6-hexylamino-2,4(1H,3H)-pyrimidinedione | 72255-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-hexylamino-2,4(1H,3H)-pyrimidinedione
• 英文别名: PSB-1584；6-Hexylamino-1H-pyrimidine-2,4-dione；6-(hexylamino)-1H-pyrimidine-2,4-dione
• CAS: 72255-76-6
• 化学式: C₁₀H₁₇N₃O₂
• 分子量: 211.264
• InChiKey: SDXQSUJXSHUIBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hexylamino-2,4(1H,3H)-pyrimidinedione 在 ammonium cerium(IV) nitrate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 10-Hexyl-8-methoxy-10H-pyrimido[4,5-b]quinoline-2,4,6,9-tetraone
  参考文献：
  名称：

  Kimachi, Tetsutaro; Tamura, Yoshinori; Bessho, Kiyoshi, Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 697 - 700

  摘要：

  DOI：
• 作为产物：
  描述：

  己-2-烯-1-胺 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 正丁醇 为溶剂， 20.0~125.0 ℃ 、172.37 kPa 条件下， 反应 14.0h， 生成 6-hexylamino-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights

  摘要：

  The orphan G protein-coupled receptor (GPCR) GPR84 is expressed on immune cells mediating proinflammatory and immunostimulatory effects. In this study, we prepared the fully efficacious, nonbiased GPR84 agonist 6-hexylamino-2,4(1H,3H)-pyrimidinedione (6) in tritium-labeled form ([H-3]PSB-1584) by hydrogenation of a hexenyl-substituted precursor with tritium gas. The radio-ligand was characterized by kinetic, saturation, and competition assays using membranes of Chinese hamster ovary cells recombinantly expressing the human GPR84. [H-3]6 reversibly labeled the receptor with high affinity (K-D 2.08 nM). Structurally diverse orthosteric and allosteric ligands, including newly designed and synthesized compounds, were studied in competition binding assays. A homology model of GPR84 was generated to perform docking studies rationalizing the experimental data. The radioligand was additionally used for labeling GPR84 in native cells and tissues. [H-3]6 constitutes the first GPR84 agonist radioligand representing a powerful tool for this poorly investigated GPCR, which has potential as a future drug target.

  DOI：

  10.1021/acs.jmedchem.9b01339

文献信息

• An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights
  作者：Meryem Köse、Thanigaimalai Pillaiyar、Vigneshwaran Namasivayam、Elisabetta De Filippo、Katharina Sylvester、Trond Ulven、Ivar von Kügelgen、Christa E. Müller

  DOI：10.1021/acs.jmedchem.9b01339

  日期：2020.3.12

  The orphan G protein-coupled receptor (GPCR) GPR84 is expressed on immune cells mediating proinflammatory and immunostimulatory effects. In this study, we prepared the fully efficacious, nonbiased GPR84 agonist 6-hexylamino-2,4(1H,3H)-pyrimidinedione (6) in tritium-labeled form ([H-3]PSB-1584) by hydrogenation of a hexenyl-substituted precursor with tritium gas. The radio-ligand was characterized by kinetic, saturation, and competition assays using membranes of Chinese hamster ovary cells recombinantly expressing the human GPR84. [H-3]6 reversibly labeled the receptor with high affinity (K-D 2.08 nM). Structurally diverse orthosteric and allosteric ligands, including newly designed and synthesized compounds, were studied in competition binding assays. A homology model of GPR84 was generated to perform docking studies rationalizing the experimental data. The radioligand was additionally used for labeling GPR84 in native cells and tissues. [H-3]6 constitutes the first GPR84 agonist radioligand representing a powerful tool for this poorly investigated GPCR, which has potential as a future drug target.
• Kimachi, Tetsutaro; Tamura, Yoshinori; Bessho, Kiyoshi, Journal of the Chemical Society. Perkin transactions I, 1993, # 6, p. 697 - 700
  作者：Kimachi, Tetsutaro、Tamura, Yoshinori、Bessho, Kiyoshi、Yoneda, Fumio

  DOI：——

  日期：——