7α-methyl-17α-ethynyl-17β-hydroxy-19-norandrosta-1,4-dien-3-one | 1155267-21-2

• 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: 7α-methyl-17α-ethynyl-17β-hydroxy-19-norandrosta-1,4-dien-3-one
• 英文别名: Δ(1,4)-tibolone；7α-methyl-17α-ethynyl-17β-hydroxy-19-norandrost-1,4-dien-3-one；7α-methyl-17α-ethynl-17β-hydroxy-19-norandrost-1,4-dien-3-one；(7R,8R,9S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-6,7,8,9,10,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 1155267-21-2
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: OAUSWWWFAKCHPK-KIURNNQRSA-N

物化性质

• 熔点：
  196-200 °C
• 沸点：
  454.9±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  替勃龙 在 Cunninghamella elegans (ATCC 10028b) 作用下， 以 丙酮 为溶剂， 反应 144.0h， 生成 7α-methyl-17α-ethynyl-17β-hydroxy-19-norandrosta-1,4-dien-3-one 、 7α-methyl-17α-ethynyl-11α,15β,17β-trihydroxy-19-norandrost-5(10)-en-3-one 、 (7alpha,17alpha)-17,19-二羟基-7-甲基-19-去甲孕甾-4-烯-20-炔-3-酮
  参考文献：
  名称：

  Method of producing tibolone metabolites by fermentation with Rhizopus stolonifer

  摘要：

  一种生产地泼龙代谢产物的新方法，包括将地泼龙与根霉菌（ATCC 12938）发酵，从而形成Δ4-地泼龙（C21H28O2）、6β-羟基地泼龙和15β-羟基地泼龙（C21H28O3）。

  公开号：

  US08148556B2

文献信息

• Biotransformation of tissue-specific hormone tibolone with fungal culture Trichothecium roseum
  作者：Syed Adnan Ali Shah、Sadia Sultan、M. Zaimi bin Mohd Noor

  DOI：10.1016/j.molstruc.2013.03.046

  日期：2013.6

  tissue-specific hormone tibolone (1) with Trichothecium roseum (ATCC 13411) has being carried out for the first time. Two new and three known metabolites 2–6 were isolated from fermentation of tibolone (1) with Trichothecium roseum and their structures were characterized by 2D NMR spectroscopy and mass spectrometry. The relative stereochemistry of new metabolites 5 and 6 was deduced by 2D NOESY experiments

  摘要 基于全细胞的生物转化是类固醇生物转化的重要工具。它可用于合成具有多种结构的生物有效化合物。组织特异性激素替勃龙 (1) 与玫瑰红毛霉 (ATCC 13411) 的生物转化已首次进行。两种新的和三种已知的代谢物 2-6 从具有玫瑰红毛霉的替勃龙 (1) 发酵中分离出来，它们的结构通过 2D NMR 光谱和质谱进行表征。新代谢物 5 和 6 的相对立体化学是通过 2D NOESY 实验推导出来的。还进行了培养对替勃龙结构修饰和时间进程研究的影响。
• Alpha-glucosidase and tyrosinase inhibitors from fungal hydroxylation of tibolone and hydroxytibolones
  作者：M. Iqbal Choudhary、S. Adnan Ali Shah、Atta-ur-Rahman、Shamsun-Nahar Khan、Mahmud Tareq Hassan Khan

  DOI：10.1016/j.steroids.2010.05.017

  日期：2010.12

  Sixteen new and one known metabolites 4-20 were obtained by incubation of tibolone (1) and hydroxytibolones (2 and 3) with various fungi. Their structures were elucidated by means of a homo and heteronuclear 2D NMR and by HREI-MS techniques. The relative stereochemistry was deduced by 2D NOESY experiment. Metabolites of tibolone (1) exhibited significant inhibitory activities against alpha-glucosidase and tyrosinase enzymes. Hydroxylations at C-6, C-10, C-11, C-15 positions and alpha,beta-unsaturation at C-1/C-2, C-4/C-5 showed potent inhibitory activities against these enzymes. (C) 2010 Elsevier Inc. All rights reserved.