N-(2-chlorophenyl)-4-(3-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 1018229-17-8

• 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-(2-chlorophenyl)-4-(3-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: N-(2-chlorophenyl)-6-methyl-4-(3-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 1018229-17-8
• 化学式: C₁₈H₁₅ClN₄O₃S
• 分子量: 402.861
• InChiKey: CJABSKLEBRIZKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 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：
  131
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻氯苯胺 以 乙醇 、 甲苯 为溶剂， 生成 N-(2-chlorophenyl)-4-(3-nitrophenyl)-6-methyl-2-thioxo-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

• Novel Biginelli dihydropyrimidines with potential anticancer activity: A parallel synthesis and CoMSIA study
  作者：B.R. Prashantha Kumar、Gopu Sankar、R.B. Nasir Baig、Srinivasan Chandrashekaran

  DOI：10.1016/j.ejmech.2009.05.014

  日期：2009.10

  Novel Biginelli dihydropyrimidines of biological interest were prepared using p-toluene sulphonic acid as an efficient catalyst. All the thirty-two synthesised dihydropyrimidines were evaluated for their in vitro antioxidant activity using DPPH method. Only, compounds 28 and 29 exhibited reasonably good antioxidant activity. Furthermore, the synthesised Biginelli compounds were subjected for their

  使用对甲苯磺酸作为有效催化剂制备了具有生物学意义的新型比吉内利二氢嘧啶。使用DPPH方法评估了所有32种合成的二氢嘧啶的体外抗氧化活性。仅化合物28和29表现出相当好的抗氧化活性。此外，合成的Biginelli化合物具有针对MCF-7人乳腺癌细胞的体外抗癌活性。以10μg的浓度测试标题化合物。就细胞毒性百分数而言，化合物表现出的活性从弱到中等，从中等到高。其中，化合物10和11表现出显着的抗癌活性。为了阐明其抗癌活性的三维结构-活性关系（3D QSAR），我们对它们进行了比较分子相似性指数分析（CoMSIA）。描述了有关其合成，分析，抗氧化活性，抗癌活性和3D QSAR研究的插图。
• 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.