5α-cholestane-2,3-dione | 5300-86-7

• 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: 5α-cholestane-2,3-dione
• 英文别名: 5a-Cholestane-2,3-dione；(5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2,3-dione
• CAS: 5300-86-7
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: BYSWDNBNMZHMHK-XPFWUWIUSA-N

物化性质

• 沸点：
  486.9±14.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  5α-cholestane-2,3-dione 在 硝酸丙酯 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到2-hydroxy-4α-nitro-5α-cholest-1-en-3-one
  参考文献：
  名称：

  光诱导去除甾族六元α,α'-二硝基环酮中的硝基基团

  摘要：

  2,4-Dinitro-5α- 和 5β-cholestan-3-ones 是由母体 3-ones 用改进的标准方法二硝化制备的。光谱表明，在乙醇中，这些 α,α'-二硝基酮以其烯醇形式存在。这些二硝基酮在乙醇中的光解产生二酚，这是由于去除了它们的两个硝基而产生的。根据合成获得的假设中间体的辐照结果，我们提出了可能导致硝基去除的路径。

  DOI：

  10.1246/bcsj.62.1107
• 作为产物：
  描述：

  5-Alpha-胆甾烷-3-酮 在 potassium tert-butylate 、 氧气 作用下， 以 叔丁醇 为溶剂， 以74%的产率得到5α-cholestane-2,3-dione
  参考文献：
  名称：

  Synthesis and Biological Activity Of Unsymmetrical Bis-Steroidal Pyrazines Related to the Cytotoxic Marine Natural Product Cephalostatin 1

  摘要：

  A mild, high-yielding synthesis of symmetrical steroidal pyrazines was achieved from the dimerization of 2-amino-3-ketosteroids, which were produced in situ from the triphenylphosphine-water reduction of the corresponding alpha-azido ketone. 2-Azidocholestan-3-one gave the dimeric steroidal pyrazine very cleanly, and two known dimeric pyrazines based on androstanone were also made using this methodology. Both C-2-symmetric geometric isomers of the dimeric steroidal pyrazine derived from cholestane were prepared by reaction of 2,3-diaminocholestane with cholestane-2,3-dione. A route to unsymmetrical bis-steroidal pyrazines was based on the observation that alpha-acetoxy ketones react with alpha-amino oximes directly with no need for oxidation of intermediate dihydropyrazines. Heating either 2 beta,17 beta-dihydroxyandrostan-3-one diacetate or 2 beta,17 beta-dihydroxyhecogenin-3-one diacetate with 2-amino-3-methoxyiminocholestane in toluene at 145 degrees C gave the corresponding unsymmetrical pyrazine in moderate yield. Five of the steroidal pyrazines were evaluated in the National Cancer Institute's new in vitro, disease-oriented antitumor screen, but none showed sufficient activity to warrant in vivo investigation.

  DOI：

  10.1021/jo00101a052

文献信息

• Cationic, Steroid-Based Imidazolium Amphiphiles Show Tunable Backbone-Dependent Membrane Selectivity in Fungi
  作者：Tristan Wegner、Rebecca Elias、Lena Roling、Nikita Raj、Volker Gerke、Micha Fridman、Frank Glorius

  DOI：10.1021/acsinfecdis.2c00164

  日期：2022.9.9

  imidazolium amphiphiles that show tunable antifungal activity in a variety of fungal pathogens of the genus Candida. We show that adoption of an ergosterol-derived backbone increases antifungal activity while modestly affecting hemolytic activity, thereby increasing overall selectivity by more than 8-fold in comparison to cholesterol-derived imidazolium salts. We hypothesize that this effect is caused by

  据报道，阳离子两亲物显示出广泛的抗菌活性。由于它们具有一般的细胞膜透化作用模式，因此对这些分子产生抗菌素耐药性的可能性很低。然而，由于它们对微生物细胞膜的选择性低，因此它们的应用往往受到毒性的限制。在此，我们报告了一个基于阳离子类固醇的咪唑两亲化合物库，这些化合物在念珠菌属的多种真菌病原体中显示出可调谐的抗真菌活性. 我们表明，采用麦角甾醇衍生的骨架可增加抗真菌活性，同时适度影响溶血活性，从而与胆固醇衍生的咪唑盐相比，将总体选择性提高 8 倍以上。我们假设这种效应是由麦角甾醇衍生的盐优先整合到真菌膜中导致膜紊乱增加引起的。我们认为这些发现为开发改进的两亲性杀菌剂提供了一个有用的平台。
• The oxidation of Δ2, Δ2,4 and Δ4,6 steroids with RuO4
  作者：Domenica Musumeci、Giovanni N Roviello、Donato Sica

  DOI：10.1016/j.steroids.2003.11.003

  日期：2004.3

  In order to find new ways for the functionalization of the A and B rings of the steroid nucleus, the reaction of 5alpha-androst-2-en-17beta-ol 17-acetate (1), cholesta-2,4-diene (4) and cholesta-4,6-dien-3beta-ol 3-acetate (7) was examined using stoichiometric amounts of ruthenium tetraoxide to yield 1,2-cis diols and/or alpha-hydroxy ketones. The reaction of 5alpha-cholest-2-en-3-ol 3-acetate (9) with ruthenium tetraoxide was also carried out and afforded, apart from an alpha-hydroxy ketone, also a diketone and a seco-dicarboxylic acid. The structures of all new steroids, including stereochemical details, were deduced by analysis of spectral data. (C) 2004 Elsevier Inc. All rights reserved.
• Hajos, Gyoergy; Snatzke, Guenter; Fueloep, Vilmos, Liebigs Annalen der Chemie, 1989, p. 25 - 30
  作者：Hajos, Gyoergy、Snatzke, Guenter、Fueloep, Vilmos、Kalman, Alajos

  DOI：——

  日期：——
• Synthesis and Chiroptical Properties of 5a-Cholest-2-eno[2,3-b]pyrazine Derivatives
  作者：György Hajós、G殤ther Snatzke

  DOI：10.3987/com-88-s25

  日期：——
• SUGINOME, HIROSHI;KUROKAWA, YOSHITAKA;ORITO, KAZUHIKO, BULL. CHEM. SOC. JAP., 61,(1988) N1, C. 4005-4014
  作者：SUGINOME, HIROSHI、KUROKAWA, YOSHITAKA、ORITO, KAZUHIKO

  DOI：——

  日期：——