Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives
6-Heteryl-5-methylthieno[2,3-<i>d</i>]pyrimidin-2,4(1<i>H</i>,3<i>H</i>)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-<i>a</i>]pyridin-2-yl)-5-methyl-3-phenylt...
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MDPI AG
2022-02-01
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| Online Access: | https://www.mdpi.com/1422-8599/2022/1/M1331 |
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| author | Sergiy V. Vlasov Hanna I. Severina Oleksandr V. Borysov Konstantin Yu. Krolenko Pavlo E. Shynkarenko Narzullo B. Saidov Vitaliy S. Vlasov Victoriya A. Georgiyants |
| author_facet | Sergiy V. Vlasov Hanna I. Severina Oleksandr V. Borysov Konstantin Yu. Krolenko Pavlo E. Shynkarenko Narzullo B. Saidov Vitaliy S. Vlasov Victoriya A. Georgiyants |
| author_sort | Sergiy V. Vlasov |
| collection | DOAJ |
| description | 6-Heteryl-5-methylthieno[2,3-<i>d</i>]pyrimidin-2,4(1<i>H</i>,3<i>H</i>)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-<i>a</i>]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione with 2-aminopyridine. The obtained heterocyclic hybrid was further modified by alkylation with 2-chloroarylacetamides. Antimicrobial activity studies for the synthesized compounds using the agar well diffusion method revealed their moderate activity against <i>S. aureus</i>, <i>E. coli</i> and <i>B. subtilis</i>. According to the double dilution assay MIC value results for 6-(imidazo[1,2-<i>a</i>]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dioneagainst <i>P. aeruginosa</i> was less than the value determined for the reference drug streptomycin. The docking study of the synthesized compounds to the active site of TrmD isolated from <i>P. aeruginosa</i> did not show their effective inhibitory activity. |
| first_indexed | 2024-03-09T13:12:50Z |
| format | Article |
| id | doaj.art-b2760063f9f34bc0a06ca5df2dea66f6 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T13:12:50Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-b2760063f9f34bc0a06ca5df2dea66f62023-11-30T21:39:31ZengMDPI AGMolbank1422-85992022-02-0120221M133110.3390/M1331Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide DerivativesSergiy V. Vlasov0Hanna I. Severina1Oleksandr V. Borysov2Konstantin Yu. Krolenko3Pavlo E. Shynkarenko4Narzullo B. Saidov5Vitaliy S. Vlasov6Victoriya A. Georgiyants7Department of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., 61002 Kharkiv, UkraineDepartment of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., 61002 Kharkiv, UkraineEnamine Ltd., 78 Chervonotkatska St., 02094 Kyiv, UkraineEnamine Ltd., 78 Chervonotkatska St., 02094 Kyiv, UkraineEnamine Ltd., 78 Chervonotkatska St., 02094 Kyiv, UkraineDepartment of Pharmacy, Tajik National University, 17 Rudaki St., Dushanbe 734025, TajikistanDepartment of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., 61002 Kharkiv, UkraineDepartment of Pharmaceutical Chemistry, National University of Pharmacy, 53 Pushkinska St., 61002 Kharkiv, Ukraine6-Heteryl-5-methylthieno[2,3-<i>d</i>]pyrimidin-2,4(1<i>H</i>,3<i>H</i>)-diones are of great interest as the promising objects for the search of antibacterials. In this communication, we obtained 6-(imidazo[1,2-<i>a</i>]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione by interaction of 6-(bromoacetyl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione with 2-aminopyridine. The obtained heterocyclic hybrid was further modified by alkylation with 2-chloroarylacetamides. Antimicrobial activity studies for the synthesized compounds using the agar well diffusion method revealed their moderate activity against <i>S. aureus</i>, <i>E. coli</i> and <i>B. subtilis</i>. According to the double dilution assay MIC value results for 6-(imidazo[1,2-<i>a</i>]pyridin-2-yl)-5-methyl-3-phenylthieno[2,3-<i>d</i>]pyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dioneagainst <i>P. aeruginosa</i> was less than the value determined for the reference drug streptomycin. The docking study of the synthesized compounds to the active site of TrmD isolated from <i>P. aeruginosa</i> did not show their effective inhibitory activity.https://www.mdpi.com/1422-8599/2022/1/M1331thieno[2,3-<i>d</i>]pyrimidineimidazo[1,2-<i>a</i>]pyridinealkylationantimicrobial activity |
| spellingShingle | Sergiy V. Vlasov Hanna I. Severina Oleksandr V. Borysov Konstantin Yu. Krolenko Pavlo E. Shynkarenko Narzullo B. Saidov Vitaliy S. Vlasov Victoriya A. Georgiyants Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives Molbank thieno[2,3-<i>d</i>]pyrimidine imidazo[1,2-<i>a</i>]pyridine alkylation antimicrobial activity |
| title | Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives |
| title_full | Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives |
| title_fullStr | Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives |
| title_full_unstemmed | Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives |
| title_short | Synthesis and Antimicrobial Evaluation of 2-(6-Imidazo[1,2-<i>a</i>]pyridin-2-yl-5-methyl-2,4-dioxo-3-phenyl-3,4-dihydrothieno[2,3-<i>d</i>]pyrimidin-1(2<i>H</i>)-yl)-<i>N</i>-arylacetamide Derivatives |
| title_sort | synthesis and antimicrobial evaluation of 2 6 imidazo 1 2 i a i pyridin 2 yl 5 methyl 2 4 dioxo 3 phenyl 3 4 dihydrothieno 2 3 i d i pyrimidin 1 2 i h i yl i n i arylacetamide derivatives |
| topic | thieno[2,3-<i>d</i>]pyrimidine imidazo[1,2-<i>a</i>]pyridine alkylation antimicrobial activity |
| url | https://www.mdpi.com/1422-8599/2022/1/M1331 |
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