3-(3-溴苯基)-1-(2-羟基-5-甲基苯基)丙-2-烯-1-酮 | 539857-05-1

• 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
• 中文名称: 3-(3-溴苯基)-1-(2-羟基-5-甲基苯基)丙-2-烯-1-酮
• 英文名称: (Z)-3-(3-Bromo-phenyl)-1-(2-hydroxy-5-methyl-phenyl)-propenone
• 英文别名: 3-(3-Bromophenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one；3-(3-bromophenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one
• CAS: 539857-05-1
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: WSYHMFMMQSFAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-溴苯基)-1-(2-羟基-5-甲基苯基)丙-2-烯-1-酮 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 生成 2-(3-bromophenyl)-3-hydroxy-6-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

  摘要：

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma

  DOI：

  10.1080/07391102.2020.1805364
• 作为产物：
  描述：

  2-羟基-5-甲基苯乙酮 、 间溴苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到3-(3-溴苯基)-1-(2-羟基-5-甲基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  新型二氢嘧啶-2-亚砜衍生物作为有效抗菌剂的设计，合成和生物学评价：实验和分子对接方法

  摘要：

  简介：二氢嘧啶骨架代表了重要的一类具有药理活性的含氮杂环化合物。由于具有潜在的生物学活性，具有二氢嘧啶部分的多种分子在药物化学中具有重要作用。 方法：通过在碱性醇溶液中将各种取代的查耳酮与硫脲缩合，以简洁的方式设计和合成了一系列3,4-二氢嘧啶-2（1H）-硫酮衍生物。为了研究它们的生物学意义，测试了这些化合物对各种细菌和真菌菌株的体外抗菌潜力。此外，实验结果得到了分子对接研究的支持。 结果与讨论：用常规光谱技术对新合成的化合物进行了表征。在抗菌活性的情况下，化合物5（40.3±0.44 mm），12和13（近35 mm）对耐甲氧西林的金黄色葡萄球菌表现出最高的抑制区。 （MRSA）细菌菌株与标准药物头孢克肟相比。这些化合物显示出对所有尝试的真菌菌株中等至良好的活性。在对接分析中，发现化合物8（-6.4017 Kcal / mol）和化合物10（-6.1319 Kcal / mol）对青霉素结合蛋白（PDB

  DOI：

  10.2174/1570180815666180209151516

文献信息

• Design, Synthesis and Biological Evaluation of Novel Dihydropyrimidine- 2-Thione Derivatives as Potent Antimicrobial Agents: Experimental and Molecular Docking Approach
  作者：Ehsan Ullah Mughal、Amina Sadiq、Muhammad Hamayun、Muhammad Naveed Zafar、Nighat Fatima、Muhammad Arfat Yameen、Syed Aun Muhammad、Amara Mumtaz、Ishtiaq Ahmed、Tehseen Fatima

  DOI：10.2174/1570180815666180209151516

  日期：2018.9.25

  potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial

  简介：二氢嘧啶骨架代表了重要的一类具有药理活性的含氮杂环化合物。由于具有潜在的生物学活性，具有二氢嘧啶部分的多种分子在药物化学中具有重要作用。 方法：通过在碱性醇溶液中将各种取代的查耳酮与硫脲缩合，以简洁的方式设计和合成了一系列3,4-二氢嘧啶-2（1H）-硫酮衍生物。为了研究它们的生物学意义，测试了这些化合物对各种细菌和真菌菌株的体外抗菌潜力。此外，实验结果得到了分子对接研究的支持。 结果与讨论：用常规光谱技术对新合成的化合物进行了表征。在抗菌活性的情况下，化合物5（40.3±0.44 mm），12和13（近35 mm）对耐甲氧西林的金黄色葡萄球菌表现出最高的抑制区。 （MRSA）细菌菌株与标准药物头孢克肟相比。这些化合物显示出对所有尝试的真菌菌株中等至良好的活性。在对接分析中，发现化合物8（-6.4017 Kcal / mol）和化合物10（-6.1319 Kcal / mol）对青霉素结合蛋白（PDB
• Popat; Nimavat; Kachhadia, Journal of the Indian Chemical Society, 2003, vol. 80, # 7, p. 707 - 708
  作者：Popat、Nimavat、Kachhadia、Joshi

  DOI：——

  日期：——
• Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies
  作者：Jamshaid Ashraf、Ehsan Ullah Mughal、Amina Sadiq、Maryam Bibi、Nafeesa Naeem、Anser Ali、Anam Massadaq、Nighat Fatima、Asif Javid、Muhammad Naveed Zafar、Bilal Ahmad Khan、Muhammad Faizan Nazar、Amara Mumtaz、Muhammad Nawaz Tahir、Masoud Mirzaei

  DOI：10.1080/07391102.2020.1805364

  日期：2021.12.12

  To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened forin vitroagainst mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis,H-1-,C-13-NMR) and mass spectrometry (EI-MS). The structure of compound15was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibioticsi.e.Cefixime and Clotrimazole. Amongst the series, the compounds2, 4, 5, 6, 7, 10, 11, 14and22exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound2(IC50= 0.280 +/- 0.010 mu g/ml) was found almost sixfold and derivative5(IC50= 0.230 +/- 0.020 mu g/ml) about sevenfold more active as compared to standard Kojic acid (IC50=1.79 +/- 0.6 mu g/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma