5,6-dimethyl-2-phenylpyrimidin-4(3H)-one | 86739-33-5

• 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: 5,6-dimethyl-2-phenylpyrimidin-4(3H)-one
• 英文别名: 5,6-dimethyl-2-phenyl-3H-pyrimidin-4-one；5,6-Dimethyl-2-phenyl-3H-pyrimidin-4-on；5,6-dimethyl-2-phenyl-4(3H)-pyrimidinone；5,6-dimethyl-2-phenyl-1H-pyrimidin-4-one；4,5-dimethyl-2-phenyl-1H-pyrimidin-6-one
• CAS: 86739-33-5
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: JZKBFYMLSCHWIN-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C(Solv: ethanol (64-17-5))
• 沸点：
  321.6±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-dimethyl-2-phenylpyrimidin-4(3H)-one 在 三氯氧磷 作用下， 生成 4-chloro-5,6-dimethyl-2-phenyl-pyrimidine
  参考文献：
  名称：

  Discovery of selective PDE4B inhibitors

  摘要：

  In this study the first PDE4B selective inhibitor is described. Optimization of lead 2-arylpyrimidine derivatives afforded a series of potent PDE4B inhibitors with >100-fold selectivity over the PDE4D isozyme. With a good pharmacokinetic profile, a selected compound exhibited potent anti-inflammatory effects in vivo and showed less emesis compared with Cilomilast. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.121
• 作为产物：
  描述：

  6-甲基-2-苯基嘧啶-4-酮 、 过氧化二异丙苯 以 溶剂黄146 为溶剂， 反应 5.0h， 以65%的产率得到5,6-dimethyl-2-phenylpyrimidin-4(3H)-one
  参考文献：
  名称：

  嘧啶酮和吡啶酮与过氧化二枯基的金属自由基CH甲基化

  摘要：

  介绍了一种在无金属条件下用过氧化二枯基（DCP）与嘧啶酮和吡啶酮进行自由基甲基化的新方法。50 g规模的反应可以在所需的条件下安全地进行...

  DOI：

  10.1039/c6gc03355e

文献信息

• Ultrasound-Promoted Synthesis of 4-Pyrimidinols and Their Tosyl Derivatives
  作者：Moisés Domínguez、Matías Vidal、Macarena García-Arriagada、Marcos Rezende

  DOI：10.1055/s-0035-1562788

  日期：——

  the prepared tosylates with phenylboronic acid. Ultrasound irradiation promoted the cyclocondensation of β-keto esters and amidines in good to excellent yields to form sixteen highly substituted 4-pyrimidinols. Tosylation of these compounds, in another ultrasound-promoted conversion, formed 4-pyrimidyl tosylates in high yields. The use of the developed protocol as an alternative route to 4-arylpyrimidines

  摘要 超声波辐照以良好至优异的产率促进了β-酮酯和am的环缩合反应，形成了十六个高度取代的4-嘧啶醇。这些化合物的甲苯磺酸化，在另一个超声促进的转化中，以高收率形成了4-嘧啶甲苯磺酸盐。所制备的甲苯磺酸盐与苯基硼酸的Suzuki-Miyaura交叉偶联的三个例子说明了使用已开发的方案作为替代4-芳基嘧啶的方法。 超声波辐照以良好至优异的产率促进了β-酮酯和am的环缩合反应，形成了十六个高度取代的4-嘧啶醇。这些化合物的甲苯磺酸化，在另一个超声促进的转化中，以高收率形成了4-嘧啶甲苯磺酸盐。所制备的甲苯磺酸盐与苯基硼酸的Suzuki-Miyaura交叉偶联的三个例子说明了使用已开发的方案作为替代4-芳基嘧啶的方法。
• [EN] BICYCLIC HETEROARYL DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS HÉTÉROARYLES BICYCLIQUES EN TANT QU'INHIBITEURS DE KINASE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2013078254A1

  公开（公告）日：2013-05-30

  The present invention provides compounds, including resolved enantiomers, resolved diastereomers, solvates and pharmaceutically acceptable salts thereof, comprising the Formula 1: wherein Het, X, R1 and R2 are as defined herein.

  本发明提供了化合物，包括已分离的对映体、已分离的异构体、溶剂合物和其药学上可接受的盐，其化学式如下：其中Het、X、R1和R2的定义如本文所述。
• Acetamide derivative, process for preparing the same, and a
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：US05972946A1

  公开（公告）日：1999-10-26

  An acetamide derivative of the formula (I): ##STR1## wherein X is --0-- or --NR.sub.4 --, R.sub.1 is H, lower alkyl, lower alkenyl or cyclolalkyl-lower-alkyl, R.sub.2 is lower alkyl, cycloalkyl, substituted or unsubstituted phenyl, etc., R.sub.3 is H, lower alkyl or hydroxy-lower alkyl, R.sub.4 is H, lower alkyl, etc., R.sub.5 is H, lower alkyl, lower alkenyl, hydroxy-lower alkyl, etc., R.sub.6 is H, lower alkyl, CF.sub.3, substituted or unsubstituted phenyl, or R.sub.5 and R.sub.6 may optionally combine to form --(CH.sub.2)n--, R.sub.7 is H, halogen, lower alkyl, lower alkoxy, CF.sub.3, OH, NH.sub.2, etc., R.sub.8 is H, halogen, lower alkyl or lower alkoxy, or a pharmaceutically acceptable acid addition salt thereof. The compounds of the present invention selectively act on the peripheral-type BZ.omega..sub.3 -receptor, and show excellent pharmacological activities, and hence, they are useful in the prophylaxis or treatment of central nervous disorders such as anxiety-related diseases, depression, epilepsy, etc.

  (I)式的乙酰胺衍生物：其中X为--O--或--NR.sub.4 --，R.sub.1为H、低烷基、低烯基或环烷基-低烷基，R.sub.2为低烷基、环烷基、取代或未取代的苯基等，R.sub.3为H、低烷基或羟基-低烷基，R.sub.4为H、低烷基等，R.sub.5为H、低烷基、低烯基、羟基-低烷基等，R.sub.6为H、低烷基、CF.sub.3、取代或未取代的苯基，或R.sub.5和R.sub.6可选择结合形成--(CH.sub.2)n--，R.sub.7为H、卤素、低烷基、低烷氧基、CF.sub.3、OH、NH.sub.2等，R.sub.8为H、卤素、低烷基或低烷氧基，或其药用可接受的酸盐。本发明的化合物选择性作用于外周型BZ.omega..sub.3-受体，表现出优异的药理活性，因此在预防或治疗与焦虑相关的疾病、抑郁症、癫痫等中枢神经系统紊乱方面具有用处。
• Pinner, Chemische Berichte, 1889, vol. 22, p. 1610
  作者：Pinner

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of Novel Sigma-1 Receptor Antagonists Based on Pyrimidine Scaffold As Agents for Treating Neuropathic Pain
  作者：Yu Lan、Yin Chen、Xudong Cao、Juecheng Zhang、Jie Wang、Xiangqing Xu、Yinli Qiu、Tan Zhang、Xin Liu、Bi-Feng Liu、Guisen Zhang

  DOI：10.1021/jm501207r

  日期：2014.12.26

  The discovery and synthesis of a new series of pyrimidines as potent sigma-1 receptor (sigma R-1) antagonists, associated with pharmacological antineuropathic pain activity, are the focus of this article. The new compounds were evaluated in vitro in sigma-1 and sigma-2 receptor binding assays. The nature of the pyrimidine scaffold was crucial for activity, and a basic amine was shown to be necessary according to the known pharmacophoric model. The most promising derivative was 5-chloro-2-(4-chlorophenyl)-4-methyl-6-(3-(piperidin-1-yl)propoxy)pyrimidine (137), which exhibited a high binding affinity to sigma R-1 receptor (K-i sigma(1) = 1.06 nM) and good sigma-1/2 selectivity (1344-fold). In in vivo tests, compound 137 exerted dose-dependent antinociceptive effects in mice formalin model and rats CCI models of neuropathic pain. In addition, no motor impairments were found in rotarod tests; acceptable pharmacokinetic properties were also noted. These data suggest compound 137 may constitute a novel class of drugs for the treatment of neuropathic pain.