Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives
Abstract In this study, a new series of aryl azo thiazolopyrimidine and thiazolopyridopyrimidine derivatives was synthesized using novel 6-aryl-4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3,4-dihydropyrimidine-2(1H)-thione and 5-aryl-7-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinoli...
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2025-05-01
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| Series: | BMC Chemistry |
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| Online Access: | https://doi.org/10.1186/s13065-025-01506-1 |
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| author | Jihan Qurban Sara A. Alqarni Adel I. Alalawy Nawaa Ali H. Alshammari Gadeer R. S. Ashour Maryam M. Alnoman Hanadi A. Katuah Nashwa M. El-Metwaly |
| author_facet | Jihan Qurban Sara A. Alqarni Adel I. Alalawy Nawaa Ali H. Alshammari Gadeer R. S. Ashour Maryam M. Alnoman Hanadi A. Katuah Nashwa M. El-Metwaly |
| author_sort | Jihan Qurban |
| collection | DOAJ |
| description | Abstract In this study, a new series of aryl azo thiazolopyrimidine and thiazolopyridopyrimidine derivatives was synthesized using novel 6-aryl-4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3,4-dihydropyrimidine-2(1H)-thione and 5-aryl-7-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one scaffolds as key intermediates. Structural elucidation of all intermediates and final products was performed via IR, UV, 1H/13C-NMR, and mass spectrometry. Among the forty synthesized compounds, several exhibited significant in vitro antimicrobial activities, particularly derivatives 11a, 11b, 7a, and 7b, with potent inhibition against S. aureus, E. coli, and C. albicans. Molecular docking studies using the bacterial DNA gyrase B subunit (Protein Data Bank (PDB): 1aj6) revealed favorable binding interactions, especially for 11b, which demonstrated the best docking score and strong π–H interactions. Furthermore, DFT-based molecular modeling confirmed the stability and high electronic reactivity of selected bioactive compounds, with low HOMO–LUMO energy gaps and favorable electrostatic potential profiles. Structure–activity relationship (SAR) analysis indicated that electronic effects, lipophilicity, and heteroaromatic substitution patterns critically influence antimicrobial potency. These findings support the potential of thiazolopyridopyrimidine derivatives as promising scaffolds for future antimicrobial drug development. |
| format | Article |
| id | doaj-art-e80c567ccb9341e5ab814d65a0b2ea8c |
| institution | OA Journals |
| issn | 2661-801X |
| language | English |
| publishDate | 2025-05-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj-art-e80c567ccb9341e5ab814d65a0b2ea8c2025-08-20T02:39:04ZengBMCBMC Chemistry2661-801X2025-05-0119112710.1186/s13065-025-01506-1Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivativesJihan Qurban0Sara A. Alqarni1Adel I. Alalawy2Nawaa Ali H. Alshammari3Gadeer R. S. Ashour4Maryam M. Alnoman5Hanadi A. Katuah6Nashwa M. El-Metwaly7Department of Chemistry, College of Science, Umm Al-Qura UniversityDepartment of Chemistry, College of Science, University of JeddahDepartment of Biochemistry, Faculty of Science, University of TabukDepartment of Chemistry, College of Science, Northern Border UniversityDepartment of Chemistry, College of Science, Umm Al-Qura UniversityBiology Department, Faculty of Science, Taibah UniversityDepartment of Chemistry, College of Science, Umm Al-Qura UniversityDepartment of Chemistry, College of Science, Umm Al-Qura UniversityAbstract In this study, a new series of aryl azo thiazolopyrimidine and thiazolopyridopyrimidine derivatives was synthesized using novel 6-aryl-4-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-3,4-dihydropyrimidine-2(1H)-thione and 5-aryl-7-(2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij]quinolin-9-yl)-2-thioxo-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one scaffolds as key intermediates. Structural elucidation of all intermediates and final products was performed via IR, UV, 1H/13C-NMR, and mass spectrometry. Among the forty synthesized compounds, several exhibited significant in vitro antimicrobial activities, particularly derivatives 11a, 11b, 7a, and 7b, with potent inhibition against S. aureus, E. coli, and C. albicans. Molecular docking studies using the bacterial DNA gyrase B subunit (Protein Data Bank (PDB): 1aj6) revealed favorable binding interactions, especially for 11b, which demonstrated the best docking score and strong π–H interactions. Furthermore, DFT-based molecular modeling confirmed the stability and high electronic reactivity of selected bioactive compounds, with low HOMO–LUMO energy gaps and favorable electrostatic potential profiles. Structure–activity relationship (SAR) analysis indicated that electronic effects, lipophilicity, and heteroaromatic substitution patterns critically influence antimicrobial potency. These findings support the potential of thiazolopyridopyrimidine derivatives as promising scaffolds for future antimicrobial drug development.https://doi.org/10.1186/s13065-025-01506-1ChalconesPyrimidinethion derivativesAntibacterial activityMolecular docking |
| spellingShingle | Jihan Qurban Sara A. Alqarni Adel I. Alalawy Nawaa Ali H. Alshammari Gadeer R. S. Ashour Maryam M. Alnoman Hanadi A. Katuah Nashwa M. El-Metwaly Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives BMC Chemistry Chalcones Pyrimidinethion derivatives Antibacterial activity Molecular docking |
| title | Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives |
| title_full | Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives |
| title_fullStr | Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives |
| title_full_unstemmed | Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives |
| title_short | Antimicrobial activity, synthesis, and docking study of some novel arylazo-1,3-thiazolopyrimidine and arylazo-1,3-thiazolopyridopyrimidine derivatives |
| title_sort | antimicrobial activity synthesis and docking study of some novel arylazo 1 3 thiazolopyrimidine and arylazo 1 3 thiazolopyridopyrimidine derivatives |
| topic | Chalcones Pyrimidinethion derivatives Antibacterial activity Molecular docking |
| url | https://doi.org/10.1186/s13065-025-01506-1 |
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