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

التفاصيل البيبلوغرافية
العنوان: Novel Alkyl(aryl)-Substituted 2,2-Difluoro-6-(trichloromethyl)-2 H -1,3,2-oxazaborinin-3-ium-2-uides: Synthesis, Antimicrobial Activity, and CT-DNA Binding Evaluations.
المؤلفون: Rosa WC; Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Rocha IO; Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Rodrigues MB; Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Coelho HS; Laboratório de Pesquisas Micológicas (LAPEMI), Departamento de Microbiologia e Parasitologia, Universidade Federal de Santa Maria, Santa Maria, Brazil.; Instituto Federal de Educação, Ciência e Tecnologia Farroupilha, Santa Maria, Brazil., Denardi LB; Laboratório de Pesquisas Micológicas (LAPEMI), Departamento de Microbiologia e Parasitologia, Universidade Federal de Santa Maria, Santa Maria, Brazil., Ledur PC; Laboratório de Pesquisas Micológicas (LAPEMI), Departamento de Microbiologia e Parasitologia, Universidade Federal de Santa Maria, Santa Maria, Brazil., Zanatta N; Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Acunha TV; Laboratório de Bioinorgânica e Materiais Porfirínicos, Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Iglesias BA; Laboratório de Bioinorgânica e Materiais Porfirínicos, Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil., Bonacorso HG; Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, Santa Maria, Brazil.
المصدر: Frontiers in pharmacology [Front Pharmacol] 2020 Sep 02; Vol. 11, pp. 1328. Date of Electronic Publication: 2020 Sep 02 (Print Publication: 2020).
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Frontiers Media] Country of Publication: Switzerland NLM ID: 101548923 Publication Model: eCollection Cited Medium: Print ISSN: 1663-9812 (Print) Linking ISSN: 16639812 NLM ISO Abbreviation: Front Pharmacol Subsets: PubMed not MEDLINE
أسماء مطبوعة: Original Publication: [Lausanne : Frontiers Media]
مستخلص: The synthesis, antimicrobial activity evaluations, biomolecule-binding properties (DNA), and absorption and emission properties of a new series of ( Z )-1,1,1-trichloro-4-alkyl(aryl)amino-4-arylbut-3-en-2-ones (4, 5) and 2,2-difluoro-3-alkyl(aryl)amino-4-aryl-6-(trichloromethyl)-2 H -1,3,2-oxazaborinin-3-ium-2-uides (6, 7) in which 3(4)-alkyl(aryl) = H, Me, iso -propyl, n -butyl, C 6 H 5 , 4-CH 3 C 6 H 4 , 4-CH 3 OC 6 H 4 , 4-NO 2 C 6 H 4 , 4-FC 6 H 4 , 4-BrC 6 H 4 , 2-naphthyl, is reported. A series of β-enaminoketones (4, 5) is synthesized from the O,N-exchange reaction of some amines (3) with ( Z )-1,1,1-trichloro-4-methoxy-4-aryl-but-3-en-2-ones (1, 2) at 61-90% yields. Subsequently, reactions of the resulting β-enaminoketones with an appropriate source of boron (BF 3 .OEt 2 ) gave the corresponding oxazaborinine derivatives (6, 7) at 50-91% yields. UV-Vis and emission properties of biomolecule-binding properties for the DNA of these new BF 2 -β-enamino containing CCl 3 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 4d, 4e, 6e , and 6f showed the best results and are very significant against P. zopfii , which causes diseases in humans and animals.
(Copyright © 2020 Rosa, Rocha, Rodrigues, Coelho, Denardi, Ledur, Zanatta, Acunha, Iglesias and Bonacorso.)
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فهرسة مساهمة: Keywords: DNA-binding assays; antimicrobial agents; difluoro-organoboron complexes; photophysical properties; β-enaminoketones
تواريخ الأحداث: Date Created: 20201005 Latest Revision: 20240329
رمز التحديث: 20240329
مُعرف محوري في PubMed: PMC7493717
DOI: 10.3389/fphar.2020.01328
PMID: 33013370
قاعدة البيانات: MEDLINE
الوصف
تدمد:1663-9812
DOI:10.3389/fphar.2020.01328