2-丙烯酸,2-羟基环己基酯 | 179756-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-丙烯酸,2-羟基环己基酯
• 英文名称: 2-[4-[4-(7-methoxy-1-naphthyl)piperazino]butyl]-4-methyl-2H,4H-1,2,4-triazin-3,5-dione
• 英文别名: 4-Methyl-2-(4-(4-(7-methoxynaphtalene-1-yl)piperazinyl)butyl)-3,5-dioxo-(2H,4H)-1,2,4-triazine；2-[4-[4-(7-methoxynaphthalen-1-yl)piperazin-1-yl]butyl]-4-methyl-1,2,4-triazine-3,5-dione
• CAS: 179756-59-3
• 化学式: C₂₃H₂₉N₅O₃
• 分子量: 423.515
• InChiKey: GKTQBPYMIGXPKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-甲氧基-1-萘胺 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 12.0h， 生成 2-丙烯酸,2-羟基环己基酯
  参考文献：
  名称：

  Synthesis and in Vivo Validation of [O-Methyl-¹¹C]2-{4-[4-(7-methoxynaphthalen-1-yl)piperazin- 1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione:  A Novel 5-HT_1A Receptor Agonist Positron Emission Tomography Ligand

  摘要：

  Antagonist 5-HT1A PET ligands are available, but an agonist ligand would give more information about signal transduction capacity. Synthesis and in vivo evaluation of [O-methyl-C-11]2-{4-[4-(7-methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (10), a potential high affinity (K-i = 1.36 nM) 5-HT1A agonist PET tracer is described. Piperazine 10 is a 5-HT1A agonist with an EC50 comparable to serotonin, based on cAMP formation and GTP(gamma)S binding assays. Radiosynthesis of [C-11]10 has been achieved by reacting 2-{4-[4-(7-hydroxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazitle-3,5-dione (9) and [C-11]CH3OTf in 25 +/- 5% (n = 15) yield at the end of synthesis (EOS). The chemical and radiochemical purities of [C-11]10 were > 99% with a specific activity 1500 +/- 300 Ci/mmol (n = 15). PET studies in anesthetized baboon demonstrate [C-11]10 specific binding, in brain regions rich in 5-HTIA receptors. Binding of [C-11]10 was blocked by WAY 100635 and 8-OH-DPAT. The regional brain volumes of distribution (V-T) of [C-11]10 in baboon correlate with [C-11]WAY100635 V-T in baboons. These data provide evidence that [C-11]10 is the first promising agonist PET tracer for the 5-HTIA receptors.

  DOI：

  10.1021/jm050725j

文献信息

• Synthesis and in Vivo Validation of [<i>O</i>-Methyl-¹¹C]2-{4-[4-(7-methoxynaphthalen-1-yl)piperazin- 1-yl]butyl}-4-methyl-2<i>H</i>-[1,2,4]triazine-3,5-dione:  A Novel 5-HT_1A Receptor Agonist Positron Emission Tomography Ligand
  作者：J. S. Dileep Kumar、Vattoly J. Majo、Shu-Chi Hsiung、Matthew S. Millak、Kuo-Peing Liu、Hadassah Tamir、Jaya Prabhakaran、Norman R. Simpson、Ronald L. Van Heertum、J. John Mann、Ramin V. Parsey

  DOI：10.1021/jm050725j

  日期：2006.1.1

  Antagonist 5-HT1A PET ligands are available, but an agonist ligand would give more information about signal transduction capacity. Synthesis and in vivo evaluation of [O-methyl-C-11]2-4-[4-(7-methoxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazine-3,5-dione (10), a potential high affinity (K-i = 1.36 nM) 5-HT1A agonist PET tracer is described. Piperazine 10 is a 5-HT1A agonist with an EC50 comparable to serotonin, based on cAMP formation and GTP(gamma)S binding assays. Radiosynthesis of [C-11]10 has been achieved by reacting 2-4-[4-(7-hydroxynaphthalen-1-yl)piperazin-1-yl]butyl}-4-methyl-2H-[1,2,4]triazitle-3,5-dione (9) and [C-11]CH3OTf in 25 +/- 5% (n = 15) yield at the end of synthesis (EOS). The chemical and radiochemical purities of [C-11]10 were > 99% with a specific activity 1500 +/- 300 Ci/mmol (n = 15). PET studies in anesthetized baboon demonstrate [C-11]10 specific binding, in brain regions rich in 5-HTIA receptors. Binding of [C-11]10 was blocked by WAY 100635 and 8-OH-DPAT. The regional brain volumes of distribution (V-T) of [C-11]10 in baboon correlate with [C-11]WAY100635 V-T in baboons. These data provide evidence that [C-11]10 is the first promising agonist PET tracer for the 5-HTIA receptors.
• Synthesis and evaluation of arylpiperazines derivatives of 3,5-dioxo-(2 H ,4 H )-1,2,4-triazine as 5-HT 1A R ligands
  作者：J.S. Dileep Kumar、Vattoly J. Majo、Jaya Prabhakaran、J. John Mann

  DOI：10.1016/j.bmcl.2014.07.048

  日期：2014.10

  5-HT1AR agonist or partial agonists are established drug candidates for psychiatric and neurological disorders. We have reported the synthesis and evaluation of a series of high affinity 5-HT1AR partial agonist PET imaging agents with greater selectivity over α-1AR. The characteristic of these molecules are 3,5-dioxo-(2H,4H)-1,2,4-triazine skeleton tethered to an arylpiperazine unit through an alkyl side chain. The most potent 5-HT1AR agonistic properties were found to be associated with the molecules bearing C-4 alkyl group as the linker. Therefore development of 3,5-dioxo-(2H,4H)-1,2,4-triazine bearing arylpiperazine derivatives may provide high affinity selective 5-HT1AR ligands. Herein we describe the synthesis and evaluation of the binding properties of a series of arylpiperazine analogues of 3,5-dioxo-(2H,4H)-1,2,4-triazine.