New 3,4-Annelated Coumarin Derivatives: Synthesis, Antimicrobial Activity, Antioxidant Capacity, and Molecular Modeling

Radulović, Niko S.; Stojanović, Gordana; Vukićević, Rastko D.; Dekić, Vidoslav; Dekić, Biljana; Palić, Radosav

doi:10.1007/s00706-006-0537-6

Cited by 29 publications

(21 citation statements)

References 5 publications

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“…However, at its highest concentration, the compound 12 inhibited mycelial growth of 16.94 %, while at the lowest concentrations no antifungal activity was found. Antiaflatoxigenic activity of 26.78 % was found for the compound 6 (ethyl substituent, position 4…”

Section: Resultsmentioning

confidence: 99%

Antifungal and antiaflatoxigenic activities of coumarinyl thiosemicarbazides against Aspergillus flavus NRRL 3251

Kovač

Kovač²,

Strelec

et al. 2017

Archives of Industrial Hygiene and Toxicology

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The antifungal and antiaflatoxigenic effects of two series of coumarinyl thiosemicarbazides on Aspergillus flavus NRRL 3251 were studied. Fungi were grown in YES medium for 72 h at 29 °C in the presence of 0, 0.1, 1, and 10 µg mL -1 of coumarinyl thiosemicarbazides: one series with substitution in position 7 and another with substitution in position 4 of the coumarin core. Dry mycelia weight determination was used for antifungal activity estimation, while the aflatoxin B1 content in YES media, determined by the dilute and shoot LC-MS/MS technique, was used for the antiaflatoxigenic effect estimation. Standard biochemical assays were used for oxidative status marker (TBARS, SOD, CAT, and GPX) determination in A. flavus NRRL 3251 mycelia. Results show that 7-substituted-coumarinyl thiosemicarbazides possess a better antifungal and antiaflatoxigenic activity than 4-substituted ones. The most prominent substituted compound was the compound 3, N-(4-chlorophenyl)-2- (2-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)acetyl)hydrazine-1-carbothioamide, which completely inhibited aflatoxin production at the concentration of 10 µg mL -1. Oxidative stress response of A. flavus exposed to the selected compounds points to the modulation of oxidative stress as a possible reason of aflatoxin production inhibition.

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Section: Resultsmentioning

confidence: 99%

Antifungal and antiaflatoxigenic activities of coumarinyl thiosemicarbazides against Aspergillus flavus NRRL 3251

Kovač

Kovač²,

Strelec

et al. 2017

Archives of Industrial Hygiene and Toxicology

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“…The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against pathogenic strains. The current results together with previous ones (Dekić et al, 2010a,b;Radulović et al, 2006Radulović et al, , 2011 showed that a heteroatom needs to be present in the arylamino substituent for such a derivative to show any significant antimicrobial activity.…”

Section: Resultsmentioning

confidence: 48%

“…Some of these compounds showed strong to moderate activity in reducing the microbial growth compared to the activity of standard antibiotics (Radulović et al, 2006). A recent QSAR study of the antimicrobial activity of some 3-nitro-coumarins has put forward some new arguments in this direction (Debeljak et al, 2007) and concluded that 4-aminoaryl substituted compounds possessed the greatest chance of being antimicrobial agents.…”

Section: Introductionmentioning

confidence: 99%

“…We have previously made synthetic efforts in the direction of creating coumarin derivatives with antimicrobial and/or antioxidant activities (Radulović et al, 2006(Radulović et al, , 2011Dekić et al, 2007aDekić et al, , b, 2008Dekić et al, , 2010a. Some of these compounds showed strong to moderate activity in reducing the microbial growth compared to the activity of standard antibiotics (Radulović et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

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Influence of the aryl substituent identity in 4-arylamino-3-nitrocoumarins on their antimicrobial activity

Deki¹,

Radulovi²,

Vukievi³

et al. 2011

Afr. J. Pharm. Pharmacol.

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Two new and six previously known coumarin derivatives with promising biological properties were synthesized in moderate to good yields by reaction of 4-chloro-3-nitro-coumarin and the appropriate arylamine in ethyl acetate in the presence of triethylamine. The synthesized compounds were evaluated for their in vitro antibacterial and antifungal activities against pathogenic strains. A correlation between the aryl substituent identity and antimicrobial activity was discussed.

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“…Bearing in mind the wide range of bioactivities, we thought it worthwhile to synthesize new coumarin derivatives. As a continuation of our previous work [3], we report on the synthesis and characterization of new derivatives containing the coumarin moiety.…”

Section: Introductionmentioning

confidence: 98%

Synthesis and structure of novel 3,4‐annelated coumarin derivatives

Dekić

Dekić²,

Dekić³

et al. 2008

Journal of Heterocyclic Chem

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Condensation of 4‐chloro‐2‐oxo‐2H‐chromene‐3‐carbonitrile (1) with heteroarylamines 2a‐d in acetonitrile containing a catalytic amount of triethylamine followed by spontaneous intramolecular cyclization gave the novel coumarin derivatives 3a‐d, respectively. These compounds underwent acid hydrolysis giving the corresponding oxoderivatives 4a‐d. The structural assignments of the synthesized compounds were based on elemental, IR, 1H and 13C NMR analyses.

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New 3,4-Annelated Coumarin Derivatives: Synthesis, Antimicrobial Activity, Antioxidant Capacity, and Molecular Modeling

Cited by 29 publications

References 5 publications

Antifungal and antiaflatoxigenic activities of coumarinyl thiosemicarbazides against Aspergillus flavus NRRL 3251

Antifungal and antiaflatoxigenic activities of coumarinyl thiosemicarbazides against Aspergillus flavus NRRL 3251

Influence of the aryl substituent identity in 4-arylamino-3-nitrocoumarins on their antimicrobial activity

Synthesis and structure of novel 3,4‐annelated coumarin derivatives

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