3α-Hydroxy-5α-pregn-16-en-20-one | 21080-60-4

• 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
• 英文名称: 3α-Hydroxy-5α-pregn-16-en-20-one
• 英文别名: 3alpha-Hydroxy-5alpha-pregn-16-en-20-one；1-[(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 21080-60-4
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: SFXPZLCQRZASKK-CGHSHZOCSA-N

物化性质

• 熔点：
  219-222 °C
• 沸点：
  443.7±45.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3α-Hydroxy-5α-pregn-16-en-20-one 在 吡啶 、 盐酸羟胺 作用下， 反应 3.0h， 以90%的产率得到3α-hydroxy-20-hydroxyimino-5α-pregn-16-ene
  参考文献：
  名称：

  Synthesis and antitumor activity of some 5α-steroid derivatives

  摘要：

  DOI：

  10.1007/s10600-009-9206-4
• 作为产物：
  描述：

  5alpha-孕甾-3alpha-醇-20-酮 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 9.0h， 生成 3α-Hydroxy-5α-pregn-16-en-20-one
  参考文献：
  名称：

  16,17-脱氢-庚烷酮的体外和体内活性：17,20键扭转能量分析和D环构象。

  摘要：

  目的某些神经活性的孕激素类固醇（也称为“ epalons”）是GABA受体的变构调节剂，并已被证明是有效的抗惊厥药，抗焦虑药，镇静/催眠药和麻醉剂。这项研究的目的是计算在16,17位引入双键的结构后果，并确定这种修饰是否会选择性降低镇静活性，但保持神经活性类固醇的强效惊厥活性。方法我们研究了在自然发生的神经活性类固醇，3 alpha-hydroxy-5 alpha-pregnan-20-one（3 alpha，5 alpha-P）和3 alpha--中引入16,17双键的生物化学和行为效应。 hydroxy-5 beta-pregnan-20-one（3 alpha，5 beta-P）和三种合成的神经活性类固醇衍生物，3 alpha-hydroxy-3 beta-methyl-5 alpha-pregnan-20-one（3 alpha，3 beta Me，5 alpha-P），3 alpha-hydroxy-5

  DOI：

  10.1023/a:1016019327120

文献信息

• Nonenzymatic synthesis of corttcosteroids and related compounds. I. Synthesis of 9,11-unsaturated steroids based on tigogenin
  作者：R. G. Karpenko、G. S. Grinenko、M. G. Davitishvili、O. F. Malyutina

  DOI：10.1007/bf00757966

  日期：1987.12

  hydroxyl or a keto group at the ll-position of the steroid molecule.. The problem of the synthesis of corticosteroids from the commonly used steroid raw material with an unsubstituted ring C (diosgenin and soiasodin) has already been solved by microbiological llhydroxylation. The chemical methods of functionalization of the deactivated steroid ring C were found to be practically inapplicable [5], but the microbiological

  皮质类固醇结构的特征之一是在类固醇分子的ll-位存在羟基或酮基。 (diosgenin and soiasodin) 已经通过微生物 11 羟基化得到解决。发现失活的类固醇环 C 的化学功能化方法实际上不适用 [5]，但有机合成中的微生物过程相当费力，需要昂贵的设备和特殊条件。
• System for delivering therapeutic agents into living cells and cells nuclei
  申请人：Segev David

  公开号：US20060160763A1

  公开（公告）日：2006-07-20

  A novel class of oligomeric compounds designed for forming conjugates with biologically active substances and delivering these substances to a desired bodily target are disclosed. Novel conjugates of these oligomeric compounds and biologically active moieties, pharmaceutical compositions containing such conjugates, and uses thereof as delivery systems for delivering the biologically active substances to a desired target are further disclosed. Processes of preparing the conjugates and the oligomeric compounds and novel intermediates designed for and used in these processes are also disclosed.

  本发明披露了一种新型寡聚化合物，旨在与生物活性物质形成共轭物，并将这些物质传递到所需的身体靶点。本发明还披露了这些寡聚化合物和生物活性基团的新型共轭物，包含这种共轭物的药物组合物以及将其用作传递生物活性物质到所需靶点的传递系统的用途。本发明还披露了制备共轭物和寡聚化合物的过程以及设计和用于这些过程的新型中间体。
• Allopregnanolone (3α-Hydroxy-5α-pregnan-20-one) Derivatives with a Polar Chain in Position 16α: Synthesis and Activity
  作者：Barbora Slavíková、Zdena Krištofíková、Hana Chodounská、Miloš Buděšínský、Fernando J. Durán、Adriana S. Veleiro、Gerardo Burton、Alexander Kasal

  DOI：10.1021/jm801454a

  日期：2009.4.9

  The lipophilic nature of allopregnanolone prevents its user-friendly application in human medicine. On inspiration by previously prepared allopregnanolone with a 16 alpha-bound tetraethylammonium salt, an attempt was made to produce allopregnanolone analogues with polar groups introduced into position 16 alpha with the goal of increasing water solubility, brain accessibility, and potency of neuroactive steroids. The Michael addition to derivatives of pregn-16-en-20-one was the key reaction step. The link between the steroid skeleton and the new side chain was either a methylene group (when diethyl malonate was added) or an oxygen atom (when a hydroxy derivative was added). [S-35]TBPS displacement was used to evaluate the products. Several carbamates (but not their parent alcohols) displaced TBPS from the picrotoxin binding site on GABA(A) receptors. Although none of them was more potent than the above ammonium salt, which stimulated this study, their nonionic nature should not prevent their passage into the brain.
• Sterols. CVIII. The Preparation of Dihydroandrosterone and Related Compounds from Diosgenin and Tigogenin
  作者：Russell E. Marker

  DOI：10.1021/ja01867a012

  日期：1940.10
• Butenandt et al., Chemische Berichte, 1939, vol. 72, p. 1617,1621
  作者：Butenandt et al.

  DOI：——

  日期：——