FAUC 113 | 221470-50-4

• 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: FAUC 113
• 英文别名: Pyrazolo[1,5-a]pyridine, 3-[[4-(4-chlorophenyl)-1-piperazinyl]methyl]-；3-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]pyrazolo[1,5-a]pyridine
• CAS: 221470-50-4
• 化学式: C₁₈H₁₉ClN₄
• 分子量: 326.829
• InChiKey: XVPRVMIFXXOEFR-UHFFFAOYSA-N

物化性质

• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  FAUC 113 、 甲酸乙酯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以78%的产率得到3-[4-(4-Chloro-phenyl)-piperazin-1-ylmethyl]-pyrazolo[1,5-a]pyridine-7-carbaldehyde
  参考文献：
  名称：

  Di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives: synthesis, dopamine receptor binding and ligand efficacy

  摘要：

  Based on the lead molecule FAUC 113, a series of di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives was synthesized and investigated for their dopamine receptor binding profile. The carbonitrile 11a (FAUC 327) showed excellent pharmacological properties combining high D4 affinity (K-i = 1.5 nM) and selectivity with significant intrinsic activity (31%) in low nanomolar concentrations (EC50 = 1.5 nM), (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00814-9
• 作为产物：
  描述：

  吡唑并[1,5-A]吡啶-3-甲酸乙酯 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 草酰氯 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 56.5h， 生成 FAUC 113
  参考文献：
  名称：

  Azaindole derivatives with high affinity for the dopamine D4 receptor: Synthesis, ligand binding studies and comparison of molecular electrostatic potential maps

  摘要：

  Piperazinylmethyl substituted pyrazolo[1,5-a]pyridines and related heterocycles were synthesized and found to recognize selectively the dopamine D4 receptor. For the most potent derivative 10d a Ki value of 2.0 nM was observed. SAR studies including the comparison of molecular isopotential surfaces were performed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00692-1

文献信息

• Synthesis and in vitro evaluation of iodine labelled pyrazolo[1,5-<i>a</i>]pyridines as highly selective dopamine D4 receptor ligands
  作者：O. Prante、S. Löber、H. Hübner、P. Gmeiner、T. Kuwert

  DOI：10.1002/jlcr.508

  日期：2001.10.30

  Two 131I-labelled radioligands, namely 3-(4-[131I]iodophenylpiperazin-1-ylmethyl)-pyrazolo[1,5-a]pyridine and 3-(4-chlorophenylpiperazin-1-ylmethyl)-7-[131I]iodopyrazolo[1,5-a]pyridine, which are required for studies or binding of these ligands to the D4 receptor, have been synthesized in 80% and 32% radiochemical yields, respectively; the radiochemical purity in each case was >97%. For the second radioligand a kit preparation, based on iododestannylation followed by solid-phase extraction, was possible. In vitro characterization using CHO-cells expressing different dopamine receptor subtypes gave Ki values of 3.1 and 2.6 nM. Both radioligands are highly selective for the D4 subtype as compared to other dopamine subtypes. Copyright © 2001 John Wiley & Sons, Ltd.

  已合成两种131I标记的放射性配体:3-(4-[131I]碘苯基哌嗪-1-基甲基)-吡唑并[1,5-a]吡啶和3-(4-氯苯基哌嗪-1-基甲基)-7-[131I]碘吡唑并[1,5-a]吡啶,放射化学产率分别为80%和32%,放射化学纯度均>97%。第二种放射性配体可以通过碘代脱锡反应后固相萃取的试剂盒制备。使用表达不同多巴胺受体亚型的CHO细胞进行体外表征,得到Ki值分别为3.1和2.6 nM。与其他多巴胺亚型相比,这两种放射性配体对D4亚型具有高度选择性。
• Azaindole derivatives with high affinity for the dopamine D4 receptor: Synthesis, ligand binding studies and comparison of molecular electrostatic potential maps
  作者：Stefan Löber、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(98)00692-1

  日期：1999.1

  Piperazinylmethyl substituted pyrazolo[1,5-a]pyridines and related heterocycles were synthesized and found to recognize selectively the dopamine D4 receptor. For the most potent derivative 10d a Ki value of 2.0 nM was observed. SAR studies including the comparison of molecular isopotential surfaces were performed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives: synthesis, dopamine receptor binding and ligand efficacy
  作者：Stefan Löber、Tarek Aboul-Fadl、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(01)00814-9

  日期：2002.2

  Based on the lead molecule FAUC 113, a series of di- and trisubstituted pyrazolo[1,5-a]pyridine derivatives was synthesized and investigated for their dopamine receptor binding profile. The carbonitrile 11a (FAUC 327) showed excellent pharmacological properties combining high D4 affinity (K-i = 1.5 nM) and selectivity with significant intrinsic activity (31%) in low nanomolar concentrations (EC50 = 1.5 nM), (C) 2002 Elsevier Science Ltd. All rights reserved.