ethyl1,2,3,4-tetrahydro-6-methyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxylate | 5629-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl1,2,3,4-tetrahydro-6-methyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxylate
• 英文别名: ethyl-4-(1,3-diphenylpyrazol-4-yl)-6-methyl-2-thioxo-1,3,4-trihydropyrimidine-5-carboxylate；ethyl 4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(1,3-diphenylpyrazol-4-yl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 5629-90-3；306281-18-5
• 化学式: C₂₃H₂₂N₄O₂S
• 分子量: 418.519
• InChiKey: YEGXGQSCEIRUAR-UHFFFAOYSA-N

物化性质

• 沸点：
  291.4±33.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl1,2,3,4-tetrahydro-6-methyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxylate 在 sodium hydroxide 作用下， 以68 %的产率得到4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid
  参考文献：
  名称：

  作为潜在钙通道阻滞剂的新型嘧啶衍生物的设计、合成、分子建模和生物学评价

  摘要：

  嘧啶在现代医学领域发挥着重要作用。它们具有广泛的生物活性，如抗菌、抗癌、抗过敏、抗利什曼原虫、抗氧化剂等。此外，近年来，3,4-二氢嘧啶-2(1H)酮吸引了研究人员通过Biginelli反应合成它们，并评估其作为著名钙通道阻滞剂硝苯地平生物等排体的抗高血压活性。我们的新目标化合物是通过硫脲1、乙酰乙酸乙酯2和/或1H-吲哚-2-甲醛、2-氯喹啉-3-甲醛、1,3-二苯基-1H-吡唑-4-甲醛的一锅反应制备的, 3a–c 在酸性介质 (HCl) 中生成嘧啶 4a–c，进而水解为羧酸衍生物 5a–c，再用 SOCl2 氯化，得到酰氯 6a–c。最后，后者与一些选定的芳香胺（即苯胺、对甲苯胺和对硝基苯胺）反应，生成酰胺 7a–c、8a–c 和 9a–c。通过TLC监测检查所制备的化合物的纯度，并通过不同的光谱技术（例如IR、1HNMR、13CNMR和质谱）确认结构。体内抗高血压活性评价表明，化合

  DOI：

  10.3390/molecules28124869
• 作为产物：
  描述：

  N-(1-phenylethylidene)phenylhydrazine 在 对甲苯磺酸 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 ethyl1,2,3,4-tetrahydro-6-methyl-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis and in vitro anticancer and antitubercular activity of diarylpyrazole ligated dihydropyrimidines possessing lipophilic carbamoyl group

  摘要：

  A series of dihydropyrimidine derivatives were synthesized by utilizing Biginelli reaction and evaluated for their in vitro anticancer activity against MCF-7 human breast cancer (HBC) cell line using sulforhodamine B (SRB) assay and antitubercular activity against Mycobacterium tuberculosis (MTB) H(37)Rv using Microplate Alamar Blue Assay (MABA). Compounds 13p, 13t were exhibited 70.6% and 63.7% of HBC cell growth inhibition at 10 mu M concentration. Interestingly compound 13p was also found to be the most potent in the series against MTB H(37)Rv with MIC value of 0.125 mu g/mL. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.02.101

文献信息

• Reaction with Hydrazonoyl Halides 64: Synthesis of Some New Triazolino[4,3-<i>a</i>]pyrimidines, 1,3,4-Thiadiazoles, and 5-Arylazothiazoles
  作者：Abdou O. Abdelhamid、Abdelgawad A. Fahmi、Basma S. Baaui

  DOI：10.1002/jhet.945

  日期：2012.9

  benzofuran moiety were prepared from the reaction of 2‐(2‐phenylhydrazono)‐1‐(5‐bromobenzofuran‐2‐yl)‐2‐chloroethanone with each of potassium thiocyanate, potassium selenocyanate, alkyl carbodithioate, and pyrmidine‐2‐thione derivatives. All the newly synthesized compounds were confirmed by elemental analysis, spectral data, and alternative route synthesis whenever possible.

  由2-（-）的反应制得2,3-二氢-1,3,4-噻二唑，2,3-二氢-1,3,4-硒代二唑和含苯并呋喃部分的三唑啉并[4,3- a ]嘧啶。 2-苯基肼基）-1-（5-溴苯并呋喃-2-基）-2-氯乙酮与硫氰酸钾，硒氰酸钾，碳二硫代烷基酯和嘧啶-2-硫酮衍生物中的每一种。所有新合成的化合物均通过元素分析，光谱数据和可能的替代路线合成得到确认。
• 4-Functionally Substituted 3-Heterylpyrazoles: XIII. 3-Aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones)
  作者：M. K. Bratenko、V. A. Chornous、M. V. Vovk

  DOI：10.1007/s11178-005-0127-9

  日期：2005.1

  Cyclocondesation of 3-aryl(heteryl)pyrazole-4-carbaldehydes with ethyl acetoacetate and urea (thiourea) in the presence of FeCl3 · 6H2O afforded 3-aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  3-芳基(杂基)吡唑-4-甲醛与乙酰乙酸乙酯和脲(硫脲)在FeCl3·6H2O存在下环缩合得到3-芳基(杂基)-4-(4-吡唑基)-1,2,3， 4-四氢嘧啶-2-酮（硫酮）。
• Sarasija; Ashok; Sudershan, Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 3, p. 349 - 352
  作者：Sarasija、Ashok、Sudershan、Shivaraj

  DOI：——

  日期：——
• Synthesis of some new Ethyl 4-(1,3-Diarylpyrazol-4-yl)-6-methyl-2-thioxo-1,3,4-trihydropyrimidine-5-carboxylates
  作者：G. Jagath Reddy、D. Latha、K. Srinivasa Rao

  DOI：10.1515/hc.2004.10.4-5.331

  日期：2004.1
• Synthesis and in vitro anticancer and antitubercular activity of diarylpyrazole ligated dihydropyrimidines possessing lipophilic carbamoyl group
  作者：Rama Krishna Yadlapalli、O.P. Chourasia、Kiranmayi Vemuri、Manjula Sritharan、Ramu Sridhar Perali

  DOI：10.1016/j.bmcl.2012.02.101

  日期：2012.4

  A series of dihydropyrimidine derivatives were synthesized by utilizing Biginelli reaction and evaluated for their in vitro anticancer activity against MCF-7 human breast cancer (HBC) cell line using sulforhodamine B (SRB) assay and antitubercular activity against Mycobacterium tuberculosis (MTB) H(37)Rv using Microplate Alamar Blue Assay (MABA). Compounds 13p, 13t were exhibited 70.6% and 63.7% of HBC cell growth inhibition at 10 mu M concentration. Interestingly compound 13p was also found to be the most potent in the series against MTB H(37)Rv with MIC value of 0.125 mu g/mL. (C) 2012 Published by Elsevier Ltd.