2-Amino-5,6-diphenyl-4(3H)-pyrimidinon | 66376-75-8

• 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: 2-Amino-5,6-diphenyl-4(3H)-pyrimidinon
• 英文别名: 2-amino-5,6-diphenylpyrimidin-4(3H)-one；2-amino-5,6-diphenyl-3H-pyrimidin-4-one；2-Amino-5,6-diphenyl-3H-pyrimidin-4-on；2-amino-4,5-diphenyl-1H-pyrimidin-6-one
• CAS: 66376-75-8
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: HVDNXYLJMBRMTI-UHFFFAOYSA-N

物化性质

• 熔点：
  319 °C
• 沸点：
  466.0±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-2,3-二苯基丙烯腈 在 sulfur 作用下， 生成 2-Amino-5,6-diphenyl-4(3H)-pyrimidinon
  参考文献：
  名称：

  Eicher, Thoephil; Franke, Guenter, Liebigs Annalen der Chemie, 1981, # 8, p. 1337 - 1353

  摘要：

  DOI：

文献信息

• HTS followed by NMR based counterscreening. Discovery and optimization of pyrimidones as reversible and competitive inhibitors of xanthine oxidase
  作者：Johan Evenäs、Fredrik Edfeldt、Matti Lepistö、Naila Svitacheva、Anna Synnergren、Britta Lundquist、Mia Gränse、Anna Rönnholm、Mikael Varga、John Wright、Min Wei、Sherrie Yue、Junfeng Wang、Chong Li、Xuan Li、Gang Chen、Yong Liao、Gang Lv、Ann Tjörnebo、Frank Narjes

  DOI：10.1016/j.bmcl.2014.01.050

  日期：2014.3

  based inhibitors of xanthine oxidase is described. After a high-throughput screening campaign, an NMR based counterscreen was used to distinguish actives, which interact with XO in a reversible manner, from assay artefacts. This approach identified pyrimidone 1 as a reversible and competitive inhibitor with good lead-like properties. A hit to lead campaign gave compound 41, a nanomolar inhibitor of hXO

  描述了新型，非嘌呤的黄嘌呤氧化酶抑制剂的鉴定。经过高通量筛选活动后，基于NMR的反筛选用于区分活性物，这些活性物以可逆方式与XO相互作用，与分析伪像分离。该方法将嘧啶酮1鉴定为可逆的竞争性抑制剂，具有良好的铅样性质。导致先头运动获得化合物41，一种hXO的纳摩尔抑制剂，口服给药后在高尿酸血症大鼠模型中具有功效。
• Hitchings et al., Journal of the Chemical Society, 1956, p. 1019,1023, 1024
  作者：Hitchings et al.

  DOI：——

  日期：——
• Structural studies on bioactive compounds. Part 29
  作者：Duncan R. Hannah、Edward C. Sherer、Roy V. Davies、Roger B. Titman、Charles A. Laughton、Malcolm F.G. Stevens

  DOI：10.1016/s0968-0896(00)00017-1

  日期：2000.4

  The immunological agent bropirimine 5 is a tetra-substituted pyrimidine with anticancer and interferon-inducing properties. Synthetic routes to novel 5-aryl analogues of bropirimine have been developed and their potential molecular recognition properties analysed by molecular modelling methods. Sterically challenged 2-amino-5-halo-6-phenylpyrimidin-4-ones (halo = Br or I) are poor substrates for palladium catalysed Suzuki cross-coupling reactions with benzeneboronic acid because the basic conditions of the reaction converts the amphoteric pyrimidinones to their unreactive enolic forms. Palladium-mediated reductive dehalogenation of the pyrimidinone substrates effectively competes with cross-coupling. 2-Amino-5-halo-4-methoxy-6-phenylpyrimidines can be converted to a range of 5-aryl derivatives with the 5-iodopyrimidines being the most efficient substrates. Hydrolysis of the 2-amino-5-aryl-4-methoxy-6-phenylpyrimidines affords the required pyrimidin-4-ones in high yields. Semi-empirical quantum mechanical calculations show how the nature of the 5-substituent influences the equilibrium between the 1H- and 3H-tautomeric forms, and the rotational freedom about the bond connecting the 6-phenyl group and the pyrimidine ring. Both of these factors may influence the biological properties of these compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.
• EICHER, T.;GRANKE, G., LIEBIGS ANN. CHEM., 1981, N 8, 1337-1353
  作者：EICHER, T.、GRANKE, G.

  DOI：——

  日期：——
• Eicher, Thoephil; Franke, Guenter, Liebigs Annalen der Chemie, 1981, # 8, p. 1337 - 1353
  作者：Eicher, Thoephil、Franke, Guenter

  DOI：——

  日期：——