ethyl 4-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate | 310440-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-5-carboxylate
• 英文别名: ethyl 4-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-[3-(4-chlorophenyl)-1-phenylpyrazol-4-yl]-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 310440-80-3
• 化学式: C₂₃H₂₁ClN₄O₃
• 分子量: 436.898
• InChiKey: RSCJZQSUGBIMQY-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C(Solv: ethanol (64-17-5))
• 沸点：
  588.6±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 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：
  85.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)乙烷-1-酮苯基腙 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 ethyl 4-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,2,3,4-tetrahydro-6-methyl-2-oxopyrimidine-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

• Synthesis of novel 4-pyrazolyl-2-oxo-1,2,3,4-tetrahydropyrimidines promoted by phosphotungstic acid
  作者：Ganesabaskaran Sivaprasad、Paramasivan T. Peramal

  DOI：10.1002/jhet.5570420518

  日期：2005.7

  Phosphotungstic acid, a keggin's type heteropoly acid catatalysed Biginelli reaction was carried out using pyrazole aldehyde, ethyl acetoacetate and urea to synthesis novel 4-pyrazolyl -2-oxo-1,2,3,4-tetrahydropy- rimidines.

  使用吡唑醛，乙酰乙酸乙酯和尿素进行磷钨酸（一种Keggin型杂多酸催化的Biginelli反应），合成了新颖的4-吡唑基-2-氧代-1,2,3,4-四氢嘧啶-嘧啶。
• 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：——
• Novel dihydropyrimidines as a potential new class of antitubercular agents
  作者：Amit R. Trivedi、Vimal R. Bhuva、Bipin H. Dholariya、Dipti K. Dodiya、Vipul B. Kataria、Viresh H. Shah

  DOI：10.1016/j.bmcl.2010.08.046

  日期：2010.10

  A small library of 30 dihydropyrimidines was synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Two compounds, ethyl 4-[3-(4-fluorophenyl)-1-phenyl- 1H-pyrazol-4-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5 carboxylate 4a and ethyl 4-[3-(4-nitrophenyl)- 1-phenyl-1H-pyrazol-4-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 4d were found to be the most active compounds in vitro with MIC of 0.02 mu g/mL against MTB and were more potent than isoniazid. (C) 2010 Elsevier Ltd. All rights reserved.
• Methods and Compositions for the Treatment of RAS Associated Disorders
  申请人：Ratner Nancy

  公开号：US20120302581A1

  公开（公告）日：2012-11-29

  The instant disclosure relates to compositions that may be useful as therapeutic agents for the treatment of disorders associated or caused by Ras deregulation or dysregulation, for example, disorders associated with alterations in the NF1 gene such as neurofibromatosis type I, fungal infections such as those caused by Candida albicans , and proliferative disorders such as glioblastoma.