(E)-1-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one | 137580-98-4

• 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-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• 英文别名: (E)-4-hydroxy-3',4'-dimethoxychalcone；4-hydroxy-3'.4'-dimethoxy-trans-chalcone；4-Hydroxy-3'.4'-dimethoxy-trans-chalkon
• CAS: 137580-98-4
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: HQNPNDMBXWMBLJ-WEVVVXLNSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到(E)-1-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

  摘要：

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.02.007
• 作为产物：
  描述：

  4-methoxymethoxy-benzaldehyde 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 生成 (E)-1-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  通过狄尔斯-阿尔德反应，LiAlH 4介导的异构化和酸介导的环化反应，以生物启发的方式合成了帕洛德桑格人的三环核

  摘要：

  的环己烯部分的三环6,7-二芳基四氢-6- ħ -苯并[ c ^ ] palodesangrens的色烯核心可在仿生和步骤-经济的方式由所述富电子（之间的Diels-Alder反应来组装ë） -1,3-丁二烯芳烃为二烯，缺电子查耳酮为亲二烯体。在LiAlH 4将酮还原为相应的醇的过程中，内和外异构体的混合物经历了一种新的非对映收敛的LiAlH 4。-介导的异构化以在C10a处安装所需的立体化学。随后在酸性条件下的吡喃环闭合将立体化学安装在剩余的C6上。总体而言，可以分三步制备palodesangrens的三环核，产率最高可达38％。

  DOI：

  10.1021/acs.joc.8b00668

文献信息

• Design, synthesis and evaluation of chalcone Mannich base derivatives as multifunctional agents for the potential treatment of Alzheimer’s disease
  作者：Xiaoyu Zhang、Qing Song、Zhongcheng Cao、Yan Li、Chaoquan Tian、Ziyi Yang、Heng Zhang、Yong Deng

  DOI：10.1016/j.bioorg.2019.03.043

  日期：2019.6

  A series of chalcone Mannich base derivatives were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer’s disease based on the multi-target directed ligands design strategy. In vitro assays demonstrated that most of the derivatives exerted potent selective inhibitory potency on AChE with good multifunctional properties. Among them, representative compound 7c

  基于多靶点定向配体设计策略，设计，合成和评估了一系列查尔酮曼尼希碱衍生物，作为治疗阿尔茨海默氏病的多功能药物。体外试验表明，大多数衍生物对AChE都具有强大的选择性抑制作用，并具有良好的多功能性能。其中，代表性的化合物7c中显示出中度抑制效力为的Ee的AChE（IC 50  = 0.44μM）和MAO-B的抑制（IC 50  = 1.21μM），自诱导的良好的抑制作用β 1-42聚集（55.0％，在25μM时），生物金属螯合性能，适度的抗氧化活性，是Trolox的1.93倍。此外，对AChE抑制的动力学分析和分子模型研究均显示7c表现出混合型抑制，同时与AChE的CAS和PAS结合。另外，7c还显示出高的BBB渗透性。这些性质表明7c可能是用于治疗AD的有前途的多功能剂。
• v.Wacek; David, Chemische Berichte, 1937, vol. 70, p. 190,193
  作者：v.Wacek、David

  DOI：——

  日期：——
• Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates
  作者：Chao-Yun Cai、Li Rao、Yong Rao、Jin-Xuan Guo、Zhi-Zun Xiao、Jing-Yu Cao、Zhi-Shu Huang、Bo Wang

  DOI：10.1016/j.ejmech.2017.02.007

  日期：2017.4

  Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as aglucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards aglucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good a-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 mu M concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line). (C) 2017 Elsevier Masson SAS. All rights reserved.
• Bioinspired Diastereoconvergent Synthesis of the Tricyclic Core of Palodesangrens via Diels–Alder Reaction, LiAlH₄-Mediated Isomerization, and Acid-Mediated Cyclization
  作者：Poramate Songthammawat、Sirilak Wangngae、Koki Matsumoto、Chuthamat Duangkamol、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1021/acs.joc.8b00668

  日期：2018.5.4

  electron-deficient chalcones as the dienophile. During the reduction of ketone to the corresponding alcohol by LiAlH4, the mixture of endo and exo isomers underwent a novel diastereoconvergent LiAlH4-mediated isomerization to install the desired stereochemistry at C10a. Subsequent pyran ring closure under acidic conditions installed the stereochemistry at the remaining C6. Overall, the tricyclic core of palodesangrens

  的环己烯部分的三环6,7-二芳基四氢-6- ħ -苯并[ c ^ ] palodesangrens的色烯核心可在仿生和步骤-经济的方式由所述富电子（之间的Diels-Alder反应来组装ë） -1,3-丁二烯芳烃为二烯，缺电子查耳酮为亲二烯体。在LiAlH 4将酮还原为相应的醇的过程中，内和外异构体的混合物经历了一种新的非对映收敛的LiAlH 4。-介导的异构化以在C10a处安装所需的立体化学。随后在酸性条件下的吡喃环闭合将立体化学安装在剩余的C6上。总体而言，可以分三步制备palodesangrens的三环核，产率最高可达38％。