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 . .

TY  - JOUR
AU  - Sirakanyan, Samvel N
AU  - Kartsev, Victor G.
AU  - Geronikaki, Athina
AU  - Spinelli, D.
AU  - Petrou, Anthi
AU  - Hakobyan, Elmira K.
AU  - Glamočlija, Jasmina
AU  - Ivanov, Marija
AU  - Soković, Marina
AU  - Hovakimyan, Anush A.
PY  - 2020
UR  - http://www.eurekaselect.com/183263/article
UR  - http://www.ncbi.nlm.nih.gov/pubmed/32598259
UR  - https://radar.ibiss.bg.ac.rs/123456789/3915
AB  - BACKGROUND From the literature it is known that many derivatives of fused thienopyrimidines and furopyrimidines possess broad spectrum of biological activity. OBJECTIVES The current studies describe the synthesis and evaluation of antimicrobial activity of some new N-1,3-thiazol-2- ylacetamides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines. METHOD By cyclocondensation of ethyl 1-aminofuro(thieno)[2,3-b]pyridine-2-carboxylates 1with Formamide were converted to the pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidin-7(8)-ones 2.Alkylation of compound 2 with 2-chloro-N-1,3-thiazol-2- ylacetamide led to the aimed N-1,3-thiazol-2-ylaceta-mides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 3. Starting from compound 2 the relevant S-alkylated derivatives of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 6 were also synthesized. RESULTS All compounds showed antibacterial activity to non-resistant strains. Compounds 3a-3m showed antibacterial activity with MIC/MBC at 0.08-2.31 mg/mL/0.11-3.75 mg/mL .Two the most active compounds 3j and 6b appeared to be more active than MRSA than reference drugs. These compounds exhibitedalso better effect to biofilm formation than reference drugs. Half of the tested compounds appeared to be equipotent/more potent than ketoconazole and more potent than bifonazole. A docking analysis has furnished useful information about the interactions occurring between the tested compounds and the different enzymes. CONCLUSION Gram-negative and Gram-positive bacteria and fungi showed different response towards tested compounds, indicating that different substituents may lead to different modes of action or that the metabolism of some bacteria/fungi was better able to overcome the effect of the compounds or adapt to it.
T2  - Current Topics in Medicinal Chemistry
T1  - Synthesis, evaluation of antimicrobial activity and molecular docking of new N-1,3-thiazol-2-ylacetamides of condensed pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines.
IS  - 24
VL  - 20
DO  - 10.2174/1568026620666200628145308
SP  - 2192
EP  - 2209
ER  - 

@article{
author = "Sirakanyan, Samvel N and Kartsev, Victor G. and Geronikaki, Athina and Spinelli, D. and Petrou, Anthi and Hakobyan, Elmira K. and Glamočlija, Jasmina and Ivanov, Marija and Soković, Marina and Hovakimyan, Anush A.",
year = "2020",
abstract = "BACKGROUND From the literature it is known that many derivatives of fused thienopyrimidines and furopyrimidines possess broad spectrum of biological activity. OBJECTIVES The current studies describe the synthesis and evaluation of antimicrobial activity of some new N-1,3-thiazol-2- ylacetamides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines. METHOD By cyclocondensation of ethyl 1-aminofuro(thieno)[2,3-b]pyridine-2-carboxylates 1with Formamide were converted to the pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidin-7(8)-ones 2.Alkylation of compound 2 with 2-chloro-N-1,3-thiazol-2- ylacetamide led to the aimed N-1,3-thiazol-2-ylaceta-mides of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 3. Starting from compound 2 the relevant S-alkylated derivatives of pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines 6 were also synthesized. RESULTS All compounds showed antibacterial activity to non-resistant strains. Compounds 3a-3m showed antibacterial activity with MIC/MBC at 0.08-2.31 mg/mL/0.11-3.75 mg/mL .Two the most active compounds 3j and 6b appeared to be more active than MRSA than reference drugs. These compounds exhibitedalso better effect to biofilm formation than reference drugs. Half of the tested compounds appeared to be equipotent/more potent than ketoconazole and more potent than bifonazole. A docking analysis has furnished useful information about the interactions occurring between the tested compounds and the different enzymes. CONCLUSION Gram-negative and Gram-positive bacteria and fungi showed different response towards tested compounds, indicating that different substituents may lead to different modes of action or that the metabolism of some bacteria/fungi was better able to overcome the effect of the compounds or adapt to it.",
journal = "Current Topics in Medicinal Chemistry",
title = "Synthesis, evaluation of antimicrobial activity and molecular docking of new N-1,3-thiazol-2-ylacetamides of condensed pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines.",
number = "24",
volume = "20",
doi = "10.2174/1568026620666200628145308",
pages = "2192-2209"
}

Sirakanyan, S. N., Kartsev, V. G., Geronikaki, A., Spinelli, D., Petrou, A., Hakobyan, E. K., Glamočlija, J., Ivanov, M., Soković, M.,& Hovakimyan, A. A.. (2020). Synthesis, evaluation of antimicrobial activity and molecular docking of new N-1,3-thiazol-2-ylacetamides of condensed pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines.. in Current Topics in Medicinal Chemistry, 20(24), 2192-2209.
https://doi.org/10.2174/1568026620666200628145308

Sirakanyan SN, Kartsev VG, Geronikaki A, Spinelli D, Petrou A, Hakobyan EK, Glamočlija J, Ivanov M, Soković M, Hovakimyan AA. Synthesis, evaluation of antimicrobial activity and molecular docking of new N-1,3-thiazol-2-ylacetamides of condensed pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines.. in Current Topics in Medicinal Chemistry. 2020;20(24):2192-2209.
doi:10.2174/1568026620666200628145308 .

Sirakanyan, Samvel N, Kartsev, Victor G., Geronikaki, Athina, Spinelli, D., Petrou, Anthi, Hakobyan, Elmira K., Glamočlija, Jasmina, Ivanov, Marija, Soković, Marina, Hovakimyan, Anush A., "Synthesis, evaluation of antimicrobial activity and molecular docking of new N-1,3-thiazol-2-ylacetamides of condensed pyrido[3',2':4,5]furo(thieno)[3,2-d]pyrimidines." in Current Topics in Medicinal Chemistry, 20, no. 24 (2020):2192-2209,
https://doi.org/10.2174/1568026620666200628145308 . .