4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-N-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 1373441-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-N-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 1,2,3,4-tetrahydro-6-methyl-N-(4-nitrophenyl)-4-(1,3-diphenyl-1H-pyrazol-4-yl)-2-thioxopyrimidine-5-carboxamide；4-(1,3-diphenylpyrazol-4-yl)-6-methyl-N-(4-nitrophenyl)-2-thioxo-3,4-dihydro-1H-pyrimidine-5-carboxamide；4-(1,3-diphenylpyrazol-4-yl)-6-methyl-N-(4-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 1373441-69-0
• 化学式: C₂₇H₂₂N₆O₃S
• 分子量: 510.576
• InChiKey: GMOIPGLLWLNERS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(4-硝基-苯胺基)-巴豆酸-(4-硝基-苯胺) 在 盐酸 、 水 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 7.5h， 生成 4-(1,3-diphenyl-1H-pyrazol-4-yl)-6-methyl-N-(4-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  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

• Design, Synthesis, Molecular Modeling, and Biological Evaluation of Novel Pyrimidine Derivatives as Potential Calcium Channel Blockers
  作者：Yasser M. Zohny、Samir M. Awad、Maha A. Rabie、Omar Awad Alsaidan

  DOI：10.3390/molecules28124869

  日期：——

  spectroscopy. The in vivo evaluation of the antihypertensive activity revealed that compounds 4c, 7a, 7c, 8c, 9b and 9c had comparable antihypertensive properties with Nifedipine. On the other hand, the in vitro calcium channel blocking activity was evaluated by IC50 measurement and results revealed that compounds 4c, 7a, 7b, 7c, 8c, 9a, 9b, and 9c had comparable calcium channel blocking activity with the

  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