3-oxo-17α-pregna-4-ene-7α-(methylacetylthia)-21,17-carbolactone | 123955-61-3

• 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: 3-oxo-17α-pregna-4-ene-7α-(methylacetylthia)-21,17-carbolactone
• 英文别名: methyl 2-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl]sulfanylacetate
• CAS: 123955-61-3
• 化学式: C₂₅H₃₄O₅S
• 分子量: 446.608
• InChiKey: JONRZROTYWLLSS-KWTQDISESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  95
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  螺内酯 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.67h， 生成 3-oxo-17α-pregna-4-ene-7α-(methylacetylthia)-21,17-carbolactone
  参考文献：
  名称：

  A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone

  摘要：

  Spironolactone is a renal competitive aldosterone antagonist. One of its most important metabolite is the 7 alpha-methylthio spironolactone: thus it is very important to have an efficient and safe access to this compound, for pharmacokinetic studies. In this context, we synthesized this metabolite by thioalkylation of 7 alpha-thio spironolactone using Hunig's base with a very good yield. We also used our procedure to prepare, with an easy work-up and high yields, 7 alpha-thioether and thioester derivatives of spironolactone, that could be useful for further Structure-Activity Relationships studies. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.005

文献信息

• A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone
  作者：Géraldine Agusti、Sandrine Bourgeois、Nathalie Cartiser、Hatem Fessi、Marc Le Borgne、Thierry Lomberget

  DOI：10.1016/j.steroids.2012.09.005

  日期：2013.1

  Spironolactone is a renal competitive aldosterone antagonist. One of its most important metabolite is the 7 alpha-methylthio spironolactone: thus it is very important to have an efficient and safe access to this compound, for pharmacokinetic studies. In this context, we synthesized this metabolite by thioalkylation of 7 alpha-thio spironolactone using Hunig's base with a very good yield. We also used our procedure to prepare, with an easy work-up and high yields, 7 alpha-thioether and thioester derivatives of spironolactone, that could be useful for further Structure-Activity Relationships studies. (c) 2012 Elsevier Inc. All rights reserved.