(Z)-2-(2-hydroxybenzylidene)benzofuran-3(2H)-one

• 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-(2-hydroxybenzylidene)benzofuran-3(2H)-one
• 英文别名: (2Z)-2-(2-hydroxybenzylidene)-1-benzofuran-3(2H)-one；(2Z)-2-[(2-hydroxyphenyl)methylidene]-1-benzofuran-3-one
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: TVCLXWLVYCIOMW-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl ((2E,4E)-5-phenylpenta-2,4-dien-1-yl) carbonate 、 (Z)-2-(2-hydroxybenzylidene)benzofuran-3(2H)-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 C₅₂H₃₄F₁₂NO₂P 作用下， 以 甲苯 为溶剂， 以81 %的产率得到
  参考文献：
  名称：

  不对称 2,4-二烯基化/[4 + 2] 环化级联通过自动串联钯催化构建融合框架

  摘要：

  已提出邻位官能化芳基烯酮和 2,4-二烯基碳酸酯之间的钯催化串联反应，通过连续的 2,4-二烯化/迈克尔加成/π-σ-π 异构化/烯丙基烷基化进行。大量具有融合和螺环框架的对映体富集结构以中等到优异的产率和立体选择性构建。值得注意的是，二烯化中间体的固有分子内 Diels-Alder 反应模式可通过 Pd(0)-π-Lewis 碱催化得到很好的逆转。

  DOI：

  10.1021/acs.orglett.3c01084
• 作为产物：
  描述：

  dalmaisione D 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以4 mg的产率得到(Z)-2-(2-hydroxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  Polyphenolic Glycosides and Oligosaccharide Multiesters from the Roots of Polygala dalmaisiana

  摘要：

  Four new polyphenolic glycosides, dalmaisiones A-D (1-4), 16 new oligosaccharide multiesters, dalmaisioses A-P (5, 7-21), and one known tetrasaccharide multiester, reiniose G (6), were isolated from the roots of Polygala dalmaisiana. The structures of the new compounds were elucidated on the basis of chemical and spectroscopic evidence.

  DOI：

  10.1021/np010434n

文献信息

• Suppression of LPS-induced NF-κB activity in macrophages by the synthetic aurone, (Z)-2-((5-(hydroxymethyl) furan-2-yl) methylene) benzofuran-3(2H)-one
  作者：Hyo S. Park、David E. Nelson、Zachary E. Taylor、James B. Hayes、Kirsten D. Cunningham、Brock A. Arivett、Rajarshi Ghosh、Larissa C. Wolf、Kimberley M. Taylor、Mary B. Farone、Scott T. Handy、Anthony L Farone

  DOI：10.1016/j.intimp.2016.12.004

  日期：2017.2

  investigated their ability to suppress pro-inflammatory signaling in human monocyte (THP-1) and murine macrophage-like (RAW 267.4) cell lines. One of these derivatives, (Z)-2-((5-(hydroxymethyl) furan-2-yl) methylene) benzofuran-3(2H)-one (aurone 1), was found to inhibit LPS-induced secretion of the pro-inflammatory cytokines, tumor-necrosis factor α (TNFα), interleukin 1β (IL-1β), and IL-8 by THP-1 cells

  抑制细胞因子的反应经常被证明对许多慢性炎症和自身免疫性疾病具有有希望的治疗作用。但是，与长期使用当前疗法相关的严重副作用，例如过敏反应和中风风险增加，已将注意力集中在靶向调节炎症的细胞内信号传导机制（例如NF-κB）上。我们合成了一系列的非天然金酮衍生物，并研究了它们抑制人类单核细胞（THP-1）和鼠类巨噬细胞样（RAW 267.4）细胞系促炎性信号传导的能力。发现这些衍生物之一，（Z）-2-（（5-（羟甲基）呋喃-2-基）亚甲基）苯并呋喃-3（2H）-一（Aurone 1），可抑制LPS诱导的脯氨酸分泌。炎症细胞因子，肿瘤坏死因子α（TNFα），THP-1细胞产生白介素1β（IL-1β）和IL-8。为了研究该机制，我们探讨了金黄色素1对THP-1和RAW264.7中LPS诱导的MAPK和NF-κB信号传导的影响。尽管aurone 1预处理对ERK，JNK或p38 MAPK的磷酸化没有影响
• [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。
• Antifungal activity of substituted aurones
  作者：Caleb L. Sutton、Zachary E. Taylor、Mary B. Farone、Scott T. Handy

  DOI：10.1016/j.bmcl.2017.01.012

  日期：2017.2

  spp. are on the rise with infections by this genus accounting for the most severe fungal infections following chemotherapy, implantation procedures, and in patients with HIV/AIDS. A series of simple aurone analogs were synthesized and screened for antifungal activity versus Candida spp. Several compounds displayed activity at 100 μM, with two having IC50 values below 20 μM for three species of Candida

  新型抗真菌剂的需求量很大，因为目前使用的抗真菌剂的耐药性正在增加。尤其是念珠菌引起的机会性真菌感染。由于该属的感染正在增加，这是化学疗法，植入程序以及艾滋病毒/艾滋病患者中最严重的真菌感染。合成了一系列简单的金酮类似物，并针对念珠菌属进行了抗真菌活性筛选。几种化合物在100μM下显示出活性，其中两种对三种念珠菌的IC 50值低于20μM 。此处测试的化合物之一还显示出抗生物膜活性，可促进中成熟期的生长。
• Aurones: Small Molecule Visible Range Fluorescent Probes Suitable for Biomacromolecules
  作者：Natasha Shanker、Ozlem Dilek、Kamalika Mukherjee、Dennis W. McGee、Susan L. Bane

  DOI：10.1007/s10895-011-0919-y

  日期：2011.11

  Aurones, derivatives of 2-benylidenebenzofuran-3(2H)-one, are natural products that serve as plant pigments. There have been reports that some of these substances fluoresce, but little information about their optical properties is in the literature. In this report, series of aurone derivatives were synthesized as possible fluorescent probes that can be excited by visible light. We found that an amine substituent shifted the lowest energy absorption band from the near-UV to the visible region of the electromagnetic spectrum. Four amine-substituted aurone derivatives were synthesized to explore the effect of this substituent on the absorption and emission properties of the aurone chromophore. The emission maxima and intensities of the molecules are strongly dependent on the nature of the substituent and the solvent polarity. Overall, the emission intensity increases and the maximum wavelength decreases in less polar solvents; thus, the aurones may be useful probes for hydrophobic sites on biological molecules. A limited investigation with model protein, nucleic acid and fixed cells supports this idea. It is known that the sulfur analog of aurone can undergo photo-induced E/Z isomerization. This possibility was investigated for one of the aminoaurones, which was observed to reversible photoisomerize. The two isomers have similar absorption spectra, but the emission properties are distinct. We conclude that appropriately substituted aurones are potentially useful as biological probes and photoswitches.

  黄酮，一种2-苯基亚胺苯并呱-3(2H)-酮的衍生物，是一种作为植物色素的天然产物。有报道称这些物质中有一些具有荧光特性，但关于它们的光学性质的文献资料很少。在这篇报告中，我们合成了一系列作为可见光激发的荧光探针的黄酮衍生物。我们发现，一个胺取代基将最低能量吸收带从近紫外区转移到了电磁谱的可见区域。合成了四种胺取代的黄酮衍生物，以探讨该取代基对黄酮色素的吸收和发射特性的影响。分子的发射峰值和强度在很大程度上取决于取代基的性质和溶剂的极性。总体而言，在极性较小的溶剂中，发射强度增加而峰值波长下降；因此，黄酮可能作为生物分子上疏水位点的有用探针。对模型蛋白质、核酸和固定细胞的有限研究支持了这一观点。已知黄酮的硫类类似物可以发生光诱导的E/Z异构化。我们对一种氨基黄酮进行了这方面的研究，观察到其可逆光异构反应。这两种异构体具有相似的吸收光谱，但发射特性有所不同。我们得出结论，适当取代的黄酮在生物探针和光开关方面具有潜在的应用价值。
• Versatile and Expeditious Synthesis of Aurones via Au^I-Catalyzed Cyclization
  作者：Hassina Harkat、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo702197b

  日期：2008.2.1

  Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3‘,4‘-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4‘-chloroaurone)

  可以以三步程序方便地形成Aurones，包括金I催化的2-（1-羟基丙-2-炔基）苯酚的环化反应，这是高度区域选择性和立体选择性的关键步骤。从取代的水杨醛开始可以得到各种各样的衍生物。实现了天然4,6,3'，4'-四甲氧基金龙的合成和两种天然产物（dalmaisione D和4'-氯金龙）的结构修饰。

表征谱图