1-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one | 402939-95-1

• 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: 1-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 1-(2,4-Dichlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 402939-95-1
• 化学式: C₁₆H₁₂Cl₂O₂
• 分子量: 307.176
• InChiKey: ZMEDBKYDRYWFLR-UHFFFAOYSA-N

物化性质

• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 乙腈 为溶剂， 反应 3.67h， 生成 1-[(2,4-dichlorophenyl)[4-(4-methoxyphenyl)-1H-pyrrol-3-yl]methyl]-1H-imidazole
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1H-pyrrolyl)(phenyl)methyl-1H-imidazole Derivatives as Antiprotozoal Agents

  摘要：

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.

  DOI：

  10.1021/acs.jmedchem.8b01464
• 作为产物：
  描述：

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

  某些新型含氟羟基吡唑啉作为潜在的抗癌和抗氧化剂的合成及药理评价

  摘要：

  乳腺癌可能是女性中最普遍的癌症。对治疗剂的抗药性的发展以及对乳腺癌细胞的靶向治疗的缺乏为寻找新的治疗化合物提供了动力。考虑到这一目标，通过多步反应序列合成了一系列新的基于3-氟-4-甲氧基苯基的1,3,5-三取代芳基-5-羟基吡唑啉类似物4a-1。通过IR，1 H NMR，13 C NMR，LC-MS和元素分析证实了新合成的化合物的结构。筛选它们的体外抗癌和体外抗氧化活性。在测试的化合物4h，4c中，尤其是4i对乳腺癌细胞系显示出有希望的细胞毒性作用。当针对DPPH自由基进行测试时，还发现该化合物具有抗氧化活性。总的来说，这项工作为抗癌和抗氧化活性的潜在前景的发展做出了贡献。

  DOI：

  10.1016/j.ejmech.2015.09.029

文献信息

• Synthesis and pharmacological evaluation of some new fluorine containing hydroxypyrazolines as potential anticancer and antioxidant agents
  作者：Dinesha、Shivapura Viveka、Bolli Keerthi Priya、K. Sreedhara Ranganath Pai、Shivalingegowda Naveen、Neratur K. Lokanath、Gundibasappa Karikannar Nagaraja

  DOI：10.1016/j.ejmech.2015.09.029

  日期：2015.11

  Breast cancer is probably the most prevalent cancer in women. The development of resistance to therapeutic agents and lack of targeted therapy for breast cancer cells provide motivation to identify new compounds for the treatment. With this objective in mind, a new series of 3-fluoro-4-methoxyphenyl group based 1,3,5-trisubstituted aryl-5-hydroxypyrazoline analogues 4a–l was synthesized through multi-step

  乳腺癌可能是女性中最普遍的癌症。对治疗剂的抗药性的发展以及对乳腺癌细胞的靶向治疗的缺乏为寻找新的治疗化合物提供了动力。考虑到这一目标，通过多步反应序列合成了一系列新的基于3-氟-4-甲氧基苯基的1,3,5-三取代芳基-5-羟基吡唑啉类似物4a-1。通过IR，1 H NMR，13 C NMR，LC-MS和元素分析证实了新合成的化合物的结构。筛选它们的体外抗癌和体外抗氧化活性。在测试的化合物4h，4c中，尤其是4i对乳腺癌细胞系显示出有希望的细胞毒性作用。当针对DPPH自由基进行测试时，还发现该化合物具有抗氧化活性。总的来说，这项工作为抗癌和抗氧化活性的潜在前景的发展做出了贡献。
• Synthesis and antifungal activity of chalcone derivatives
  作者：Yuanyuan Zheng、Xuesong Wang、Sumei Gao、Min Ma、Guiming Ren、Huabing Liu、Xiaohong Chen

  DOI：10.1080/14786419.2015.1007973

  日期：2015.10.2

  In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifungal activity against Sclerotinia sclerotiorum, Helminthosprium maydis, Botrytis cinerea, Rhizoctonia solani and Gibberella zeae. Among them, the inhibition of growth for compound 30 against S. sclerotiorum showed 89.9%, with the median effective concentrations (EC50) of 15.4gmL(-1). The inhibition of growth for compounds 28, 29 and 30 at a concentration of 100gmL(-1) against H. maydis is 90.3%, 90.7% and 91.1%, with EC50 of 15.1, 18.3 and 18.1gmL(-1), respectively.
• Design, Synthesis, and Bioactivities Screening of a Diaryl Ketone-Inspired Pesticide Molecular Library as Derived from Natural Products
  作者：Hong Zhang、Hong Jin、Lan-zhu Ji、Ke Tao、Wei Liu、Hao-yu Zhao、Tai-ping Hou

  DOI：10.1111/j.1747-0285.2011.01082.x

  日期：2011.7

  Three natural products, 1,5‐diphenylpentan‐1‐one, 1,5‐diphenylpent‐2‐en‐1‐one, and 3‐hydroxy‐1,5‐diphenylpentan‐1‐one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as ‘pharmacophores’, a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)‐1‐(2,4‐dichlorophenyl)‐3‐(furan‐2‐yl)‐ ‐prop‐2‐en‐1‐one (III2) was 1.20 mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
• Synthesis, Molecular Docking and Biological Evaluation of Some Novel Heterocyclic Derivatives
  作者：Flefel, Eman M.、Tantawy、Fayed、Sayed, Hayam H.、Khedr

  DOI：10.21608/ejchem.2012.1164

  日期：2012.8.30
• Design, Synthesis, and Biological Evaluation of New 1-(Aryl-1<i>H</i>-pyrrolyl)(phenyl)methyl-1<i>H</i>-imidazole Derivatives as Antiprotozoal Agents
  作者：Francesco Saccoliti、Valentina Noemi Madia、Valeria Tudino、Alessandro De Leo、Luca Pescatori、Antonella Messore、Daniela De Vita、Luigi Scipione、Reto Brun、Marcel Kaiser、Pascal Mäser、Claudia M. Calvet、Gareth K. Jennings、Larissa M. Podust、Giacomo Pepe、Roberto Cirilli、Cristina Faggi、Annalise Di Marco、Maria Rosaria Battista、Vincenzo Summa、Roberta Costi、Roberto Di Santo

  DOI：10.1021/acs.jmedchem.8b01464

  日期：2019.2.14

  We have designed and synthesized a series of new imidazole-based compounds structurally related to an antiprotozoal agent with nanomolar activity which we identified recently. The new analogues possess micromolar activities against Trypanosoma brucei rhodesiense and Leishmania donovani and nanomolar potency against Plasmodium falciparum. Most of the analogues displayed IC50 within the low nanomolar range against Trypanosoma cruzi, with very high selectivity toward the parasite. Discussion of structure activity relationships and in vitro biological data for the new compounds are provided against a number of different protozoa. The mechanism of action for the most potent derivatives (Si, 6a-c, and 8b) was assessed by a target-based assay using recombinant T. cruzi GYPS1. Bioavailability and efficacy of selected hits were assessed in a T. cruzi mouse model, where 6a and 6b reduced parasitemia in animals >99% following intraperitoneal administration of 25 mg/kg/day dose for 4 consecutive days.