Z-2-[(4-N,N-dimethylaminophenyl)methylene]benzo[b]furan-3-one | 112980-33-3

• 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-[(4-N,N-dimethylaminophenyl)methylene]benzo[b]furan-3-one
• 英文别名: Z-2-[(4-(N,N-dimethylamino)phenyl)methylene]benzofuran-3-one；(Z)-2-(4-(dimethylamino)benzylidene)benzofuran-3(2H)-one；(2Z)-2-[(4-dimethylaminophenyl)methylene]benzofuran-3-one；(2Z)-2-[[4-(dimethylamino)phenyl]methylidene]-1-benzofuran-3-one
• CAS: 112980-33-3
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: BDLCKVSBCPDQJX-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2'-hydroxy-4-dimethylaminochalcone 在 吡啶 、 mercury(II) diacetate 作用下， 反应 3.0h， 以82%的产率得到Z-2-[(4-N,N-dimethylaminophenyl)methylene]benzo[b]furan-3-one
  参考文献：
  名称：

  Synthesis, crystal structure and two-photon excited fluorescence properties of three aurone derivatives

  摘要：

  Three aurone derivatives, Z-2-[(4-N,N-dimethylaminophenyl)methylene] benzofuran-3-one (1), Z-2-[(N-ethylcarbazol-3-yl)methylene]benzofuran-3-one (2) and Z-2-[(pyren-1-yl)methylene]benzofuran-3-one (3) have been synthesized by the cyclization of 2'-hydroxychalcones. Their crystal structure, single-and two-photon related absorption and fluorescence properties have been examined. Pumped by 860 nm laser pulses in femtosecond regime, the compounds exhibit strong yellow-green two-photon excited fluorescence at 539 nm (1), 505 nm (2) and 524 nm (3) in THF with two-photon absorption (TPA) cross-section being 1536GM (1), 608GM (2) and 236GM (3). (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.11.018

文献信息

• Probing the aurone scaffold against Plasmodium falciparum: Design, synthesis and antimalarial activity
  作者：Marta P. Carrasco、Ana S. Newton、Lídia Gonçalves、Ana Góis、Marta Machado、Jiri Gut、Fátima Nogueira、Thomas Hänscheid、Rita C. Guedes、Daniel J.V.A. dos Santos、Philip J. Rosenthal、Rui Moreira

  DOI：10.1016/j.ejmech.2014.04.076

  日期：2014.6

  were also prepared. Screening against the chloroquine resistant Plasmodium falciparum W2 strain identified novel aurones with IC50 values in the low micromolar range. The most potent compounds contained a basic moiety, with the ability to accumulate in acidic digestive vacuole of the malaria parasite. However, none of those aurones revealed significant activity against hemozoin formation and falcipain-2

  通过苯并呋喃酮和适当取代的苯甲醛的直接醛醇缩合反应合成了包含44个不同取代的金酮衍生物的文库。引入了使用钯催化方案的微波增强合成，作为扩展金质支架周围化学空间的有力策略。另外，还制备了在环A处含有7-氨基甲基-6-羟基取代图案的曼尼希碱衍生物。针对耐氯喹的恶性疟原虫W2菌株进行筛选，鉴定出具有IC 50的新型金质值在低微摩尔范围内。最有效的化合物包含一个碱性部分，具有在疟原虫的酸性消化液中积累的能力。然而，这些金黄色素均未显示出对血zo素形成和falcipain-2的显着活性，falcipain-2是在恶性疟原虫感染的血液阶段表达的两个经过验证的靶标，并在该寄生虫的消化液中起作用。总的来说，这项研究突出了（i）金氧烷作为使用钯催化方法快速递送先导化合物进行进一步优化的合成程序平台的有用性，以及（ii）新型金酮衍生物作为有前景的抗疟疾化合物的潜力。
• [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。
• Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile
  作者：Somepalli Venkateswarlu、Gopala K. Panchagnula、Aditya L. Gottumukkala、Gottumukkala V. Subbaraju

  DOI：10.1016/j.tet.2007.04.048

  日期：2007.7

  along with six structural analogs. The products obtained were Z-isomers and these were converted into E-isomers by photoisomerization. The E and Z isomers of aurones showed distinct proton and carbon chemical shifts. However, the spectroscopic data of either Z-4′-chloroaurone (1a) or its E-isomer (2a) did not match with those reported for the natural product and thus requires revision of the structure

  4'-Chloroaurone（1a），是唯一从海洋来源获悉的金盏花，Spatoglossum variabile是由2-羟基苯乙酮与六个结构类似物合成的。所得产物为Z-异构体，并且通过光异构化将其转化为E-异构体。黄金的E和Z异构体表现出明显的质子和碳化学位移。但是，Z -4'-chloroaurone（1a）或它的E-异构体（2a）的光谱数据）与报告的天然产品不匹配，因此需要修改指定的结构。报道的天然产物的质子NMR光谱数据与已知的异香豆素报道的数据相符（5）。评估了合成的E和Z的金黄色元素的抗氧化和抗菌活性。所述金酮Z -2-[（3,4-二羟基苯基）亚甲基]苯并[ b ]呋喃-3-酮具有显着的抗氧化活性。有趣的是，Z-金黄色素对革兰氏阳性和革兰氏阴性细菌有活性，而相应的E-金黄色素是无活性的。
• [EN] THERAPEUTIC AURONES<br/>[FR] AURONES THÉRAPEUTIQUES
  申请人：MIDDLE TENNESSEE STATE UNIV

  公开号：WO2017180644A1

  公开（公告）日：2017-10-19

  Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

  发现替代的金莲素具有抗锥虫、抗真菌和免疫调节活性。该发明提供了新型金莲素化合物、药物组合物和方法，涵盖医学和兽医应用。
• Design of Aurone‐Based Dual‐State Emissive (DSE) Fluorophores
  作者：Daria V. Berdnikova、Sören Steup、Michael Bolte、Markus Suta

  DOI：10.1002/chem.202300356

  日期：——

  Aurone derivatives were introduced as easily accessible dual-state emissive (DSE) fluorophores along with the description of molecular design principles. Facile one-step synthesis in combination with biological activities make DSE aurones unique tool for biomedical applications.

  介绍了Aurone 衍生物作为易于获得的双态发射 (DSE) 荧光团以及分子设计原理的描述。简便的一步合成与生物活性相结合，使 DSE aurones 成为生物医学应用的独特工具。