Eleftheriou, Phaedra

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  • Eleftheriou, Phaedra (5)
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Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties

Geronikaki, Athina; Kartsev, Victor; Eleftheriou, Phaedra; Petrou, Anthi; Glamočlija, Jasmina; Ćirić, Ana; Soković, Marina

(Bentham Science Publishers Ltd., 2020)

TY  - JOUR
AU  - Geronikaki, Athina
AU  - Kartsev, Victor
AU  - Eleftheriou, Phaedra
AU  - Petrou, Anthi
AU  - Glamočlija, Jasmina
AU  - Ćirić, Ana
AU  - Soković, Marina
PY  - 2020
UR  - https://www.eurekaselect.com/186178/article
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/4000
AB  - Background: Although a great number of the targets of antimicrobial therapy have been achieved, it remains among the first fields of pharmaceutical research, mainly because of the development of resistant strains. Docking analysis may be an important tool in the research for the development of more effective agents against specific drug targets or multi-target agents 1-3. Methods: In the present study, based on docking analysis, ten tetrahydrothiazolo[2,3-a]isoindole derivatives were chosen for the evaluation of the antimicrobial activity. Results: All compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species being, in some cases, more potent than ampicillin and streptomycin against all species. The most sensitive bacteria appeared to be S. aureus and En. Cloacae, while M. flavus, E. coli and P. aeruginosa were the most resistant ones. The compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited good antifungal activity better than reference drugs bifonazole (1.4 – 41 folds) and ketoconazole (1.1 – 406 folds) against all fungal species. In order to elucidate the mechanism of action, docking studies on different antimicrobial targets were performed. Conclusion: According to docking analysis, the antifungal activity can be explained by the inhibition of the CYP51 enzyme for most compounds with a better correlation of the results obtained for the P.v.c. strain (linear regression between estimated binding Energy and log(1/MIC) with R 2 =0.867 and p=0.000091 or R 2 = 0.924, p= 0.000036, when compound 3 is excluded.
PB  - Bentham Science Publishers Ltd.
T2  - Current Topics in Medicinal Chemistry
T1  - Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties
IS  - 29
VL  - 20
DO  - 10.2174/1568026620666200922114735
SP  - 2681
EP  - 2691
ER  - 
@article{
author = "Geronikaki, Athina and Kartsev, Victor and Eleftheriou, Phaedra and Petrou, Anthi and Glamočlija, Jasmina and Ćirić, Ana and Soković, Marina",
year = "2020",
abstract = "Background: Although a great number of the targets of antimicrobial therapy have been achieved, it remains among the first fields of pharmaceutical research, mainly because of the development of resistant strains. Docking analysis may be an important tool in the research for the development of more effective agents against specific drug targets or multi-target agents 1-3. Methods: In the present study, based on docking analysis, ten tetrahydrothiazolo[2,3-a]isoindole derivatives were chosen for the evaluation of the antimicrobial activity. Results: All compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species being, in some cases, more potent than ampicillin and streptomycin against all species. The most sensitive bacteria appeared to be S. aureus and En. Cloacae, while M. flavus, E. coli and P. aeruginosa were the most resistant ones. The compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited good antifungal activity better than reference drugs bifonazole (1.4 – 41 folds) and ketoconazole (1.1 – 406 folds) against all fungal species. In order to elucidate the mechanism of action, docking studies on different antimicrobial targets were performed. Conclusion: According to docking analysis, the antifungal activity can be explained by the inhibition of the CYP51 enzyme for most compounds with a better correlation of the results obtained for the P.v.c. strain (linear regression between estimated binding Energy and log(1/MIC) with R 2 =0.867 and p=0.000091 or R 2 = 0.924, p= 0.000036, when compound 3 is excluded.",
publisher = "Bentham Science Publishers Ltd.",
journal = "Current Topics in Medicinal Chemistry",
title = "Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties",
number = "29",
volume = "20",
doi = "10.2174/1568026620666200922114735",
pages = "2681-2691"
}
Geronikaki, A., Kartsev, V., Eleftheriou, P., Petrou, A., Glamočlija, J., Ćirić, A.,& Soković, M.. (2020). Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties. in Current Topics in Medicinal Chemistry
Bentham Science Publishers Ltd.., 20(29), 2681-2691.
https://doi.org/10.2174/1568026620666200922114735
Geronikaki A, Kartsev V, Eleftheriou P, Petrou A, Glamočlija J, Ćirić A, Soković M. Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties. in Current Topics in Medicinal Chemistry. 2020;20(29):2681-2691.
doi:10.2174/1568026620666200922114735 .
Geronikaki, Athina, Kartsev, Victor, Eleftheriou, Phaedra, Petrou, Anthi, Glamočlija, Jasmina, Ćirić, Ana, Soković, Marina, "Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole-3-1,1-dioxidederivatives with antimicrobial activity and docking assisted prediction of the mechanism of their antibacterial and antifungal properties" in Current Topics in Medicinal Chemistry, 20, no. 29 (2020):2681-2691,
https://doi.org/10.2174/1568026620666200922114735 . .
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3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

Horishny, Volodymyr; Kartsev, Victor; Matiychuk, Vasyl; Geronikaki, Athina; Anthi, Petrou; Pogodin, Pavel; Poroikov, Vladimir; Ivanov, Marija; Kostić, Marina; Soković, Marina; Eleftheriou, Phaedra

(MDPI AG, 2020)

TY  - JOUR
AU  - Horishny, Volodymyr
AU  - Kartsev, Victor
AU  - Matiychuk, Vasyl
AU  - Geronikaki, Athina
AU  - Anthi, Petrou
AU  - Pogodin, Pavel
AU  - Poroikov, Vladimir
AU  - Ivanov, Marija
AU  - Kostić, Marina
AU  - Soković, Marina
AU  - Eleftheriou, Phaedra
PY  - 2020
UR  - https://www.mdpi.com/1424-8247/13/9/229
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3942
AB  - Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was S. aureus (American Type Culture Collection ATCC 6538), while L. monocytogenes (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound 5d (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9–113.8 μM, and Minimal bactericidal concentration MBC at 57.8–118.3 μM). Three most active compounds 5d, 5g, and 5k being evaluated against three resistant strains, Methicillin resistant Staphilococcus aureus (MRSA), P. aeruginosa, and E. coli, were more potent against MRSA than ampicillin (MIC at 248–372 μM, MBC at 372–1240 μM). At the same time, streptomycin (MIC at 43–172 μM, MBC at 86–344 μM) did not show bactericidal activity at all. The compound 5d was also more active than ampicillin towards resistant P. aeruginosa strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480–640 μM, and MFC at 640–800 μM) and ketoconazole (MIC 285–475 μM and MFC 380–950 μM). The best activity was exhibited by compound 5g. The most sensitive fungal was T. viride (IAM 5061), while A. fumigatus (human isolate) was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds 5d, 5g, 5k, 7c using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of E. coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.
PB  - MDPI AG
T2  - Pharmaceuticals
T1  - 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation
IS  - 9
VL  - 13
DO  - 10.3390/ph13090229
SP  - 229
ER  - 
@article{
author = "Horishny, Volodymyr and Kartsev, Victor and Matiychuk, Vasyl and Geronikaki, Athina and Anthi, Petrou and Pogodin, Pavel and Poroikov, Vladimir and Ivanov, Marija and Kostić, Marina and Soković, Marina and Eleftheriou, Phaedra",
year = "2020",
abstract = "Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was S. aureus (American Type Culture Collection ATCC 6538), while L. monocytogenes (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound 5d (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9–113.8 μM, and Minimal bactericidal concentration MBC at 57.8–118.3 μM). Three most active compounds 5d, 5g, and 5k being evaluated against three resistant strains, Methicillin resistant Staphilococcus aureus (MRSA), P. aeruginosa, and E. coli, were more potent against MRSA than ampicillin (MIC at 248–372 μM, MBC at 372–1240 μM). At the same time, streptomycin (MIC at 43–172 μM, MBC at 86–344 μM) did not show bactericidal activity at all. The compound 5d was also more active than ampicillin towards resistant P. aeruginosa strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480–640 μM, and MFC at 640–800 μM) and ketoconazole (MIC 285–475 μM and MFC 380–950 μM). The best activity was exhibited by compound 5g. The most sensitive fungal was T. viride (IAM 5061), while A. fumigatus (human isolate) was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds 5d, 5g, 5k, 7c using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of E. coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.",
publisher = "MDPI AG",
journal = "Pharmaceuticals",
title = "3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation",
number = "9",
volume = "13",
doi = "10.3390/ph13090229",
pages = "229"
}
Horishny, V., Kartsev, V., Matiychuk, V., Geronikaki, A., Anthi, P., Pogodin, P., Poroikov, V., Ivanov, M., Kostić, M., Soković, M.,& Eleftheriou, P.. (2020). 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation. in Pharmaceuticals
MDPI AG., 13(9), 229.
https://doi.org/10.3390/ph13090229
Horishny V, Kartsev V, Matiychuk V, Geronikaki A, Anthi P, Pogodin P, Poroikov V, Ivanov M, Kostić M, Soković M, Eleftheriou P. 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation. in Pharmaceuticals. 2020;13(9):229.
doi:10.3390/ph13090229 .
Horishny, Volodymyr, Kartsev, Victor, Matiychuk, Vasyl, Geronikaki, Athina, Anthi, Petrou, Pogodin, Pavel, Poroikov, Vladimir, Ivanov, Marija, Kostić, Marina, Soković, Marina, Eleftheriou, Phaedra, "3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation" in Pharmaceuticals, 13, no. 9 (2020):229,
https://doi.org/10.3390/ph13090229 . .
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Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones.

Tratrat, Christophe; Haroun, Michelyne; Xenikakis, Iakovos; Liaras, Konstantinos; Tsolaki, Evangelia; Eleftheriou, Phaedra; Petrou, Anthi; Aldhubiab, Bandar; Attimarad, Mahesh; Venugopala, Katharigatta N.; Harsha, Sree; Elsewedy, Heba S.; Geronikaki, Athina; Soković, Marina

(2019)

TY  - JOUR
AU  - Tratrat, Christophe
AU  - Haroun, Michelyne
AU  - Xenikakis, Iakovos
AU  - Liaras, Konstantinos
AU  - Tsolaki, Evangelia
AU  - Eleftheriou, Phaedra
AU  - Petrou, Anthi
AU  - Aldhubiab, Bandar
AU  - Attimarad, Mahesh
AU  - Venugopala, Katharigatta N.
AU  - Harsha, Sree
AU  - Elsewedy, Heba S.
AU  - Geronikaki, Athina
AU  - Soković, Marina
PY  - 2019
UR  - http://www.eurekaselect.com/169442/article
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3358
AB  - BACKGROUND Thiazole derivates as well as chalcones, are very important scaffold for medicinal chemistry. Literature survey revealed that they possess wide spectrum of biological activities among which are anti-inflammatory and antimicrobial. OBJECTIVES The current studies describe the synthesis and evaluation of antimicrobial activity of twenty eight novel thiazole-based chalcones. METHODS The designed compounds were synthesized using classical methods of organic synthesis. The in vivo evaluation of antimicrobial activity was performed by microdilution method. RESULTS All compounds have shown antibacterial properties better than that of ampicillin and in many cases better than streptomycin. As far as the antifungal activity is concerned, all compounds possess much higher activity than reference drugs bifonazole and ketoconazole. The most sensitive bacterial species was B. cereus (MIC 6.5-28.4 µmol × 10-2/mL and MBC 14.2-105.0 µmol × 10-2/mL) while the most resistant ones were L. monocytogenes (MIC 21.4-113.6 µmol × 10-2/mL) and E. coli (MIC 10.7- 113.6 µmol × 10-2/mL) and MBC at 42.7-358.6 µmol × 10-2/mL and 21.4-247.2 µmol × 10-2/mL, respectively. All the compounds exhibited antibacterial activity against the three resistant strains, MRSA, P. aeruginosa and E.coli. with MIC and MBC in the range of 0.65-11.00 µmol/mL × 10-2 and 1.30-16.50 µmol/mL × 10-2. Docking studies were performed. CONCLUSION Twenty-eight novel thiazole-based chalcones were designed, synthesized and evaluated for antimicrobial activity. The results showed that these derivatives could be lead compounds in search of new potent antimicrobial agents. Docking studies indicated that DNA gyrase, GyrB and MurA inhibition may explain the antibacterial activity.
T2  - Current Topics in Medicinal Chemistry
T1  - Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones.
IS  - 5
VL  - 19
DO  - 10.2174/1568026619666190129121933
SP  - 356
EP  - 375
ER  - 
@article{
author = "Tratrat, Christophe and Haroun, Michelyne and Xenikakis, Iakovos and Liaras, Konstantinos and Tsolaki, Evangelia and Eleftheriou, Phaedra and Petrou, Anthi and Aldhubiab, Bandar and Attimarad, Mahesh and Venugopala, Katharigatta N. and Harsha, Sree and Elsewedy, Heba S. and Geronikaki, Athina and Soković, Marina",
year = "2019",
abstract = "BACKGROUND Thiazole derivates as well as chalcones, are very important scaffold for medicinal chemistry. Literature survey revealed that they possess wide spectrum of biological activities among which are anti-inflammatory and antimicrobial. OBJECTIVES The current studies describe the synthesis and evaluation of antimicrobial activity of twenty eight novel thiazole-based chalcones. METHODS The designed compounds were synthesized using classical methods of organic synthesis. The in vivo evaluation of antimicrobial activity was performed by microdilution method. RESULTS All compounds have shown antibacterial properties better than that of ampicillin and in many cases better than streptomycin. As far as the antifungal activity is concerned, all compounds possess much higher activity than reference drugs bifonazole and ketoconazole. The most sensitive bacterial species was B. cereus (MIC 6.5-28.4 µmol × 10-2/mL and MBC 14.2-105.0 µmol × 10-2/mL) while the most resistant ones were L. monocytogenes (MIC 21.4-113.6 µmol × 10-2/mL) and E. coli (MIC 10.7- 113.6 µmol × 10-2/mL) and MBC at 42.7-358.6 µmol × 10-2/mL and 21.4-247.2 µmol × 10-2/mL, respectively. All the compounds exhibited antibacterial activity against the three resistant strains, MRSA, P. aeruginosa and E.coli. with MIC and MBC in the range of 0.65-11.00 µmol/mL × 10-2 and 1.30-16.50 µmol/mL × 10-2. Docking studies were performed. CONCLUSION Twenty-eight novel thiazole-based chalcones were designed, synthesized and evaluated for antimicrobial activity. The results showed that these derivatives could be lead compounds in search of new potent antimicrobial agents. Docking studies indicated that DNA gyrase, GyrB and MurA inhibition may explain the antibacterial activity.",
journal = "Current Topics in Medicinal Chemistry",
title = "Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones.",
number = "5",
volume = "19",
doi = "10.2174/1568026619666190129121933",
pages = "356-375"
}
Tratrat, C., Haroun, M., Xenikakis, I., Liaras, K., Tsolaki, E., Eleftheriou, P., Petrou, A., Aldhubiab, B., Attimarad, M., Venugopala, K. N., Harsha, S., Elsewedy, H. S., Geronikaki, A.,& Soković, M.. (2019). Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones.. in Current Topics in Medicinal Chemistry, 19(5), 356-375.
https://doi.org/10.2174/1568026619666190129121933
Tratrat C, Haroun M, Xenikakis I, Liaras K, Tsolaki E, Eleftheriou P, Petrou A, Aldhubiab B, Attimarad M, Venugopala KN, Harsha S, Elsewedy HS, Geronikaki A, Soković M. Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones.. in Current Topics in Medicinal Chemistry. 2019;19(5):356-375.
doi:10.2174/1568026619666190129121933 .
Tratrat, Christophe, Haroun, Michelyne, Xenikakis, Iakovos, Liaras, Konstantinos, Tsolaki, Evangelia, Eleftheriou, Phaedra, Petrou, Anthi, Aldhubiab, Bandar, Attimarad, Mahesh, Venugopala, Katharigatta N., Harsha, Sree, Elsewedy, Heba S., Geronikaki, Athina, Soković, Marina, "Design, Synthesis, Evaluation of Antimicrobial Activity and Docking Studies of New Thiazole-based Chalcones." in Current Topics in Medicinal Chemistry, 19, no. 5 (2019):356-375,
https://doi.org/10.2174/1568026619666190129121933 . .
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5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.

Fesatidou, Maria; Zagaliotis, Panagiotis; Camoutsis, Charalampos; Petrou, Anthi; Eleftheriou, Phaedra; Tratrat, Christophe; Haroun, Micheline; Geronikaki, Athina; Ćirić, Ana; Soković, Marina

(2018)

TY  - JOUR
AU  - Fesatidou, Maria
AU  - Zagaliotis, Panagiotis
AU  - Camoutsis, Charalampos
AU  - Petrou, Anthi
AU  - Eleftheriou, Phaedra
AU  - Tratrat, Christophe
AU  - Haroun, Micheline
AU  - Geronikaki, Athina
AU  - Ćirić, Ana
AU  - Soković, Marina
PY  - 2018
UR  - https://www.sciencedirect.com/science/article/pii/S0968089618310277?via%3Dihub
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3127
AB  - In continuation of our efforts to develop new compounds with antimicrobial properties we describe design, synthesis, molecular docking study and evaluation of antimicrobial activity of seventeen novel 2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-arylidene-1,3-thiazolidin-4-ones. All compounds showed antibacterial activity against eight Gram positive and Gram negative bacterial species. Twelve out of seventeen compounds were more potent than streptomycin and all compounds exhibited higher potency than ampicillin. Compounds were also tested against three resistant bacterial strains: MRSA, P. aeruginosa and E. coli. The best antibacterial potential against ATCC and resistant strains was observed for compound 8 (2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-(4-nitrobenzylidene)-1,3thiazolidin-4-one). The most sensitive bacterium appeared to be S. typhimirium, followed by B. cereus while L. monocitogenes and M. flavus were the most resistant. Compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited antifungal activity better than the reference drugs bifonazole and ketokonazole (3-115 times). It was found that compound 8 appeared again to be the most potent. Molecular docking studies on E. coli MurB, MurA as well as C. albicans CYP 51 and dihydrofolate reductase were used for the prediction of mechanism of antibacterial and antifungal activities confirming the experimental results.
T2  - Bioorganic & Medicinal Chemistry
T1  - 5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.
DO  - 10.1016/j.bmc.2018.08.004
ER  - 
@article{
author = "Fesatidou, Maria and Zagaliotis, Panagiotis and Camoutsis, Charalampos and Petrou, Anthi and Eleftheriou, Phaedra and Tratrat, Christophe and Haroun, Micheline and Geronikaki, Athina and Ćirić, Ana and Soković, Marina",
year = "2018",
abstract = "In continuation of our efforts to develop new compounds with antimicrobial properties we describe design, synthesis, molecular docking study and evaluation of antimicrobial activity of seventeen novel 2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-arylidene-1,3-thiazolidin-4-ones. All compounds showed antibacterial activity against eight Gram positive and Gram negative bacterial species. Twelve out of seventeen compounds were more potent than streptomycin and all compounds exhibited higher potency than ampicillin. Compounds were also tested against three resistant bacterial strains: MRSA, P. aeruginosa and E. coli. The best antibacterial potential against ATCC and resistant strains was observed for compound 8 (2-{[5-(adamantan-1-yl)-1,3,4-thiadiazol-2-yl]-imino}-5-(4-nitrobenzylidene)-1,3thiazolidin-4-one). The most sensitive bacterium appeared to be S. typhimirium, followed by B. cereus while L. monocitogenes and M. flavus were the most resistant. Compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited antifungal activity better than the reference drugs bifonazole and ketokonazole (3-115 times). It was found that compound 8 appeared again to be the most potent. Molecular docking studies on E. coli MurB, MurA as well as C. albicans CYP 51 and dihydrofolate reductase were used for the prediction of mechanism of antibacterial and antifungal activities confirming the experimental results.",
journal = "Bioorganic & Medicinal Chemistry",
title = "5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.",
doi = "10.1016/j.bmc.2018.08.004"
}
Fesatidou, M., Zagaliotis, P., Camoutsis, C., Petrou, A., Eleftheriou, P., Tratrat, C., Haroun, M., Geronikaki, A., Ćirić, A.,& Soković, M.. (2018). 5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.. in Bioorganic & Medicinal Chemistry.
https://doi.org/10.1016/j.bmc.2018.08.004
Fesatidou M, Zagaliotis P, Camoutsis C, Petrou A, Eleftheriou P, Tratrat C, Haroun M, Geronikaki A, Ćirić A, Soković M. 5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation.. in Bioorganic & Medicinal Chemistry. 2018;.
doi:10.1016/j.bmc.2018.08.004 .
Fesatidou, Maria, Zagaliotis, Panagiotis, Camoutsis, Charalampos, Petrou, Anthi, Eleftheriou, Phaedra, Tratrat, Christophe, Haroun, Micheline, Geronikaki, Athina, Ćirić, Ana, Soković, Marina, "5-Adamantan thiadiazole-based thiazolidinones as antimicrobial agents. Design, synthesis, molecular docking and evaluation." in Bioorganic & Medicinal Chemistry (2018),
https://doi.org/10.1016/j.bmc.2018.08.004 . .
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New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents

Incerti, Matteo; Vicini, Paola; Geronikaki, Athina; Eleftheriou, Phaedra; Tsagkadouras, Athanasios; Zoumpoulakis, Panagiotis; Fotakis, Charalmpos; Ćirić, Ana; Glamočlija, Jasmina; Soković, Marina

(2017)

TY  - JOUR
AU  - Incerti, Matteo
AU  - Vicini, Paola
AU  - Geronikaki, Athina
AU  - Eleftheriou, Phaedra
AU  - Tsagkadouras, Athanasios
AU  - Zoumpoulakis, Panagiotis
AU  - Fotakis, Charalmpos
AU  - Ćirić, Ana
AU  - Glamočlija, Jasmina
AU  - Soković, Marina
PY  - 2017
UR  - http://xlink.rsc.org/?DOI=C7MD00334J
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/2926
AB  - A series of 21 novel N-[2-phenyl-4-oxo-1,3-thiazolidin-3-yl]-1,2-benzothiazole-3-carboxamides/acetamides (4a–4p) as well as a series of N′-(halophenylmethylidene)-1,2-benzothiazole-3-acetohydrazides (3h–3p) have been synthesized and evaluated for their antimicrobial activity against eight bacterial and eight fungal species, among them plant, animal and human pathogens and food contaminating species. All compounds appeared to be potent and the best activity was exhibited by compound 4d with MIC in the range of 10.7–21.4 μmol mL−1 × 10−2 and MBC of 21.4–40.2 μmol mL−1 × 10−2. The best antifungal activity was observed for compounds 4p and 3h. Elucidation of the relationship between the antimicrobial activity and molecular properties of the synthesized compounds was also performed. Synthetic intermediates were also tested with several exhibiting good antimicrobial activities. Docking studies for some compounds were performed.
T2  - MedChemComm
T2  - MedChemComm
T1  - New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents
IS  - 11
VL  - 8
DO  - 10.1039/C7MD00334J
SP  - 2142
EP  - 2154
ER  - 
@article{
author = "Incerti, Matteo and Vicini, Paola and Geronikaki, Athina and Eleftheriou, Phaedra and Tsagkadouras, Athanasios and Zoumpoulakis, Panagiotis and Fotakis, Charalmpos and Ćirić, Ana and Glamočlija, Jasmina and Soković, Marina",
year = "2017",
abstract = "A series of 21 novel N-[2-phenyl-4-oxo-1,3-thiazolidin-3-yl]-1,2-benzothiazole-3-carboxamides/acetamides (4a–4p) as well as a series of N′-(halophenylmethylidene)-1,2-benzothiazole-3-acetohydrazides (3h–3p) have been synthesized and evaluated for their antimicrobial activity against eight bacterial and eight fungal species, among them plant, animal and human pathogens and food contaminating species. All compounds appeared to be potent and the best activity was exhibited by compound 4d with MIC in the range of 10.7–21.4 μmol mL−1 × 10−2 and MBC of 21.4–40.2 μmol mL−1 × 10−2. The best antifungal activity was observed for compounds 4p and 3h. Elucidation of the relationship between the antimicrobial activity and molecular properties of the synthesized compounds was also performed. Synthetic intermediates were also tested with several exhibiting good antimicrobial activities. Docking studies for some compounds were performed.",
journal = "MedChemComm, MedChemComm",
title = "New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents",
number = "11",
volume = "8",
doi = "10.1039/C7MD00334J",
pages = "2142-2154"
}
Incerti, M., Vicini, P., Geronikaki, A., Eleftheriou, P., Tsagkadouras, A., Zoumpoulakis, P., Fotakis, C., Ćirić, A., Glamočlija, J.,& Soković, M.. (2017). New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents. in MedChemComm, 8(11), 2142-2154.
https://doi.org/10.1039/C7MD00334J
Incerti M, Vicini P, Geronikaki A, Eleftheriou P, Tsagkadouras A, Zoumpoulakis P, Fotakis C, Ćirić A, Glamočlija J, Soković M. New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents. in MedChemComm. 2017;8(11):2142-2154.
doi:10.1039/C7MD00334J .
Incerti, Matteo, Vicini, Paola, Geronikaki, Athina, Eleftheriou, Phaedra, Tsagkadouras, Athanasios, Zoumpoulakis, Panagiotis, Fotakis, Charalmpos, Ćirić, Ana, Glamočlija, Jasmina, Soković, Marina, "New N -(2-phenyl-4-oxo-1,3-thiazolidin-3-yl)-1,2-benzothiazole-3-carboxamides and acetamides as antimicrobial agents" in MedChemComm, 8, no. 11 (2017):2142-2154,
https://doi.org/10.1039/C7MD00334J . .
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