Cholest-4-en-3β,6α-diol-3-monoacetat | 65082-82-8

• 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: Cholest-4-en-3β,6α-diol-3-monoacetat
• 英文别名: 3β-acetoxy-6α-hydroxy-4-cholestene；[(3S,6S,8S,9S,10R,13R,14S,17R)-6-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 65082-82-8
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: LMHDVSKJERKBHQ-MNGHIMFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cholest-4-en-3β,6α-diol-3-monoacetat 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 生成 Acetic acid (3S,4R,5R,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-6-hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthren-3-yl ester 、 Acetic acid (3S,4S,5S,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-6-hydroxy-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[4,5]cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  甾体骨架中双脂环族醇的立体控制环氧化的研究：从cholest-4-en-3β，6β-制备八种非对映体纯的环氧化物；-3β，6α-; -3α，6β-和-3α，6α-二醇

  摘要：

  从cholest-4-en-3β，6β制备了八种非对映体纯的环氧化物；-3β，6α-; -3α，6β-和-3α，6α-二醇通过空间，保护基和氧化剂的组合作用对甾体骨架内双脂环式醇系统的立体控制的环氧化作用。

  DOI：

  10.1016/s0957-4166(01)00174-4
• 作为产物：
  描述：

  6-oxo-5a-cholestane-3β,5-diol 3-acetate 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 生成 Cholest-4-en-3β,6α-diol-3-monoacetat
  参考文献：
  名称：

  Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 2415 - 2437

  摘要：

  DOI：

文献信息

• Oxidation with selenium dioxide: the first report of solvent-selective steroidal aromatization, efficient access to 4β,7α-dihydroxy steroids, and syntheses of natural diaromatic ergosterols
  作者：Pranab Ghosh、Jayanta Das、Antara Sarkar、Seik Weng Ng、Edward R.T. Tiekink

  DOI：10.1016/j.tet.2012.05.110

  日期：2012.8

  Selenium dioxide oxidation of cholesterol reveals a solvent-dependent product selectivity and facile one-pot synthesis of three derivatives, including aromatic analogues of naturally occurring ergosterol. Efficient access to 4β,7α-dihydroxy cholesterol is described. Analogous chemistry of β-sitosterol and diosgenin is also reported. The protocol is found effective to synthesize two diaromatic ergosterol

  胆固醇的二氧化硒氧化显示出溶剂依赖性的产物选择性和三种衍生物的轻松一锅合成，其中包括天然麦角固醇的芳香类似物。描述了有效获取4β，7α-二羟基胆固醇的方法。还报道了β-谷甾醇和薯os皂苷元的相似化学。发现该方案对于合成两种二芳族麦角固醇天然产物是有效的。通过X射线晶体学证明了代表性的二芳族胆固醇衍生物和三乙酰化的4β，7α-二羟基胆固醇衍生物的分子结构的简要描述。
• Improved synthesis and in vitro evaluation of the cytotoxic profile of oxysterols oxidized at C4 (4α- and 4β-hydroxycholesterol) and C7 (7-ketocholesterol, 7α- and 7β-hydroxycholesterol) on cells of the central nervous system
  作者：Thomas Nury、Mohammad Samadi、Amira Zarrouk、Jean Marc Riedinger、Gérard Lizard

  DOI：10.1016/j.ejmech.2013.09.028

  日期：2013.12

  Whereas the biological activities of oxysterols oxidized at C7 (7-ketocholesterol (71(C), 76-hydroxycholesterol (7 6-0HC), 7 alpha-hydroxycholesterol (7 alpha-OHC)) are well documented, those of oxysterols oxidized at C4 (4 beta-hydroxycholesterol (4 beta-OHC), 4 alpha-hydroxycholesterol (4 alpha-OHC)) are not well known, especially on the cells of the central nervous system. Therefore, an improved methodology has been validated for 4 beta-OHC and 4 alpha-OHC synthesis, and the effects on cell viability and cell growth of these molecules were studied on immortalized, tumoral and normal brain cells (158N, C6 and SK-N-BE cells, and mixed primary cultures of astrocytes and oligodendrocytes). Whereas inhibition of cell growth with 7KC, 7 6-OHC, and 7 alpha-OHC is associated with a decrease of cell viability (cytotoxic activities), our data establish that 4 beta-OHC and 4a-OHC have no effect on cell viability, and no or minor effect on cell growth evocating cytostatic properties. Thus, comparatively to oxysterols oxidized at C7, the toxicity of oxysterols oxidized at C4 is in the following range of order: 7KC > 76-OHC > 7 alpha-OHC > (4 alpha-OHC > 4 alpha-OHC). Interestingly, to date, 4 beta-0HC and 4a-OHC are the only oxysterols identified with cytostatic properties suggesting that these molecules, whereas not cytotoxic, may have some interests to counteract cell proliferation. (C) 2013 Elsevier Masson SAS. All rights reserved.