(E)-2,4-dimethoxy-2'-hydroxychalcone

• 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)-2,4-dimethoxy-2'-hydroxychalcone
• 英文别名: (E)-3-(2,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one；2,4-Dimethoxy-2'-hydroxychalcone
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: ORIBPRISLKRPRQ-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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)-2,4-dimethoxy-2'-hydroxychalcone 在 selenium(IV) oxide 、 戊醇 、 氢碘酸 、 苯酚 作用下， 生成 7-羟基-2-(2-羟基苯基)-4H-苯并吡喃-4-酮
  参考文献：
  名称：

  Gallagher et al., Journal of the Chemical Society, 1953, p. 3770,3777

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2,4-Dimethoxy-phenyl)-3-hydroxy-1-(2-hydroxy-phenyl)-propan-1-one 在 oxonium 作用下， 生成 (E)-2,4-dimethoxy-2'-hydroxychalcone
  参考文献：
  名称：

  Synthesis and preliminary biological evaluation of 4,6-disubstituted 3-cyanopyridin-2(1H)-ones, a new class of calcium entry blockers

  摘要：

  The preparation of 3-cyano-4,6-diaryl-pyridin-2(1H)-ones 4a . h, calcium entry blockers related to diltiazem, is described starting from 1,3-diaryl-2-propen-1-ones 5. On preliminary pharmacological tests all compounds are active and some of them show calcium antagonistic activity superior or comparable to diltiazem. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00361-9

文献信息

• Silica gel supported InBr3 and InCl3: new catalysts for the facile and rapid oxidation of 2′-hydroxychalcones and flavanones to their corresponding flavones under solvent free conditions
  作者：Naseem Ahmed、Hasrat Ali、Johan E. van Lier

  DOI：10.1016/j.tetlet.2004.11.062

  日期：2005.1

  Silica gel supported InBr3 or InCl3 (15–20 mol %) were explored as a new solid-support catalysts for the facile and efficient oxidation, under solvent free conditions, of 2′-hydroxychalcones and flavanones to yield the corresponding flavones in >80% yield. The catalysts are easily prepared, stable, and efficient under mild reaction conditions.

  硅胶负载的InBr 3或InCl 3（15–20 mol％）被研究为一种新型的固体载体催化剂，可在无溶剂条件下方便，有效地氧化2'-羟基查耳酮和黄烷酮，以产生>的相应黄酮。 80％的产率。在温和的反应条件下，该催化剂易于制备，稳定且有效。
• Evaluation and Discovery of Novel Synthetic Chalcone Derivatives as Anti-Inflammatory Agents
  作者：Jianzhang Wu、Jianling Li、Yuepiao Cai、Yong Pan、Faqing Ye、Yali Zhang、Yunjie Zhao、Shulin Yang、Xiaokun Li、Guang Liang

  DOI：10.1021/jm200946h

  日期：2011.12.8

  Major anti-inflammatory agents, steroids and cyclooxygenase, were proved to have serious side effects. Here, a series of chalcone derivatives were synthesized and screened for anti-inflammatory activities. QSAR study revealed that the presence of electron-withdrawing groups in B-ring and electron-donating groups in A-ring of chalcones was important for inhibition of LPS-induced IL-6 expression. Further

  事实证明，主要的抗炎药，类固醇和环氧合酶具有严重的副作用。在这里，合成了一系列查尔酮衍生物，并筛选了抗炎活性。QSAR研究表明，查耳酮的B环中有吸电子基团，而A环中有供电子基团对于抑制LPS诱导的IL-6表达很重要。此外，化合物22，23，26，40，和47抑制TNF-α和IL-6释放的剂量依赖的方式和降低LPS诱导的TNF-α，IL-1β，IL-6，IL-12，和COX-2 mRNA的产生。从机械上讲，化合物23和26干扰JNK /NF-κB信号传导并剂量依赖性地阻止ERK和p38激活。另外，23和26对LPS诱导的死亡显示出显着的保护作用，并且能够阻断巨噬细胞中高葡萄糖激活的细胞因子谱。总之，这些数据显示了一系列在炎性疾病中具有潜在治疗作用的抗炎查耳酮。
• ¹H and¹³C NMR spectral assignments of 2′-hydroxychalcones
  作者：Yeonjoong Yong、Seunghyun Ahn、Doseok Hwang、Hyuk Yoon、Geunhyeong Jo、Young Hwa Kim、Sang Ho Kim、Dongsoo Koh、Yoongho Lim

  DOI：10.1002/mrc.3949

  日期：2013.6

  natural sources are well known. In this study, 24 2′‐hydroxychalcones bearing methoxy substituents were synthesized, among which five are new. The NMR data for all synthesized chalcones are described for the first time. The complete assignments of the 1H and 13C NMR data can be used for the identification of newly discovered and widely isolated, synthesized chalcones. Copyright © 2013 John Wiley & Sons, Ltd

  查耳酮对药物化学家很感兴趣，因为它们的结构可以很容易地被各种官能团修饰。来自天然来源的查耳酮的合成和生物活性是众所周知的。在这项研究中，合成了 24 个带有甲氧基取代基的 2'-羟基查尔酮，其中五个是新的。首次描述了所有合成查耳酮的 NMR 数据。1H 和 13C NMR 数据的完整归属可用于鉴定新发现和广泛分离的合成查耳酮。版权所有 © 2013 John Wiley & Sons, Ltd.
• Structure–activity relationships of antileishmanial and antimalarial chalcones
  作者：Mei Liu、Prapon Wilairat、Simon L Croft、Agnes Lay-Choo Tan、Mei-Lin Go

  DOI：10.1016/s0968-0896(03)00233-5

  日期：2003.7

  lipophilic chalcones, in particular those with 4'-hydroxyl-substituted B rings and hetero/polyaromatic A rings. In contrast, chalcones with good antimalarial activity have alkoxylated B rings and electron-deficient A rings. Visualization of the steric and electrostatic fields generated from comparative molecular field analysis (CoMFA) indicate that the ring A of chalcones make a more significant contribution

  测试了一系列含氧查耳酮（已在早期评估了其抗疟活性）（恶性疟原虫K1）对利什曼原虫杜鹃花的抗疟原虫活性。构效关系的比较表明，这两种活动存在不同的理化和结构要求。抗利什曼活性与较少的亲脂性查耳酮有关，特别是具有4'-羟基取代的B环和杂/多芳族A环的亲脂查耳酮。相反，具有良好抗疟疾活性的查耳酮具有烷氧基化的B环和缺电子的A环。比较分子场分析（CoMFA）产生的空间和静电场的可视化表明，查耳酮的A环对抗疟药活性的贡献更大，而A环和B环均对抗疟疾活性很重要。尽管有不同的要求，但还是发现了两个烷氧基化的查耳酮（8、19），它们结合了良好的抗疟和抗疟疾活性。
• Synthesis of a library of glycosylated flavonols
  作者：Zhitao Li、George Ngojeh、Paul DeWitt、Zhi Zheng、Min Chen、Brendan Lainhart、Vincent Li、Peter Felpo

  DOI：10.1016/j.tetlet.2008.10.032

  日期：2008.12

  products isolated from plants. Some glycosylated flavonols showed very interesting biological activities. A library of flavonols has been made through Algar-Flynn-Oyamada reaction from 2'-hydroxyacetophenones and benzaldehydes. Glycosylation of these flavonols with various glycosyl donors affords a library of glycosylated flavonols. These compounds are potentially useful pharmacologically active compounds

  黄酮醇是从植物中分离出来的一类重要的天然产物。一些糖基化的黄酮醇表现出非常有趣的生物学活性。通过Algar-Flynn-Oyamada反应，由2'-羟基苯乙酮和苯甲醛制得黄酮醇。这些黄酮醇与各种糖基供体的糖基化提供了糖基化黄酮醇的文库。这些化合物可能是有用的药理活性化合物，并将对其生物学活性进行研究。

表征谱图