(E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4-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)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: 4-dimethylamino-2'-hydroxy-4'-methoxy-trans-chalcone；4-Dimethylamino-2'-hydroxy-4'-methoxy-trans-chalkon；(E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: JFCDSZVRDJZDRF-IZZDOVSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以68%的产率得到2-(4-Dimethylamino-phenyl)-7-methoxy-chroman-4-one
  参考文献：
  名称：

  摘要：

  Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors: therefore. in an effort to develop novel anti breast cancer agents. B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern.Methods. A series of flavanones was prepared by cyclisation of 2'-hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity or these compounds was investigated using human placental microsomes and radiolabeled [1.2,6,7-H-3]-androstenedione as substrate.Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring subtitution pattern. Hydroxylation at position 3' and/or 4' enhanced the anti-aromatase activity thus, 3'.4'-dihydroxy-7-methoxyflavanone was found to he twice more potent than aminoglutethimide. the first aromatase inhibitor clinically used.Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these Compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

  DOI：

  10.1023/a:1014490817731
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 73.0h， 生成 (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  设计，合成和评估新型二甲基氨基查尔酮-O-烷基胺衍生物作为潜在的对抗阿尔茨海默氏病的多功能药物

  摘要：

  一种新型系列二甲基氨基chalcone-的ö设计并合成了α-烷基胺衍生物，作为用于治疗AD的多功能剂。所有目标化合物均表现出显着的抑制和分解Aβ聚集的能力，并充当潜在的选择性AChE抑制剂，生物金属螯合剂和选择性MAO-B抑制剂。在这些化合物中，化合物TM-6对自诱导的Aβ聚集表现出最大的抑制活性（IC50 = 0.88μM），并且对自诱导的Aβ聚集表现出良好的分解能力（95.1％，25μM），TEM图像，分子对接研究分子动力学模拟为它的高效率提供了合理的解释，并且还发现它是一种出色的抗氧化剂（ORAC-FL值为2.1eq。），最佳的AChE抑制剂（IC50 = 0.13μM）和MAO-B抑制剂（IC50 = 1.0μM），以及良好的神经保护剂。紫外-可见光谱和ThT荧光分析表明，化合物TM-6不仅是抑制Cu2 +诱导的Aβ聚集（95.3％，25μM）的良好生物金属螯合剂，而且还可以分解结构良好的Aβ原纤维（88

  DOI：

  10.1016/j.ejmech.2021.113310

文献信息

• Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones
  作者：Alix Tordo、Erwann Jeanneau、Mathieu Bordy、Yann Bretonnière、Jens Hasserodt

  DOI：10.1039/d1tc03096e

  日期：——

  Fifteen easily assembled ESIPT-active 2′-hydroxychalcones were prepared to identify deep-red crystal-state fluorophores with increased quantum yields. Systematic single-crystal XRD analysis furnished trends in the structure–property relationship.

  制备了15种易于组装的ESIPT活性2'-羟基查尔酮，以识别具有增加量子产率的深红色晶体态荧光物质。系统的单晶XRD分析提供了结构-性质关系的趋势。
• 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
• Dhara, Mrinal G.; Mallik, Uttam K.; Mallik, Asok K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 11, p. 1214 - 1217
  作者：Dhara, Mrinal G.、Mallik, Uttam K.、Mallik, Asok K.

  DOI：——

  日期：——
• Haenni, 1921, vol. 1, p. 107,108
  作者：Haenni

  DOI：——

  日期：——
• Design, synthesis and evaluation of novel dimethylamino chalcone-O-alkylamines derivatives as potential multifunctional agents against Alzheimer’s disease
  作者：Zhipei Sang、Qing Song、Zhongcheng Cao、Yong Deng、Zhenghuai Tan、Li Zhang

  DOI：10.1016/j.ejmech.2021.113310

  日期：2021.4

  derivatives was designed and synthesized as multifunctional agents for the treatment of AD. All the target compounds exhibited significant abilities to inhibit and disaggregate Aβ aggregation, and acted as potential selective AChE inhibitors, biometal chelators and selective MAO-B inhibitors. Among these compounds, compound TM-6 showed the greatest inhibitory activity against self-induced Aβ aggregation (IC50 = 0

  一种新型系列二甲基氨基chalcone-的ö设计并合成了α-烷基胺衍生物，作为用于治疗AD的多功能剂。所有目标化合物均表现出显着的抑制和分解Aβ聚集的能力，并充当潜在的选择性AChE抑制剂，生物金属螯合剂和选择性MAO-B抑制剂。在这些化合物中，化合物TM-6对自诱导的Aβ聚集表现出最大的抑制活性（IC50 = 0.88μM），并且对自诱导的Aβ聚集表现出良好的分解能力（95.1％，25μM），TEM图像，分子对接研究分子动力学模拟为它的高效率提供了合理的解释，并且还发现它是一种出色的抗氧化剂（ORAC-FL值为2.1eq。），最佳的AChE抑制剂（IC50 = 0.13μM）和MAO-B抑制剂（IC50 = 1.0μM），以及良好的神经保护剂。紫外-可见光谱和ThT荧光分析表明，化合物TM-6不仅是抑制Cu2 +诱导的Aβ聚集（95.3％，25μM）的良好生物金属螯合剂，而且还可以分解结构良好的Aβ原纤维（88