(E)-5'-bromo-2'-hydroxy-3-nitrochalcone | 1021684-65-0

• 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)-5'-bromo-2'-hydroxy-3-nitrochalcone
• 英文别名: 5'-bromo-2'-hydroxy-3-nitrochalcone；(E)-1-(5-bromo-2-hydroxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one
• CAS: 1021684-65-0
• 化学式: C₁₅H₁₀BrNO₄
• 分子量: 348.153
• InChiKey: XLABBOMUYJLDLL-GQCTYLIASA-N

物化性质

• 沸点：
  514.2±50.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-5'-bromo-2'-hydroxy-3-nitrochalcone 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以68%的产率得到3-amino-5'-bromo-2'-hydroxychalcone
  参考文献：
  名称：

  Reductive Coupling Reactions of 2-Nitrochalcones and their β-Hydroxy-analogues: New Syntheses of 2-Arylquinoline and 2-Aryl-4-hydroxyquinoline Derivatives

  摘要：

  A one-pot synthesis of novel 2-arylquinolines and 2-aryl-4-hydroxyquinolines was developed from the intramolecular reductive coupling reactions of 2-nitrochalcones and 3-hydroxy-1-phenyl-3-(2-nitrophenyl)-2-propen-1-ones. Depending on the reduction method and on the presence of electron donating substituents on the A ring of 2-nitrochalcones one can modulate the formation of 2-arylquinolines, their N-oxides, and of 2-aminochalcones. The reduction of 3-hydroxy-1-(2-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-ones with stannous chloride in hydrochloric acid gave 2 '-aminoflavones and with ammonium formate and Pd/C yielded 2-(2-hydroxyaryl)-4-hydroxyquinolines.

  DOI：

  10.1007/s00706-007-0647-9
• 作为产物：
  描述：

  2-羟基-5-溴苯乙酮 、 间硝基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以69%的产率得到(E)-5'-bromo-2'-hydroxy-3-nitrochalcone
  参考文献：
  名称：

  多靶点2'-羟基查耳酮作为治疗神经退行性疾病及其合并症的潜在药物

  摘要：

  阿尔茨海默病 (AD) 和帕金森病 (PD) 等神经退行性疾病 (NDD) 的复杂性需要多向治疗。通过联合抑制胆碱酯酶 (ChE) 和单胺氧化酶 (MAO、MAO-A 和 MAO-B) 来恢复神经递质水平，并结合对抗淀粉样蛋白 β (Aβ) 聚集的策略，可能构成一种治疗性强的多靶点方法。 NDD 的治疗。 查尔酮是黄酮类化合物的一个亚类，具有广泛的生物活性。我们在此报告了作为 MAO-A 和 MAO-B 抑制剂的 2'-羟基查耳酮的合成。化合物5c (IC 50 = 0.031 ± 0.001 μM)、 5a (IC 50 = 0.084 ± 0.003 μM)、 2c (IC 50 = 0.095 ± 0.019 μM) 和2a (IC 50 = 0.111 ± 0.006 μM) 是最有效、选择性最强的和人 (h)MAO-B 亚型的可逆抑制剂。 hMAO-B抑制剂1a 、 2a和5a还

  DOI：

  10.1016/j.neuropharm.2021.108837

文献信息

• Efficient Synthesis of Nitroflavones by Cyclodehydrogenation of 2′-Hydroxychalcones and by the Baker-Venkataraman Method
  作者：Ana I. R. N. A. Barros、Artur M. S. Silva

  DOI：10.1007/s00706-006-0550-9

  日期：2006.12

  Several nitroflavone derivatives were synthesized by cyclodehydrogenation of 2'-hydroxychalcones and by the Baker-Venkataraman approach, starting from 2'-hydroxyacetophenones and benzoic acid derivatives. Nitroflavones synthesised by the first synthetic approach were obtained in better global yields than those obtained by the later method. The structures of all new compounds were elucidated by microanalyses, 1D and 2D NMR, IR, and mass spectroscopic measurements.
• A two step synthesis of BzR/GABAergic active flavones via a Wacker-related oxidation
  作者：Michael Lorenz、M. Shahjahan Kabir、James M. Cook

  DOI：10.1016/j.tetlet.2009.12.107

  日期：2010.2

  A general route for the synthesis of biologically important flavones is reported via a two step sequence employing a catalytic Wacker-Cook oxidation(4b) as the key step. (C) 2009 Elsevier Ltd. All rights reserved.
• Reductive Coupling Reactions of 2-Nitrochalcones and their β-Hydroxy-analogues: New Syntheses of 2-Arylquinoline and 2-Aryl-4-hydroxyquinoline Derivatives
  作者：Ana I. R. N. A. Barros、André F. R. Dias、Artur M. S. Silva

  DOI：10.1007/s00706-007-0647-9

  日期：2007.6

  A one-pot synthesis of novel 2-arylquinolines and 2-aryl-4-hydroxyquinolines was developed from the intramolecular reductive coupling reactions of 2-nitrochalcones and 3-hydroxy-1-phenyl-3-(2-nitrophenyl)-2-propen-1-ones. Depending on the reduction method and on the presence of electron donating substituents on the A ring of 2-nitrochalcones one can modulate the formation of 2-arylquinolines, their N-oxides, and of 2-aminochalcones. The reduction of 3-hydroxy-1-(2-hydroxyphenyl)-3-(2-nitrophenyl)-2-propen-1-ones with stannous chloride in hydrochloric acid gave 2 '-aminoflavones and with ammonium formate and Pd/C yielded 2-(2-hydroxyaryl)-4-hydroxyquinolines.
• Multitarget 2′-hydroxychalcones as potential drugs for the treatment of neurodegenerative disorders and their comorbidities
  作者：Fabiola Kamecki、Damijan Knez、Diego Carvalho、Carolina Marcucci、Marina Rademacher、Josefina Higgs、Simon Žakelj、Alejandra Marcos、Felicitas de Tezanos Pinto、Juan Andrés Abin-Carriquiry、Stanislav Gobec、Natalia Colettis、Mariel Marder

  DOI：10.1016/j.neuropharm.2021.108837

  日期：2021.12

  mouse brain homogenates. Molecular modelling rationalised the binding mode of 2′-hydroxychalcones in the active site of hMAO-B. Additionally, several derivatives inhibited murine acetylcholinesterase (mAChE) (IC50 values from 4.37 ± 0.83 μM to 15.17 ± 6.03 μM) and reduced the aggregation propensity of Aβ. Moreover, some derivatives bound to the benzodiazepine binding site (BDZ-bs) of the γ-aminobutyric

  阿尔茨海默病 (AD) 和帕金森病 (PD) 等神经退行性疾病 (NDD) 的复杂性需要多向治疗。通过联合抑制胆碱酯酶 (ChE) 和单胺氧化酶 (MAO、MAO-A 和 MAO-B) 来恢复神经递质水平，并结合对抗淀粉样蛋白 β (Aβ) 聚集的策略，可能构成一种治疗性强的多靶点方法。 NDD 的治疗。 查尔酮是黄酮类化合物的一个亚类，具有广泛的生物活性。我们在此报告了作为 MAO-A 和 MAO-B 抑制剂的 2'-羟基查耳酮的合成。化合物5c (IC 50 = 0.031 ± 0.001 μM)、 5a (IC 50 = 0.084 ± 0.003 μM)、 2c (IC 50 = 0.095 ± 0.019 μM) 和2a (IC 50 = 0.111 ± 0.006 μM) 是最有效、选择性最强的和人 (h)MAO-B 亚型的可逆抑制剂。 hMAO-B抑制剂1a 、 2a和5a还