2',4'-二羟基-2-甲氧基查耳酮 | 108051-21-4

• 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
• 中文名称: 2',4'-二羟基-2-甲氧基查耳酮
• 中文别名: 2'，4'-二羟基-2-甲氧基查耳酮；2’,4’-二羟基-2-甲氧基查耳酮
• 英文名称: (E)-1-(2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)-2-propen-1-one
• 英文别名: 2'.4'-dihydroxy-2-methoxy-trans-chalcone；2'.4'-Dihydroxy-2-methoxy-trans-chalkon；2',4'-Dihydroxy-2-methoxychalcone；(E)-1-(2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)prop-2-en-1-one
• CAS: 108051-21-4；104236-78-4
• 化学式: C₁₆H₁₄O₄
• 分子量: 270.285
• InChiKey: ODLVGCCGMXGMGZ-RMKNXTFCSA-N

物化性质

• 熔点：
  175-178°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2',4'-二羟基-2-甲氧基查耳酮 在 氯仿 、 溴 作用下， 生成 3'.5'-dibromo-2'.4'-dihydroxy-2-methoxy-trans-chalcone
  参考文献：
  名称：

  Vandrewalla; Jadhav, Proceedings - Indian Academy of Sciences, Section A, 1948, vol. 28, p. 125,130

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 盐酸 、 barium dihydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 2',4'-二羟基-2-甲氧基查耳酮
  参考文献：
  名称：

  一些吡唑衍生物的合成及其与P-糖蛋白的亲和力结合的初步研究。

  摘要：

  合成了一系列取代的吡唑啉，并通过直接结合至包含ATP结合位点和调节剂相互作用区的纯化蛋白结构域，评估了它们的抗癌活性以及抑制P-糖蛋白介导的多药耐药性的能力。已经发现化合物2a和e以更大的亲和力与P-糖蛋白结合。

  DOI：

  10.1016/j.bmcl.2005.05.067

文献信息

• Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-ß-D-Glycopyranosyl Chalcone analogues with molecular docking studies
  作者：GONCA ÇELİK、GİZEM TATAR YILMAZ、HÜSEYİN ŞAHİN、BURAK BARUT、NURETTİN YAYLI

  DOI：10.55730/1300-0527.3527

  日期：——

  16a-c, and 17a-c) were tested for their enzyme inhibition activity against α-glycosidase, tyrosinase, and AChE with in vitro and in silico analysis. Amongst them, compounds 12a-c, 16a-c, and 17a-c displayed moderate or less enzyme inhibition activity against α-glycosidase while other compounds 7a-c and 8a-c) were not active. Remarkably interesting enzyme inhibition effects, with IC50 values below 30.59

  在本研究中，设计、合成并表征了一些新型单-和二-O-β-D-吡喃葡萄糖基查耳酮类似物。通过在乙醇溶液中碱催化的克莱森-施密特缩合反应，以良好的产率合成了查耳酮衍生物。然后这些查尔酮与TAGBr（2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基溴）在干燥丙酮中在无水条件下在0-5℃下反应。通过 Zemplen 方法用 NaOCH3 在无水甲醇中进行脱酰化，得到取代的查尔酮-O-糖苷（单-和二-O-β-D-吡喃糖基查尔酮类似物）。基于红外、核磁共振光谱数据和质谱分析，阐明了所有合成化合物的化学结构。此外，通过体外和计算机分析测试了化合物（7a-c、8a-c、12a-c、16a-c 和 17a-c）对 α-糖苷酶、酪氨酸酶和 AChE 的酶抑制活性。其中，化合物12a-c、16a-c和17a-c对α-糖苷酶表现出中等或较低的酶抑制活性，而其他化合物7a-c和8a-c)则没有活性。7c 对酪氨酸酶具有非常有趣的酶抑制作用，IC50
• Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)
  作者：Lei Ma、Zhengyi Yang、Chenjing Li、Zhiyuan Zhu、Xu Shen、Lihong Hu

  DOI：10.3109/14756366.2010.543420

  日期：2011.10.1

  According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of beta-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A- and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC(50) = 0.27 mu M).
• Synthesis and Selective Inhibitory Activity of 1-Acetyl-3,5-diphenyl-4,5-dihydro-(1<i>H</i>)-pyrazole Derivatives against Monoamine Oxidase
  作者：Franco Chimenti、Adriana Bolasco、Fedele Manna、Daniela Secci、Paola Chimenti、Olivia Befani、Paola Turini、Valentina Giovannini、Bruno Mondovì、Roberto Cirilli、Francesco La Torre

  DOI：10.1021/jm031042b

  日期：2004.4.1

  A novel series of 1-acetyl-3-(4-hydroxy- and 2,4-dihydroxyphenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole derivatives 1 - 12 have been synthesized and investigated for the ability to selectively inhibit the activity of the A and B isoforms of monoamine oxidase (MAO). The new synthesized compounds 1-12 proved to be more reversible, potent, and selective inhibitors of MAO-A than of MAO-B. Knowing that stereochemistry may be an important modulator of biological activity, we performed the semipreparative chromatographic enantioseparation of the most potent, selective, and chiral compounds, 6 and 11. The separated enantiomers were then submitted to in vitro biological evaluation while increasing their inhibitory activity and A selectivity. The (-)-6 enantiomer shows Ki(MAO-A) 2 nM and SI = 165 000, (+)-6 shows Ki(MAO-A) = 6 nM and SI = 166 666, (-)-11 shows Ki(MAO-A) = 4 nM and SI = 80 000, and (+)-11 shows Ki(MAO-A) = 7 nM and SI = 38 571.
• Synthesis and activity of a new series of chalcones as aldose reductase inhibitors
  作者：Fabio Severi、Stefania Benvenuti、Luca Costantino、Gabriella Vampa、Michele Melegari、Luciano Antolini

  DOI：10.1016/s0223-5234(99)80010-5

  日期：1998.11

  A new series of chalcone derivatives has been synthesized and tested in vitro in order to assess their ability to inhibit aldose reductase enzyme (ALR2) and their specificity towards the target enzyme with respect to other oxidoreductases, such as aldehyde reductase, sorbitol dehydrogenase, and glutathione reductase. All the compounds display affinity for ALR2. The X-ray crystal structure of 1-(2,4-dihydroxyphenyl)-3-(2-methoxyphenyl)propen-1-one was determined. (C) Elsevier, Paris.
• Studies in Cell Suspension Cultures of Cassia didymobotrya. Part VI. The Biotransformation of Chalcones to Aurones and Auronols
  作者：Bruno Botta、Giuliano Delle Monache、Maria Cristina De Rosa、Rosalba Scurria、Alberto Vitali、Vittorio Vinciguerra、Pilar Menendez、Domenico Misiti

  DOI：10.3987/com-96-7414

  日期：——

  Cell-free extracts derived from tissue cultures of Cassia didymobotrya, which previously had been reported to convert 4-hydroxychalcones to flavones and biflavanones, catalyze the biotransformation of 2-hydroxychalcones to aurones and auronols. The aurone was shown to be the direct precursor of auronol.