3α-hydroxy-1β,11α-epoxy-5α-pregnan-20-one | 1032410-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 3α-hydroxy-1β,11α-epoxy-5α-pregnan-20-one
• 英文别名: 1-[(1R,3S,4S,7S,8S,11S,13S,15R,16S,17S)-13-hydroxy-3,16-dimethyl-18-oxapentacyclo[13.2.1.03,7.08,17.011,16]octadecan-4-yl]ethanone
• CAS: 1032410-50-6
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: OQORSKKNPQZFPN-TWTWHMCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,3aR,3a1S,4aR,4a1S,5aS,6S,8aS,8bS,10aS)-6-acetyl-3a1,5a-dimethylhexadecahydro-1H-cyclopenta[1,2]phenanthro[4,5-bcd]furan-2-yl formate 在 potassium hydrogencarbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以75%的产率得到3α-hydroxy-1β,11α-epoxy-5α-pregnan-20-one
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs

  摘要：

  Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3 alpha-hydroxy-11,19-epoxypregn-4- ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[H-3] butylbicycloorthobenzoate as radiolabeled ligand for the GABA(A) receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1 alpha, 11 alpha-Epoxypregnanolone (6) was more active than pregnanolone (2). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.048

文献信息

• Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs
  作者：Lautaro D. Alvarez、Adriana S. Veleiro、Ricardo F. Baggio、María T. Garland、Valeria C. Edelsztein、Héctor Coirini、Gerardo Burton

  DOI：10.1016/j.bmc.2008.01.048

  日期：2008.4.1

  Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3 alpha-hydroxy-11,19-epoxypregn-4- ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[H-3] butylbicycloorthobenzoate as radiolabeled ligand for the GABA(A) receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1 alpha, 11 alpha-Epoxypregnanolone (6) was more active than pregnanolone (2). (C) 2008 Elsevier Ltd. All rights reserved.