4',4-dihydroxychalcone

• 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: 4',4-dihydroxychalcone
• 英文别名: 1,3-bis(4-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: FZQLEXXZAVVCCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4',4-dihydroxychalcone 在 盐酸 、 sodium tetrahydroborate 、 copper(l) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 24.17h， 生成 (E)-4,4'-(3-ethenyl-1-propene-1,3-diyl)bisphenol
  参考文献：
  名称：

  Synthesis of norlignans and in vitro inhibitory activity of antigen-induced degranulation

  摘要：

  The synthesis and biological evaluation of a series of novel norlignans are described. Norlignans were evaluated for their inhibitory activity on the release of beta-hexosaminidase, a marker of degranulation, from RBL-2H3 cells induced by the IgE-antigen complex. The results showed that norlignans 4c and 4e potently inhibited degranulation, with IC50 values of 18.3 and 17.9 mu M, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.033
• 作为产物：
  描述：

  4,4’-二甲氧基查耳酮 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到4',4-dihydroxychalcone
  参考文献：
  名称：

  4-Fluoro-3′,4′,5′-trimethoxychalcone as a new anti-invasive agent. From discovery to initial validation in an in vivo metastasis model

  摘要：

  Invasion and metastasis are responsible for 90% of cancer-related mortality. Herein, we report on our quest for novel, clinically relevant inhibitors of local invasion, based on a broad screen of natural products in a phenotypic assay. Starting from micromolar chalcone hits, a predictive QSAR model for diaryl propenones was developed, and synthetic analogues with a 100-fold increase in potency were obtained. Two nanomolar hits underwent efficacy validation and eADMET profiling; one compound was shown to increase the survival time in an artificial metastasis model in nude mice. Although the molecular mechanism(s) by which these substances mediate efficacy remain(s) unrevealed, we were able to eliminate the major targets commonly associated with antineoplastic chalcones. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.029

文献信息

• Antibacterial and anti‐inflammatory activity of valproic acid‐pyrazole conjugates as a potential agent against periodontitis
  作者：Lei Dong、Ling Fang、Xinxiang Dai、Jia Zhang、Jia Wang、Pei Xu

  DOI：10.1002/ddr.21851

  日期：2022.2

  Periodontitis is a serious global concern. Therefore, in the present study, we intend to synthesize novel valproic-acid pyrazole conjugates as a novel agent against periodontitis. The molecules were developed in a facile synthetic route and obtained in excellent yields. The entire set of molecules were screened for antibacterial activity against a battery of micro-organisms responsible for periodontitis

  牙周炎是一个严重的全球问题。因此，在本研究中，我们打算合成新型丙戊酸吡唑偶联物作为抗牙周炎的新型药物。这些分子以一种简便的合成路线开发，并以优异的收率获得。对整套分子进行了针对一系列引起牙周炎的微生物的抗菌活性筛选，例如牙龈卟啉单胞菌、中间假单胞菌、具核梭菌和大肠杆菌，它们在这些微生物中表现出相当大的抑制活性。测试系列中最有效的化合物，化合物7c在对大肠杆菌的时间-杀灭曲线中显示出杀菌活性。化合物7c还显示在 LPS 刺激的 RAW264.7 细胞中抑制 NF-ĸB 转录活性，IC 50为 19.23 μM。还研究了化合物7c在大鼠实验性牙周炎中对氧化应激（MDA、SOD 和 GSH）、炎症（TNF-α、IL-1β 和 IL-6）和细胞凋亡的各种指标的影响。已发现化合物7c以剂量依赖性方式显着抑制氧化应激、炎症和细胞凋亡。如蛋白质印迹分析所示，化合物7c还抑制COX-2和iNOS的表达。
• POTENTIAL ANTICANCER AGENTS III. URETHANE-TYPE NITROGEN MUSTARDS OF SOME SYNTHETIC ESTROGENS
  作者：I. Niculescu-Duvăz、V. Feyns、E. Grant、E. Tărnăuceanu

  DOI：10.1139/v66-166

  日期：1966.5.1

  not available

  不可用
• Dicyanatochalcones and method for the production thereof
  申请人：Lonza AG

  公开号：US06653497B1

  公开（公告）日：2003-11-25

  Dicyanatochalcones of general formula: wherein R1 to R8, independent of one another, represent hydrogen, C1-4-alkyl, C1-4-alkoxy or halogen. The compounds can be produced from corresponding dicyanatochalcones by reacting them with chlorine cyanide or bromine cyanide and with a tertiary amine. The compounds are suited for producing polytriazine resins exhibiting good mechanical properties, a low dielectric constant and a good behavior in fire.

  通式为：其中R1至R8，相互独立，表示氢、C1-4-烷基、C1-4-烷氧基或卤素。这些化合物可通过将相应的二氰基茚酮与氯氰或溴氰以及三级胺反应而制得。这些化合物适用于生产表现出良好机械性能、低介电常数和良好防火性能的聚三嗪树脂。
• Eco-Friendly and Efficient Greener Process for the Synthesis of Chalcones and Pyrazolones Using the Supramolecular Catalyst β-Cyclodextrin
  作者：Priyanka K. Bhadke、Akshata R. Pahelkar、Yatin U. Gadkari、John M. Naik、Vikas N. Telvekar

  DOI：10.1080/00304948.2022.2034462

  日期：2022.7.4

  Published in Organic Preparations and Procedures International: The New Journal for Organic Synthesis (Vol. 54, No. 4, 2022)

  （2022 年）。使用超分子催化剂 β-环糊精合成查耳酮和吡唑啉酮的环保高效绿色工艺。国际有机制剂和程序。领先于印刷。
• Nano titania-supported sulfonic acid: An efficient and reusable catalyst for a range of organic reactions under solvent free conditions
  作者：Salman Rahmani、Ali Amoozadeh、Eskandar Kolvari

  DOI：10.1016/j.catcom.2014.07.002

  日期：2014.11

  gravimetric analysis (TGA). The catalytic activity of n-TSA was investigated in the synthesis of important organic derivatives such as pyrimidones, benzothiazoles and chalcones. All of the reactions are very fast and the yields are good to excellent. The catalyst was easily separated and reused for several runs without appreciable loss of its catalytic activity.

  纳米二氧化钛负载的磺酸（n-TSA）可以很容易地由纳米二氧化钛（氧化钛）与氯磺酸作为磺化剂的反应制得，并通过FT-IR光谱，扫描电子显微镜（SEM）和X射线进行表征衍射（XRD）和热重分析（TGA）。在合成重要的有机衍生物（如嘧啶酮，苯并噻唑和查耳酮）中，研究了n-TSA的催化活性。所有的反应都非常快，收率良好至极好。催化剂易于分离，可重复使用几次，而不会明显降低其催化活性。