1-Methyl-5α-androsten-(1)-dion-(3,17) | 1424-01-7

• 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: 1-Methyl-5α-androsten-(1)-dion-(3,17)
• 英文别名: 1-Methyl-5alpha-androst-1-ene-3,17-dione；(5S,8R,9S,10S,13S,14S)-1,10,13-trimethyl-5,6,7,8,9,11,12,14,15,16-decahydro-4H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 1424-01-7
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: STLDQAJEGPFPIE-SWEGMTMGSA-N

物化性质

• 熔点：
  142-144 °C
• 沸点：
  428.6±45.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷；乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1-Methyl-5α-androsten-(1)-dion-(3,17) 生成 阿他美坦
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  1-雄烯二酮 在 copper(l) chloride 作用下， 生成 1-Methyl-5α-androsten-(1)-dion-(3,17)
  参考文献：
  名称：

  Pelc,B., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 3089 - 3095

  摘要：

  DOI：

文献信息

• Aspergillus niger-mediated biotransformation of methenolone enanthate, and immunomodulatory activity of its transformed products
  作者：Zahid Hussain、Nida Dastagir、Shabbir Hussain、Almas Jabeen、Salman Zafar、Rizwana Malik、Saira Bano、Abdul Wajid、M. Iqbal Choudhary

  DOI：10.1016/j.steroids.2016.04.007

  日期：2016.8

  Two fungal cultures Aspergillus niger and Cunninghamella blakesleeana were used for the biotransformation of methenolone enanthate (1). Biotransformation with A. niger led to the synthesis of three new (2-4), and three known (5-7) metabolites, while fermentation with C. blakesleeana yielded metabolite 6. Substrate 1 and the resulting metabolites were evaluated for their immunomodulatory activities. Substrate 1 was found to be inactive, while metabolites 2 and 3 showed a potent inhibition of ROS generation by whole blood (IC50= 8.60 and 7.05 mu g/mL), as well as from isolated polymorphonuclear leukocytes (PMNs) (IC50= 14.0 and 4.70 mu g/mL), respectively. Moreover, compound 3 (34.21%) moderately inhibited the production of TNF-alpha, whereas 2 (88.63%) showed a potent inhibition of TNF-alpha produced by the THP-1 cells. These activities indicated immunomodulatory potential of compounds 2 and 3. All products were found to be non-toxic to 3T3 mouse fibroblast cells. (C) 2016 Elsevier Inc. All rights reserved.
• Verfahren zur Herstellung von 1-Methyl-androsta-1,4-dien-3,17-dion und die neuen Zwischenprodukte für dieses Verfahren
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0290378B1

  公开（公告）日：1992-01-02
• ——
  作者：PETZOLDT KARL

  DOI：——

  日期：——
• VERFAHREN ZUR HERSTELLUNG VON 1-METHYL-1,4-ANDROSTADIEN-3,17-DION
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0217840A1

  公开（公告）日：1987-04-15
• 2-IOD-3-KETO-$g(D)?4 -STEROIDE, VERFAHREN ZU IHRER HERSTELLUNG, SOWIE DEREN WEITERVERARBEITUNG
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0528876A1

  公开（公告）日：1993-03-03