2'-hydroxy-4'-methoxydihydrochalcone | 22141-31-7

• 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'-methoxydihydrochalcone
• 英文别名: 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropan-1-one；2′-hydroxy-4′-methoxydihydrochalcone
• CAS: 22141-31-7
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: FQCZZYGBJVMLOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2'-hydroxy-4'-methoxydihydrochalcone 在 Bu₄NHSO₄ potassium carbonate 、 二乙胺 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 7-methoxyhomoisoflavanone
  参考文献：
  名称：

  Pinkey; Jain, P. K.; Grover, S. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 365 - 367

  摘要：

  DOI：
• 作为产物：
  描述：

  丹皮酚 在 palladium on activated charcoal 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2'-hydroxy-4'-methoxydihydrochalcone
  参考文献：
  名称：

  Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

  摘要：

  Eleven 4'-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 mu M. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the a, beta-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

  DOI：

  10.1016/j.bmc.2018.10.045

文献信息

• Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones <i>via</i> palladium(<scp>ii</scp>)-catalyzed oxidative cyclization
  作者：Seung Hwan Son、Yang Yil Cho、Hyung-Seok Yoo、Soo Jin Lee、Young Min Kim、Hyu Jeong Jang、Dong Hwan Kim、Jeong-Won Shin、Nam-Jung Kim

  DOI：10.1039/d1ra01672e

  日期：——

  Divergent and versatile synthetic routes to flavones and flavanones via efficient Pd(II) catalysis are disclosed. These Pd(II) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives, via discriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic

  公开了通过有效的 Pd( II ) 催化合成黄酮和黄烷酮的不同且通用的合成路线。根据氧化剂和添加剂，这些 Pd( II ) 催化剂分别以高度原子经济的方式通过涉及脱氢的区分氧化环化序列，方便地从 2'-羟基二氢查耳酮中提供各种黄酮和黄烷酮作为常见的中间体。
• Versatile formation of Ru(II) hydrazone complexes: Structure, theoretical studies and catalytic activity in α-alkylation
  作者：Kaliyappan Murugan、Subbarayan Vijayapritha、Venkatachalam Kavitha、Periasamy Viswanathamurthi

  DOI：10.1016/j.poly.2020.114737

  日期：2020.11

  lattices. DFT calculations were carried out to explain the solid structures of complexes 1-3. Moreover, the synthesized complexes were screened as catalysts for the α-alkylation of ketones with alcohols. The effect of various parameters, such as base, solvent, temperature, time, substituents and also catalyst loading, on the catalytic activity were analyzed. The results depict that the complex 3 was found

  摘要新的1-（蒽-10-基）亚甲基）-2-（苯并[d]噻唑-2-基）肼（BHA）和1-（蒽-10-基）亚甲基）-2-（喹啉-2）在氯仿-乙醇介质中，以1：1的摩尔比使[yl]肼（QHA）配体与[RuHCl（CO）（E）3]（E = PPh3或AsPh3）或[RuCl2（AsPh3）3]反应以合成新的钌配合物。通过元素分析，IR，NMR（1H，13C和31P）光谱，ESI-质谱和单晶XRD技术分析了所有新的钌配合物。XRD的单晶研究揭示了钌离子周围的八面体几何形状。研究还表明，配位体通过形成五个或四个成员的螯合环，与钌金属配位，在配合物1、3和4中作为单阴离子双齿N ^ N供体，在配合物2中作为中性双齿N ^ N供体。通过Hirshfeld表面分析研究了晶格中的分子内相互作用。结果表明，π堆积接触在晶格中起重要作用。进行DFT计算以解释配合物1-3的固体结构。此外，合成的配合物被筛选为酮与醇
• Synthesis and structural characterization of facile ruthenium(II) hydrazone complexes: Efficient catalysts in α-alkylation of ketones with primary alcohols via hydrogen auto transfer
  作者：Subbarayan Vijayapritha、Kaliyappan Murugan、Periasamy Viswanathamurthi、Paranthaman Vijayan、Chinnasamy Kalaiarasi

  DOI：10.1016/j.ica.2020.119887

  日期：2020.11

  successfully applied as catalysts in α -alkylation of aliphatic and aromatic ketones with alcohols via borrowing hydrogen strategy. Various parameters such as base, solvent, temperature, time and catalyst loading on the catalytic activity were analyzed. From the results, the catalyst 1 was found to be the best catalyst for α-alkylation reaction to obtain excellent yield. The catalytic system has a broad

  摘要为了开发新的配合物，新的Ru（II）配合物（1-3）由[Ru（SAL-HBT）（CO）（AsPh3）2]，[Ru（VAN） -HBT）（CO）（AsPh3）2]和[Ru（NAP-HBT）（CO）Cl（AsPh3）2] [SAL-HBT =（水杨基（（2-（苯并噻唑-2基）肼基）甲基苯酚））， VAN-HBT = 2-（（（2-（苯并噻唑-2-基）肼基）甲基）-6甲氧基苯酚）和NAP-HBT =萘基-2-（（2-（苯并噻唑-2-基）肼基）甲基苯酚）合成。通过令人满意的元素分析，各种光谱技术（IR，（1H，13C）NMR）以及质谱法确定了它们的身份。钌（II）离子具有扭曲的八面体几何形状的六配位体。在配合物1和2中，配体通过形成N 1 N供体5元和N 2 O供体6元螯合环而以双阴离子三齿形式配位。然而，在配合物3中，配体通过形成N 1 N供体五元环以单阴离子二齿形式配位。新的钌（II）羰基
• 1-Benzopyran-4-one Antioxidants as Aldose Reductase Inhibitors
  作者：Luca Costantino、Giulio Rastelli、Maria Cristina Gamberini、Joe A. Vinson、Pratima Bose、Anna Iannone、Mariagrazia Staffieri、Luciano Antolini、Antonella Del Corso、Umberto Mura、Albano Albasini

  DOI：10.1021/jm980441h

  日期：1999.6.1

  e derivatives was synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. Some of the compounds obtained display inhibitory activity similar to that of Sorbinil but are more selective than Quercetin and Sorbinil with respect to the closely related enzyme, aldehyde reductase, and also possess antioxidant activity. Remarkably, these compounds

  从类黄酮槲皮素的抑制活性开始，合成了一系列4H-1-苯并吡喃-4-酮衍生物，并测试了其对醛糖还原酶（一种涉及糖尿病并发症出现的酶）的抑制作用。获得的一些化合物显示出与索比尼尔相似的抑制活性，但是就紧密相关的酶，醛还原酶而言，比槲皮素和索比尼尔更具选择性，并且还具有抗氧化活性。值得注意的是，这些化合物比羧酸具有更高的pKa值，这一特性可能使这些化合物的药代动力学非常有趣。
• Subtle Structural Differences Trigger Inhibitory Activity of Propafenone Analogues at the Two Polyspecific ABC Transporters: P-Glycoprotein (P-gp) and Breast Cancer Resistance Protein (BCRP)
  作者：Theresa Schwarz、Floriane Montanari、Anna Cseke、Katrin Wlcek、Lene Visvader、Sarah Palme、Peter Chiba、Karl Kuchler、Ernst Urban、Gerhard F. Ecker

  DOI：10.1002/cmdc.201500592

  日期：2016.6.20

  and breast cancer resistance protein (BCRP) are widely recognized for their role in cancer multidrug resistance and absorption and distribution of compounds. Furthermore, they are linked to drug–drug interactions and toxicity. Nevertheless, due to their polyspecificity, a molecular understanding of the ligand‐transporter interaction, which allows designing of both selective and dual inhibitors, is

  跨膜ABC转运蛋白P-糖蛋白（P-gp）和乳腺癌耐药蛋白（BCRP）因其在癌症多药耐药以及化合物的吸收和分布中的作用而被广泛认可。此外，它们与药物-药物相互作用和毒性有关。然而，由于它们的多特异性，对配体-转运蛋白相互作用的分子理解，允许设计选择性和双重抑制剂，仍处于起步阶段。该研究包括合成、计算机预测和体外测试的组合方法，以确定触发转运蛋白选择性的分子特征。一系列 15 种具有不同刚性和碱性取代基的普罗帕酮类似物的合成和测试为选择性和双重抑制剂提供了第一个趋势。结果表明，氮原子上取代基的灵活性以及氮原子的碱性都触发了转运蛋白的选择性。此外，P-gp 化合物的抑制活性似乎比 BCRP 受 logP 的影响更大。因此，进一步利用这些差异应该可以为这两种多特异性 ABC 转运蛋白设计特异性抑制剂。