5-pregnen-20-one-3β-yl propionate | 54552-01-1

• 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: 5-pregnen-20-one-3β-yl propionate
• 英文别名: 3β-propionyloxypregnenolone；3β-propionyloxy-pregn-5-en-20-one；3β-Propionyloxy-pregn-5-en-20-on；[(3S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] propanoate
• CAS: 54552-01-1
• 化学式: C₂₄H₃₆O₃
• 分子量: 372.548
• InChiKey: YDVRGLSUPTYULK-VGHKYRARSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  465.7±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-pregnen-20-one-3β-yl propionate 在 selenium(IV) oxide 、 sodium acetate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 3β-propionyloxy-17-[1',2',3'-selenadiazol-4'-yl]pregnenolon
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 17-[1′,2′,3′]-selenadiazolylpregnenolone compounds

  摘要：

  Using pregnenolone as a starting material, some 3-substituted 17-[1',2',3']-selenadiazolylpregnenolone derivatives were synthesized, and their structures were characterized by IR, NMR and HRMS. The in vitro antitumor activity of the compounds was assayed against PC-3, SKOV3, T47D, MCF-7 and HEK293T cell lines. The results show that some compounds display selective antiproliferative activity against PC-3 and SKOV3 cells lines and are almost inactive to normal kidney epithelial cells (HEK293T). The IC50 value are much better than that of abiraterone (positive control).

  DOI：

  10.1016/j.steroids.2018.10.004
• 作为产物：
  描述：

  孕烯醇酮 、 丙酸酐 生成 5-pregnen-20-one-3β-yl propionate
  参考文献：
  名称：

  Sterols. CXLIII. The Conversion of 5-Pregnen-3(β)-ol-20-one to Dehydro-iso-androsterone^*

  摘要：

  DOI：

  10.1021/ja01258a009

文献信息

• Fatty Acid Steryl, Stanyl, and Steroid Esters by Esterification and Transesterification in Vacuo Using <i>Candida rugosa</i> Lipase as Catalyst
  作者：Nikolaus Weber、Petra Weitkamp、Kumar D. Mukherjee

  DOI：10.1021/jf000830w

  日期：2001.1.1

  Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degreesC. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5 alpha -pregnan-3 beta -ol-20-one or 5-pregnen-3 beta -ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C, rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.