6-amino-2-pentylsulfanyl-3H-pyrimidin-4-one

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-amino-2-pentylsulfanyl-3H-pyrimidin-4-one
• 英文别名: 4-amino-2-pentylsulfanyl-1H-pyrimidin-6-one
• 化学式: C₉H₁₅N₃OS
• 分子量: 213.304
• InChiKey: ZTGOICKKTYHRSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  92.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-2-pentylsulfanyl-3H-pyrimidin-4-one 在 吡啶 、 三氯氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 7-N,7-N-diethyl-5-pentylsulfanyl-[1,3]thiazolo[4,5-d]pyrimidine-2,7-diamine
  参考文献：
  名称：

  Hit-to-Lead studies: The discovery of potent, orally bioavailable thiazolopyrimidine CXCR2 receptor antagonists

  摘要：

  A Hit-to-Lead optimisation programme was carried out on a high throughput screening hit, the thiazolopyrimidine 1, resulting in the discovery of the potent, orally bioavailable CXCR2 antagonist 29. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.091
• 作为产物：
  描述：

  6-氨基-2-硫脲嘧啶 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以68%的产率得到6-amino-2-pentylsulfanyl-3H-pyrimidin-4-one
  参考文献：
  名称：

  6-Amino-2-mercapto-3H-pyrimidin-4-one derivatives as new candidates for the antagonism at the P2Y12 receptors

  摘要：

  P2Y(12) plays an important role in platelet aggregation, which makes it an interesting target for antithrombotic agents. Compounds that antagonize P2Y(12) include the active metabolites of thienopyridines and molecules that are structurally related to ATP, which is an antagonist of P2Y(12). During the last few years, our group has been working on the development of P2Y(12) receptors antagonists that are based on an extremely simple chemical structure, the 6-amino-2-mercapto-3H-pyrimidin-4-one, variously substituted at the sulfur and oxygen functions. This nucleus represents the simplified combination of two known P2Y(12) antagonists: the active metabolite of the thienopyridines and ATP derivatives. The effects of the synthesized compounds were tested on ADP-induced human platelet aggregation, using light transmission aggregometry. None of the tested compounds induced platelet aggregation, while some of them, at concentration of 10 (4) M, partially inhibited platelet aggregation induced by ADP 10 (6) M. The most potent compound, 6b, antagonized the inhibitory effect of 2-methylthio-ADP on the forskolin-induced accumulation of cyclic-AMP in CHO FlpIN cells expressing recombinant human P2Y(12)-receptors. In addition, none of the tested compounds, including 6b, interfered with ligand binding to P1 receptors. Our results suggest that some of the synthesized compounds are specific antagonists of P2 receptors, and in particular of P2Y(12) and suggest that further development of this structurally new series of compounds as P2Y(12) receptors antagonists is recommended. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.061

文献信息

• Synthesis and Biological Evaluation of New Imidazole, Pyrimidine, and Purine Derivatives and Analogs as Inhibitors of Xanthine Oxidase
  作者：Giuliana Biagi、Alberto Costantini、Luca Costantino、Irene Giorgi、Oreste Livi、Piergiorgio Pecorari、Marcella Rinaldi、Valerio Scartoni

  DOI：10.1021/jm950876u

  日期：1996.1.1

  imidazole, 2,4,5-trisubstituted pyrimidine, 2-substituted purine, thiazolo[3,2-alpha]purine, [1,3]thiazino[3,2-alpha]purine, thiazolo[2,3-i]purine, [1,3]thiazino-[2,3-i]purine, and 6-substituted pyrazolo[3,4-d]pyrimidine were synthesized and tested as inhibitors of the xanthine oxidase enzyme. Of those, some 4-(acylamino)-5-carbamoylimidazoles and 2-thioalkyl-substituted purines exhibited very good inhibitory

  4,5-二取代咪唑，2,4,5-三取代嘧啶，2-取代嘌呤，噻唑并[3,2-α]嘌呤，[1,3]噻嗪并[3,2-α]嘌呤，噻唑的几种衍生物合成了[2,3-i]嘌呤，[1,3]噻嗪基-[2,3-i]嘌呤和6-取代的吡唑并[3,4-d]嘧啶，并作为黄嘌呤氧化酶的抑制剂进行了测试。其中，一些4-（酰基氨基）-5-氨基甲酰咪唑和2-硫代烷基取代的嘌呤表现出非常好的抑制活性，比别嘌呤醇的抑制作用至少强500倍。根据抑制剂别嘌呤醇结合的已知机理，可将6-正烷基吡唑并[3，4-d]嘧啶的无效归因于烷基链，这可能阻碍与钼的配位。咪唑衍生物的有效性，与之相反，4，5-二氨基-2-（硫代烷基）-6-羟基嘧啶表示五元环在与酶相互作用中的相对重要性。此外，有角环化的[1,3]噻嗪基[2,3-i]嘌呤酮具有显着的功效，构成了有趣的一类新抑制剂，并且线性环化衍生物的活性较弱，这使我们能够表征更多恰好面对底物次黄嘌呤的N（1）-C（2）位置的酶的亲脂性区域。