TY  - JOUR
AU  - Sirakanyan, Samvel
AU  - Kartsev, Victor
AU  - Spinelli, Domenico
AU  - Geronikaki, Athina
AU  - Petrou, Anthi
AU  - Ivanov, Marija
AU  - Glamočlija, Jasmina
AU  - Soković, Marina
AU  - Hakobyan, Elmira
AU  - Hovakimyan, Anush
PY  - 2021
UR  - https://onlinelibrary.wiley.com/doi/10.1002/ardp.202000208
UR  - http://www.ncbi.nlm.nih.gov/pubmed/33029832
UR  - https://radar.ibiss.bg.ac.rs/123456789/3916
AB  - In this study, we report the synthesis and antimicrobial activity of some new disubstituted piperazines. Thus, 3-chlorocyclopenta[c]pyridines and 6-chloropyrano[3,4-c]pyridine 1 under mild reaction conditions with piperazine gave the 3(6)-piperazine-substituted cyclopenta[c]pyridines and pyrano[3,4-c]pyridine 2. Furthermore, the latter, by alkylation with 2-chloro-N-1,3-thiazol-2-ylacetamide, led to the formation of the target compounds. The evaluation of the antibacterial activity revealed that 3k was the most potent compound. The most sensitive bacterium was found to be Listeria monocytogenes, whereas Staphylococcus aureus was the most resistant one. Three compounds, 3d, 3g, and 3k, were tested also against the following resistant strains: methicillin-resistant S. aureus (MRSA), Escherichia coli, and Pseudomonas aeruginosa. All three compounds appeared to be more potent than ampicillin against MRSA. Moreover, compound 3d showed a better activity than the reference drug ampicillin against P. aeruginosa, whereas 3g was more efficient against E. coli. The best antifungal activity was observed again for compound 3k. The most resistant fungi appeared to be Aspergillus fumigatus, whereas Trichoderma viride seemed the most sensitive one toward the compounds tested. Molecular docking studies on E. coli MurB, as well as on Candida albicans CYP51 and dihydrofolate reductase, were used for the prediction of the mechanisms of the antibacterial and antifungal activities, confirming the experimental results.
PB  - Wiley-VCH Verlag
T2  - Archiv der Pharmazie
T1  - Synthesis and antimicrobial activity of new 2-piperazin-1-yl-N-1,3-thiazol-2-ylacetamides of cyclopenta[c]pyridines and pyrano[3,4-c]pyridines.
IS  - 1
VL  - 354
DO  - 10.1002/ardp.202000208
SP  - e2000208
SP  - 2000208
ER  - 

@article{
author = "Sirakanyan, Samvel and Kartsev, Victor and Spinelli, Domenico and Geronikaki, Athina and Petrou, Anthi and Ivanov, Marija and Glamočlija, Jasmina and Soković, Marina and Hakobyan, Elmira and Hovakimyan, Anush",
year = "2021",
abstract = "In this study, we report the synthesis and antimicrobial activity of some new disubstituted piperazines. Thus, 3-chlorocyclopenta[c]pyridines and 6-chloropyrano[3,4-c]pyridine 1 under mild reaction conditions with piperazine gave the 3(6)-piperazine-substituted cyclopenta[c]pyridines and pyrano[3,4-c]pyridine 2. Furthermore, the latter, by alkylation with 2-chloro-N-1,3-thiazol-2-ylacetamide, led to the formation of the target compounds. The evaluation of the antibacterial activity revealed that 3k was the most potent compound. The most sensitive bacterium was found to be Listeria monocytogenes, whereas Staphylococcus aureus was the most resistant one. Three compounds, 3d, 3g, and 3k, were tested also against the following resistant strains: methicillin-resistant S. aureus (MRSA), Escherichia coli, and Pseudomonas aeruginosa. All three compounds appeared to be more potent than ampicillin against MRSA. Moreover, compound 3d showed a better activity than the reference drug ampicillin against P. aeruginosa, whereas 3g was more efficient against E. coli. The best antifungal activity was observed again for compound 3k. The most resistant fungi appeared to be Aspergillus fumigatus, whereas Trichoderma viride seemed the most sensitive one toward the compounds tested. Molecular docking studies on E. coli MurB, as well as on Candida albicans CYP51 and dihydrofolate reductase, were used for the prediction of the mechanisms of the antibacterial and antifungal activities, confirming the experimental results.",
publisher = "Wiley-VCH Verlag",
journal = "Archiv der Pharmazie",
title = "Synthesis and antimicrobial activity of new 2-piperazin-1-yl-N-1,3-thiazol-2-ylacetamides of cyclopenta[c]pyridines and pyrano[3,4-c]pyridines.",
number = "1",
volume = "354",
doi = "10.1002/ardp.202000208",
pages = "e2000208-2000208"
}

Sirakanyan, S., Kartsev, V., Spinelli, D., Geronikaki, A., Petrou, A., Ivanov, M., Glamočlija, J., Soković, M., Hakobyan, E.,& Hovakimyan, A.. (2021). Synthesis and antimicrobial activity of new 2-piperazin-1-yl-N-1,3-thiazol-2-ylacetamides of cyclopenta[c]pyridines and pyrano[3,4-c]pyridines.. in Archiv der Pharmazie
Wiley-VCH Verlag., 354(1), e2000208.
https://doi.org/10.1002/ardp.202000208

Sirakanyan S, Kartsev V, Spinelli D, Geronikaki A, Petrou A, Ivanov M, Glamočlija J, Soković M, Hakobyan E, Hovakimyan A. Synthesis and antimicrobial activity of new 2-piperazin-1-yl-N-1,3-thiazol-2-ylacetamides of cyclopenta[c]pyridines and pyrano[3,4-c]pyridines.. in Archiv der Pharmazie. 2021;354(1):e2000208.
doi:10.1002/ardp.202000208 .

Sirakanyan, Samvel, Kartsev, Victor, Spinelli, Domenico, Geronikaki, Athina, Petrou, Anthi, Ivanov, Marija, Glamočlija, Jasmina, Soković, Marina, Hakobyan, Elmira, Hovakimyan, Anush, "Synthesis and antimicrobial activity of new 2-piperazin-1-yl-N-1,3-thiazol-2-ylacetamides of cyclopenta[c]pyridines and pyrano[3,4-c]pyridines." in Archiv der Pharmazie, 354, no. 1 (2021):e2000208,
https://doi.org/10.1002/ardp.202000208 . .