2'-amino-3β-hydroxy-4'H-4'-phenyl-5α-androstan[16,17:5',6']pyridin-3'-carbonitrile | 1415001-47-6

• 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: 2'-amino-3β-hydroxy-4'H-4'-phenyl-5α-androstan[16,17:5',6']pyridin-3'-carbonitrile
• CAS: 1415001-47-6
• 化学式: C₂₉H₃₇N₃O
• 分子量: 443.632
• InChiKey: XRLXYNIDEIGMLD-JBXZJMPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.07
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2'-amino-3β-hydroxy-4'H-4'-phenyl-5α-androstan[16,17:5',6']pyridin-3'-carbonitrile 在 乙酸酐 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 Petroleum ether 为溶剂， 生成 3'-amino-3β-hydroxy-4'-imino-5'-phenyl-5α-androstan[16,17:6',7']-5'H-pyrido[2',3'-d]pyrimidine
  参考文献：
  名称：

  One-pot three-component synthesis of novel heterocyclic steroids as a central antioxidant and anti-inflammatory agents

  摘要：

  Oxidative stress and inflammation have been implicated in several neurodegenerative and developmental brain disorders. The present work was devoted to the design and synthesis of novel steroid derivatives bearing promising heterocyclic moiety that would act to reduce neuro-inflammation and oxidative stress in brain. The novel heterocyclic steroids were synthesized and their chemical structures were confirmed by studying their analytical and spectral data. The tested compounds were assayed in the model of neuroinflammation produced in rats by cerebral lipopolysacharide injection. The intracerebral administration of bacterial endotoxin resulted in cerebral inflammatory state evidenced by increased malondialdehyde (MDA), decreased reduced glutathione (GSH) level, increased nitric oxide as well 35 increased acetylcholinesterase (AChE) activity in the brain. Compounds 6, 10, 8b and 13a markedly increased reduced glutathione. Malondialadehyde and nitric oxide levels were reduced to normal values after treatment with all tested compounds. AChE activity was normalized by compound 8b and reduced to below normal values by compounds 10 and 14a. These results are exciting in that these agents might be useful candidates in treatment of cerebral inflammation. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.001
• 作为产物：
  描述：

  表雄酮 、 苯甲醛 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 以85%的产率得到2'-amino-3β-hydroxy-4'H-4'-phenyl-5α-androstan[16,17:5',6']pyridin-3'-carbonitrile
  参考文献：
  名称：

  One-pot three-component synthesis of novel heterocyclic steroids as a central antioxidant and anti-inflammatory agents

  摘要：

  Oxidative stress and inflammation have been implicated in several neurodegenerative and developmental brain disorders. The present work was devoted to the design and synthesis of novel steroid derivatives bearing promising heterocyclic moiety that would act to reduce neuro-inflammation and oxidative stress in brain. The novel heterocyclic steroids were synthesized and their chemical structures were confirmed by studying their analytical and spectral data. The tested compounds were assayed in the model of neuroinflammation produced in rats by cerebral lipopolysacharide injection. The intracerebral administration of bacterial endotoxin resulted in cerebral inflammatory state evidenced by increased malondialdehyde (MDA), decreased reduced glutathione (GSH) level, increased nitric oxide as well 35 increased acetylcholinesterase (AChE) activity in the brain. Compounds 6, 10, 8b and 13a markedly increased reduced glutathione. Malondialadehyde and nitric oxide levels were reduced to normal values after treatment with all tested compounds. AChE activity was normalized by compound 8b and reduced to below normal values by compounds 10 and 14a. These results are exciting in that these agents might be useful candidates in treatment of cerebral inflammation. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.09.001