2'-hydroxy-4',6'-di(methoxymethoxy)-3-bromo-chalcone | 1134396-07-8

• 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: 2'-hydroxy-4',6'-di(methoxymethoxy)-3-bromo-chalcone
• 英文别名: 3-(3-Bromophenyl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 1134396-07-8
• 化学式: C₁₉H₁₉BrO₆
• 分子量: 423.26
• InChiKey: NEUIZAVGWMUUCV-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  578.4±50.0 °C(predicted)
• 密度：
  1.419±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4',6'-di(methoxymethoxy)-3-bromo-chalcone 在 sodium acetate 作用下， 生成 (+/-)-5,7-dimethoxymethoxy-3'-bromo-flavanone
  参考文献：
  名称：

  甘草素衍生物抗阿尔茨海默病活性的设计、合成和胆碱酯酶抑制试验

  摘要：

  海洋环境是发现功能材料的丰富资源，海藻因其在生物学和医学中的潜在用途而受到认可。甘草素已从马尾藻中分离和鉴定。为了寻找新的抗阿尔茨海默病活性，我们设计并合成了 32种 7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 3a-3p ) 和 5-羟基-7-异戊二烯氧基-2,3-二氢黄烷酮衍生物 ( 4a- 4p）作为基于甘草素作为先导化合物的胆碱酯酶抑制剂。对乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 的抑制筛选表明，所有合成的化合物在体外均具有有效的 AChE 抑制活性，但对 BuChE 的抑制活性减弱至较弱. 动力学研究表明，化合物 4o 通过双重结合位点能力抑制 AChE。此外，所有化合物均显示出自由基清除作用。最后，4o在AChE活性位点的分子对接模拟与所得药理结果吻合较好。

  DOI：

  10.1016/j.bmcl.2021.128306
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 2'-hydroxy-4',6'-di(methoxymethoxy)-3-bromo-chalcone
  参考文献：
  名称：

  Zhao, Dong-Hai; Sui, Xin; Qu, You-Le, Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1129 - 1132

  摘要：

  DOI：

文献信息

• Flavonoids as Vasorelaxant Agents: Synthesis, Biological Evaluation and Quantitative Structure Activities Relationship (QSAR) Studies
  作者：Xiaowu Dong、Yanming Wang、Tao Liu、Peng Wu、Jiadi Gao、Jianchao Xu、Bo Yang、Yongzhou Hu

  DOI：10.3390/molecules16108257

  日期：——

  A series of 2-(2-diethylamino)-ethoxychalcone and 6-prenyl(or its isomers)-flavanones 10a,b and 11a–g were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pretreated with 1 μM phenylephrine (PE). Several compounds showed potent vasorelaxant activities. Compound 10a (EC50 = 7.6 μM, Emax = 93.1%), the most potent one, would be a promising structural template for development of novel and more efficient vasodilators. Further, 2D-QSAR analysis of compounds 10a,b and 11c-e as well as thirty previously synthesized flavonoids 1-3 and 12-38 using Enhanced Replacement Method-Multiple Linear Regression (ERM-MLR) was further performed based on an optimal set of molecular descriptors (H5m, SIC2, DISPe, Mor03u and L3m), leading to a reliable model with good predictive ability (Rtrain2 = 0.839, Qloo2 = 0.733 and Rtest2 = 0.804). The results provide good insights into the structure- activity relationships of the target compounds.

  一系列2-（2-二乙基氨基）-乙氧基查尔酮和6-异戊烯基（或其异构体）-黄烷酮10a、b和11a-g被合成并评估了其对预处理有1μM苯肾上腺素（PE）的大鼠主动脉环的血管舒张活性。几个化合物显示出强效的血管舒张活性。化合物10a（EC50=7.6μM，Emax=93.1%），是最强效的，将成为开发新型更有效的血管扩张剂的有前景的结构模板。此外，基于一组最优分子描述符（H5m、SIC2、DISPe、Mor03u和L3m），对化合物10a、b和11c-e以及之前合成的三十个黄酮类化合物1-3和12-38使用增强替换方法-多元线性回归（ERM-MLR）进行了二维定量构效关系分析，得到了一个具有良好预测能力的可靠模型（Rtrain2=0.839，Qloo2=0.733和Rtest2=0.804）。结果为目标化合物的结构-活性关系提供了良好的见解。
• Synthesis and biological evaluation of novel hybrid chalcone derivatives as vasorelaxant agents
  作者：Xiaowu Dong、Lilin Du、Zhichao Pan、Tao Liu、Bo Yang、Yongzhou Hu

  DOI：10.1016/j.ejmech.2010.05.054

  日期：2010.9

  the vasorelaxant activities of chalcones, nine hybrid chalcone derivatives conjugated with nitric oxide (NO) donor or 1,4-dihydropyridyl (1,4-DHP) moiety were designed and synthesized based on molecular hybridization strategy. Their vasorelaxant activities were evaluated in aortic rings with endothelium pre-contracted with phenylephrine (PE). All of these compounds showed preferable vasorelaxant activities

  为了进一步改善查尔酮的血管舒张活性，基于分子杂交策略设计合成了九种杂化查尔酮衍生物，它们与一氧化氮（NO）供体或1,4-二氢吡啶基（1,4-DHP）部分共轭。他们的血管舒张活性被评估在主动脉环与苯肾上腺素（PE）预收缩的内皮细胞。所有这些化合物均表现出优选的血管舒张活性，比其母体化合物更有效。化合物8c和15c是最有效的化合物，将成为开发新型血管松弛剂的有前途的结构模板。
• Synthesis, biological evaluation and quantitative structure-activities relationship of flavonoids as vasorelaxant agents
  作者：Xiaowu Dong、Tao Liu、Jingying Yan、Peng Wu、Jing Chen、Yongzhou Hu

  DOI：10.1016/j.bmc.2008.11.052

  日期：2009.1

  A series of flavonoid derivatives were designed, synthesized. Their vasorelaxant activities were evaluated experimentally against rat aorta rings pretreated with phenylephrine (PE). Among them, 6-hydroxy-8-allyl- 4'-chloro-flavanone 8q exhibited the highest vasodilatory activity (EC50 = 4.6 mu M, E-max = 95.1%). The 3D-QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method, and a statistically reliable model with good predictive power (r(2) = 0.872 and q(cv)(2) = 0.496) was established. The contour plots of CoMFA model provide a good insight into the structure-activity relationships of these compounds and may be used to design more potent flavonoids derivatives as vasorelaxant agents. (C) 2008 Elsevier Ltd. All rights reserved.
• Microwave-Assisted Mannich Reaction of 2-Hydroxy-chalcones
  作者：Xiaowu Dong、Tao Liu、Jing Chen、Huazhou Ying、Yongzhou Hu

  DOI：10.1080/00397910802431107

  日期：2009.1.28

  A series of Mannich base derivatives of 2-hydroxy-chalcones were obtained expediently in good to excellent yields by microwave-assisted Mannich reaction. The regioselectivity of the reaction occurred preferentially at the C-3 position of the 2-hydroxy-chalcone backbone. In comparison with conventional results, results from microwave possesses give better yields in shorter times. Further vasorelaxation assay showed that 2-hydroxy-3-((4-methylpiperazin-1-yl)methyl)-4,6-dimethoxymethoxy-3'-bromo-chalcone 8 significantly decreased maximal PE-induced contraction (Emax=1005.97%, EC50=10.20.51M).
• Synthesis and studies on antidepressant activity of 2′,4′,6′-trihydroxychalcone derivatives
  作者：Xin Sui、Ying-Chun Quan、Yue Chang、Rui-Peng Zhang、Yin-Feng Xu、Li-Ping Guan

  DOI：10.1007/s00044-011-9640-2

  日期：2012.7

  In this study, we synthesized a series of 2',4',6'-trihydroxychalcone derivatives and evaluated their antidepressant activities. The results of the nine compounds showed significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 2-bromo-2',4',6'-trihydroxychalcone (3h) was found to be the most potent, and it was observed that compound 3h at dose of 10, 20, and 40 mg/kg significantly reduced the duration of immobility times in the FST and TST in mice 30 min after treatment.