N-([1,2,5]thiadiazolo[3,4-b]pyridin-5-yl)piperazine | 944247-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-([1,2,5]thiadiazolo[3,4-b]pyridin-5-yl)piperazine
• 英文别名: 5-Piperazin-1-yl-[1,2,5]thiadiazolo[3,4-b]pyridine；5-piperazin-1-yl-[1,2,5]thiadiazolo[3,4-b]pyridine
• CAS: 944247-21-6
• 化学式: C₉H₁₁N₅S
• 分子量: 221.286
• InChiKey: VZATXQANFZPGIG-UHFFFAOYSA-N

物化性质

• 沸点：
  398.0±32.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  82.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-([1,2,5]thiadiazolo[3,4-b]pyridin-5-yl)piperazine 、 9,10-二氢麦角酸 在 吡啶 作用下， 生成 [(6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-[4-([1,2,5]thiadiazolo[3,4-b]pyridin-5-yl)piperazin-1-yl]methanone
  参考文献：
  名称：

  Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor

  摘要：

  Non-peptidic compounds containing the octahydro-indolo[4,3-fg]quinoline (ergoline) structural element have been optimized into derivatives with high affinity (pK(d) r sst(1) > 9) and selectivity (> 1000-fold for h sst(1) over h sst(2)-h sst(5)) for the somatostatin sst(1) receptor. In functional assays, these ergolines act as antagonists at human recombinant sst(1) receptors. Pharmacokinetic studies in rodents reveal good oral bioavailability and brain penetration for some of these compounds. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.12.030
• 作为产物：
  描述：

  4-(5,6-diaminopyridine-2-yl)piperazine 在 N-亚磺酰苯胺 作用下， 以 甲苯 为溶剂， 生成 N-([1,2,5]thiadiazolo[3,4-b]pyridin-5-yl)piperazine
  参考文献：
  名称：

  SAR of the arylpiperazine moiety of obeline somatostatin sst1 receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.04.078

文献信息

• Decahydroisoquinoline derivatives as novel non-peptidic, potent and subtype-selective somatostatin sst3 receptor antagonists
  作者：Thomas Troxler、Konstanze Hurth、Karl-Heinrich Schuh、Philippe Schoeffter、Daniel Langenegger、Albert Enz、Daniel Hoyer

  DOI：10.1016/j.bmcl.2010.01.063

  日期：2010.3

  Starting from non-peptidic sst(1)-selective somatostatin receptor antagonists, first compounds with mixed sst(1)/sst(3) affinity were identified by directed structural modifications. Systematic optimization of these initial leads afforded novel, enantiomerically pure, highly potent and sst(3)-subtype selective somatostatin antagonists based on a (4S,4aS,8aR)-decahydroisoquinoline-4-carboxylic acid core moiety. These compounds can efficiently be synthesized and show promising PK properties in rodents. (C) 2010 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.
• 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.
• Ergoline derivatives as highly potent and selective antagonists at the somatostatin sst1 receptor
  作者：Thomas Troxler、Albert Enz、Daniel Hoyer、Daniel Langenegger、Peter Neumann、Paul Pfäffli、Philippe Schoeffter、Konstanze Hurth

  DOI：10.1016/j.bmcl.2007.12.030

  日期：2008.2

  Non-peptidic compounds containing the octahydro-indolo[4,3-fg]quinoline (ergoline) structural element have been optimized into derivatives with high affinity (pK(d) r sst(1) > 9) and selectivity (> 1000-fold for h sst(1) over h sst(2)-h sst(5)) for the somatostatin sst(1) receptor. In functional assays, these ergolines act as antagonists at human recombinant sst(1) receptors. Pharmacokinetic studies in rodents reveal good oral bioavailability and brain penetration for some of these compounds. (C) 2007 Elsevier Ltd. All rights reserved.