(E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-prop-2-en-1-one

• 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-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-prop-2-en-1-one
• 英文别名: (E)-1-(2,4-dihydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one；(E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-2-propen-1-one；(E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one；3,4',4-trihydroxychalcone；3,4,4'-trihydroxychalcone；4',3,4-trihydroxychalcone
• 化学式: C₁₅H₁₂O₄
• 分子量: 256.258
• InChiKey: UPERCWWUZZKHCL-LREOWRDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-prop-2-en-1-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以89%的产率得到(E)-4-(3-(4-acetoxyphenyl)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate
  参考文献：
  名称：

  通过狄尔斯-阿尔德反应，LiAlH 4介导的异构化和酸介导的环化反应，以生物启发的方式合成了帕洛德桑格人的三环核

  摘要：

  的环己烯部分的三环6,7-二芳基四氢-6- ħ -苯并[ c ^ ] palodesangrens的色烯核心可在仿生和步骤-经济的方式由所述富电子（之间的Diels-Alder反应来组装ë） -1,3-丁二烯芳烃为二烯，缺电子查耳酮为亲二烯体。在LiAlH 4将酮还原为相应的醇的过程中，内和外异构体的混合物经历了一种新的非对映收敛的LiAlH 4。-介导的异构化以在C10a处安装所需的立体化学。随后在酸性条件下的吡喃环闭合将立体化学安装在剩余的C6上。总体而言，可以分三步制备palodesangrens的三环核，产率最高可达38％。

  DOI：

  10.1021/acs.joc.8b00668
• 作为产物：
  描述：

  3,4-二(四氢吡喃-2-氧基)苯甲醛 在 barium hydroxide octahydrate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 (E)-3-(3,4-dihydroxyphenyl)-1-(4-hydroxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  Geometrically and Conformationally Restrained Cinnamoyl Compounds as Inhibitors of HIV-1 Integrase:  Synthesis, Biological Evaluation, and Molecular Modeling

  摘要：

  Various cinnammoyl-based structures were synthesized and tested in enzyme assays as inhibitors of the HIV-1 integrase (IN). The majority of compounds were designed as geometrically or conformationally constrained analogues of caffeic acid phenethyl ester (CAPE) and were characterized by a syn disposition of the carbonyl group with respect to the vinylic double bond. Since the cinnamoyl moiety present in flavones such as quercetin (inactive on HIV-1-infected cells) is frozen in an anti arrangement, it was hoped that fixing our compounds in a syn disposition could favor anti-HIV-1 activity in cell-based assays. Geometrical and conformational properties of the designed compounds were taken into account through analysis of X-ray structures available from the Cambridge Structural Database. The polyhydroxylated analogues were prepared by reacting 3,4-bis(tetrahydropyran-2-yloxy)benzaldehyde with various compounds having active methylene groups such as 2-propanone, cyclopentanone, cyclohexanone, 1,3-diacetylbenzene, 2,4-dihydroxyacetophenone, 2,3-dihydro-1-indanone, 2,3-dihydro-1,3-indandione, and others. While active against both 3'-processing and strand-transfer reactions, the new compounds, curcumin included, failed to inhibit the HIV-1 multiplication in acutely infected MT-4 cells. Nevertheless, they specifically inhibited the enzymatic reactions associated with IN, being totally inactive against other viral (HIV-1 reverse transcriptase) and cellular (RNA polymerase II) nucleic acid-processing enzymes. On the other hand, title compounds were endowed with remarkable antiproliferative activity, whose potency correlated neither with the presence of catechols (possible source of reactive quinones) nor with inhibition of topoisomerases. The SARs developed for our compounds led to novel findings concerning the molecular determinants of IN inhibitory activity within the class of cinnamoyl-based structures. We hypothesize that these compounds bind to IN featuring the cinnamoyl residue C=C-C=O in a syn disposition, differently from flavone derivatives characterized by an anti arrangement about the same fragment. Certain inhibitors, lacking one of the two pharmacophoric catechol hydroxyls, retain moderate potency thanks to nonpharmacophoric fragments (i.e., a m-methoxy group in curcumin) which favorably interact with an "accessory" region of IN. This region is supposed to be located adjacent to the binding site accommodating the pharmacophoric dihydroxycinnamoyl moiety. Disruption of coplanarity in the inhibitor structure abolishes activity owing to poor shape complementarity with the target or an exceedingly high strain energy of the coplanar conformation.

  DOI：

  10.1021/jm9707232

文献信息

• Synthesis of 4-(2-Amino)ethoxy-3′,4′-dihydroxychalcones and Their Antioxidant and Cytotoxic Effects on Human Tumor Cells
  作者：Hyoung Ja Kim、Seung Hwan Kim、Young Hun Lee、Dong Woon Kim、Kilwoong Mo、Hye Jin Kim、Sang Hoon Park、Changbae Jin、Nam-Jung Kim、Yong Sup Lee

  DOI：10.1002/bkcs.10253

  日期：2015.5

  Recently, many reports revealed that there are close correlations between antioxidant and anticancer activities of compounds. In this study, we designed 4‐hydroxy‐3′,4′‐dihydroxychalcone (2) as a ring‐opened analog of luteolin, which has been known to possess both antioxidant and anticancer activities, and then introduced aminoethyl moieties to this chalcone structure to increase water solubility by

  最近，许多报道表明，化合物的抗氧化剂和抗癌活性之间有着密切的联系。在这项研究中，我们设计了4-羟基-3'，4'-二羟基查耳酮（2）作为木犀草素的开环类似物，已知该木犀草素同时具有抗氧化和抗癌活性，然后将氨乙基部分引入该查耳酮结构中通过转化为HCl盐来增加水溶性。合成的氨基烷基取代的查耳酮3a–3d在三种不同的测定系统中显示出强大的抗氧化活性，并针对四种测试的肿瘤细胞系具有抗癌活性。
• 2′,5′-Dihydroxychalcone as a Potent Chemical Mediator and Cyclooxygenase Inhibitor
  作者：Chun-Nan Lin、Tai-Hua Lee、Mei-Feng Hsu、Jih-Pyang Wang、Feng-Nien Ko、Che-Ming Teng

  DOI：10.1111/j.2042-7158.1997.tb06837.x

  日期：2011.4.12

  Eleven chalcone derivatives have been tested for their inhibitory effects on platelet aggregation in rabbit platelet suspension and the activation of mast cells and neutrophils.

  Arachidonic acid-induced platelet aggregation was potently inhibited by almost all the compounds and some also had a potent inhibitory effect on collagen-induced platelet aggregation and cyclooxygenase. Some hydroxychalcone derivatives showed strong inhibitory effects on the release of β-glucuronidase and lysozyme, and on superoxide formation by rat neutrophils stimulated with the peptide fMet-Leu-Phe (fMLP). We found that the anti-inflammatory effect of 2′,5′-dihydroxychalcone was greater than that of trifluoperazine. 2′,5′-Dihydroxy and 2′,3,4,4′-tetrahydroxyl chalcones, even at low concentration (50 μm), tested in platelet-rich plasma from man almost completely inhibited secondary aggregation induced by adrenaline.

  These results suggest that the anti-platelet effects of the chalcones are mainly a result of inhibition of thromboxane formation.

  摘要：对十一种查尔酮衍生物进行了测试，以评估它们对兔血小板悬液中血小板聚集、肥大细胞和中性粒细胞激活的抑制作用。花生四烯酸诱导的血小板聚集几乎被所有化合物强烈抑制，有些化合物对胶原诱导的血小板聚集和环氧化酶也有强烈的抑制作用。一些羟基查尔酮衍生物显示出对β-葡萄糖苷酸酶和溶菌酶释放，以及对受到fMet-Leu-Phe（fMLP）肽激活的大鼠中性粒细胞产生的超氧化物的强烈抑制作用。我们发现，2′,5′-二羟基查尔酮的抗炎效果大于三氟她嗪。即使在低浓度（50 μm）下，在人体富含血小板的血浆中，2′,5′-二羟基和2′,3,4,4′-四羟基查尔酮几乎完全抑制了由肾上腺素诱导的继发性聚集。这些结果表明，查尔酮的抗血小板作用主要是通过抑制血栓素形成实现的。
• Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema
  作者：Kangsan Roh、Jung-hun Lee、Hee Kang、Kye Won Park、Youngju Song、Sukchan Lee、Jin-Mo Ku

  DOI：10.1016/j.ejmech.2020.112280

  日期：2020.7

  factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50% suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb

  在本文中，我们证明，butein（1）可以通过抑制肿瘤坏死因子α（TNF-α）的产生来预防小鼠淋巴水肿模型中的肿胀。合成并评估了Butein衍生物，以鉴定具有体外抗炎活性的化合物。其中，20μM化合物7j，7m和14a在脂多糖刺激后表现出50％的抑制小鼠腹膜巨噬细胞TNF-α产生的作用。在鼠淋巴水肿模型中，化合物14a表现出最强的效力，体外IC50为14.6μM，肢体体积抑制了70％。在药代动力学研究中，通过口服给药，前药策略使化合物1的动力学溶解度增加了6倍，血液中的活性代谢产物水平提高了5倍，从而使化合物14a处于血液中。
• Sulfonamide chalcone as a new class of α-glucosidase inhibitors
  作者：Woo Duck Seo、Jin Hyo Kim、Jae Eun Kang、Hyung Won Ryu、Marcus J. Curtis-Long、Hyun Sun Lee、Min Suk Yang、Ki Hun Park

  DOI：10.1016/j.bmcl.2005.08.087

  日期：2005.12

  Chalcones 1-20, a new class of glycosidase inhibitors, were synthesized, and their glycosidase inhibitory activities were investigated. Non-aminochalcones 1-12 had no inhibitory activity, however, aminochalcones 13-20 had strong glycosidase (alpha-glucosidase, alpha-amylase, and beta-amylase) inhibitory activities. In particular, sulfonamide chalcones 17-20 had more potent alpha-glucosidase inhibitory

  合成了新型糖苷酶抑制剂Chalcones 1-20，并研究了它们对糖苷酶的抑制活性。非氨基查耳酮1-12没有抑制活性，但是氨基查耳酮13-20具有很强的糖苷酶（α-葡萄糖苷酶，α-淀粉酶和β-淀粉酶）抑制活性。特别地，磺酰胺查耳酮17-20比胺化查尔酮13-16具有更有效的α-葡糖苷酶抑制活性。4'-（对甲苯磺酰胺）-3,4-二羟基查尔酮20（IC（50）= 0.4microM）是对抗α-葡萄糖苷酶的最佳抑制剂，这些磺酰胺查耳酮显示出非竞争性抑制作用。
• COMPOSITION FOR INDUCING DIFFERENTIATION INTO BEIGE AND BROWN ADIPOCYTES AND METHOD OF INDUCING THE SAME
  申请人：RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY

  公开号：US20150374643A1

  公开（公告）日：2015-12-31

  A composition for inducing differentiation into beige adipocytes from white adipocytes, including butein, a butein derivative, or a pharmaceutically available salt thereof as an active ingredient, and a method of inducing the differentiation are provided. Increases in expressions of UCP-1 and PRDM4 are confirmed using the active ingredient, that is, the butein or butein derivative, and therefore the composition is expected to be used in preventing or treating obesity, and more basically, for target treatment.

  本发明提供了一种用于将白色脂肪细胞分化为米色脂肪细胞的组合物，包括布丁、布丁衍生物或其药学上可用的盐作为活性成分，并提供了一种诱导分化的方法。使用活性成分即布丁或布丁衍生物，已确认UCP-1和PRDM4表达的增加，因此预计该组合物可用于预防或治疗肥胖症，更基本地，用于目标治疗。