1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid,ethyl ester | 106720-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid,ethyl ester
• 英文别名: 2-benzylsulfanyl-6-methyl-4-(3-nitro-phenyl)-1, 4-dihydro-pyrimidine-5-carboxylic acid ethyl ester；ethyl 2-(benzylthio)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate；1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid, ethyl ester；ethyl 2-benzylsulfanyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate
• CAS: 106720-49-4
• 化学式: C₂₁H₂₁N₃O₄S
• 分子量: 411.481
• InChiKey: WBCZVFKMXNYNCA-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C
• 沸点：
  553.8±60.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid,ethyl ester 生成 diethyl 2-benzylsulfanyl-6-methyl-4-(3-nitrophenyl)-4H-pyrimidine-3,5-dicarboxylate
  参考文献：
  名称：

  ATWAL, KARNAIL;ROVNYAK, GEORGE C.

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-dihydro-2-<<(4-methoxyphenyl)methyl>thio>-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid ethyl ester 在 potassium carbonate 、 三氟乙酸 、 乙硫醇 作用下， 以 四氢呋喃 为溶剂， 生成 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-[(phenylmethyl)thio]-5-pyrimidinecarboxylic acid,ethyl ester
  参考文献：
  名称：

  Atwal, Karnail S.; O'Reilly, Brian C.; Gougoutas, Jack Z., Heterocycles, 1987, vol. 26, # 5, p. 1189 - 1192

  摘要：

  DOI：

文献信息

• A Cs2CO3-mediated simple and selective method for the alkylation and acylation of 3,4-dihydropyrimidin-2(1H)-thiones
  作者：Salil Putatunda、Arijit Chakraborty

  DOI：10.1016/j.crci.2013.12.006

  日期：2014.10

  excellent yields in the presence of Cs2CO3, a mild base. The method evidences a selective S-alkylation when using acyl chlorides as efficient acylating agents at room temperature on the 2-thioxo-dihydropyrimidone moiety. A possible mechanistic interpretation of the different selectivities in case of alkylation and acylation was done with the help of a geometry optimization process.

  摘要 在 Cs2CO3（一种弱碱）存在下，合成了 3,4-二氢嘧啶-2(1H)-硫酮的烷基和酰基衍生物，收率非常好。该方法证明了在室温下使用酰氯作为 2-硫代-二氢嘧啶酮部分上的有效酰化剂时的选择性 S-烷基化。在几何优化过程的帮助下，对烷基化和酰化的不同选择性进行了可能的机械解释。
• 2-substituted thio or oxy-4-aryl or
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04728652A1

  公开（公告）日：1988-03-01

  1,4-Dihydropyrimidines of the formula ##STR1## wherein X is sulfur or oxygen and R.sub.4 is aryl or heterocyclo and disclosed. These compounds are useful as cardiovacular agents, particularly anti-hypertensive agents, due to their vasodilator activity.

  该公式为##STR1##的1,4-二氢嘧啶化合物，其中X为硫或氧，R.sub.4为芳基或杂环基。这些化合物可用作心血管药物，特别是抗高血压药物，因为它们具有扩血管活性。
• Pyrimidinecarboxylic acid derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04753946A1

  公开（公告）日：1988-06-28

  Pyridine compounds of the formula ##STR1## wherein R.sub.4 is aryl or heterocyclo are disclosed. These compounds are useful as cardiovascular agents due to their calcium entry blocking vasodilator activity.

  公开了化学式为##STR1##的吡啶化合物，其中R.sub.4是芳基或杂环烷基。这些化合物由于其钙通道阻滞血管扩张剂活性而可用作心血管药物。
• Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines
  作者：Karnail S. Atwal、George C. Rovnyak、Joseph Schwartz、Suzanne Moreland、Anders Hedberg、Jack Z. Gougoutas、Mary F. Malley、David M. Floyd

  DOI：10.1021/jm00167a035

  日期：1990.5

  2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.
• Synthesis of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines as a new class of antifilarial agents
  作者：B.K. Singh、Mridul Mishra、Nisha Saxena、G.P. Yadav、P.R. Maulik、M.K. Sahoo、R.L. Gaur、P.K. Murthy、R.P. Tripathi

  DOI：10.1016/j.ejmech.2008.01.038

  日期：2008.12

  A series of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines (8-21) were synthesized in good yields by alkylation of 5-methyl-6-phenyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ethyl esters (2-7) with different alkyl or aralkyl halides in the presence of a combination of anhydrous K2CO3 and catalytic amount of tetrabutyl ammonium bromide. The title compounds were evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro and in vivo at various concentrations. One of the compounds (18) showed promising antifilarial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.