N-(3-chloro-4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide | 1088497-36-2

• 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-(3-chloro-4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 1088497-36-2
• 化学式: C₁₈H₁₄ClFN₄O₄
• 分子量: 404.785
• InChiKey: USKYFSGILQIYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 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：
  5

反应信息

• 作为产物：
  描述：

  N-(3-chloro-4-fluorophenyl)-2-acetylacetamide 、 对硝基苯甲醛 、 尿素 在 盐酸 作用下， 以 甲醇 为溶剂， 以59%的产率得到N-(3-chloro-4-fluorophenyl)-6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
  参考文献：
  名称：

  Synthesis, screening for antitubercular activity and 3D-QSAR studies of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxamides

  摘要：

  Multi-drug resistance to commonly used antitubercular drugs has propelled the development of new structural classes of antitubercular agents. This paper reports the synthesis, evaluation and 3D-QSAR analysis of a set of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides as antitubercular agents. Substituted acetoacetanilides were reacted with various aromatic aldehydes and urea which yielded the tetrahydropyrimidine derivatives with a phenyl carbamoyl group at C-5 position, and with various substitutions on the 4-phenyl and the N-phenyl aromatic rings. All compounds were screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. The QSAR models were generated on a training set of 23 molecules. The molecules were aligned using the atom-fit and field-fit techniques. The CoMFA and CoMSIA models generated on the molecules aligned by the atom-fit method show a correlation coefficient (r(2)) of 0.98 and 0.95 with cross-validated r(2)(q(2)) of 0.68 and 0.58, respectively. The 3D-QSAR models were externally validated against a test set of 7 molecules for which the predictive r(2) (r(pred)(2)) is recorded as 0.41 and 0.32 for the CoMFA and CoMSIA models, respectively. The CoMFA and CoMSIA contours helped to design some new molecules with improved activity. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.08.004

文献信息

• Synthesis, screening for antitubercular activity and 3D-QSAR studies of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxamides
  作者：Vijay Virsodia、Raghuvir R.S. Pissurlenkar、Dinesh Manvar、Chintan Dholakia、Priti Adlakha、Anamik Shah、Evans C. Coutinho

  DOI：10.1016/j.ejmech.2007.08.004

  日期：2008.10

  Multi-drug resistance to commonly used antitubercular drugs has propelled the development of new structural classes of antitubercular agents. This paper reports the synthesis, evaluation and 3D-QSAR analysis of a set of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides as antitubercular agents. Substituted acetoacetanilides were reacted with various aromatic aldehydes and urea which yielded the tetrahydropyrimidine derivatives with a phenyl carbamoyl group at C-5 position, and with various substitutions on the 4-phenyl and the N-phenyl aromatic rings. All compounds were screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. The QSAR models were generated on a training set of 23 molecules. The molecules were aligned using the atom-fit and field-fit techniques. The CoMFA and CoMSIA models generated on the molecules aligned by the atom-fit method show a correlation coefficient (r(2)) of 0.98 and 0.95 with cross-validated r(2)(q(2)) of 0.68 and 0.58, respectively. The 3D-QSAR models were externally validated against a test set of 7 molecules for which the predictive r(2) (r(pred)(2)) is recorded as 0.41 and 0.32 for the CoMFA and CoMSIA models, respectively. The CoMFA and CoMSIA contours helped to design some new molecules with improved activity. (C) 2007 Elsevier Masson SAS. All rights reserved.