(5'R)-17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one | 1207630-79-2

• 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: (5'R)-17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
• 英文别名: (8S,9S,10R,13S,14S,17S)-17-[(5R)-2-(4-bromophenyl)-4,5-dihydro-1,3-oxazol-5-yl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1207630-79-2
• 化学式: C₂₈H₃₄BrNO₂
• 分子量: 496.487
• InChiKey: VMCDZYSKPLPOLA-RLRFXSNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5'R)-17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3β-ol 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 以46%的产率得到(5'R)-17β-[2-(4-bromophenyl)-4,5-dihydrooxazol-5-yl]androst-5-en-3-one
  参考文献：
  名称：

  Steroselective synthesis of some steroidal oxazolines, as novel potential inhibitors of 17α-hydroxylase-C17,20-lyase

  摘要：

  17 beta-Oxazolinyl steroids 7a-g and 8a-g were synthesized. The Lewis acid-catalysed reactions of (20R)-3 beta-acetoxy-21-azidomethyl-20-hydroxypregn-5-ene with substituted aromatic aldehydes led to the formation of 3 beta-acetoxyandrost-5-enes substituted in position 17 beta with oxazolinyl residues (7a-g). Oppenauer oxidation of the 3 beta-hydroxy-exo-heterocyclic steroids yielded the corresponding Delta(4)-3-ketosteroids. The inhibitory effects (IC50) of both 3-hydroxy compounds 7a-g and their Delta(4)-3-keto counterparts 8a-g on rat testicular C-17,C-20-lyase were investigated with an in vitro radioligand incubation technique. The 3-chlorophenyl- (8d), and the 4-bromophenyl-17 beta-(2-oxazolin-5-yl)androst-4-en-3-one derivatives(8f) were found to be modest inhibitors (IC50=4.8 and 5.0 mu M, respectively). (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.08.001

文献信息

• Steroselective synthesis of some steroidal oxazolines, as novel potential inhibitors of 17α-hydroxylase-C17,20-lyase
  作者：Dóra Ondré、János Wölfling、István Tóth、Mihály Szécsi、János Julesz、Gyula Schneider

  DOI：10.1016/j.steroids.2009.08.001

  日期：2009.11

  17 beta-Oxazolinyl steroids 7a-g and 8a-g were synthesized. The Lewis acid-catalysed reactions of (20R)-3 beta-acetoxy-21-azidomethyl-20-hydroxypregn-5-ene with substituted aromatic aldehydes led to the formation of 3 beta-acetoxyandrost-5-enes substituted in position 17 beta with oxazolinyl residues (7a-g). Oppenauer oxidation of the 3 beta-hydroxy-exo-heterocyclic steroids yielded the corresponding Delta(4)-3-ketosteroids. The inhibitory effects (IC50) of both 3-hydroxy compounds 7a-g and their Delta(4)-3-keto counterparts 8a-g on rat testicular C-17,C-20-lyase were investigated with an in vitro radioligand incubation technique. The 3-chlorophenyl- (8d), and the 4-bromophenyl-17 beta-(2-oxazolin-5-yl)androst-4-en-3-one derivatives(8f) were found to be modest inhibitors (IC50=4.8 and 5.0 mu M, respectively). (C) 2009 Elsevier Inc. All rights reserved.