androstanedione | 846-46-8

• 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: androstanedione
• 英文别名: 5α-androstan-3,17-dione；(5α)-androstane-3,17-dione；3,17-Diketo-(5α,10β,13β)androstan；5α-Androst-4-en-3,17-dion；3,17-Dioxo-5α-androstan；5α-Androstandion-(3,17)；(5alpha,8xi,9xi,14xi)-Androstane-3,17-dione；(5S,10S,13S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 846-46-8；1229-12-5；2942-88-3；2943-09-1；3986-81-0；4034-63-3；4069-05-0；5982-99-0；10085-16-2；72029-07-3；94991-77-2；102339-28-6
• 化学式: C₁₉H₂₈O₂
• 分子量: 288.43
• InChiKey: RAJWOBJTTGJROA-LWTCHCTNSA-N

物化性质

• 熔点：
  165-167 °C(Solv: ligroine (8032-32-4))
• 沸点：
  411.2±38.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  androstanedione 在 silica gel 、 铜 氢气 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.32 kPa 条件下， 反应 2.5h， 生成 Epiandrosteron
  参考文献：
  名称：

  Cu/SiO2-catalyzed hydrogenation of cyclohexanones under very mild conditions

  摘要：

  Unsubstituted and alkyl-substituted cyclohexanotics. including 3-oxo-steroids, can be easily hydrogenated to the corresponding alcohols at I atm of H-2 and 60 90degreesC over a 8% Cu/SiO2 non-toxic. reusable catalyst with excellent selectivity (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(02)00671-8
• 作为产物：
  描述：

  4-androstene-3,17-dione 在 盐酸 、 palladium on activated charcoal 、 氢气 、 对甲苯磺酸 、 原甲酸三乙酯 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 androstanedione
  参考文献：
  名称：

  一种司坦唑醇中间体雄甾-17α-甲基-17β-羟基-3-酮的合成方法

  摘要：

  本发明提供一种司坦唑醇中间体雄甾‑17α‑甲基‑17β‑羟基‑3‑酮的合成方法，该方法是以4‑雄烯二酮为原料，通过3位、17位酮基双缩酮，5位烯键催化氢化，3位、17位双缩酮水解制备化合物5α‑雄甾烷‑3,17二酮；再通过3位酮基双醚化，17位格氏加成，最后水解制备化合物雄甾‑17α‑甲基‑17β‑羟基‑3‑酮，HPLC纯度99.0%以上。本发明方法路线简短，生产工艺容易控制，环境友好，生产成本低，适合工业规模化生产。

  公开号：

  CN109438538A

文献信息

• Synthetic Scope of Alcohol Transfer Dehydrogenation Catalyzed by Cu/Al2O3: A New Metallic Catalyst with Unusual Selectivity
  作者：Federica Zaccheria、Nicoletta Ravasio、Rinaldo Psaro、Achille Fusi

  DOI：10.1002/chem.200501619

  日期：2006.8.16

  dehydrogenation reaction from the substrate alcohol to styrene catalyzed by a heterogeneous, reusable copper catalyst under very mild liquid-phase experimental conditions (90 degrees C, N(2)) and shows unusual selectivity. Thus, the method is selective for the oxidation of secondary and allylic alcohols even in the presence of unprotected primary and benzylic alcohols. Electronic effects and the choice

  已经建立了对包括环己醇和甾族醇在内的多种醇进行厌氧氧化的方法。它依赖于在非常温和的液相实验条件（90摄氏度，N（2））下，由多相，可重复使用的铜催化剂催化的从底物醇到苯乙烯的转移脱氢反应，并显示出不同寻常的选择性。因此，即使在未保护的伯醇和苄醇的存在下，该方法对于氧化仲醇和烯丙基醇也是选择性的。电子效应和氢受体的选择解释了所观察到的选择性。
• MEDICINAL APPLICATIONS OF BENZOIC ACID HYDRAZONES SYNTHESIZED ON THE BASIS OF STEROIDAL TIGOGENIN
  申请人：Shelar Ashok Ranganath

  公开号：US20110178317A1

  公开（公告）日：2011-07-21

  Novel benzoic acid hydrazones of 5α-androstan-3,17-dione have been prepared on the basis of steroidal tigogenin of the plant Yucca gloriosa . The hydrazones of the General Formula (I), General Formula (II) and General Formula (III) as shown in the accompanying FIGURE of the drawing are synthesized. The hydrazones have shown promising anti-T.B., anti-cancer and anti-HIV activity revealing immense potential as more efficacious, less toxic drugs with fewer undesirable side effects. They could also prove valuable in correcting hormonal abnormalities that cause severe health problems.

  5α-雄甾烷-3,17-二酮的新型苯甲酸肼已经根据植物优格龙胆甾原甙制备。根据图纸中显示的一般式(I)、一般式(II)和一般式(III)，合成了这些肼。这些肼显示出有希望的抗结核、抗癌和抗艾滋病活性，表明它们具有更有效、毒性更小、副作用更少的巨大潜力。它们还可能在纠正引起严重健康问题的激素异常方面具有价值。
• Chemoselectivity in molybdenum catalyzed alcohol and aldehyde oxidations
  作者：Barry M. Trost、Yoshiro Masuyama

  DOI：10.1016/s0040-4039(00)99832-0

  日期：1984.1

  Hydrogen peroxide in the presence of (NH4)6Mo7O24 · 4H2O and potassium carbonate is a chemoselective method to oxidize secondary alcohols to ketones and to oxidize aldehydes to acids, the latter also accelerated by cerium chloride.

  在（NH 4）6 Mo 7 O 24 ·4H 2 O和碳酸钾存在下的过氧化氢是一种化学选择方法，可将仲醇氧化为酮，并将醛氧化为酸，后者也可通过氯化铈加速。
• Baeyer-Villiger Oxidation of Some C19 Steroids by Penicillium lanosocoeruleum
  作者：Alina Świzdor

  DOI：10.3390/molecules181113812

  日期：——

  The biotransformation of androsterone (1), epiandrosterone (2), androstanedione (3) and DHEA (dehydroepiandrosterone) (4) by Penicillium lanosocoeruleum—a fungal species not used in biotransformations so far—were described. All the substrates were converted in high yield (70%–99%) into D ring δ-lactones. The oxidation of 1 produced 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5). The oxidation of 2 led to 3β-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (6). The biotransformation of 3 resulted in the formation of 3α-hydroxy-17a-oxa-D-homo-5α-androstan-17-one (5) and 17a-oxa-D-homo-5α-androstan-3,17-dione (7). An analysis of the transformation progress of the studied substrates as a function of time indicates that the Baeyer-Villiger monooxygenase of this fungus does not accept the 3β-hydroxy-5-ene functionality of steroids. In this microorganism steroidal 3β-hydroxy-dehydrogenase (3β-HSD) was active, and as a result DHEA (4) was transformed exclusively to testololactone (8). Apart from the observed oxidative transformations, a reductive pathway was revealed with the C-3 ketone being reduced to a C-3α-alcohol. It is demonstrated for the first time that the reduction of the 3-keto group of the steroid nucleus can occur in the presence of a ring-D lactone functionality.

  描述了青霉 (Penicillium lanosocoeruleum)（一种迄今为止未用于生物转化的真菌物种）对雄酮 (1)、表雄酮 (2)、雄烷二酮 (3) 和 DHEA（脱氢表雄酮）(4) 的生物转化。所有底物均以高产率（70%–99%）转化为 D 环 δ-内酯。 1 的氧化产生 3α-羟基-17a-oxa-D-homo-5α-androstan-17-one (5)。 2 的氧化生成 3β-羟基-17a-oxa-D-homo-5α-androstan-17-one (6)。 3的生物转化导致形成3α-羟基-17a-oxa-D-homo-5α-androstan-17-one (5) 和 17a-oxa-D-homo-5α-androstan-3,17-dione ( 7).对所研究底物的转化进程随时间的分析表明，该真菌的 Baeyer-Villiger 单加氧酶不接受类固醇的 3β-羟基-5-烯官能团。在该微生物中，类固醇 3β-羟基脱氢酶 (3β-HSD) 具有活性，因此 DHEA (4) 仅转化为睾丸内酯 (8)。除了观察到的氧化转化之外，还揭示了还原途径，其中 C-3 酮被还原为 C-3α-醇。首次证明类固醇核的 3-酮基团的还原可以在 D 环内酯官能团存在的情况下发生。
• INDOMETHACIN ANALOGS FOR THE TREATMENT OF CASTRATE-RESISTANT PROSTATE CANCER
  申请人：Vanderbilt University

  公开号：US20140371261A1

  公开（公告）日：2014-12-18

  Provided are compositions for inhibiting a biological activity of an aldoketo reductase family 1, member C3 (AKR1 C3) polypeptide. In some embodiments, the compositions are indomethacin derivatives that are AKR1 C3-specific inhibitors. Also provided are methods for producing disclosed indomethacin derivatives that substantially lack cyclooxygenase inhibitory activity but that have AKR1C3 inhibitory activity, methods for inhibiting AKR1C3 polypeptide biological activities, and methods for treating prostate tumors in subjects.

  提供了一些用于抑制醛酮还原酶家族1成员C3（AKR1 C3）多肽生物活性的组合物。在某些实施例中，这些组合物是AKR1 C3特异性抑制剂的吲哚美辛衍生物。还提供了制备所述吲哚美辛衍生物的方法，这些方法基本上缺乏环氧合酶抑制活性，但具有AKR1C3抑制活性，以及抑制AKR1C3多肽生物活性的方法和治疗受试者的前列腺肿瘤的方法。