) as a prodrug of 1-testosterone (4) was prepared in four steps from 17 beta-Acetoxy-S alpha-androstan-3-one (stanolone acetate) (1) in high yield. Thus, stanolone acetate (1) was brominated in the presence of hydrogen chloride in acetic acid to give 17 beta-acetoxy-2-bromo-5 alpha-androstan-3-one (2), which underwent dehydrobromination using lithium carbonate as base with lithium bromide as an additive to give 17 beta-acetoxy-5 alpha-androst-l-en-3-one (3) in almost quantitative yield with 97% of purity. Compound (3) was hydrolyzed with sodium hydroxide to give 17 beta-hydroxy-5 alpha-androst-1-en-3-one (4,1-testosterone), which was oxidized with chromium trioxide to afford 5 alpha-androst-1-ene-3,17-dione (5). The overall yield of 5 was 78.2% with purity of 99%. In this method, the formation of 4-ene was diminished when 1-ene was introduced, and its mechanism was also discussed. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.09.008

文献信息

• Synthesis of α,β-unsaturated ketone from α-iodo ketone using photoirradiation
  作者：Shun-Jun Ji、Eiji Takahashi、T.Tomoyoshi Takahashi、C.Akira Horiuchi

  DOI：10.1016/s0040-4039(99)02010-9

  日期：1999.12

  Irradiation of α-iodo ketone in hexane under a nitrogen atmosphere with a high-pressure mercury lamp (λ>300nm) at room temperature afforded the corresponding α,β-unsaturated ketones in good yield. This reaction affords a new, clean and convenient synthetic method for the α,β-unsaturated ketone.

  在室温下在氮气气氛下用高压汞灯（λ> 300nm）照射α-碘酮在己烷中的辐射，以良好的收率得到相应的α，β-不饱和酮。该反应为α，β-不饱和酮提供了一种新的，清洁的和方便的合成方法。
• Efficient approach to novel 1α-triazolyl-5α-androstane derivatives as potent antiproliferative agents
  作者：Zalán Kádár、Ádám Baji、István Zupkó、Tibor Bartók、János Wölfling、Éva Frank

  DOI：10.1039/c1ob06086d

  日期：——

  Stereoselective 1,4-Michael addition of azoimide to 17β-acetoxy-5α-adrost-1-en-3-one was carried out to furnish a 1α-azido-3-ketone, which was reduced to give the 3β- and 3α-hydroxy epimers in a ratio of 5 : 2. The Cu(I)-catalyzed 1,3-dipolar cycloaddition of the major isomer to terminal alkynes afforded 1α-triazolyl derivatives, which were deacetylated to the corresponding 3β,17β-diols or oxidized to the analogous 3-ketones. However, the ability of the minor 1α,3α-azidoalcohol to undergo similar cyclization was found to be affected significantly by the steric bulk of the substituents on the alkyne reaction partner. All triazolyl compounds were tested in vitro on three malignant gynecological cell lines (HeLa, MCF7 and A2780).

  立体选择性的1,4-迈克尔加成反应将偶氮亚胺加成到17β-乙酰氧基-5α-雄甾-1-烯-3-酮上，得到1α-叠氮-3-酮，将其还原得到3β-和3α-羟基差向异构体，比例为5:2。铜(I)催化的1,3-偶极环加成反应将主要异构体与端炔反应，形成1α-三唑基衍生物，随后去乙酰化得到相应的3β,17β-二醇，或氧化得到类似的3-酮。然而，次要的1α,3α-叠氮醇进行类似环化的能力受到炔反应伴侣上取代基立体阻碍的显著影响。所有三唑基化合物都在体外对三种恶性妇科细胞系（HeLa、MCF7和A2780）进行了测试。
• [EN] ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS<br/>[FR] COMPOSÉS CIBLANT DES RÉCEPTEURS HORMONAUX NUCLÉAIRES ANTICANCÉREUX
  申请人：NUVATION BIO INC

  公开号：WO2021097046A1

  公开（公告）日：2021-05-20

  The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)

  该披露涉及抗癌化合物，这些化合物是公式Al、A2、A3或A4的抗癌PARP抑制剂，通过连接剂与类固醇结合，从而使类固醇将该共轭物靶向到细胞核，以及其制备和使用的方法。
• Insights into the Synthesis of Steroidal<i>A</i>-Ring Olefins
  作者：Carla L. Varela、Fernanda M. F. Roleira、Saul C. P. Costa、Alexandra S. C. T. Pinto、Ana I. O. S. Martins、Rui A. Carvalho、Natércia A. Teixeira、Georgina Correia-da-Silva、Elisiário Tavares-da-Silva

  DOI：10.1002/hlca.201300082

  日期：2014.1

  The classical synthesis, followed by purification of the steroidal A‐ring Δ1‐olefin, 5α‐androst‐1‐en‐17‐one (5), from the Δ1‐3‐keto enone, (5α,17β)‐3‐oxo‐5‐androst‐1‐en‐17‐yl acetate (1), through a strategy involving the reaction of Δ1‐3‐hydroxy allylic alcohol, 3β‐hydroxy‐5α‐androst‐1‐en‐17β‐yl acetate (2), with SOCl2, was revisited in order to prepare and biologically evaluate 5 as aromatase inhibitor

  经典合成，随后是甾体的纯化甲形环Δ 1烯烃，5 α -雄甾-1-烯-17-酮（5）中，从Δ 1 -3酮烯酮，（5 α，17 β）-3-氧代-5-雄甾-1-烯-17-基乙酸酯（1），通过涉及Δ的反应的策略1 -3-羟基烯丙基醇，3- β羟基-5- α -雄甾-1-烯-17- β基乙酸酯（2）中，用的SOCl 2，是为了重新制备和生物学评价5作为乳腺癌的芳香化酶抑制剂。令人惊讶地，随后策略也得到同分异构的Δ 2烯烃6作为副产物，这只能NMR分析的基础上被检测到。纯化和检测程序的优化使我们可以达到化合物5生物学检测所需的96％纯度。相同的合成策略应用于，使用Δ 4 -3-酮烯酮，3-氧代雄甾-4-烯-17- β -基乙酸甲酯（8），作为起始原料，以制备有效的芳香酶抑制剂Δ 4烯烃，雄甾‐4‐en‐17‐一（15）。出乎意料的是，另一种芳香化酶抑制剂Δ3,5形成了二烯，rost-3,5-dien-
• Regio- and stereoselective access to novel ring-condensed steroidal isoxazolines
  作者：Gergő Mótyán、Zalán Kádár、Dóra Kovács、János Wölfling、Éva Frank

  DOI：10.1016/j.steroids.2014.05.019

  日期：2014.9

  Novel 5α-androstanes containing an isoxazoline moiety condensed to ring A or D were efficiently synthetized by 1,3-dipolar cycloadditions of aryl nitrile oxides to steroidal α,β-unsaturated ketones. During the ring closures, regioisomers in which the O terminus of the nitrile oxide dipoles is attached to the β-carbon of the dipolarophile were formed in a stereoselective manner to furnish exclusively

  通过芳基腈氧化物与甾体 α,β-不饱和酮的 1,3-偶极环加成反应有效地合成了含有缩合到环 A 或 D 上的异恶唑啉部分的新型 5α-雄甾烷。在闭环过程中，氧化腈偶极子的 O 末端连接到偶极体的 β-碳上的区域异构体以立体选择性的方式形成，以专门提供 1α,2α- 或 15β,16β-稠合杂环。六元环 A 的环烯酮部分被证明比五元环 D 的反应性低，但所有反应都受到腈氧化物取代模式的显着影响。主要产物的 17-脱乙酰导致芳构化或同时羟基化，这取决于应用于环 A 稠合杂环的碱，