(Z)-2-(3,4-dimethoxybenzylidene)benzofuran-3(2H)-one | 63831-46-9

• 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)-2-(3,4-dimethoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 3',4'-dimethoxyaurone；2-veratrylidene-benzofuran-3-one；2-Veratryliden-benzofuran-3-on；3',4'-Dimethoxy-aurone；(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 63831-46-9
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: FJYHPGCVLUAPLZ-YBEGLDIGSA-N

物化性质

• 熔点：
  160-161 °C
• 沸点：
  455.6±45.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3,4-dimethoxybenzylidene)benzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到(Z)-2-(3,4-dihydroxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Aurones as histone deacetylase inhibitors: Identification of key features

  摘要：

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.019
• 作为产物：
  描述：

  (2E)-3-(3,4-二甲氧基苯基)-1-(2-羟基苯基)-2-丙烯-1-酮 在 mercury(II) diacetate 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 (Z)-2-(3,4-dimethoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Aurones as histone deacetylase inhibitors: Identification of key features

  摘要：

  In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET- based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 mu M in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.019

文献信息

• Synthesis of aurones under neutral conditions using a deep eutectic solvent
  作者：Ian Hawkins、Scott T. Handy

  DOI：10.1016/j.tet.2013.08.060

  日期：2013.11

  Of the various methods available for their synthesis, the simplest involves the condensation of a coumaranone with an aldehyde. This reaction can be performed under acidic or basic conditions. We have recently discovered an effectively neutral set of conditions that employ the deep eutectic solvent comprised of choline chloride and urea as both solvent and catalyst. Modest to good yields can be achieved

  Aurones是黄酮类天然产物家族中一个有趣但很少研究的成员。在可用于合成的各种方法中，最简单的方法涉及香豆素与醛的缩合。该反应可以在酸性或碱性条件下进行。最近，我们发现了一组有效的中性条件，它们采用由氯化胆碱和尿素组成的深共熔溶剂作为溶剂和催化剂。对于多种醛，可以实现中等至良好的产率，从而促进从生物学和光谱学角度对金刚烷的进一步研究。
• A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds
  作者：Julian Garrec、Alexis Archambeau、Anaïs Scuiller、Xueyang Liu、Marie Cordier

  DOI：10.1055/s-0040-1706038

  日期：2021.6

  A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

  描述了钯催化的1-氮代烯与(2-羟甲基)烯丙基碳酸酯之间的氧杂-(4+4)-环加成反应。以花槿素衍生的氮代烯以较高的产率提供多环的1,5-氧杂环己烷。有趣的是，线性的氮代烯也参与其中，并产生具有完全区域选择性的单环杂环化合物。进行了密度泛函理论计算以深入了解这一观察结果。

• Discovery of benzofuran-3(2 H )-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis
  作者：Sheng Wang、Lei Xu、Yu-Ting Lu、Yu-Fei Liu、Bing Han、Ting Liu、Jie Tang、Jia Li、Jiangping Wu、Jing-Ya Li、Li-Fang Yu、Fan Yang

  DOI：10.1016/j.ejmech.2017.02.048

  日期：2017.4

  kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried

  死亡相关的蛋白激酶相关的凋亡诱导激酶2（DRAK2）是一种丝氨酸/苏氨酸激酶，在多种细胞死亡信号传导途径中起关键作用。发现抑制DRAK2可有效保护胰岛β细胞免于凋亡，因此DRAK2抑制剂代表了治疗糖尿病的有前途的治疗策略。目前仅知道靶向DRAK2的化学实体很少。我们进行了高通量筛选，并将化合物4鉴定为中度DRAK2抑制剂，IC50值为3.15μM。随后对命中化合物4的SAR研究导致开发出新型的benzofuRAn-3（2H）-DRAK2抑制剂系列，具有针对26种所选激酶的增强的效能和有利的选择性。重要的是，大多数有效化合物40（IC50 = 0.33μM）和41（IC50 = 0。发现25μM）以剂量依赖性方式保护胰岛β细胞免于凋亡。这些数据支持以下观点：DRAK2的小分子抑制剂代表了治疗糖尿病的有前途的策略。
• An Efficient Synthesis of Aurone Derivatives by the Tributylphosphine-catalyzed Regioselective Cyclization of <i>o</i>-Alkynoylphenols
  作者：Koya Saito、Masahito Yoshida、Takayuki Doi

  DOI：10.1246/cl.140910

  日期：2015.2.5

  An organocatalytic regioselective synthesis of aurones from o-alkynoylphenols was achieved. A catalytic amount of tributylphosphine selectively induced the 5-exo cyclization of o-alkynoylphenols under ambient conditions leading to aurone derivatives in high to excellent yields.

  实现了从o-烷炔酰基苯酚的有机催化区选择性合成黄烷酮的方法。少量的三丁基膦在常温下选择性诱导o-烷炔酰基苯酚的5-exo环化，产生黄烷酮衍生物，收率高至优异。
• [EN] AURONES AND METHODS OF USING AURONES TO TREAT TUBERCULOSIS<br/>[FR] AURONES ET MÉTHODES D'UTILISATION D'AURONES POUR TRAITER LA TUBERCULOSE
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2020223439A1

  公开（公告）日：2020-11-05

  This disclosure describes compounds, compositions, and methods for treating or preventing infection or disease including, in some specific embodiments, treating or preventing tuberculosis and/or infection with Mycobacterium tuberculosis (Mtb). In one aspect, this disclosure describes aurones including, for example, aurone 9504, aurone 9505, aurone 9501, aurone 9510, aurone AA2A, and aurone AA8, compositions including aurones, and methods of using aurones for treating or preventing tuberculosis.

  这份披露描述了治疗或预防感染或疾病的化合物、组合物和方法，包括在某些具体实施例中，治疗或预防结核病和/或结核分枝杆菌（Mtb）感染。在一个方面，这份披露描述了包括aurone 9504、aurone 9505、aurone 9501、aurone 9510、aurone AA2A和aurone AA8在内的aurones，包括aurones的组合物，以及使用aurones治疗或预防结核病的方法。