3β-hydroxy-17-keto-17-methyl-16-nitrile-16,17-seco-5-androstene | 361342-72-5

• 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: 3β-hydroxy-17-keto-17-methyl-16-nitrile-16,17-seco-5-androstene
• 英文别名: 3β-hydroxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-nitrile；3β-hydroxy-17-oxo-17-methyl-16,17-secoandrost-5-ene-16-nitrile；2-[(1S,2S,4aS,4bR,7S,10aR)-2-acetyl-7-hydroxy-2,4b-dimethyl-1,3,4,4a,5,6,7,8,10,10a-decahydrophenanthren-1-yl]acetonitrile
• CAS: 361342-72-5
• 化学式: C₂₀H₂₉NO₂
• 分子量: 315.456
• InChiKey: ZHNFZMTUJVVASP-APNJTCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-17-keto-17-methyl-16-nitrile-16,17-seco-5-androstene 在 环己酮 、 aluminum tri-tert-butoxide 作用下， 生成 17-methyl-3,17-dioxo-16,17-seco-4-androstene-16-nitrile
  参考文献：
  名称：

  Structure–activity relationships in 4- and 5-androstene: 3β-acetoxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-carbonitrile and 17-methyl-3,17-dioxo-16,17-seco-4-androstene-16-carbonitrile

  摘要：

  The title compounds, C22H31NO3 and C20H27NO2, have similar conformations except in the molecular geometry and the bonding of two of the rings. These differences lead to marked differences in the biological activities of these compounds. Molecules of both compounds are linked by weak C-H...O hydrogen bonds in the crystal structures.

  DOI：

  10.1107/s0108270104017457
• 作为产物：
  描述：

  (3S,8R,9S,10R,13S,14S,17R)-3,17-Dihydroxy-10,13,17-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one oxime 在 sodium ethanolate 作用下， 以 吡啶 、 乙醇 为溶剂， 生成 3β-hydroxy-17-keto-17-methyl-16-nitrile-16,17-seco-5-androstene
  参考文献：
  名称：

  Structure–activity relationships in 4- and 5-androstene: 3β-acetoxy-17-methyl-17-oxo-16,17-seco-5-androstene-16-carbonitrile and 17-methyl-3,17-dioxo-16,17-seco-4-androstene-16-carbonitrile

  摘要：

  The title compounds, C22H31NO3 and C20H27NO2, have similar conformations except in the molecular geometry and the bonding of two of the rings. These differences lead to marked differences in the biological activities of these compounds. Molecules of both compounds are linked by weak C-H...O hydrogen bonds in the crystal structures.

  DOI：

  10.1107/s0108270104017457

文献信息

• New D-modified androstane derivatives as aromatase inhibitors☆
  作者：Katarina M. Penov Gaši、Slobodanka M. Stanković、János J. Csanádi、Evgenija A. Djurendić、Marija N. Sakač、Ljubica Medić Mijačević、Otto N. Arcson、Srdjan Z. Stojanović、Silvana Andrić、Dora Molnar Gabor、Radmila Kovačević

  DOI：10.1016/s0039-128x(01)00096-4

  日期：2001.8

  Starting from a 16-oximino derivative of 5-androstene the newly-synthesized 16-oximino-17-hydroxy-17-substituted derivatives 2-4 gave by the Beckmann fragmentation reaction the corresponding D-seco derivatives 6-9. Besides, in the case of the 17-hydroxy-17-methyl-16-oximino derivative 2, as a result of the rearrangement, the hydrolysis product 5 of the 16-oximino group with the opposite configuration

  从5-雄甾烯的16-氧亚氨基衍生物开始，新合成的16-氧亚氨基17-羟基-17-取代的衍生物2-4通过贝克曼裂解反应得到相应的D-seco衍生物6-9。此外，在17-羟基-17-甲基-16-肟基衍生物2的情况下，由于重排，获得了在C-17处具有相反构型的16-肟基的水解产物5。通过Oppenauer氧化和/或用2,3-二氯-5,6-二氰基苯并醌（DDQ）脱水7，可获得相应的衍生物12、13和14。通过适当的X射线结构分析明确证明了6和12的结构。抗芳香化酶活性的动力学分析表明，与其他雄烯衍生物相比，化合物12在去核大鼠卵巢中的表达最高（IC（50）为0.42 microM）。与氨基戊二酰亚胺（AG）活性相比，它低3.5倍。抑制是竞争性的，K（i）为0.27 microM。在D-seco衍生物中引入其他不饱和单元（化合物13和14）不会增加抗芳香化酶活性。