n-butyl-3-keto-5α-androstane-17β-hemisuccinamide | 131943-83-4

• 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: n-butyl-3-keto-5α-androstane-17β-hemisuccinamide
• 英文别名: [(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] 4-(butylamino)-4-oxobutanoate
• CAS: 131943-83-4
• 化学式: C₂₇H₄₃NO₄
• 分子量: 445.643
• InChiKey: ZBYATHKHUNHTLK-YOLSHIOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dihydrotestosterone hemisuccinate 、 正丁胺 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以147 mg的产率得到n-butyl-3-keto-5α-androstane-17β-hemisuccinamide
  参考文献：
  名称：

  Synthesis and androgen receptor binding of dihydrotestosterone hemisuccinate homologs

  摘要：

  Dihydrotestosterone-succinyl-agarose is the most common form of androgen affinity column. To investigate the effect of variation in the number of methylene groups between the ester and amide functions, a homologous series, varying the number of methylenes between the functional groups, has been synthesized and evaluated. In addition, since structure studies show 17 alpha-methyldihydrotestosterone binds with high affinity, a 17 alpha-carboxymethyl ligand (3) was studied. Relative binding affinities of the dicarboxylates (assayed as the n-butyl amides) range from 0.003 to 0.044 (dihydrotestosterone = 1.00), while there was no detectable binding for 3. Only the suberate binds better than the much-used succinate, and it would be a likely candidate for an affinity ligand.

  DOI：

  10.1016/0039-128x(90)90041-9

文献信息

• Synthesis and androgen receptor binding of dihydrotestosterone hemisuccinate homologs
  作者：Mark E. Stobaugh、Robert T. Blickenstaff

  DOI：10.1016/0039-128x(90)90041-9

  日期：1990.6

  Dihydrotestosterone-succinyl-agarose is the most common form of androgen affinity column. To investigate the effect of variation in the number of methylene groups between the ester and amide functions, a homologous series, varying the number of methylenes between the functional groups, has been synthesized and evaluated. In addition, since structure studies show 17 alpha-methyldihydrotestosterone binds with high affinity, a 17 alpha-carboxymethyl ligand (3) was studied. Relative binding affinities of the dicarboxylates (assayed as the n-butyl amides) range from 0.003 to 0.044 (dihydrotestosterone = 1.00), while there was no detectable binding for 3. Only the suberate binds better than the much-used succinate, and it would be a likely candidate for an affinity ligand.