6-methyl-2(1H)-oxo-4-(4-chlorophenyl)-3,4-dihydropyrimidine-5-(2'-chlorophenyl)carboxamide | 421576-05-8

• 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: 6-methyl-2(1H)-oxo-4-(4-chlorophenyl)-3,4-dihydropyrimidine-5-(2'-chlorophenyl)carboxamide
• 英文别名: N-(2-chlorophenyl)-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide；N-(2-chlorophenyl)-4-(4-chlorophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 421576-05-8
• 化学式: C₁₈H₁₅Cl₂N₃O₂
• 分子量: 376.242
• InChiKey: SFBJTKKSJZFAHN-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

• 作为反应物：
  描述：

  6-methyl-2(1H)-oxo-4-(4-chlorophenyl)-3,4-dihydropyrimidine-5-(2'-chlorophenyl)carboxamide 以 乙腈 为溶剂， 反应 2.5h， 以90%的产率得到N-(2-chlorophenyl)-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxamide
  参考文献：
  名称：

  光诱导的2-氧-1,2,3,4-四氢嘧啶-5-羧酰胺的脱氢反应

  摘要：

  通过将各种2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides（THPMs）暴露于紫外光下，研究其光敏性，以阐明位于4-上的取代基的性质的影响。杂环的5-位和氧气或氩气气氛对反应速率的影响。在氩气下的反应速率比在氧气下的反应速率更快，并且受THPM环4和5位上取代基的性质影响。此外，发现THPM-酰胺的脱氢比相应的5-乙氧基羰基-和5-乙酰基-THPM的脱氢更快。与溶液光化学相反，通过固态照射没有观察到变化。

  DOI：

  10.1007/s13738-012-0097-0
• 作为产物：
  描述：

  2-氯乙酰乙酰替苯胺 、 4-氯苯甲醛 、 尿素 在 氯化锆(IV) 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以74%的产率得到6-methyl-2(1H)-oxo-4-(4-chlorophenyl)-3,4-dihydropyrimidine-5-(2'-chlorophenyl)carboxamide
  参考文献：
  名称：

  Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-5-carboxamides

  摘要：

  在回流条件和微波辐射下合成了带有5位羰基基团的各种二氢嘧啶酮衍生物。使用催化量的四氯化锆作为高效催化剂进行高效的三组分Biginelli反应，导致这些化合物的形成。

  DOI：

  10.1515/znb-2010-0408

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.
• Ultrasound assisted dehydrogenation of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
  作者：Hamid R. Memarian、Mousa Soleymani

  DOI：10.1016/j.ultsonch.2010.10.006

  日期：2011.5

  Dehydrogenation of various 2-oxo-1,2,3.4-tetrahydropyrimidine-5-carboxamides (THPMs) to 2-oxo-1,2-dihydropyrimidine-5-carboxamides (DHPMs) using tetrabutylammonium peroxydisulfate (TBAPS) as an efficient oxidizing agent under thermal and sono-thermal conditions has been investigated. In contrast to the thermal reaction, a decrease of the amount of oxidant and an increase of the rate of reaction are observed by simultaneously applying heat and ultrasound. The nature of both C-4 and C-5 substituents on the heterocyclic ring influences the rate of reaction under both conditions. The proposed electron-transfer-induced dehydrogenation in this study is supported by conductometric studies. (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-5-carboxamides
  作者：Mousa Soleymani、Hamid Reza Memarian

  DOI：10.1515/znb-2010-0408

  日期：2010.4.1

  The synthesis of various dihydropyrimidinone derivatives bearing carbamoyl moieties in 5-position under reflux conditions and microwave irradiation is described. An efficient three-component Biginelli reaction using catalytic amounts of zirconium(IV) chloride as an efficient catalyst leads to the formation of these compounds.

  在回流条件和微波辐射下合成了带有5位羰基基团的各种二氢嘧啶酮衍生物。使用催化量的四氯化锆作为高效催化剂进行高效的三组分Biginelli反应，导致这些化合物的形成。
• Light-induced dehydrogenation of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
  作者：H. R. Memarian、M. Soleymani、H. Sabzyan

  DOI：10.1007/s13738-012-0097-0

  日期：2012.10

  an oxygen or argon atmosphere on the rate of reaction. The rate of reaction is faster under argon than under oxygen and is influenced by the nature of the substituent on the 4- and 5-positions of the THPM ring. Furthermore, it is found that the dehydrogenation of THPM-amides is faster than that of the corresponding 5-ethoxycarbonyl- and 5-acetyl-THPMs. In contrast to the solution photochemistry, no

  通过将各种2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides（THPMs）暴露于紫外光下，研究其光敏性，以阐明位于4-上的取代基的性质的影响。杂环的5-位和氧气或氩气气氛对反应速率的影响。在氩气下的反应速率比在氧气下的反应速率更快，并且受THPM环4和5位上取代基的性质影响。此外，发现THPM-酰胺的脱氢比相应的5-乙氧基羰基-和5-乙酰基-THPM的脱氢更快。与溶液光化学相反，通过固态照射没有观察到变化。