17α-azido-5β-androstan-3α-ol | 1321605-05-3

• 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: 17α-azido-5β-androstan-3α-ol
• 英文别名: (3R,5R,8R,9S,10S,13S,14S,17R)-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-ol
• CAS: 1321605-05-3
• 化学式: C₁₉H₃₁N₃O
• 分子量: 317.475
• InChiKey: QCDRTITWRLVLFH-ULTMTAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17α-azido-5β-androstan-3α-ol 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 1.58h， 生成 N-(3α-hydroxy-5β-androstan-17α-yl)-pentafluorobenzamide
  参考文献：
  名称：

  Neuroactive steroids with perfluorobenzoyl group

  摘要：

  During an initial study in searching for the alternative derivatives suitable for photolabeling of neuroactive steroids, perfluorobenzoates and perfluorobenzamides in position 17 of 5 beta-androstan-3 alpha-ol were synthesized from the corresponding 17-hydroxy and 17-amino derivatives. After transformation into glutamates or sulfates, 17 alpha-epimers had comparable inhibitory activity at NMDA receptors to the natural neurosteroid (20-oxo-5 beta-pregnan-3 beta-yl sulfate), however, were more potent (2- to 36-fold) than their 17 beta-substituted analogs. In one case, fluorine in position 4' of perfluorobenzoate group was substituted with azide and activity of the final glutamate was retained comparing with the corresponding perfluorobenzoate. The series was expanded with perfluorobenzoyl derivatives of pregnanolone: Perfluorobenzamide of glutamate and perfluorobenzoate of 11 alpha-hydroxy pregnanolone were prepared and tested. From nine tested compounds, four of them exhibit very good inhibition activity and can serve as promising leads for photolabeling experiments. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.07.004
• 作为产物：
  描述：

  本胆烷-17β-醇-3-酮 在 sodium tetrahydroborate 、 迭氮酸 、 cerium(III) chloride heptahydrate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 乙酸乙酯 、 苯 为溶剂， 反应 0.33h， 生成 17α-azido-5β-androstan-3α-ol
  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