17α-acetoxy-11β-hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione | 1613729-92-2

• 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
• 英文名称: 17α-acetoxy-11β-hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione
• CAS: 1613729-92-2
• 化学式: C₂₅H₃₂O₅
• 分子量: 412.526
• InChiKey: UHYFCJNWGRKACN-AVXHDLFRSA-N

反应信息

• 作为产物：
  描述：

  醋酸美伦孕酮 在 Cunninghamella blakesleeana 作用下， 以 丙酮 为溶剂， 反应 336.0h， 以20 mg的产率得到17α-acetoxy-11β-hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione
  参考文献：
  名称：

  Fungal transformation and T-cell proliferation inhibitory activity of melengestrol acetate and its metabolite

  摘要：

  Biotransformation of melengestrol acetate (MGA, 17 alpha-acetoxy-6-methyl-16-methylenepregna-4, 6-diene-3,20-dione) (1) was investigated for the first time by using fungal cultures. Incubation of compound I with Cunninghamella blakesleeana yielded a new major metabolite, 17 alpha-acetoxy-11 beta-hydroxy-6-methyl-16-methylenepregna-4,6-diene-3,20-dione (2). The metabolite 2 was purified by using HPLC, followed by characterization through H-1- and C-13-NMR and other spectroscopic techniques. Single crystal X-ray diffraction analysis was used to deduce the three dimensional structures of melengestrol acetate (1) and metabolite 2 for the first time. T-cell proliferation assay was employed to evaluate the immunosuppressant effect of compounds 1 and 2 with IC50 = 0.5 +/- 0.07 and 0.6 +/- 0.08 mu g/mL, respectively. The results indicated that these compounds possess sixfold potent T-cell proliferation inhibitory activity as compared to the standard prednisolone (IC50 < 3.1 mu g/mL). Both compounds were found to be non-toxic in a 3T3 (mouse fibroblast) cell-based cytotoxicity assay. This discovery of potent anti-inflammatory activity of compounds 1 and 2 can lead the way to develop new immunosuppressant compounds for clinical application. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.04.012