2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone | 118075-12-0

• 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-4,4',6'-trimethoxymethoxylchalcone
• 英文别名: 2'-hydroxy-4,4',6'-trimethoxymethoxychalcone；2'-Hydroxy-4,4',6'-tris(methoxymethoxy)chalcone；1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[4-(methoxymethoxy)phenyl]prop-2-en-1-one
• CAS: 118075-12-0
• 化学式: C₂₁H₂₄O₈
• 分子量: 404.417
• InChiKey: ZXLLXKCREJNXEP-UHFFFAOYSA-N

物化性质

• 沸点：
  586.1±50.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以79%的产率得到2',4,4',6'-四羟基查耳酮
  参考文献：
  名称：

  一类A环具有甲基的醌式查尔酮化合物，制法 与抗炎活性

  摘要：

  本发明公开了一类A环具有甲基的醌式查尔酮类化合物及其制备方法与抗炎活性应用。本发明的化合物具有通式(Ⅰ)所示的结构，其制备方法包括以下步骤：(1)合成2‑羟基‑4,6‑二甲氧甲氧基苯乙酮，(2)合成2′‑羟基‑4′,6′‑二甲氧甲氧基查尔酮衍生物，(3)合成2′,4′,6′‑三羟基查尔酮衍生物，(4)合成一类A环具有甲基的醌式查尔酮类化合物。本发明的化合物制备方法简单并且具有明显的抗炎作用。

  公开号：

  CN105085218B
• 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， 反应 48.0h， 生成 2'-hydroxy-4,4',6'-trimethoxymethoxylchalcone
  参考文献：
  名称：

  Sophoflavescenol、Flavenochromane C 和 Citrusinol 的首次全合成

  摘要：

  首次实现了槐黄烯醇 (1)、黄酮色烷 C (2) 和柑橘醇 (3) 的全合成。这三种天然存在的异戊二烯化或异戊二烯环化黄酮类化合物具有重要的生物活性，例如对某些癌细胞系的细胞毒性，或者是治疗勃起功能障碍的先导化合物。以 2,4,6-三羟基苯乙酮和取代苯甲醛为原料，合成过程包括甲氧基甲基保护、羟醛缩合、环化、二甲基二环氧乙烷氧化、O-异戊二烯化、微波辅助克莱森重排、脱保护、异戊二烯基环化和用 2 脱氢,3-二氯-5,6-二氰基-1,4-苯醌。1、2 和 3 的总产率分别为 23、17 和 16%。所有化合物均通过 1H 和 13C NMR 光谱和 MS 进行表征。

  DOI：

  10.1002/ejoc.201403689

文献信息

• 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。
• Anti-ulcer agent comprising chalcone derivative as effective ingredient
  申请人：Tsumura & Co.

  公开号：US05106871A1

  公开（公告）日：1992-04-21

  The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: ##STR1## wherein X and Y independently stand for a hydrogen atom or together form a single bond, R.sub.1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R.sub.2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R.sub.3 stands for hydroxyl group or a methoxy group, R.sub.4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R.sub.5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R.sub.6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R.sub.7 stands for a hydrogen atom or a methoxy group.

  本发明涉及一种抗溃疡剂，其包括以下通式I所表示的化合物作为有效成分，以及包含在该通式I所表示的化合物中的一种新的查尔酮衍生物： ##STR1## 其中，X和Y独立地代表氢原子或形成单键，R1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R2代表氢原子、异戊烯基、异戊基或丙基，R3代表羟基或甲氧基，R4代表氢原子、羟基或甲氧基，R5代表氢原子、羟基、甲氧基或异戊基，R6代表羟基、甲氧基或羧甲氧基，R7代表氢原子或甲氧基。
• Aurones as histone deacetylase inhibitors: Identification of key features
  作者：Vincent Zwick、Alkiviadis-Orfefs Chatzivasileiou、Nathalie Deschamps、Marina Roussaki、Claudia A. Simões-Pires、Alessandra Nurisso、Iza Denis、Christophe Blanquart、Nadine Martinet、Pierre-Alain Carrupt、Anastasia Detsi、Muriel Cuendet

  DOI：10.1016/j.bmcl.2014.10.019

  日期：2014.12

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.
• Site-Specific Fluorescent Labeling Approaches for Naringenin, an Essential Flavonone in Plant Nitrogen-Fixation Signaling Pathways
  作者：Lei Chen、Feng-Qing Li、Bi-He Hou、Guo-Fan Hong、Zhu-Jun Yao

  DOI：10.1021/jo8014165

  日期：2008.11.7

  In search of an appropriate position for the fluorescent labeling. six chemically available positions of the flavonone core of naringenin have been examined. A number of azido-containing naringenin derivatives were accordingly prepared in various site-specific fashions. and the Mild CU(I)-catalyzed Huisgen 1-3-dipolar cycloaddition successfully served as the common "Click" labeling tool in the final steps. Oil the basis of the biological activities of the first batch of labeled compounds, further optimization at the C-6 position of naringenin finally afforded naringenin-flu (27). which acquired 20% of the potency of naringenin and presented good optical properties. Entry of naringenin-flu into living Rhizobium Cells was demonstrated by in vitro fluorescent imaging experiments.
• In Vitro Osteogenic Differentiation and Antibacterial Potentials of Chalcone Derivatives
  作者：Daheui Choi、Jin Chan Park、Ha Na Lee、Ji-Hoi Moon、Hyo-won Ahn、Kwangyong Park、Jinkee Hong

  DOI：10.1021/acs.molpharmaceut.8b00288

  日期：2018.8.6

  Chalcone derivatives have been investigated as therapeutic agents for the anticancer, antioxidant, and anti-inflammatory fields. In this study, we have synthesized four different types of chalcone derivatives and demonstrated in vitro bioactivities. We divided these derivatives into two groups of chalcones on the basis of similar substituents on the aromatic rings, and we tested cell viability and proliferation potentials, which indicated that the methoxy substituent on the A ring could enhance cytotoxicity and antiproliferation potential depending on the chalcone concentration. We also investigated osteogenic differentiation of C2C12 cells by ALP staining, the early marker for osteogenesis, which demonstrated that the chalcones could not only induce activity of BMP-2 but also inhibit the activity of noggin, a BMP antagonist. In addition, chalcone bearing hydroxyl groups at the 2-, 4-, and 6-position on the A ring inhibited treptococcus mutans growth, a major causative agent of dental caries. Therefore, we concluded that the chalcone derivatives synthesized in this research can be good candidates for therapeutic agents promoting bone differentiation, with an expectation of inhibiting S. mutans, in dentistry.