Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives

Mickevičius, Vytautas; Vaickelionienė, Rita; Jonuškienė, Ilona; Mikulskiene, Gema; Kantminienė, Kristina

doi:10.1007/s00706-009-0201-z

Cited by 11 publications

(6 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The amide group determines the splitting of resonances in 1 H- and 13 C-NMR spectra due to the restricted rotation around the ( E/Z ) amide bond. The lone pair of the nitrogen atom in the azomethine group affects the neighbouring atoms and causes formation of geometrical isomers ( cis/trans ) [ 19 , 20 , 21 ]. The 13 C-NMR spectra of 4a – c exhibited a double set of resonances of CO, N=CH, pyrrolidinone ring carbons and even some of the benzene ring ones.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

et al. 2012

Self Cite

View full text Add to dashboard Cite

New 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives containing hydrazone, azole, diazole, oxadiazole fragments, as well as 2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinone derivatives were synthesized. The structure of all compounds has been confirmed by NMR, IR, mass spectra, and elemental analysis data. Methyl 1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarboxylate demonstrated potential antibacterial and antifungal activities as determined by diffusion and serial dilution methods, while N'-[(4-bromophenyl)methylidene]-1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarbohydrazide and 2-{3-[4-(1,2,3-oxadiazol-5-yl)-2-oxo-1-pyrrolidinyl]phenoxy}-3-{3-[4-(1,3,4-oxadiazol-2-yl)-2-oxo-1-pyrrolidinyl]phenoxy}naphthoquinone showed antifungal activity against Candida tenuis and Aspergillus niger at low concentrations, as determined by the serial dilution method. The substitution of the methoxy fragment by N-containing substituents in monophenoxy substituted naphthoquinones was found to decrease their activity against Mycobacterium luteum. Besides, introduction of the second phenoxy substituted fragment increased the antifungal activity against Candida tenuis and Aspergillus niger at lower concentrations.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…The pathway of synthesis of the new 1,4disubstituted pyrrolidinones is shown in Scheme 1 (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) and Scheme 2 (14)(15)(16)(17)(18)(19)(20)(21)(22)(23).…”

Section: Chemistrymentioning

confidence: 99%

“…As a continuation of our interest in the synthesis and application of new azole derivatives [23][24][25] the title compounds with O, S, and N heteroatoms were synthesized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, antibacterial and antioxidant evaluation of 4-substituted 1-(4-methoxyphenyl)pyrrolidin-2-ones

et al. 2015

View full text Add to dashboard Cite

Substituted 1-(4-methoxyphenyl)pyrrolidin-2-ones containing azole, diazole, oxadiazole, thiadiazole, and triazole fragments have been synthesized, and the characterization of the obtained products is presented. The study compounds have been analyzed for antioxidant and antibacterial activities. Two types of hetero systems-5-thioxo-4,5-dihydro-1,3,4-oxadiazole and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazineshowed a moderate activity against Rhizobium radiobacter, Xanthomonas campestris, and Escherichia coli microorganisms. Some compounds were tested for their antioxidant activity.

show abstract

“…The increasing focus on the synthesis of pyrrolidinone derivatives and the study of their biological properties encouraged us to extend the works in the synthesis and investigations of functionalized 2-pyrrolidinone derivatives [25][26][27][28] with aromatic and heterocyclic moieties in the structure.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial evaluation of novel 1-(2,6-diethylphenyl)-5-oxopyrrolidine derivatives

Žukauskas¹,

Grybaitė²,

Vaickelionienė³

et al. 2020

chemija

Self Cite

View full text Add to dashboard Cite

Synthesis of 1-(2,6-diethylphenyl)-5-oxopyrrolidine derivatives containing hydrazone, semi/thiosemicarbazide and azole moieties is described. For this purpose, the appropriate hydrazide was treated with aromatic aldehydes, ketones and phenyl iso(thio)cyanates to obtain the desired outcome. The synthesized target compounds were evaluated for their antibacterial properties. The antibacterial screening revealed promising compounds with a pyrazole and thiosemicarbazide moieties in the molecule, which in some cases appeared to be 4 times more effective than Ampicillin.

show abstract

Synthesis and properties of 1-(3-(fluoromethyl and trifluoromethyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives

Cited by 11 publications

References 35 publications

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

Synthesis, antibacterial and antioxidant evaluation of 4-substituted 1-(4-methoxyphenyl)pyrrolidin-2-ones

Synthesis and antibacterial evaluation of novel 1-(2,6-diethylphenyl)-5-oxopyrrolidine derivatives

Contact Info

Product

Resources

About