1-睾酮 | 65-06-5

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药 - 雄激素及同化激素类药
• 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: 1-睾酮
• 中文别名: 17b-羟基-5a-雄甾-1-烯-3-酮
• 英文名称: 1-testosterone
• 英文别名: 17β-hydroxy-5α-androst-1-en-3-one；17β-Hydroxy-5α-androst-1-en-3-on；(5S,8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 65-06-5
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: OKJCFMUGMSVJBG-ABEVXSGRSA-N

物化性质

• 熔点：
  157-159?C
• 沸点：
  420.5±45.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)
• 溶解度：
  乙腈：1mg/mL；乙醇：1mg/mL；甲醇：1mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi

制备方法与用途

用途： 适用于男性因内源性雄激素缺乏或不足引起的各种疾病，以及女性功能性子宫出血、乳腺癌和再生障碍性贫血等疾病的治疗。

反应信息

• 作为反应物：
  描述：

  1-睾酮 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以90 %的产率得到1-雄烯二酮
  参考文献：
  名称：

  5α-androst-1-ene-3β,17β-二醇的新型立体选择性合成

  摘要：

  详细阐述了合成代谢类固醇及其代谢物的参考化合物5α-androst-1-ene-3β,17β-二醇的高效立体选择性合成方法。合成的关键在于使用硼氢化钠-氯化铈(III)体系作为还原剂。

  DOI：

  10.1007/s11172-023-4078-5
• 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 、 sodium hydroxide 、 溴 、 lithium carbonate 、 lithium bromide 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 1-睾酮
  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

文献信息

• New classes of orally active hormonal derivatives. I. Alkyl androstan-17β-yl and alkyl 19-norandrostan-17β-yl mixed acetals
  作者：Romano Vitali、Rinaldo Gardi、Giovanni Falconi、Alberto Ercoli

  DOI：10.1016/0039-128x(66)90047-x

  日期：1966.10

  Abstract A series of alkyl steroid- 17β-yl mixed acetals of aliphatic and cyclo-aliphatic ketones have been prepared from several androstane and 19-norandrostane derivatives. By oral administration many of these compounds, which are easily hydrolizable both in vitro and in vivo , have proved to be more potent than methyltestosterone in the usual test for androgenic and myogenic activity.

  摘要 以几种雄甾烷和19-去甲雄甾烷衍生物为原料制备了一系列脂肪族和环脂肪族酮的烷基类固醇-17β-基混合缩醛。通过口服给药，这些化合物中的许多在体外和体内都容易水解，在通常的雄激素和生肌活性试验中已证明比甲基睾酮更有效。
• Structural and Configurational Dependence of the Sensory Process in Steroids
  作者：G�nther Ohloff、Bruno Maurer、Beat Winter、Wolfgang Giersch

  DOI：10.1002/hlca.19830660121

  日期：1983.2.2

  19-nortestosterone have led to the synthesis of over 60 androstane and estrane derivatives whose sensory evaluation has allowed molecular parameters to be established for release of a ‘steroid-type’ scent. Odor perception with O-containing compounds in both classes has been found to be regioselective1. Osmophoric groups at C(3) were found to be the most active and specific. Functionality at C(2) is accompanied

  睾丸激素和19-去甲睾丸激素的结构修饰已导致合成了60多种雄甾烷和雌二醇衍生物，其感官评估已为释放“类固醇型”气味建立了分子参数。两种类别的含O化合物的气味感知都具有区域选择性1。C（3）处的渗透基团是最活跃和最特异的。C（2）处的功能在很大程度上伴随着原子缺陷，并且在特殊情况下，C（1）和C（4）处的含O取代基似乎会影响受体膜。
• Synthesis of novel C17 steroidal carbamates
  作者：Vânia M.A. Moreira、Tadas S. Vasaitis、Zhiyong Guo、Vincent C.O. Njar、Jorge A.R. Salvador

  DOI：10.1016/j.steroids.2008.05.010

  日期：2008.11

  We have exploited the reaction of 1,1'-carbonylbis(2-methylimidazole) (CBMI) with several 17beta-hydroxy androstanes to synthesize a series of novel C17 steroidal carbamates. Structural elucidation features have been provided for the final compounds based on 1D and 2D NMR techniques, IR spectroscopy, and related literature. The new compounds were tested for inhibition of human cytochrome 17alpha-hydroxylase-C17

  我们利用 1,1'-羰基双 (2-甲基咪唑) (CBMI) 与几个 17beta-羟基雄甾烷的反应来合成一系列新型 C17 甾体氨基甲酸酯。已根据 1D 和 2D NMR 技术、IR 光谱和相关文献为最终化合物提供了结构解析特征。测试了新化合物对人类细胞色素 17α-羟化酶-C17,20-裂解酶 (CYP17) 和雄激素受体 (AR) 结合和功能影响的抑制作用。还评估了它们对 PC-3 细胞增殖的抑制潜力。发现化合物 11 和 23 抑制 CYP17，IC50 值分别为 17.1 和 11.5 microM。C17 处的氨基甲酸酯部分允许合成的化合物与野生型 (wt-) 和突变的 AR 紧密结合。当绑定到突变的 AR 时，发现这些化合物具有双重作用，在天然雄激素二氢睾酮 (DHT) 存在的情况下，在低浓度下刺激转录，而在测试的较高浓度下几乎完全阻断转录。化合物 8 和 12 对 PC-3 细胞增殖最有效，EC50
• FLUORESCENCE BASED DETECTION OF SUBSTANCES
  申请人：Russell David

  公开号：US20090230322A1

  公开（公告）日：2009-09-17

  A method for the fluorescent detection of a substance, the method comprising providing particles comprising a metal or a metal oxide core, wherein one or more optionally fluorescently tagged antibodies or human specific peptide nucleic acid (PNA) oligomers for binding to a substance is/are bound, directly or indirectly, to the surface of the metal or metal oxide; contacting a substrate, which may or may not have the substance on its surface, with the particles for a time sufficient to allow the antibody/PNA oligomer to bind with the substance; removing those particles which have not bound to the substrate; if the antibodies or PNA oligomers are not fluorescently tagged, contacting the substrate with one or more fluorophores that selectively bind with the antibody and/or substance, then optionally washing the substrate to remove unbound fluorophores; and illuminating the substrate with appropriate radiation to show the fluorophores on the substrate.

  一种用于荧光检测物质的方法，该方法包括提供含有金属或金属氧化核的颗粒，其中一种或多种可选择性地荧光标记的抗体或人特异性肽核酸（PNA）寡聚体，用于结合到物质上，直接或间接地结合到金属或金属氧化物的表面；将可能在其表面具有或不具有该物质的基质与这些颗粒接触一段时间，以充分允许抗体/PNA寡聚体与该物质结合；移除那些未与基质结合的颗粒；如果抗体或PNA寡聚体未被荧光标记，则将基质与一种或多种能特异性结合抗体和/或物质的荧光剂接触，然后可选择地清洗基质以去除未结合的荧光剂；并用适当的辐射照射基质以显示基质上的荧光剂。
• [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。