(E)-1-(4-bromophenyl)-3-(3-hydroxyphenyl)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-(3-hydroxyphenyl)prop-2-en-1-one
• 英文别名: 1-(4-Bromophenyl)-3-(3-hydroxyphenyl)prop-2-ene-1-one
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: OBAKZNFZACQQKK-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  哌啶 、 聚合甲醛 、 (E)-1-(4-bromophenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 以 乙醇 为溶剂， 以89 %的产率得到(E)-1-(4-bromophenyl)-3-(3-hydroxy-4-(piperidin-1-ylmethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcone Mannich base derivatives: synthesis, antimalarial activities against Plasmodium knowlesi, and molecular docking analysis

  摘要：

  关于氨基烷基查尔酮衍生物对恶性疟原虫和克雷西疟原虫的抗疟作用的研究推动了药物研发工作，以应对抗药性问题。

  DOI：

  10.1039/d3ra05361j
• 作为产物：
  描述：

  4-溴苯乙酮 、 间羟基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-1-(4-bromophenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Chalcone Mannich base derivatives: synthesis, antimalarial activities against Plasmodium knowlesi, and molecular docking analysis

  摘要：

  关于氨基烷基查尔酮衍生物对恶性疟原虫和克雷西疟原虫的抗疟作用的研究推动了药物研发工作，以应对抗药性问题。

  DOI：

  10.1039/d3ra05361j

文献信息

• Syntheses and in Vitro Antiplasmodial Activity of Aminoalkylated Chalcones and Analogues
  作者：Anke Wilhelm、Pravin Kendrekar、Anwar E. M. Noreljaleel、Efrem T. Abay、Susan L. Bonnet、Lubbe Wiesner、Carmen de Kock、Kenneth J. Swart、Jan Hendrik van der Westhuizen

  DOI：10.1021/acs.jnatprod.5b00114

  日期：2015.8.28

  A series of readily synthesized and inexpensive aminoalkylated chalcones and diarylpropane analogues (1-55) were synthesized and tested against chloroquinone-sensitive (D10 and NF54) and -resistant (Dd2 and K1) strains of Plasmodium falciparum. Hydrogenation of the enone to a diarylpropane moiety increased antiplasmodial bioactivity significantly. The influence of the structure of the amine moiety, A-ring substituents, propyl vs ethyl linker, and chloride salt formation on further enhancing antiplasmodial activity was investigated. Several compounds have IC50 values similar to or better than chloroquine (CQ). The most active compound (26) had an IC50 value of 0.01 mu M. No signs of resistance were detected, as can be expected from compounds with structures unrelated to CQ and other currently used antimalarial drugs. Toxicity tests (in vitro CHO cell assay) gave high SI indices.
• Chalcone Mannich base derivatives: synthesis, antimalarial activities against <i>Plasmodium knowlesi</i>, and molecular docking analysis
  作者：Jufrizal Syahri、Rahmiwati Hilma、Amatul Hamizah Ali、Norzila Ismail、Ng Yee Ling、Nurlaili、Beta Achromi Nurohmah、Hani Kartini Agustar、Lau Yee Ling、Jalifah Latip

  DOI：10.1039/d3ra05361j

  日期：——

  Research on the antimalarial effect of aminoalkyl chalcone derivatives against Plasmodium falciparum and Plasmodium knowlesi has bolstered efforts in drug discovery to combat cases of drug resistance.

  关于氨基烷基查尔酮衍生物对恶性疟原虫和克雷西疟原虫的抗疟作用的研究推动了药物研发工作，以应对抗药性问题。
• Synthesis, Antimicrobial Activities, and Molecular Modeling Studies of Agents for the Sortase A Enzyme
  作者：Gizem Tatar Yilmaz、Nurettin Yayli、Tamer Tüzüner、Gözde Bozdal、Merve Salmanli、Gülin Renda、Büşra Korkmaz、Arif Bozdeveci、Şengül Alpay Karaoğlu

  DOI：10.1002/cbdv.202301659

  日期：——

  Sortase A (SrtA) is an attractive target for developing new anti‐infective drugs that aim to interfere with essential virulence mechanisms, such as adhesion to host cells and biofilm formation. Herein, twenty hydroxy, nitro, bromo, fluoro, and methoxy substituted chalcone compounds were synthesized, antimicrobial activities and molecular modeling strategies against the SrtA enzyme were investigated. The most active compounds were found to be T2, T4, and T19 against Streptococcus mutans (S. mutans) with MIC values of 1.93, 3.8, 3.94 μg/mL, and docking scores of −6.46, −6.63, −6.73 kcal/mol, respectively. Also, these three active compounds showed better activity than the chlorohexidine (CHX) (MIC value: 4.88 μg/mL, docking score: −6.29 kcal/mol) in both in vitro and in silico. Structural stability and binding free energy analysis of S.mutans SrtA with active compounds were measured by molecular dynamic (MD) simulations throughout 100 nanoseconds (ns) time. It was observed that the stability of the critical interactions between these compounds and the target enzyme was preserved. To prove further, in vivo biological evaluation studies could be conducted for the most promising precursor compounds T2, T4, and T19, and it might open new avenues to the discovery of more potent SrtA inhibitors.