3-(2-Chlorophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one | 907557-90-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-Chlorophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one
• CAS: 907557-90-8
• 化学式: C₁₅H₉Cl₃O
• 分子量: 311.595
• InChiKey: KXZODUXKLAXGEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-Chlorophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-(2-chlorophenyl)-3-(3,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors

  摘要：

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.021
• 作为产物：
  描述：

  3,4-二氯苯乙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(2-Chlorophenyl)-1-(3,4-dichlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors

  摘要：

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.021

文献信息

• Solvent-Free Synthesis of Some1-Acetyl Pyrazoles
  作者：Ganesamoorthy Thirunarayanan、Krishnamoorthy Guna Sekar

  DOI：10.5012/jkcs.2013.57.5.599

  日期：2013.10.20

  N-acetyl pyrazoles including 1-(3-(3,4-dichlorophenyl)-5-(substituted phenyl)-4,5-dihydro- 1 H-pyrazole- 1-yl) ethanones have been synthesised by solvent free cyclization cum acetylation of chalcones like substituted styryl 3,4- dichlorophenyl ketones using hydrazine hydrate and acetic anhydride in presence of catalytic amount of fly-ash: H2SO4 catalyst. The yield of these N-acetyl pyrazole derivatives

  通过无溶剂环化合成了一些N-乙酰基吡唑，包括1-（3-（3,4-二氯苯基）-5-（取代的苯基）-4,5-二氢-1 H-吡唑-1-基）乙酮。在催化量的粉煤灰：H2SO4催化剂存在下，使用水合肼和乙酸酐对查尔酮类（如取代的3,4-二氯苯基苯乙烯基酮）进行乙酰化。这些N-乙酰基吡唑衍生物的产率超过75％。合成的N-乙酰基吡唑啉衍生物具有物理常数和光谱数据特征
• Design, Facile Synthesis and Characterization of Dichloro Substituted Chalcones and Dihydropyrazole Derivatives for Their Antifungal, Antitubercular and Antiproliferative Activities
  作者：Afzal B. Shaik、Richie R. Bhandare、Srinath Nissankararao、Zehra Edis、N. Ravikiran Tangirala、Shaik Shahanaaz、M. Mukhlesur Rahman

  DOI：10.3390/molecules25143188

  日期：——

  Infectious diseases caused by fungi and mycobacteria pose an important problem for humankind. Similarly, cancer is one of the leading causes of death globally. Therefore, there is an urgent need for the development of novel agents to combat the deadly problems of cancer, tuberculosis, and also fungal infections. Hence, in the present study, we designed, synthesized, and characterized 30 compounds including 15 chalcones (2–16) and 15 dihydropyrazoles (17–31) containing dichlorophenyl moiety and also screened these compounds for their antifungal, antitubercular, and antiproliferative activities. Among these compounds, the dihydropyrazoles showed excellent antifungal and antitubercular activities whereas the chalcones exhibited promising antiproliferative activity. Among the dihydropyrazoles, compound 31 containing 2-thienyl moiety showed promising antifungal activity (MIC 5.35 µM), whereas compounds 22 and 24 containing 2,4-difluorophenyl and 4-trifluoromethyl scaffolds revealed significant antitubercular activity with the MICs of 3.96 and 3.67 µM, respectively. Compound 16 containing 2-thienyl moiety in the chalcone series showed the highest anti-proliferative activity with an IC50 value of 17 ± 1 µM. The most active compounds identified through this study could be considered as starting points in the development of drugs with potential antifungal, antitubercular, and antiproliferative activities.

  真菌和分枝杆菌引起的传染病对人类构成重要问题。同样，癌症是全球死亡的主要原因之一。因此，迫切需要开发新型药物来对抗癌症、结核病以及真菌感染等致命问题。因此，在本研究中，我们设计、合成和表征了30种化合物，包括15种香豆素（2-16）和15种二氢吡唑（17-31），含有二氯苯基团，并对这些化合物进行了抗真菌、抗结核和抗增殖活性的筛选。在这些化合物中，二氢吡唑表现出优异的抗真菌和抗结核活性，而香豆素表现出有希望的抗增殖活性。在二氢吡唑中，含有2-噻吩基团的31号化合物显示出有希望的抗真菌活性（MIC为5.35 µM），而含有2,4-二氟苯基和4-三氟甲基骨架的22号和24号化合物分别显示出显著的抗结核活性，MIC分别为3.96和3.67 µM。在香豆素系列中，含有2-噻吩基团的16号化合物显示出最高的抗增殖活性，IC50值为17 ± 1 µM。通过本研究确定的最活性化合物可能被视为具有潜在抗真菌、抗结核和抗增殖活性药物开发的起点。
• Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents
  作者：Peng-Cheng Lv、Huan-Qiu Li、Juan Sun、Yang Zhou、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2010.05.034

  日期：2010.7

  Two series of pyrazole derivatives designing for potential EGFR kinase inhibitors have been discovered. Some of them exhibited significant EGFR inhibitory activity. Compound 3-(3,4-dimethylphenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide (C5) displayed the most potent EGFR inhibitory activity with IC50 of 0.07 mu M, which was comparable to the positive control erlotinib. Docking simulation was performed to position compound C5 into the EGFR active site to determine the probable binding model. Antiproliferative assay results indicating that some of the pyrazole derivatives own high antiproliferative activity against MCF-7. Compound C5 showed significant antiproliferative activity against MCF-7 with IC50 of 0.08 mu M. Therefore, compound C5 with potent inhibitory activity in tumor growth inhibition would be a potential anticancer agent. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, biological evaluation and molecular modeling of dihydro-pyrazolyl-thiazolinone derivatives as potential COX-2 inhibitors
  作者：Ke-Ming Qiu、Ru Yan、Man Xing、Hai-Hong Wang、Hong-En Cui、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.09.021

  日期：2012.11

  A series of dihydro-pyrazolyl-thiazolinone derivatives (5a-5t) have been synthesized and their biological activities were also evaluated as potential cyclooxygenase-2 (COX-2) inhibitors. Among these compounds, compound 2-(3-(3,4-dimethylphenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (5a) displayed the most potent COX-2 inhibitory activity with IC50 of 0.5 mu M, but weak to COX-1. Docking simulation was performed to position compound 5a into the COX-2 active site to determine the probable binding model. Based on the preliminary results, compound 5a with potent inhibitory activity and low toxicity would be a potential and selective anti-cyclooxygenase-2 agent. (C) 2012 Elsevier Ltd. All rights reserved.