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荧光1-(3-氨基-4-(4-(叔丁基)苯基)-6-(对甲苯基)呋喃并[2,3-b]吡啶-2-基)乙-1-酮的合成:晶体结构、荧光行为、抗菌及抗氧化研究

Synthesis of Fluorescent 1-(3-Amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one: Crystal Structure, Fluorescence Behavior, Antimicrobial and Antioxidant Studies.

作者信息

Ibrahim Mohammad M, Al-Refai Mahmoud, Al-Fawwaz Abdullah, Ali Basem F, Geyer Armin, Harms Klaus, Marsch Michael, Krüger Michelle, Osman Hasnah, Azmi Mohamad N

机构信息

Department of Chemistry, Faculty of Science, Al al-Bayt University, P.O. BOX 130040, Al-Mafraq, 25113, Jordan.

Department of Biological Sciences, Faculty of Science, Al al-Bayt University, Al-Mafraq, 25113, Jordan.

出版信息

J Fluoresc. 2018 Mar;28(2):655-662. doi: 10.1007/s10895-018-2227-2. Epub 2018 Apr 21.

Abstract

Furopyridine III, namely 1-(3-amino-4-(4-(tert-butyl)phenyl)-6-(p-tolyl)furo[2,3-b]pyridin-2-yl)ethan-1-one, synthesized from 4-(4-(tert-butyl)phenyl)-2-oxo-6-(p-tolyl)-1,2-dihydropyridine-3-carbonitrile I in two steps. The title compound is characterized by NMR, MS and its X-ray structure. The molecular structure consists of planar furopyridine ring with both phenyl rings being inclined from the furopyridine scaffold to a significant different extent. There are three intramolecular hydrogen bonds within the structure. The lattice is stabilized by N-H…O, HC-H …π and π…π intermolecular interactions leading to three-dimensional network. Compound III exhibits fluorescent properties, which are investigated. Antimicrobial potential and antioxidant activity screening studies for the title compound III and the heterocyclic derivatives, I and II, show no activity towards neither bacterial nor fungal strains, while they exhibited weak to moderate antioxidant activity compared to reference.

摘要

呋吡啶III,即1-(3-氨基-4-(4-(叔丁基)phenyl)-6-(对甲苯基)呋喃并[2,3-b]吡啶-2-基)乙-1-酮,由4-(4-(叔丁基)phenyl)-2-氧代-6-(对甲苯基)-1,2-二氢吡啶-3-腈I分两步合成。标题化合物通过核磁共振、质谱及其X射线结构进行表征。分子结构由平面呋吡啶环组成,两个苯环从呋吡啶骨架倾斜的程度有显著差异。结构内有三个分子内氢键。晶格通过N-H…O、HC-H …π和π…π分子间相互作用得以稳定,形成三维网络。化合物III表现出荧光性质,并对其进行了研究。对标题化合物III以及杂环衍生物I和II的抗菌潜力和抗氧化活性筛选研究表明,它们对细菌和真菌菌株均无活性,不过与参比物相比,它们表现出弱至中等程度的抗氧化活性。

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