17β-azido-5β-androstan-3α-yl sulfate pyridinium | 1321605-23-5

• 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: 17β-azido-5β-androstan-3α-yl sulfate pyridinium
• 英文别名: [(3R,5R,8R,9S,10S,13S,14S,17S)-17-azido-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate;pyridine
• CAS: 1321605-23-5
• 化学式: C₅H₅N*C₁₉H₃₁N₃O₄S
• 分子量: 476.64
• InChiKey: KAXIGCMMEWRTHW-IZJNMLJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-oxo-5β-androstan-17α-yl tosylate 在 sodium tetrahydroborate 、 sodium azide 、 cerium(III) chloride heptahydrate 作用下， 以 吡啶 、 甲醇 、 六甲基磷酰三胺 、 乙酸乙酯 为溶剂， 反应 17.33h， 生成 17β-azido-5β-androstan-3α-yl sulfate pyridinium
  参考文献：
  名称：

  Azido analogs of neuroactive steroids

  摘要：

  Analogs of pregnanolone (3 alpha-hydroxy-5 beta-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17 alpha- and 17 beta-azido-5 beta-androstan-3 alpha-ol), compounds with its part replaced (20-azido-21-nor-5 beta-pregnan-3 alpha-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5 beta-pregnan-3 alpha-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.04.008

文献信息

• Azido analogs of neuroactive steroids
  作者：Lukáš Vidrna、Ivan Černý、Vladimír Pouzar、Jiřina Borovská、Vojtěch Vyklický、Ladislav Vyklický、Hana Chodounská

  DOI：10.1016/j.steroids.2011.04.008

  日期：2011.9

  Analogs of pregnanolone (3 alpha-hydroxy-5 beta-pregnan-20-one), modified in position 17 were prepared. Compounds with 20-keto pregnane side chain replaced completely by azide (17 alpha- and 17 beta-azido-5 beta-androstan-3 alpha-ol), compounds with its part replaced (20-azido-21-nor-5 beta-pregnan-3 alpha-ol), and compounds with keto group only replaced ((20R)- and (20S)-20-azido-5 beta-pregnan-3 alpha-ol) were synthesized using tosylate displacements with sodium azide or Mitsunobu reaction with azoimide. All five azido steroids were converted into corresponding sulfates. Subsequent tests for inhibition of glutamate induced response on NMDA receptors revealed that modification of pregnanolone sulfate side chain with azide did not disturb the activity and some of sulfates tested were more active than parent compound. (C) 2011 Elsevier Inc. All rights reserved.