4-(2,4-dichlorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 332032-59-4

• 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: 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-N-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 332032-59-4
• 化学式: C₁₈H₁₅Cl₂N₃O₂
• 分子量: 376.242
• InChiKey: FJJCCDARQRJXHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 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：
  70.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯胺 以 乙醇 、 甲苯 为溶剂， 生成 4-(2,4-dichlorophenyl)-6-methyl-2-oxo-N-phenyl-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

• Ultrasound-Assisted Synthesis of 6-Methyl-1,2,3,4-tetrahydro-<i>N</i>-aryl-2-oxo/thio-4-arylpyrimidine-5-carboxamides Catalyzed by Uranyl Nitrate Hexahydrate
  作者：K. Venkatesan、V. S. V. Satyanarayana、A. Sivakumar

  DOI：10.1002/jccs.201300380

  日期：2014.6

  An efficient and simple method developed for the synthesis of 6‐methyl‐1,2,3,4‐tetrahydro‐N‐aryl‐2‐oxo/thio‐4‐arylpyrimidine‐5‐carboxamide derivatives (4a‐o) using UO2(NO3)2.6H2O catalyst under conventional and ultrasonic conditions. The ultrasound irradiation synthesis had shown several advantages such as milder conditions, shorter reaction times and higher yields. The structures of all the newly

  使用UO 2合成6-甲基-1,2,3,4-四氢-N-芳基-2-氧代/硫代-4-芳基嘧啶-5-羧酰胺衍生物（4a-o）的有效而简单的方法（NO 3）2 .6H 2 O催化剂在常规和超声条件下。超声辐射合成显示出一些优点，例如条件温和，反应时间更短和产率更高。所有新合成的化合物的结构均已通过FT-IR，1 H NMR，13 C NMR和质谱证实。
• Synthesis of pyrimidine carboxamide derivatives catalyzed by uranyl nitrate hexa Hydrate with their antibacterial and antioxidant studies
  作者：K. Venkatesan、V. S. V. Satyanarayana、A. Sivakumar

  DOI：10.4314/bcse.v30i1.11

  日期：——

  An efficient and simple method was developed for the synthesis pyrimidine-5-carboxamides using UO 2 (NO 3 ) 2 .6H 2 O catalyst under conventional and microwave irradiation. The synthesis of dihydropyrimidine using uranyl nitrate had shown many advantages such as easy work up, shorter reaction times and higher yields using acetonitrile as a solvent. The structures of the synthesized compounds were confirmed

  开发了一种高效简单的方法，在常规和微波辐射下，使用UO 2（NO 3）2 .6H 2 O催化剂合成嘧啶-5-甲酰胺。用硝酸铀酰合成二氢嘧啶显示出许多优点，例如易于处理，较短的反应时间和使用乙腈作为溶剂的较高产率。合成的化合物的结构通过FT-IR，1 H NMR，13 C NMR和质谱数据确认。筛选了所有合成的化合物的体外抗氧化和抗菌活性，并报道了结果。关键词：微波，硝酸铀酰，抗氧化剂，抗菌公牛。化学 Soc。埃塞俄比亚。2016，30（1），119-128。DOI：http：//dx.doi.org/10.4314/bcse.v30i1.11