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新型烷基(芳基)取代的2,2-二氟-6-(三氯甲基)-2,1,3,2-恶唑硼烷-3-鎓-2-脲:合成、抗菌活性及与CT-DNA结合评估

Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2-1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations.

作者信息

Rosa Wilian C, Rocha Inaiá O, Rodrigues Melissa B, Coelho Helena S, Denardi Laura B, Ledur Pauline C, Zanatta Nilo, Acunha Thiago V, Iglesias Bernardo A, Bonacorso Helio G

机构信息

Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil.

Laboratório de Pesquisas Micológicas (LAPEMI), Departamento de Microbiologia e Parasitologia, Universidade Federal de Santa Maria, Santa Maria, Brazil.

出版信息

Front Pharmacol. 2020 Sep 2;11:1328. doi: 10.3389/fphar.2020.01328. eCollection 2020.

Abstract

The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of ()-1,1,1-trichloro-4-alkyl(aryl)amino-4-arylbut-3-en-2-ones and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2-1,3,2-oxazaborinin-3-ium-2-uides in which 3(4)-alkyl(aryl) = H, Me, -propyl, -butyl, CH, 4-CHCH, 4-CHOCH, 4-NOCH, 4-FCH, 4-BrCH, 2-naphthyl, is reported. A series of β-enaminoketones is synthesized from the O,N-exchange reaction of some amines with ()-1,1,1-trichloro-4-methoxy-4-aryl-but-3-en-2-ones at 61-90% yields. Subsequently, reactions of the resulting β-enaminoketones with an appropriate source of boron (BF.OEt) gave the corresponding oxazaborinine derivatives at 50-91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF-β-enamino containing CCl units were also evaluated. Some compounds from the present series also exhibited potent antimicrobial effects on various pathogenic microorganisms at concentrations below those that showed cytotoxic effects. Compounds , and showed the best results and are very significant against , which causes diseases in humans and animals.

摘要

报道了一系列新的()-1,1,1-三氯-4-烷基(芳基)氨基-4-芳基丁-3-烯-2-酮和2,2-二氟-3-烷基(芳基)氨基-4-芳基-6-(三氯甲基)-2-1,3,2-氧杂硼杂环戊硼烷-3-鎓-2-化物的合成、抗菌活性评估、生物分子结合特性(DNA)以及吸收和发射特性,其中3(4)-烷基(芳基)=H、Me、-丙基、-丁基、CH、4-CHCH、4-CHOCH、4-NOCH、4-FCH、4-BrCH、2-萘基。通过一些胺与()-1,1,1-三氯-4-甲氧基-4-芳基丁-3-烯-2-酮的O,N交换反应以61-90%的产率合成了一系列β-烯胺酮。随后,所得β-烯胺酮与适当的硼源(BF.OEt)反应,以50-91%的产率得到相应的氧杂硼杂环戊硼烷衍生物。还评估了这些含CCl单元的新型BF-β-烯胺对DNA的生物分子结合特性的紫外可见和发射特性。本系列中的一些化合物在低于显示细胞毒性作用的浓度下对各种致病微生物也表现出强效抗菌作用。化合物、和显示出最佳结果,并且对在人和动物中引起疾病的非常显著。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3cfc/7493717/81150a63eb52/fphar-11-01328-g005.jpg

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