(E)-3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-2-propen-1-one | 82522-52-9

• 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)-3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-2-propen-1-one
• 英文别名: (E)-1-(4-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one；2,4'-dihydroxychalcone；2,4'-dihydroxy-trans-chalcone；2,4'-Dihydroxy-trans-chalkon；(E)-1-(4-hydroxyphenyl)-3-(2-hydroxyphenyl)-2-propen-1-one (11)；(E)-3-(2-hydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 82522-52-9
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: PYXFBLHBGUOXFY-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  水杨醛 在 三氯化硼 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 (E)-3-(2-hydroxy-phenyl)-1-(4-hydroxy-phenyl)-2-propen-1-one
  参考文献：
  名称：

  Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

  摘要：

  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).

  DOI：

  10.3109/14756366.2010.543420

文献信息

• Antitumorigenic Activities of Chalcones. I. Inhibitory Effects of Chalcone Derivatives on 32Pi-Incorporation into Phospholipids of HeLa Cells Promoted by 12-O-Tetradecanoyl-phorbol 13-Acetate(TPA).
  作者：Susumu IWATA、Takeshi NISHINO、Nobuyuki NAGATA、Yoshiko SATOMI、Hoyoku NISHINO、Shoji SHIBATA

  DOI：10.1248/bpb.18.1710

  日期：——

  More than forty chalcone derivatives were synthesized to examine their structure-activity relationship against tumorigenesis. As a primary screening test, the inhibitory activities of the chalcones for the 32Pi-incorporation into phospholipids of HeLa cells enhanced by 12-O-tetradecanoyl-phorbol 13-acetate (TPA) were examined. 3-Hydroxy-chalcone derivatives possessing methyl group in 3'-, 4'-, or 2'-position and isoliquiritigenin homologs showed potent inhibitory activities in the phosphorylation test, which suggests their antitumorigenic effects.

  合成了四十余种查耳酮衍生物，以研究其结构与抗肿瘤发生活性之间的关系。作为初步筛选测试，检测了查耳酮对12-O-十四烷酰佛波醇-13-乙酸酯（TPA）增强的HeLa细胞磷脂中32Pi掺入的抑制活性。在3'-、4'-或2'-位具有甲基的3-羟基查耳酮衍生物和异甘草素同系物在磷酸化试验中显示出强大的抑制活性，这表明它们具有抗肿瘤发生作用。
• METHODS OF DESIGNING, PREPARING, AND USING NOVEL PROTONOPHORES
  申请人：Martineau Louis C.

  公开号：US20140135359A1

  公开（公告）日：2014-05-15

  The present invention provides a computer-assisted method of generating a protonophore requiring the use of a computer including a processor. The method includes: designing the protonophore, calculating, using the processor, an estimated protonophoric activity; producing the protonophore if the estimated protonophoric activity corresponds to an U 50 of about 20 μM or less; and determining the uncoupling activity of the protonophore. The present invention also provides novel protonophores that meet the above requirement and their methods of use.

  本发明提供了一种利用计算机辅助的方法来生成需要使用处理器的质子载体。该方法包括：设计质子载体，使用处理器计算估计的质子载体活性；如果估计的质子载体活性对应于大约20微米或更少的U50，则生产质子载体；并确定质子载体的解耦活性。本发明还提供了符合上述要求的新型质子载体及其使用方法。
• XANTHOHUMOL-BASED COMPOUNDS AND COMPOSITIONS THEREOF, AND METHODS OF MAKING AND USING THE SAME
  申请人：Oregon State University

  公开号：US20160008298A1

  公开（公告）日：2016-01-14

  Disclosed herein are compounds capable of ameliorating, treating, and preventing metabolic syndrome, or risk factors associated with metabolic syndrome, such as obesity, diabetes, and/or cardiovascular disease. In some embodiments, the compounds can function as mild mitochondrial uncouplers and thereby reduce markers of metabolic syndrome by improving insulin sensitivity and glucose metabolism. Methods of making the compounds also are disclosed herein, along with compositions and formulations suitable for administration to a subject. In some embodiments, the compounds (or compositions thereof) can be formulated and administered as dietary supplements.

  本文披露了一些能够改善、治疗和预防代谢综合征或与代谢综合征相关的危险因素，如肥胖、糖尿病和/或心血管疾病的化合物。在某些实施例中，这些化合物可以作为轻度线粒体解偶联剂发挥作用，从而通过改善胰岛素敏感性和葡萄糖代谢来减少代谢综合征的标志。本文还披露了制备这些化合物的方法，以及适合用于给予受试者的组合物和配方。在某些实施例中，这些化合物（或其组合物）可以制成膳食补充剂的形式进行配方和给予。
• Synthesis, in vitro antigiardial activity, SAR analysis and docking study of substituted chalcones
  作者：David Cáceres-Castillo、Rubén M. Carballo、Ramiro Quijano-Quiñones、Gumersindo Mirón-López、Manlio Graniel-Sabido、Rosa E. Moo-Puc、Gonzalo J. Mena-Rejón

  DOI：10.1007/s00044-019-02492-5

  日期：2020.3

  A series of 15 chalcones-bearing substituents at positions 2, 4, and 5 of rings A and B were synthesized using microwave-assisted Claissen-Smichdt condensation and evaluated for their activity against Giardia lamblia and Green monkey kidney cells. Five compounds exhibited activity against G. lamblia at IC50's 3m exhibited the highest antigiardial activity (IC50 = 1.03 mu M), even more than the positive control (metronidazole, IC50 = 1.4 mu M), and selectivity (SI = 38.9). A preliminary SAR study suggested that electrophylicity has not relationship with antigiardiasic activity, and the docking study reveals that synthesized chalcones bind at zone 3 of colchicine site, therefore presumably the action mechanism of the synthesized chalcones does not follow the Michael acceptor mechanism.
• Carpenter; Hunter, Journal of Applied Chemistry, 1951, vol. 1, p. 217,223
  作者：Carpenter、Hunter

  DOI：——

  日期：——