4-methyl-N-(2-methylphenyl)-6-(3-nitrophenyl)-2-oxo-1,2,3,6-tetrahydropyrimidine-5-carboxamide | 333767-99-0

• 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-methyl-N-(2-methylphenyl)-6-(3-nitrophenyl)-2-oxo-1,2,3,6-tetrahydropyrimidine-5-carboxamide
• 英文别名: 6-methyl-4-(3-nitrophenyl)-2-oxo-N-(o-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxamide；6-methyl-N-(2-methylphenyl)-4-(3-nitrophenyl)-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 333767-99-0
• 化学式: C₁₉H₁₈N₄O₄
• 分子量: 366.376
• InChiKey: BLSDDDFBAHIOTI-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2'-甲基乙酰乙酰苯胺 、 间硝基苯甲醛 、 尿素 以64%的产率得到4-methyl-N-(2-methylphenyl)-6-(3-nitrophenyl)-2-oxo-1,2,3,6-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  Three-component synthesis of 6-aryl-4-methyl-2-oxo-1,2,3,6-tetrahydropyrimidine-5-(N-aryl)carboxamides

  摘要：

  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.

  DOI：

  10.1007/s10593-010-0594-y

文献信息

• [EN] 6 - METHYL - 4 - PHENYL - 5 - ( PHENYL OR CYCLOALKYL) CARBAMOYL - 1,2,3, 4 - TETRAHYDROPYRIMIDIN- 2 - ONE DERIVATIVES AS ANTITUBERCULAR AGENTS<br/>[FR] DÉRIVÉS DE 6 - MÉTHYL - 4 - PHÉNYL - 5 - (PHÉNYL OU CYCLOALKYL) CARBAMOYL - 1,2,3, 4 - TÉTRAHYDROPYRIMIDIN- 2 - ONE UTILISÉS EN TANT QU'AGENTS ANTITUBERCULEUX
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2011151701A1

  公开（公告）日：2011-12-08

  The present invention discloses antitubercular compounds selected from tetrahydropyrimidones/ tetrahydrothiopyrimidone derivatives of Formula (1) and its pharmaceutically acceptable salts for the treatment of Mycobacterium in the dormant phase. Formula (1) wherein, R is H, halogen, dihalogen, O-alkyl, di- O-alkyl, R1 is phenyl, chlorophenyl, nitrophenyl, diclorophenyl, cycloalkyl, preferably cyclohexyl, X is O or S.

  本发明公开了选择自公式（1）的四氢嘧啶酮/四氢硫嘧啶酮衍生物以及其药学上可接受的盐的抗结核化合物，用于治疗休眠期结核分枝杆菌。其中，公式（1）中，R为H、卤素、二卤素、O-烷基、二O-烷基，R1为苯基、氯苯基、硝基苯基、二氯苯基、环烷基，优选环己基，X为O或S。
• 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.
• 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.