(Z)-4,6-dihydroxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3(2H)-one | 1234351-34-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-4,6-dihydroxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3(2H)-one
• 英文别名: (Z)-4,6-dihydroxy-2-(3,4,5-trimethoxybenzylidene)benzofuran-3-one；4,6-dihydroxy-2-(3,4,5-trimethoxybenzylidene)benzofuran-3(2H)-one；(2Z)-4,6-dihydroxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 1234351-34-8
• 化学式: C₁₈H₁₆O₇
• 分子量: 344.321
• InChiKey: YRZCWZZZVWAACE-PQMHYQBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  间苯三酚 在 盐酸 、 sodium methylate 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 6.25h， 生成 (Z)-4,6-dihydroxy-2-[(3,4,5-trimethoxyphenyl)methylidene]-1-benzofuran-3(2H)-one
  参考文献：
  名称：

  作为有效胰腺脂肪酶抑制剂的烷氧基黄酮的设计、合成、生物学评价和分子对接

  摘要：

  橙酮是黄酮类化合物的一个小亚类。与查尔酮、黄酮和异黄酮等其他亚类不同，橙酮作为胰腺脂肪酶抑制剂尚未得到广泛研究。在这项工作中，我们研究了合成Aurone衍生物的胰腺脂肪酶抑制效力。设计并合成了属于四个系列（4,6-二羟基黄酮、6-羟基黄酮、4,6-二烷氧基黄酮和6-烷氧基黄酮）的36个化合物。通过分光光度法测定其体外抑制活性，并与槲皮素和奥利司他进行比较。具有长链（6-10 个碳）烷氧基取代基的烷氧基橙酮衍生物显示出更大的效力。其中，相对于槲皮素（IC50为86.98±3.859μM）和奥利司他（IC50为0.0334±0.0015μM），4,6-二烷氧基橙酮8表现出最高的抗胰腺脂肪酶活性（IC50为1.945±0.520μM）。荧光猝灭测量证实了烷氧基黄酮衍生物对胰腺脂肪酶的亲和力。动力学研究表明，8 通过竞争机制抑制脂肪酶（Ki 为 1.288 ± 0.282 µM）。分子对接结果阐明了

  DOI：

  10.1016/j.bmcl.2023.129574

文献信息

• Aurones as New Porcine Pancreatic α-Amylase Inhibitors
  作者：Khashayar Roshanzamir、Elaheh Kashani-Amin、Azadeh Ebrahim-Habibi、Latifeh Navidpour

  DOI：10.2174/1570180815666180712150600

  日期：2019.1.15

  Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α- amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds

  背景：Aurones（Z）-2-亚苄基苯并呋喃-3-酮衍生物是黄酮的天然结构异构体，具有广阔的药理潜力。 方法：在这项研究中，通过评估其对猪胰腺α-淀粉酶的体外生物学活性，研究了羟基化或甲氧基化金酮衍生物抑制猪胰腺α-淀粉酶的结构要求。 结果：基于体外和计算机模拟的结果，这些抑制剂的构效关系表明，（Z）-亚苄基苯并呋喃-3-酮衍生物的A或B环的OH基团的氢键与该化合物的催化残基结合位点对其抑制活性至关重要。 结论：似乎金黄色素中的OH基团抑制α-淀粉酶的方式类似于黄酮和黄酮醇中的OH基团。
• Green synthesis of aurones and related compounds under solvent-free conditions
  作者：Karima Boussafi、Didier Villemin、Nathalie Bar、Mabrouk Belghosi

  DOI：10.3184/174751916x14719593488659

  日期：2016.9

  3-Coumaranones were condensed with aldehydes on alumina or alumina–potassium fluoride without solvent under microwave irradiation or classical heating. Novel aurones and analogues bearing ferrocenyl, benzodioxole or benzodioxane groups were obtained in good yields without use of heavy metal reagents.

  在微波辐射或经典加热下，3-香豆酮与醛在氧化铝或氧化铝-氟化钾上缩合，无需溶剂。在不使用重金属试剂的情况下，以良好的收率获得了带有二茂铁、苯并二氧杂环戊烯或苯并二氧杂环己烷基团的新型金酮和类似物。
• [EN] COMPOSITIONS AND METHODS FOR INHIBITING GROUP II INTRON RNA<br/>[FR] COMPOSITIONS ET MÉTHODES POUR INHIBER DES ARN D'INTRON DE GROUPE II
  申请人：UNIV YALE

  公开号：WO2019147894A1

  公开（公告）日：2019-08-01

  The present invention provides compositions and methods for inhibiting group II intron splicing for treating or preventing a disease or disorder associated with an organism harboring an active group II intron. The present invention also provides compositions and methods for inhibiting group II intron splicing for inhibiting, preventing or reducing growth of an organism harboring an active group II intron.

  本发明提供了用于抑制II类内含子剪接的组合物和方法，用于治疗或预防与携带活跃II类内含子的生物体相关的疾病或紊乱。本发明还提供了用于抑制II类内含子剪接，以抑制、预防或减少携带活跃II类内含子的生物体生长的组合物和方法。
• Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR
  作者：Chong-Yew Lee、Eng-Hui Chew、Mei-Lin Go

  DOI：10.1016/j.ejmech.2010.03.023

  日期：2010.7

  The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P) H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E-LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity. (c) 2010 Elsevier Masson SAS. All rights reserved.
• COMPOSITIONS AND METHODS FOR INHIBITING GROUP II INTRON RNA
  申请人：YALE UNIVERSITY

  公开号：US20210139512A1

  公开（公告）日：2021-05-13

  The present invention provides compositions and methods for inhibiting group II intron splicing for treating or preventing a disease or disorder associated with an organism harboring an active group II intron. The present invention also provides compositions and methods for inhibiting group II intron splicing for inhibiting, preventing or reducing growth of an organism harboring an active group II intron.