[(3R,4aR,10aR)-6-hydroxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone | 187220-53-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: [(3R,4aR,10aR)-6-hydroxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone
• CAS: 187220-53-7
• 化学式: C₂₅H₃₀N₄O₄
• 分子量: 450.538
• InChiKey: SNEIGEIWPUPYFF-DNVFCKCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R,4aR,10aR)-6-hydroxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone 、 三甲基乙酸酐 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以43%的产率得到[(3R,4aR,10aR)-1-methyl-3-[4-(4-nitrophenyl)piperazine-1-carbonyl]-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-6-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Identification and SAR of potent and selective non-peptide obeline somatostatin sst1 receptor antagonists

  摘要：

  A novel class of non-peptide somatostatin receptor ligands bearing the octahydrobenzo[g]quinoline (obeline) structural element has been identified. SAR studies have been performed that led to the discovery of derivatives with high affinity (pK(d) r sst(I) >= 9) and selectivity (>= 150-fold for h sst(1) over h sst(2)-h sst(5)) for somatostatin receptor subtype sst(1). In a functional assay, the compounds act as antagonists at human recombinant sst, receptors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.086
• 作为产物：
  描述：

  (3R,4aR,10aR) 6-Methoxy-1-methyl-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline-3-carboxylic acid 在 吡啶 、 propylphosphonic anhydride 、 氢溴酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(3R,4aR,10aR)-6-hydroxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone
  参考文献：
  名称：

  Identification and SAR of potent and selective non-peptide obeline somatostatin sst1 receptor antagonists

  摘要：

  A novel class of non-peptide somatostatin receptor ligands bearing the octahydrobenzo[g]quinoline (obeline) structural element has been identified. SAR studies have been performed that led to the discovery of derivatives with high affinity (pK(d) r sst(I) >= 9) and selectivity (>= 150-fold for h sst(1) over h sst(2)-h sst(5)) for somatostatin receptor subtype sst(1). In a functional assay, the compounds act as antagonists at human recombinant sst, receptors. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.086

文献信息

• Identification and SAR of potent and selective non-peptide obeline somatostatin sst1 receptor antagonists
  作者：Thomas Troxler、Daniel Hoyer、Daniel Langenegger、Peter Neumann、Paul Pfäffli、Philippe Schoeffter、Dieter Sorg、Robert Swoboda、Konstanze Hurth

  DOI：10.1016/j.bmcl.2007.04.086

  日期：2007.7

  A novel class of non-peptide somatostatin receptor ligands bearing the octahydrobenzo[g]quinoline (obeline) structural element has been identified. SAR studies have been performed that led to the discovery of derivatives with high affinity (pK(d) r sst(I) >= 9) and selectivity (>= 150-fold for h sst(1) over h sst(2)-h sst(5)) for somatostatin receptor subtype sst(1). In a functional assay, the compounds act as antagonists at human recombinant sst, receptors. (C) 2007 Elsevier Ltd. All rights reserved.