(E)-1-(4-bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one

• 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: (E)-1-(4-bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-4-bromophenyl-3-(2-methoxyphenyl)prop-2-en-1-one；3-Oxo-1-<2-methoxy-phenyl>-3-<4-brom-phenyl>-propen-(1)
• 化学式: C₁₆H₁₃BrO₂
• 分子量: 317.182
• InChiKey: BQTFYNPTSBOPJK-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 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：

  (E)-1-(4-bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one 在 bis(η3-allyl-μ-chloropalladium(II)) 、 p-methylbenzaldehyde oxime 、 caesium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以87%的产率得到(E)-1-(4-hydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  高效溶剂和温度调谐访问醛肟醚和酚的功能通过Pd催化的C-O交叉偶联与芳基溴化物和溴查耳酮醛肟的†

  摘要：

  首次开发了具有功能切换选项的单一方法，用于钯催化芳基溴化物和溴代查耳酮与醛肟的C–O交叉偶联。发现配体t BuXPhos（L2）是Pd催化的醛肟与溴偶联伙伴的偶联的有效支撑配体。从肟醚到酚基或羟基的官能团转换是由溶剂或温度驱动的。该方法在短的反应时间内以良好的产率提供了优异的产物。

  DOI：

  10.1039/c9nj05124d
• 作为产物：
  描述：

  4-溴苯乙酮 、 邻甲氧基苯甲醛 生成 (E)-1-(4-bromophenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  ULTRAVIOLET ABSORPTION OF SUBSTITUTED PHENYL AND POLYCYCLIC ARYL CHALCONES

  摘要：

  报道了一系列取代的反式查尔酮对紫外和近可见光的吸收。

  DOI：

  10.1139/v64-377

文献信息

• SAR and molecular mechanism studies of monoamine oxidase inhibition by selected chalcone analogs
  作者：Raed Shalaby、Jacobus P. Petzer、Anél Petzer、Usman M. Ashraf、Ealla Atari、Fawaz Alasmari、Sivarajan Kumarasamy、Youssef Sari、Ashraf Khalil

  DOI：10.1080/14756366.2019.1593158

  日期：2019.1.1

  reversible competitive mode of inhibition. Most of the synthesized chalcone analogs showed a better selectivity toward MAO-B. However, introducing of 2,4,6-trimethoxy substituents on ring B shifted the selectivity toward MAO-A. In addition, we investigated the molecular mechanism of MAO-B inhibition by selected chalcone analogs. Our results revealed that these selected chalcone analogs increased dopamine levels

  抽象的 本研究描述了一系列22查尔酮类似物的合成。这些化合物被评估为潜在的人类MAO-A和MAO-B抑制剂。化合物对两种同工型表现出不同的选择性。发现IC 50值在微摩尔至亚微摩尔范围内。该ķ我化合物16的MAO-A和MAO-B抑制值分别为0.047和0.020μM。酶抑制剂混合物的透析表明抑制作用是可逆的竞争方式。大多数合成的查耳酮类似物对MAO-B表现出更好的选择性。然而，在环B上引入2,4,6-三甲氧基取代基使选择性向MAO-A转移。此外，我们研究了所选查耳酮类似物抑制MAO-B的分子机制。我们的结果表明，这些选定的查尔酮类似物可增加大鼠肝癌（H4IIE）细胞中的多巴胺水平，并降低MAO-B酶的相对mRNA表达。
• Quantum chemical insight into molecular structure, density functional theory calculations, vibrational dynamics, natural population analysis, Hirshfeld analysis, and molecular docking approach to chalcone 1-4-bromophenyl-3-(2-methoxyphenyl)prop-2-en-1-one
  作者：Y. Premila Rachelin、Sayantan Pradhan、C. James

  DOI：10.1080/00387010.2018.1442352

  日期：2018.3.16

  3-parameter, Lee-Yang-Parr functional was used for the optimization of geometry. The comprehensive assignments of the vibrational spectra have been performed with the aid of normal coordinate analysis. Stability of the molecule and intra/intermolecular charge transfer have been analyzed using natural bond orbital analysis. The existence of intermolecular C-H⋯O, blueshifted hydrogen bond was investigated by bond

  摘要 新型查尔酮 1-4-溴苯基-3-(2-甲氧基苯基)prop-2-en-1-one 的结构已通过傅里叶变换红外和傅里叶变换拉曼表征。使用 Becke、3 参数、Lee-Yang-Parr 泛函的密度泛函理论用于优化几何。振动谱的综合分配已经在法向坐标分析的帮助下进行。已经使用自然键轨道分析分析了分子的稳定性和分子内/分子间电荷转移。通过键长变化研究了分子间CH⋯O、蓝移氢键的存在。赫什菲尔德和二维指纹图分析已用于研究分子中存在的相互作用的性质。对接复合体给出 -8 的恒定性。
• Synthesis of novel chalcones through palladium-catalyzed C O cross-coupling reaction of bromo-chalcones with ethyl acetohydroxamate and their antiplasmodial evaluation against Plasmodium falcipuram in vitro
  作者：Reeta、Rajendran Vinoth、T.M. Rangarajan、Ayushee、Rishi Pal Singh、Manjula Singh

  DOI：10.1016/j.bioorg.2019.02.016

  日期：2019.5

  An efficient method for palladium-catalyzed CO cross-coupling of ethyl acetohydroxamate (EAcHO) with 4-bromo-chalcones has been developed to synthesize novel chalcones. The two supporting ligands, namely tBuXPhos (L7), and cataCXium®PIntB (L16) were found to be effective ligands towards the Pd-catalyzed CO cross-coupling reaction to afford the desired product in moderate to excellent yields (50-99%)

  已开发出一种有效的方法，用于钯催化的乙酰氧肟酸乙酯（EAcHO）与4-溴-查耳酮的CO交叉偶联反应，以合成新型查耳酮。发现两个支持配体，即tBuXPhos（L7）和cataCXium®PIntB（L16）是有效的配体，可实现Pd催化的CO交叉偶联反应，以中等至极好的收率（50-99％）提供所需的产物。使用[3H]次黄嘌呤掺入抑制试验，筛选偶联产物的体外血液期对恶性疟原虫（3D7）的抗血浆活性。在筛选的22种化合物中，有11种显示出良好的抗血浆活性，IC50值为6-16μg/ mL。选择的活性分子11、16、22，
• Synthesis of N-acylated pyrazolines: Spectroscopic, crystallographic, Hirshfeld Surface, lead sensing and theoretical studies
  作者：Mohammad Asad、Muhammad Nadeem Arshad、Abdullah M. Asiri、Hadi M. Marwani、Khalid A. Alamry、Mohammad Mahboob Alam、Syed Nazreen、Ahmed A. Elhenawy、Mohammed M. Rahman

  DOI：10.1016/j.molliq.2023.122340

  日期：2023.9

  spectral analyses, as well as single crystal diffraction study (Sc-XRD). An effective metal ion sensor (Lead ion) with a flat glassy carbon electrode (GCE) was produced for prospective use by coupling a conducting coating binder (PEDOT:PSS) with a thin-layer NA2Pyr modified electrode (NA2Pyr/GCE). Linear sweep voltammetry was used to detect lead (Pb2+) ions in phosphate aqueous phase. The sensitivity (11,867

  N-酰化-2-吡唑啉(NA2Pyr) 分别由查尔酮和水合肼在丙酸和三氟乙酸存在下通过一锅环缩合合成。使用 FT-IR、 1 H NMR、13 C NMR 光谱分析以及单晶衍射研究 (Sc-XRD)确定结构。通过将导电涂层粘合剂 (PEDOT:PSS) 与薄层 NA2Pyr 修饰电极 (NA2Pyr/GCE) 耦合，生产了一种具有扁平玻碳电极 (GCE) 的有效金属离子传感器（铅离子），用于预期用途。线性扫描伏安法用于检测磷酸盐水相中的铅 (Pb 2+ ) 离子。灵敏度（11,867 uAnM -1 cm -2) 的化学传感器探头是利用校准曲线斜率和调整后的电极活性表面积测量的。使用校准图的最大线性线计算线性动态范围（LDR：0.01nM 至 10.0mM）。检测限 (0.008nM) 的计算方法包括 3σ/m（其中 σ 是空白响应的标准偏差，m 是校准曲线的斜率）。这种新型电化学方法是检测
• Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics
  作者：Thanh-Dao Tran、Tuong-Ha Do、Ngoc-Chau Tran、Trieu-Du Ngo、Thi-Ngoc-Phuong Huynh、Cat-Dong Tran、Khac-Minh Thai

  DOI：10.1016/j.bmcl.2012.05.112

  日期：2012.7

  A total of 30 chalcone analogues was synthesized via a base catalyzed Claisen Schmidt condensation and screened for their in vitro antibacterial activity against Methicillin-sensitive Staphylococcus aureus (MSSA) and Methicillin-resistant Staphylococcus aureus (MRSA) alone or in combination with non beta-lactam antibiotics namely ciprofloxacin, chloramphenicol, erythromycin, vancomycin, doxycycline and gentamicin. In the checkerboard technique, fractional inhibitory concentration indices (FICI) show that the following combinations like ciprofloxacin with 25 (4'-bromo-2-hydroxychalcone); doxycycline with 21 (4-hydroxychalcone); doxycycline with 25; and doxycycline with 4 (2',2-dihydroxychalcone) were synergistic against MRSA. In term SAR study, the relationship between chalcone structure and their antibacterial activity against S. aureus and synergy with tested antibiotics were discussed. Possible mechanisms for antibacterial activity of chalcones alone as well as the synergistic effect in combinations were proposed by molecular modeling studies, respectively. Combinations of chalcones with conventional antibiotics could be an effective alternative in the treatment of infection caused by MRSA. (C) 2012 Elsevier Ltd. All rights reserved.