5-alpha-孕甾-2-烯-20-酮 | 969-72-2

• 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: 5-alpha-孕甾-2-烯-20-酮
• 英文名称: 5α-pregn-2-en-20-one
• 英文别名: 5α-Pregn-2-en-20-on；5alpha-Pregn-2-en-20-one；1-[(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 969-72-2
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: PERPPAKFLWZECF-QYYVTAPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-alpha-孕甾-2-烯-20-酮 在 三氟化硼乙醚 、 水 、 potassium carbonate 、 silver nitrate 、 间氯过氧苯甲酸 、 potassium hydroxide 、 silver(l) oxide 作用下， 以 甲醇 、 氯仿 、 苯 为溶剂， 反应 10.0h， 生成 2α,3α-epoxy-21-methoxy-5α-pregnan-20-one
  参考文献：
  名称：

  Neurosteroids: Can a 2alpha,3alpha-epoxy ring make up for the 3alpha-hydroxyl group?

  摘要：

  Seven steroid epoxides were prepared from 5 alpha-pregn-2-en-20-one and 5 alpha-pregn-3-en-20-one and their side-chain derivatives. All compounds were tested in vitro for binding to gamma-aminobutyric acid (GABA(A)) receptor, some of them also in vivo for anticonvulsant action.2 alpha,3 alpha-Epoxy-5 alpha-pregnan-20-one inhibited the TBPS binding to the GABA(A) receptor and showed a moderate anticonvulsant action in immature rats. In contrast, its 3 alpha,4 alpha-isomer was inactive. More polar epoxide derivatives, modified at the side chain were less active or inactive.Noteworthy, diol 20, the product of trans-diaxial opening of the 2 alpha,3 alpha-epoxide 4, was not able to inhibit the TBPS binding, showing that the activity of the epoxide is due to the compound itself and not to its hydrolytic product.The 3 alpha-hydroxyl group is known to be essential for the GABA(A) receptor binding. Despite the shortness of in vivo effects which are probably due to metabolic inactivation of the products prepared, our results show that the 2 alpha,3 alpha-epoxy ring is another structural pattern with ability to bind the GABA(A)R. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.11.007
• 作为产物：
  描述：

  孕烯醇酮 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 40.0~130.0 ℃ 、310.27 kPa 条件下， 反应 22.0h， 生成 5-alpha-孕甾-2-烯-20-酮
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS
  [FR] COMPOSITIONS ET MÉTHODES POUR TRAITER DES TROUBLES DU SNC

  摘要：

  本文描述了式(I)的神经活性类固醇，或其药用可接受盐；其中(II)，A，R1，R2，R3a，R4a，R4b，R5，R7a和R7b如本文所定义。在某些实施例中，这些化合物被设想为GABA调节剂。本发明还提供了包括本发明化合物的药物组合物，以及使用和治疗方法，例如用于诱导镇静和/或麻醉。

  公开号：

  WO2016061527A1

文献信息

• NEW STEROIDS HAVING INCREASED WATER SOLUBILITY AND RESISTANCE AGAINST METABOLISM, AND METHODS FOR THEIR PRODUCTION
  申请人：BACKSTROM Torbjorn

  公开号：US20080119416A1

  公开（公告）日：2008-05-22

  Steroid compounds having increased resistance against metabolism and increased water solubility are disclosed, together with methods for their production. These substances are suitable for the manufacture of pharmaceuticals for the treatment of steroid related or steroid induced CNS disorders and for use in methods of prevention, alleviation or treatment of such disorders.

  揭示了具有增加代谢抵抗力和增加水溶性的类固醇化合物，以及它们的生产方法。这些物质适用于制造用于治疗与类固醇相关或类固醇诱导的中枢神经系统疾病的药物，并用于预防、缓解或治疗此类疾病的方法。
• Synthesis and antituberculosis activity of several steroids from 3β-acetoxy-5α-pregn-16-en-20-one
  作者：M. I. Sikharulidze、N. Sh. Nadaraia、M. L. Kakhabrishvili

  DOI：10.1007/s10600-012-0265-6

  日期：2012.7

  The semicarbazone and isonicotinoylhydrazone of 5α-pregn-2-en-20-one, which was prepared from 3β-acetoxy-5α-pregn-16-en-20-one, were synthesized for the first time. The antituberculosis activity of these and semicarbazones and isonicotinoylhydrazones of saturated, unsaturated, and adamantane-modified ketosteroids synthesized by us earlier was studied in vitro experiments.

  首次合成了由3β-乙酰氧基-5α-孕甾-16-烯-20-酮制备的5α-孕甾-2-烯-20-酮的缩氨基脲和异烟酰肼。通过体外实验研究了这些化合物以及我们早期合成的饱和、不饱和和金刚烷修饰的酮甾体的缩氨基脲和异烟酰肼的抗结核活性。
• Methods, compositions, and compounds for allosteric modulation of the
  申请人：University of Southern California

  公开号：US05232917A1

  公开（公告）日：1993-08-03

  Method, compositions, and compounds for modulating brain excitability to alleviate stress, anxiety, insomnia and seizure activity using certain steroid derivatives that act at a newly identified site on the gamma-aminobutyric acid receptor-chloride ionophore (GR) complex.

  使用某些类固醇衍生物在伽马氨基丁酸受体-氯离子载体（GR）复合物上的新识别位点，调节大脑兴奋性以缓解压力、焦虑、失眠和癫痫活动的方法、组合物和化合物。
• [EN] PROCESS FOR PREPARING HIGH PURITIY ALLOPREGNANOLONE AND INTERMEDIATES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ALLOPRÉGNANOLONE À HAUTE PURETÉ ET DE SES INTERMÉDIAIRES
  申请人：BIONICE S L U

  公开号：WO2020187965A1

  公开（公告）日：2020-09-24

  The invention relates to an efficient and industrially applicable process for the preparation and purification of allopregnanolone and intermediates thereof without the assistance of column chromatography.

  该发明涉及一种高效且工业适用的过程，用于制备和纯化羟孕酮和其中间体，无需使用柱层析法的辅助。
• Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation
  作者：Gábor Mikle、Alexandra Zugó、Erzsébet Szatnik、Anita Maxim、Sándor Mahó、László Kollár

  DOI：10.1007/s11696-020-01478-7

  日期：2021.5

  5α-pregn-20-ene-20-carboxamides were synthesized from the widely accessible 3β-acetoxy-pregn-5,16-dien-20-one (PDA) using selective hydrogenation, hydrazine and iodoalkene formation, as well as palladium-catalysed aminocarbonylation. The 20-iodo-20-ene derivatives, obtained from the corresponding 20-keto derivatives via their hydrazones, served as substrates. 23 new 20-carboxamides were obtained using various N-nucleophiles

  由广泛可得的3β-乙酰氧基-pregn-5,16-合成20-羧酰胺基孕烯衍生物，例如3β-乙酰氧基-5α-pregn-20-ene-20-羧酰胺和5α-pregn-20-ene-20-羧酰胺。 Dien-20-one（PDA）使用选择性加氢，肼和碘代烯烃的形成，以及钯催化的氨基羰基化。通过相应的20酮从相应的20-酮衍生物获得的20-碘-20-烯衍生物用作底物。使用各种氮素获得了23种新的20-羧酰胺-亲核试剂，范围从简单的伯胺到α-氨基酸酯。这种方法的新颖之处在于应用轻度，中度或高产率的反应来获得原本难以获得的具有药学重要性的甾族20-羧酰胺。换句话说，代替了例如甾醇或胆酸的酶促或合成降解，使用了基本骨架的功能化（“积累”方法）。