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 . .