[(3R,4aR,10aR)-6-methoxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone | 187218-90-2

• 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-methoxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone
• CAS: 187218-90-2
• 化学式: C₂₆H₃₂N₄O₄
• 分子量: 464.564
• InChiKey: INULNSAIIZKOQE-YOSAUDMPSA-N

物化性质

• 沸点：
  684.2±55.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R,4aR,10aR)-6-methoxy-1-methyl-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-3-yl]-[4-(4-nitrophenyl)piperazin-1-yl]methanone 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 34.0h， 生成 [(3R,4aR,10aR)-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[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
• 作为产物：
  描述：

  [3R,4aR,10aR]-6-methoxy-1-methyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline-3-carboxylic acid methyl ester 在 吡啶 、 sodium hydroxide 、 propylphosphonic anhydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [(3R,4aR,10aR)-6-methoxy-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

• SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists
  作者：Konstanze Hurth、Albert Enz、Philipp Floersheim、Conrad Gentsch、Daniel Hoyer、Daniel Langenegger、Peter Neumann、Paul Pfäffli、Dieter Sorg、Robert Swoboda、Annick Vassout、Thomas Troxler

  DOI：10.1016/j.bmcl.2007.04.078

  日期：2007.7

  The SAR of over 50 derivatives of octahydrobenzo[g]quinoline (obeline)-type somatostatin sst, receptor antagonist 1 is presented, focusing on the modification of its arylpiperazine moiety. sst(1) affinities in this series cover a range of five orders of magnitude with the best derivatives displaying subnanomolar sst, affinities and > 10,000-fold selectivities over the sst, receptor subtype as well as promising pharmacokinetic properties. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.