N-phenyl-4-(3-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 333768-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-4-(3-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 6-methyl-4-(3-nitrophenyl)-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide；4-methyl-6-(3-nitrophenyl)-2-oxo-N-phenyl-1,2,3,6-tetrahydropyrimidine-5-carboxamide；6-methyl-4-(3-nitrophenyl)-2-oxo-N-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 333768-02-8
• 化学式: C₁₈H₁₆N₄O₄
• 分子量: 352.349
• InChiKey: JWJKQMQXUBCOON-UHFFFAOYSA-N

物化性质

• 熔点：
  262-264 °C(Solv: ethanol (64-17-5))
• 沸点：
  577.5±50.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯胺 以 乙醇 、 甲苯 为溶剂， 生成 N-phenyl-4-(3-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  Targeting Dormant Tuberculosis Bacilli: Results for Molecules with a Novel Pyrimidone Scaffold

  摘要：

  Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug‐resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC‐207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach – recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E‐state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure–activity relationships that will guide the design of more potent inhibitors.

  DOI：

  10.1111/cbdd.12373

文献信息

• A General, Effcient and Green Procedure for Synthesis of Dihydropyrimidine-5-carboxamides in Low Melting Betaine Hydrochloride/Urea Mixture
  作者：Peng Liu、Jianwu Hao、Zhanhui Zhang

  DOI：10.1002/cjoc.201500862

  日期：2016.6

  A simple, facile and convenient strategy has been developed for the synthesis of dihydropyrimidine‐5‐carboxamides in low melting mixture of betaine hydrochloride/urea. In this procedure, the low melting mixture of betaine hydrochloride/urea plays a triple role: as a catalyst, solvent and reactant. The present green protocol has advantages such as high yield of products, short reaction times, operational

  已经开发了一种简单，简便，方便的策略，用于在甜菜碱盐酸盐/尿素的低熔点混合物中合成二氢嘧啶-5-羧酰胺。在此过程中，甜菜碱盐酸盐/尿素的低熔点混合物起着三重作用：作为催化剂，溶剂和反应物。当前的绿色方案具有以下优点：产品产量高，反应时间短，操作简便，无需色谱分离，生态友好以及适用于大规模合成。
• Three-component synthesis of 6-aryl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine-5-(N-aryl)carboxamides
  作者：V. L. Gein、T. M. Zamaraeva、A. A. Kurbatova、M. I. Vakhrin

  DOI：10.1007/s10593-010-0594-y

  日期：2010.11

  A three-component synthesis using acetoacetanilides and a mixture of an aromatic aldehyde and urea yields 6-aryl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine-5-(N-aryl)carboxamides.
• Targeting Dormant Tuberculosis Bacilli: Results for Molecules with a Novel Pyrimidone Scaffold
  作者：Rohit R. Joshi、Avinash Barchha、Vijay M. Khedkar、Raghuvir R. S. Pissurlenkar、Sampa Sarkar、Dhiman Sarkar、Rohini R. Joshi、Ramesh A. Joshi、Anamik K. Shah、Evans C. Coutinho

  DOI：10.1111/cbdd.12373

  日期：2015.2

  Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug‐resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC‐207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach – recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E‐state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure–activity relationships that will guide the design of more potent inhibitors.