(E)-1-phenyl-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one | 1228954-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (E)-1-phenyl-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one
• 英文别名: 1-phenyl-3-(1-phenyl-3-p-tolyl-1H-pyrazole-4-yl)prop-2-en-1-one；(E)-3-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenyl-2-propen-1-one；(2E)-3-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylprop-2-en-1-one；(E)-3-[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]-1-phenylprop-2-en-1-one
• CAS: 1228954-09-3
• 化学式: C₂₅H₂₀N₂O
• 分子量: 364.447
• InChiKey: PPIHIKDLCHVTQY-WUKNDPDISA-N

物化性质

• 熔点：
  130-134 °C(Solv: ethanol (64-17-5))
• 沸点：
  564.6±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-phenyl-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one 、 4-肼基苯磺酰胺 在 盐酸 作用下， 以 水 为溶剂， 以62%的产率得到4-(1',5-diphenyl-3'-(p-tolyl)-3,4-dihydro-1'H,2H-[3,4'-bipyrazol]-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study

  摘要：

  A series of pyrazole-pyrazoline substituted with benzenesulfonamide were synthesized and evaluated for their antimalarial activity in vitro and in vivo. The compounds were active against both chloroquine (CQ) sensitive (3D7) and CQ resistant (RKL-9) strains of Plasmodium falciparum. Seven compounds (7e, 7i, 7j, 7l, 7m, 7o and 7p) exhibiting EC50 less than 2 mu M. A mechanistic study of compound 7o revealed that these compound act through the inhibition of beta-hematin. The study indicated that these compounds can serve as lead compounds for further development of potent antimalarial drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.082
• 作为产物：
  描述：

  4-methylbenzaldehyde phenylhydrazone 在 sodium hydroxide 、 三氯氧磷 作用下， 反应 5.25h， 生成 (E)-1-phenyl-3-(1-phenyl-3-(p-tolyl)-1H-pyrazol-4-yl)prop-2-en-1-one
  参考文献：
  名称：

  Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study

  摘要：

  A series of pyrazole-pyrazoline substituted with benzenesulfonamide were synthesized and evaluated for their antimalarial activity in vitro and in vivo. The compounds were active against both chloroquine (CQ) sensitive (3D7) and CQ resistant (RKL-9) strains of Plasmodium falciparum. Seven compounds (7e, 7i, 7j, 7l, 7m, 7o and 7p) exhibiting EC50 less than 2 mu M. A mechanistic study of compound 7o revealed that these compound act through the inhibition of beta-hematin. The study indicated that these compounds can serve as lead compounds for further development of potent antimalarial drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.082

文献信息

• Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory–antimicrobial agents
  作者：Pawan K. Sharma、Satish Kumar、Pawan Kumar、Pawan Kaushik、Dhirender Kaushik、Yogita Dhingra、Kamal R. Aneja

  DOI：10.1016/j.ejmech.2010.01.059

  日期：2010.6

  A new series of pyrazolylpyrazolines (5a–k) was synthesized by the reaction of appropriate chalcones (3a–k) with 4-hydrazinobenzenesulfonamide hydrochloride (4) in ethanol. All the newly synthesized target compounds (5a–k) were screened for their anti-inflammatory activity using carrageenan-induced rat paw edema assay. Compounds 5g and 5j showed pronounced anti-inflammatory activity comparable to the

  通过适当的查耳酮（3a - k）与4-肼基苯磺酰胺盐酸盐（4）在乙醇中的反应合成了一系列新的吡唑基吡唑啉（5a - k）。使用角叉菜胶诱导的大鼠爪水肿试验筛选了所有新合成的目标化合物（5a - k）的抗炎活性。化合物5g和5j的抗炎活性与参考标准尼美舒利相当，而化合物5b，5d和5h显示出良好的抗炎活性。另外，评估了合成的化合物对两种革兰氏阳性细菌和两种革兰氏阴性细菌的体外抗菌活性。四种化合物5c，5h - 5j对所有测试的革兰氏阳性和革兰氏阴性细菌菌株均表现出良好的广谱活性。在这项研究中，化合物5j具有有趣的双重抗炎和抗菌特性，可以被认为是生物活性最高的成员。
• Banpurkar, Anita R.; Perdih, Franc; Wazalwar, Sachin S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2020, vol. 59B, # 1, p. 143 - 146
  作者：Banpurkar, Anita R.、Perdih, Franc、Wazalwar, Sachin S.

  DOI：——

  日期：——
• Pyrazole-pyrazoline as promising novel antimalarial agents: A mechanistic study
  作者：Gautam Kumar、Omprakash Tanwar、Jitender Kumar、Mymoona Akhter、Supriya Sharma、C.R. Pillai、Md Mumtaz Alam、M.S. Zama

  DOI：10.1016/j.ejmech.2018.01.082

  日期：2018.4

  A series of pyrazole-pyrazoline substituted with benzenesulfonamide were synthesized and evaluated for their antimalarial activity in vitro and in vivo. The compounds were active against both chloroquine (CQ) sensitive (3D7) and CQ resistant (RKL-9) strains of Plasmodium falciparum. Seven compounds (7e, 7i, 7j, 7l, 7m, 7o and 7p) exhibiting EC50 less than 2 mu M. A mechanistic study of compound 7o revealed that these compound act through the inhibition of beta-hematin. The study indicated that these compounds can serve as lead compounds for further development of potent antimalarial drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.