2',4',6'-trimethoxychalcone

• 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',4',6'-trimethoxychalcone
• 英文别名: 2',4',6'-Tris(methoxy)chalcone；3-phenyl-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: DRGVZVJDZOMQAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',4',6'-trimethoxychalcone 在 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 42.75h， 生成 (6R,10S)-4-phenyl-2-(2,4,6-trimethoxyphenyl)-5,6,7,8,9,10-hexahydro-6,10-methanocycloocta[b]pyridine 1-oxide
  参考文献：
  名称：

  双环[3.3.1]壬烷骨架稠合的吡啶N-氧化物催化四氯化硅对内环氧化物的对映选择性开环

  摘要：

  报道了新的手性路易斯碱性有机催化剂的合成，该催化剂含有与双环 [3.3.1] 壬烷骨架稠合的吡啶 N-氧化物部分。所得吡啶N-氧化物用作中间环氧化物与四氯化硅对映选择性开环的催化剂。具有两个 2,4-二芳基取代的吡啶 N-氧化物部分的衍生物 1b 被证明是一种特别有效的催化剂，可用于降冰片烯氧化物 16i 的去对称化，以提供前所未有的 96% ee 的 Wagner-Meerwein 重排产物 20i。双功能同源物 3 带有 4-芳基取代基，与脂环族环氧化物底物表现出中等至高水平的不对称诱导（47-88% ee）。

  DOI：

  10.1002/ejoc.201500762
• 作为产物：
  描述：

  1,3,5-三甲氧基苯 、 肉桂酰氯 在 zinc(II) oxide 作用下， 反应 0.08h， 以97%的产率得到2',4',6'-trimethoxychalcone
  参考文献：
  名称：

  Zinc oxide as a regioselective and heterogeneous catalyst for the synthesis of chalcones at room temperature

  摘要：

  Zinc oxide catalyzed synthesis of chalcones has been carried out under solvent-free conditions at room temperature. Activated as well as unactivated aromatics smoothly underwent Friedel-Crafts acylation with alpha,beta-unsaturated acid chlorides furnishing excellent yields of the corresponding chalcones. The zinc oxide can be recovered and reused at least three times without any appreciable loss in activity. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2012.06.012

文献信息

• Construction and Biological Evaluation of Small Libraries Based on the Intermediates within the Total Synthesis of Uvaretin
  作者：Shashika Perera、Asantha Fernando、Johnathan Dallman、Chamitha Weeramange、Ashabha Lansakara、Thi Nguyen、Ryan J. Rafferty

  DOI：10.1002/cmdc.202001010

  日期：2021.5.18

  therapeutic agents: New bioactive agents, either as sole or combinational agents, have been constructed through the synthetic manipulation of the intermediates within the total synthesis of the uvaretin class of natural products. It was found that increasing the hydrophobic character of the phenolic core correlates to a decrease in sole agent cytotoxicity. The synthesis of new, small chemical screening libraries

  发现治疗剂：新的生物活性剂，无论是单独的还是组合的，都是通过合成操纵 uvaretin 类天然产物的全合成过程中的中间体而构建的。发现增加酚核心的疏水特性与降低单一试剂的细胞毒性相关。本文展示了由我们的 uvaretin 类天然产物的全合成路线的中间体构建的新的小型化学筛选库 (CSL) 的合成。组装了许多在查尔酮核内的酚基上具有各种取代的基于查尔酮的 CSL。通过细胞毒性研究，发现查耳酮酚核心的疏水性水平存在偏差：具有更多疏水核心的细胞毒性较小。此外，据观察，在胰腺癌细胞系 MIA PaCa-2 中用 6-硫嘌呤评估的增强作用可通过在酚核心上包含较少疏水性特征来调节。的作用存在于 uvaretin 家族中的邻羟基苄基被证明具有细胞毒性。合并在这项工作中构建的 CSL 上进行的所有构效关系研究导致构建了一种新的查尔酮杂化物，该杂化物同时具有细胞毒性烯酮基团和小分子增强的还原烯酮基团。
• Design of potent fluoro-substituted chalcones as antimicrobial agents
  作者：Serdar Burmaoglu、Oztekin Algul、Arzu Gobek、Derya Aktas Anil、Mahmut Ulger、Busra Gul Erturk、Engin Kaplan、Aylin Dogen、Gönül Aslan

  DOI：10.1080/14756366.2016.1265517

  日期：2017.1.1

  resistance, we attempted to develop novel antitubercular and antimicrobial agents. For this purpose, we developed some new fluorine-substituted chalcone analogs (3, 4, 9-15, and 20-23) using a structure-activity relationship approach. Target compounds were evaluated for their antitubercular efficacy against Mycobacterium tuberculosis H37Rv and antimicrobial activity against five common pathogenic bacterial and

  由于细菌和真菌的耐药性不断提高，我们试图开发新型的抗结核和抗菌药物。为此，我们使用结构-活性关系方法开发了一些新的氟取代的查耳酮类似物（3、4、9-15和20-23）。评价目标化合物对结核分枝杆菌H37Rv的抗结核功效以及对5种常见病原细菌和3种常见真菌菌株的抗菌活性。三个衍生物（3、9和10）显示出显着的抗结核活性，IC50值≤16,760。与查尔酮结构的B环上具有单氟取代基的三甲氧基取代基支架衍生的化合物相比，相应的羟基类似物具有更好的抑制活性。就抗菌活性而言，
• Horie, Tokunaru; Kawamura, Yasuhiko; Sakai, Chikako, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 753 - 760
  作者：Horie, Tokunaru、Kawamura, Yasuhiko、Sakai, Chikako、Akita, Ayako、Kuramoto, Masafumi

  DOI：——

  日期：——
• CHALCONE DERIVATIVES AS NRF2 ACTIVATORS
  申请人：Biswal Shyam

  公开号：US20140088052A1

  公开（公告）日：2014-03-27

  Compounds and methods for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway, including those associated with an autoimmune disease, comorbidity associated with diabetes, such as retinopathy and nephropathy, bone marrow transplant for leukemia and related cancers, bone marrow deficiencies, inborn errors of metabolism, and other immune disorders, oxidative stress, respiratory infection, ischemia, neurodegenerative disorders, radiation injury, neutropenia caused by chemotherapy, autoimmunity, and congenital neutropenic disorders, and for restoring a corticosteroid responsiveness, in a subject are provided.
• [EN] CHALCONE DERIVATIVES AS NRF2 ACTIVATORS<br/>[FR] DÉRIVÉS DE CHALCONE EN TANT QU'ACTIVATEURS DE NRF2
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2012116362A2

  公开（公告）日：2012-08-30

  Compounds and methods for treating or preventing a disease, disorder or condition associated with an Nrf2-regulated pathway, including those associated with an autoimmune disease, comorbidity associated with diabetes, such as retinopathy and nephropathy, bone marrow transplant for leukemia and related cancers, bone marrow deficiencies, inborn errors of metabolism, and other immune disorders, oxidative stress, respiratory infection, ischemia, neurodegenerative disorders, radiation injury, neutropenia caused by chemotherapy, autoimmunity, and congenital neutropenic disorders, and for restoring a corticosteroid responsiveness, in a subject are provided.