Antifungal and antioxidant activity of (Z)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one
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ZVEAGHINTSEVA, Marina, STYNGACH, Evgenia, POGREBNOI, Serghei, BARBA, Alic, GERONIKAKI, Athina, DUKA, Gh., VALICA, Vladimir, MAKAEV, Fliur. Antifungal and antioxidant activity of (Z)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one. In: Topical issues of new drugs development: Abstracts оf XXIII International Scientific And Practical Conference Of Young Scientists And Student, 21 aprilie 2016, Kharkiv. Kharkiv, Ukraine: National University of Pharmacy, 2016, Ediția a XXIII-a, pp. 57-58.
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Topical issues of new drugs development
Ediția a XXIII-a, 2016
Conferința "Topical issues of new drugs development"
Kharkiv, Ucraina, 21 aprilie 2016

Antifungal and antioxidant activity of (Z)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one


Pag. 57-58

Zveaghintseva Marina1, Styngach Evgenia1, Pogrebnoi Serghei1, Barba Alic1, Geronikaki Athina2, Duka Gh.1, Valica Vladimir3, Makaev Fliur13
 
1 Institute of Chemistry of the Academy of Sciences of Moldova,
2 Aristotle University of Thessaloniki,
3 ”Nicolae Testemițanu” State University of Medicine and Pharmacy
 
Disponibil în IBN: 7 august 2020



Teza

Introduction. The treatment of fungal infectious diseases remains a challenging problem because of the increasing number of microbial pathogens. 1,2,4-Triazole derivatives templates is a privileged structure fragments in modern medicinal chemistry considering its broad pharmacological spectrum and affinity for various bio targets of these class heterocyclic compounds. The current interest in the development of new agents can be partially ascribed both to the increasing emergence of fungal resistance to antibiotic therapy and to newly emerging pathogens, reinforces the need for the development of new and potent chemical entities or an improvement in the activity of well-known 1,2,4-triazole derivatives. Considering this statement, the synthesis of analogues can be seen as an efficient approach to optimize an active chemical structure and design new drugs, since simple structural changes can lead to better biological activities through modifications of physicochemical properties.
Aim. The aim of this investigation dedicated to the development of selective synthesis of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one and the study of antifungal as well as antioxidant properties.
Materials and methods. The target compound was synthesized starting from 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone and 3,5-di-tert-butyl-4-hydroxybenzaldehyde. Final compound was evaluated for antioxidant generation ability on of DPPH▪, and screened for antifungal activity against fungi. In order to determine the reaction stoichiometry, different molar ratios, expressed as moles of antioxidant per mole of DPPH▪, were tested, ranging from 0.1 to 10. For each molar ratio, the remaining concentration of DPPH▪ at the plateau was determined and graphed, and EC50 was read on the graph as the molar ratio which reduces half of the initial DPPH▪ concentration, was determined from the graph. A lower EC50 value is associated with a stronger DPPH radical scavenging capacity under the same testing conditions. These results for clarity were also expressed in terms of antiradical power
(ARP) calculated as ARP=1/EC50 in which larger ARP values represented a larger scavenging capacity. The number of reduced DPPH▪ molecules per one molecule of antioxidant was defined as ζ = 1/(2 x EC50). The results obtained for EC50, ζ and ARP of the studied compounds were compared to those of ionol (control). Antifungal activity has been tested on Aspergillus ochraceus (ATCC 12066), Aspergillus flavus (ATCC 9643), Aspergillus fumigatus (plant isolate), Aspergillus niger (ATCC 6275), Aspergillus versicolor (ATCC 11730), Penicillium funiculosum (ATCC 36839), Penicillium ochrochloron (ATCC 95 9112), Trichoderma viride (IAM 5061) and Candida albicans (ATCC 10231) by the diffusion plate method. The test compound was dissolved in dimethylsulfoxide (1 mL), mixed with potato dextrose agar PDA at concentrations of 50, 100, 150 and 200 μg/mL and poured onto sterile Petri dishes (with diameter of 9 cm). A 6 mm disc containing mycelia was transferred to the center of PDA plate. Tree replications were maintained for each concentration and DMSO was used as a control solvent then the inoculated plates were incubated at 37 °C for 4 days and the zone of inhibition was observed and measured. Results and discussion. The target compound was synthesized under a Knoevenagel condensation by nucleophilic addition of 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone to 3,5-di-tert-butyl-4-hydroxybenzaldehyde followed by a dehydration reaction. The compound was characterized by mp, elemental analyses and spectroscopic data and the Z- configuration at C=C double bond could be established unambiguously by 1H NMR as well as 13C NMR spectroscopy.
Antifungal activity of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one was tested against eight fungal strains. Minimal inhibitory and minimal fungicidal concentration was determined using microdilution method. The tested compound showed antifungal activities in the MIC range of 0.3-38.6 μmol x 10-2/ml and MFC range of 0.6-77.2 μmol x 10-2/ml. It was observed that 1-{(1R,3S,4S,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]heptan-3-yl}-3-methyl-1H-imidazol-3-ium (S)-2-[(S)-1,2-dihydroxyethyl]-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate 2 shows a similar radical scavenging capacity to that of ionol. Conclusions. Heterocyclic compound based on 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone and 3,5-di-tert-butyl-4-hydroxybenzaldehyde, possessing strong antifungal activity with concomitant very good antioxidant are potential leads for developing efficacious double action therapeutics.