17β-acetoxy-5'-aminothieno[2',3':2,3]-5α-androstane-4'-carbonitrile | 871731-16-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 17β-acetoxy-5'-aminothieno[2',3':2,3]-5α-androstane-4'-carbonitrile
• 英文别名: [(1S,2S,10S,13R,14S,17S,18S)-6-amino-7-cyano-2,18-dimethyl-5-thiapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),6-dien-17-yl] acetate
• CAS: 871731-16-7
• 化学式: C₂₄H₃₂N₂O₂S
• 分子量: 412.596
• InChiKey: KNEKRHPESGRJFU-CRCQEFMESA-N

物化性质

• 熔点：
  212-214 °C(Solvent: Ethanol)
• 沸点：
  567.4±50.0 °C(predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17β-acetoxy-5'-aminothieno[2',3':2,3]-5α-androstane-4'-carbonitrile 、 尿素 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以65%的产率得到17β-acetoxy-6''-amino-1''H-2''-oxopyrimidino[5'',4'':4',5']thieno[2',3':2,3]-5α-androstane
  参考文献：
  名称：

  Novel synthesized aminosteroidal heterocycles intervention for inhibiting iron-induced oxidative stress

  摘要：

  The objective of this study was to elucidate the potential role of novel synthesized aminosteroidal heterocyclic compounds 2, 5, 9b and 10c against iron-induced oxidative stress with particular insight on erythrocyte ghosts in male rats. Chronic iron supplementation (3000 mg kg(-1) diet) for 6 weeks significantly increased plasma iron and ferritin levels. It also produced significant increase in plasma TNF-alpha and NO levels. Lipid metabolism was also affected by excess iron, so that plasma and erythrocyte membrane total cholesterol, triglycerides, phospholipids and total lipid levels were significantly elevated. In consequence, a significant increase in plasma leptin level was detected. Iron overload clearly induces oxidative stress as indicated by the significant increase in both plasma and erythrocyte membrane lipid peroxidation levels. Noteworthy, excess iron not only decreased the mean value of erythrocyte membrane protein but also caused marked alterations in the membrane protein fractions with concomitant inhibition in erythrocyte membrane ATPases activity. On the other hand, treatment with the aminosteriodal heterocyclic compounds especially compounds 5, 2, and 10c in an oral dose of 5 mg kg(-1) B.W. per day could ameliorate almost all of the changes in plasma and erythrocyte ghosts components induced by iron overload. The efficacious role of these novel synthesized aminosteriods in preventing iron-induced oxidative stress may be mediated through their iron chelating properties, anti-lipid peroxidation activities and membrane stabilizing actions. The encouraging results obtained in the present study lend credence to substantial investigation to assess the use of these compounds as a potent line of therapy to retard the pathogenesis of iron overload diseases. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.012
• 作为产物：
  描述：

  (10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基)乙酸酯 、 丙二腈 在 sulfur 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到17β-acetoxy-5'-aminothieno[2',3':2,3]-5α-androstane-4'-carbonitrile
  参考文献：
  名称：

  Novel synthesized aminosteroidal heterocycles intervention for inhibiting iron-induced oxidative stress

  摘要：

  The objective of this study was to elucidate the potential role of novel synthesized aminosteroidal heterocyclic compounds 2, 5, 9b and 10c against iron-induced oxidative stress with particular insight on erythrocyte ghosts in male rats. Chronic iron supplementation (3000 mg kg(-1) diet) for 6 weeks significantly increased plasma iron and ferritin levels. It also produced significant increase in plasma TNF-alpha and NO levels. Lipid metabolism was also affected by excess iron, so that plasma and erythrocyte membrane total cholesterol, triglycerides, phospholipids and total lipid levels were significantly elevated. In consequence, a significant increase in plasma leptin level was detected. Iron overload clearly induces oxidative stress as indicated by the significant increase in both plasma and erythrocyte membrane lipid peroxidation levels. Noteworthy, excess iron not only decreased the mean value of erythrocyte membrane protein but also caused marked alterations in the membrane protein fractions with concomitant inhibition in erythrocyte membrane ATPases activity. On the other hand, treatment with the aminosteriodal heterocyclic compounds especially compounds 5, 2, and 10c in an oral dose of 5 mg kg(-1) B.W. per day could ameliorate almost all of the changes in plasma and erythrocyte ghosts components induced by iron overload. The efficacious role of these novel synthesized aminosteriods in preventing iron-induced oxidative stress may be mediated through their iron chelating properties, anti-lipid peroxidation activities and membrane stabilizing actions. The encouraging results obtained in the present study lend credence to substantial investigation to assess the use of these compounds as a potent line of therapy to retard the pathogenesis of iron overload diseases. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.012