2',5'-dimethoxy-4-hydroxychalcone | 177344-59-1

• 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',5'-dimethoxy-4-hydroxychalcone
• 英文别名: (E)-1-(2,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 177344-59-1
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: NZERHZIFOYEWGN-WEVVVXLNSA-N

物化性质

• 沸点：
  495.1±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：

  2',5'-dimethoxy-4-hydroxychalcone 在 二苯硫醚 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 反应 24.0h， 以86%的产率得到1-(2,5-Dimethoxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  具有镇痛活性的α7烟碱受体二苯基丙烷正构构调节剂的氨基酸和肽前药

  摘要：

  α7烟碱乙酰胆碱受体（nAChRs）是离子通道，涉及许多CNS病理过程，包括疼痛和精神病，认知疾病和炎性疾病。与正构激动剂相比，这些通道的正构构调制相对于其他烟碱样受体构成了一种实现选择性的有趣方法。我们最近描述了新的查耳酮和1,3-二苯基丙烷作为α7nAChRs的正变构调节剂（PAM），它们被证明具有良好的镇痛活性，但药代动力学性能较差。在这里，我们报告了氨基酸和肽衍生物作为这些调节剂的前药的制备，目的是改善其体内活性生物活性。尽管缬氨酸衍生物在水溶液中显示出很短的半衰期，可以认为它们是前药，但Val-Val和Val-Pro-Val分别通过化学和酶促转化反应成为母体1,3-二苯基丙烷的合适前体。2'，5'，4-三羟基-1,3-二苯基丙烷-1-酮3的前药化合物19（Val-Val）和21（Val-Pro-Val）在体内试验中显示出显着的抗伤害感受活性。最好的化合物21在镇痛测试中显示出比其

  DOI：

  10.1016/j.ejmech.2017.10.083
• 作为产物：
  描述：

  2',5'-dimethoxy-4-(tetrahydropyran-2-yloxy)chalcone 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以3.41 g的产率得到2',5'-dimethoxy-4-hydroxychalcone
  参考文献：
  名称：

  Structure–activity relationship studies on chalcone derivatives

  摘要：

  Some chalcones exert potent anti-inflammatory activities. 2,5-Dialkoxychalcones and 2',5'-dihydroxy-4-chloro-dihydrochalcone inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)/interferon-gamma (IFN-gamma)-activated N9 microglial cells and in LPS-activated RAW 264.7 macrophage-like cells have been demonstrated in our previous reports. These compounds also suppressed the inducible NO synthase (iNOS) expression and cyclooxygenase-2 (COX-2) activity in RAW 264.7 cells. In an effort to continually develop potent anti-inflammatory agent, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with appropriate aromatic aldehyde and then evaluated their inhibitory effects on the activation of mast cells, neutrophils, macrophages, and microglial cells. Most of the 2',5-dihydroxychaclone derivatives exhibited potent inhibitory effects on the release of beta-glucuronidase and lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB). Some chalcones showed potent inhibitory effects on superoxide anion generation in rat neutrophils in response to fMLP/CB. Compounds 1 and 5 exhibited potent inhibitory effects on NO production in macrophages and microglial cells. Compound 11 showed inhibitory effect on NO production and iNOS protein expression in RAW 264.7 cells. The present results demonstrated that most of the 2', 5'-dihydroxychaclones have anti-inflammatory effects. The potent inhibitory effect of 2',5'-dibydroxy-dihydrochaclones on NO production in LPS-activated macrophage, probably through the suppression of iNOS protein expression, is proposed to be useful for the relief of septic shock. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00312-7

文献信息

• Novel chalcone derivatives and pharmaceutical compositions comprising the same
  申请人：KAOHSIUNG MEDICAL UNIVERSITY

  公开号：US20040176471A1

  公开（公告）日：2004-09-09

  Disclosed herein are novel chalcone derivatives of formulas (I), (II) and (III): 1 wherein each of the substituents is given the definition as set forth in the Specification and Claims. These compounds are demonstrated to have anti-inflammatory activities and thus can be used in the treatment of an inflammatory disorder in a subject.

  本文披露了式(I)、(II)和(III)的新型查尔酮衍生物：1其中每个取代基的定义如规范和权利要求所述。这些化合物已被证明具有抗炎活性，因此可用于治疗主体的炎症性疾病。
• Novel peripheral tetra-substituted phthalocyanines containing methoxylated chalcone group: Synthesis, spectral, electrochemical and spectroelectrochemical properties
  作者：Halise Yalazan、Duygu Akyüz、Vildan Serdaroğlu、Nuran Kahriman、Atıf Koca、Halit Kantekin

  DOI：10.1016/j.jorganchem.2020.121181

  日期：2020.4

  This paper reports the synthesis, electrochemical and spectroelectrochemical properties of peripheral tetra substituted phthalocyanines that include (E)-1-(2,5-dimethoxyphenyl)-3-(4 hydroxyphenyl)prop-2-en-1-one. Precursor phthalonitrile compound (3) for the formation of phthalocyanines was synthesized at first, then related phthalocyanine compounds CoII (Pc-4), CuII (Pc-5), ZnII (Pc-6), MnIIICl (Pc-7)

  本文报道了包括（E）-1-（2,5-二甲氧基苯基）-3-（4羟基苯基）prop-2-en-1-one在内的外围四取代酞菁的合成，电化学和光谱电化学性质。首先合成用于形成酞菁的前体酞腈化合物（3），然后合成相关的酞菁化合物Co II（Pc -4），Cu II（Pc -5），Zn II（Pc -6），Mn III Cl（Pc- 7）和无金属（PC -8）合成。所有化合物的光谱特性都通过使用流行的光谱技术来实现。用循环伏安法（CV）和方波伏安法（SWV）研究了金属酞菁（MPcs）的电化学，以确定络合物的氧化还原机理。还进行了原位光谱电化学表征，以支持氧化还原机制并确定电产生的MPc物质的光电响应。
• Severi; Costantino; Benvenuti, Medicinal Chemistry Research, 1996, vol. 6, # 2, p. 128 - 136
  作者：Severi、Costantino、Benvenuti、Vampa、Mucci

  DOI：——

  日期：——
• Synthetic 2′,5′-dimethoxychalcones as G2/M arrest-mediated apoptosis-inducing agents and inhibitors of nitric oxide production in rat macrophages
  作者：Bai-Luh Wei、Chi-Huang Teng、Jih-Pyang Wang、Shen-Jeu Won、Chun-Nan Lin

  DOI：10.1016/j.ejmech.2006.12.009

  日期：2007.5

  In an effort to develop novel antitumor or chemopreventive agents, a series of 2',5'-dimethoxychalcone derivatives were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde. In vitro screening revealed low micromolar activity (IC50) against several human cancer tines. Activity in MCF-7 cells correlated with the ability to induce G(2)/M arrest-mediated apoptosis following drug treatment by the most potent agent, 8, an observation further reinforced by fluorescence microscopy. Compounds 3, 8, and 10 showed potent inhibitory effect on NO production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophage-like cells. The present results demonstrated that 3, 8, and 10 are potential anti-inflammatory and cancer chemopreventive agents. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Amino acid and peptide prodrugs of diphenylpropanones positive allosteric modulators of α7 nicotinic receptors with analgesic activity
  作者：Beatriz Balsera、José Mulet、Salvador Sala、Francisco Sala、Roberto de la Torre-Martínez、Sara González-Rodríguez、Adrián Plata、Lieve Naesens、Asia Fernández-Carvajal、Antonio Ferrer-Montiel、Manuel Criado、María Jesús Pérez de Vega、Rosario González-Muñiz

  DOI：10.1016/j.ejmech.2017.10.083

  日期：2018.1

  preparation of amino acid and peptide derivatives as prodrugs of these modulators with the aim of improving their in vivo biological activity. While the valine derivative showed very short half life in aqueous solutions to be considered a prodrug, Val-Val and Val-Pro-Val are suitable precursors of the parent 1,3-diphenylpropanones, via chemical and enzymatic transformation, respectively. Compounds 19 (Val-Val)

  α7烟碱乙酰胆碱受体（nAChRs）是离子通道，涉及许多CNS病理过程，包括疼痛和精神病，认知疾病和炎性疾病。与正构激动剂相比，这些通道的正构构调制相对于其他烟碱样受体构成了一种实现选择性的有趣方法。我们最近描述了新的查耳酮和1,3-二苯基丙烷作为α7nAChRs的正变构调节剂（PAM），它们被证明具有良好的镇痛活性，但药代动力学性能较差。在这里，我们报告了氨基酸和肽衍生物作为这些调节剂的前药的制备，目的是改善其体内活性生物活性。尽管缬氨酸衍生物在水溶液中显示出很短的半衰期，可以认为它们是前药，但Val-Val和Val-Pro-Val分别通过化学和酶促转化反应成为母体1,3-二苯基丙烷的合适前体。2'，5'，4-三羟基-1,3-二苯基丙烷-1-酮3的前药化合物19（Val-Val）和21（Val-Pro-Val）在体内试验中显示出显着的抗伤害感受活性。最好的化合物21在镇痛测试中显示出比其