3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one | 1134396-08-9

• 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: 3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one
• 英文别名: 2'-hydroxy-4',6'-dimethoxymethoxy-3,4-methylenedioxy-chalcone；3-(1,3-Benzodioxol-5-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one；3-(1,3-benzodioxol-5-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 1134396-08-9
• 化学式: C₂₀H₂₀O₈
• 分子量: 388.374
• InChiKey: DLGAHCTWAXARRN-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107 °C
• 沸点：
  608.4±55.0 °C(predicted)
• 密度：
  1.324±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 在 palladium on activated charcoal 、 氢气 作用下， 以 四氢呋喃 为溶剂， 以79 %的产率得到3-(1,3-Benzodioxol-5-yl)-1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]propan-1-one
  参考文献：
  名称：

  [EN] METHYLOPHIOPOGONONE A DERIVATIVE, AND PREPARATION AND USE THEREOF
  [FR] DÉRIVÉ DE MÉTHYLOPHIOPOGONONE A, SA PRÉPARATION ET SON UTILISATION
  [ZH] 甲基麦冬黄酮A类衍生物及其制备和应用

  摘要：

  提供一种甲基麦冬黄酮A类衍生物及其制备和应用，具体涉及三种甲基麦冬黄酮A的衍生物，其化学结构为式I，式II，式III，以及该类衍生物的制备方法，及该类衍生物在制备预防和/或治疗心血管疾病等方面药物中的应用。

  公开号：

  WO2024027521A1
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-(benzo[d][1,3]dioxol-5-yl)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  [EN] METHYLOPHIOPOGONONE A DERIVATIVE, AND PREPARATION AND USE THEREOF
  [FR] DÉRIVÉ DE MÉTHYLOPHIOPOGONONE A, SA PRÉPARATION ET SON UTILISATION
  [ZH] 甲基麦冬黄酮A类衍生物及其制备和应用

  摘要：

  提供一种甲基麦冬黄酮A类衍生物及其制备和应用，具体涉及三种甲基麦冬黄酮A的衍生物，其化学结构为式I，式II，式III，以及该类衍生物的制备方法，及该类衍生物在制备预防和/或治疗心血管疾病等方面药物中的应用。

  公开号：

  WO2024027521A1

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.