Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones
In this study, three pyridine- and four thiophene-containing chalcone derivatives were synthesized via Claisen–Schmidt condensation reaction, where five derivatives were new. Different spectral analyses (IR, 1H NMR, HRMS) clarified the structures and these proposed compounds were screened for antimi...
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The Royal Society
2025-01-01
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| Online Access: | https://royalsocietypublishing.org/doi/10.1098/rsos.241411 |
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| author | Fahmida Akhter Sumita Saznin Marufa S. M. Anyet Ullah Shohag Hiroshi Nishino Mohammad Sayed Alam Md. Aminul Haque Mohammad Mostafizur Rahman |
| author_facet | Fahmida Akhter Sumita Saznin Marufa S. M. Anyet Ullah Shohag Hiroshi Nishino Mohammad Sayed Alam Md. Aminul Haque Mohammad Mostafizur Rahman |
| author_sort | Fahmida Akhter |
| collection | DOAJ |
| description | In this study, three pyridine- and four thiophene-containing chalcone derivatives were synthesized via Claisen–Schmidt condensation reaction, where five derivatives were new. Different spectral analyses (IR, 1H NMR, HRMS) clarified the structures and these proposed compounds were screened for antimicrobial activity by the agar disc diffusion technique. Compound 1c was conspicuously active against most of the bacterial and fungal strains. It displayed higher activity against Bacillus cereus (22.3 ± 0.6 mm), Shigella sonnei (43.3 ± 0.6 mm) and Shigella boydii (34.0 ± 1.0 mm) compared to the standard ceftriaxone (20.3 ± 0.6 mm, 40.3 ± 0.6 mm and 25.7 ± 0.6 mm, respectively). In addition, the exhibited inhibition zone of compound 1c against all fungal strains was higher than that of the standard amphotericin B. All the newly synthesized derivatives satisfied the ADME properties, and no toxicological risks were found. All compounds were docked against three protein receptors with the range of binding affinity of −6.3 to −9.6 kcal mol−1. Molecular dynamics simulation was scrutinized further for compound 1c in three protein–ligand complexes where root mean square deviation and root mean square fluctuation data were below 2 Å, proposing its stability inside and minimal structural changes. |
| format | Article |
| id | doaj-art-54b599b3b83f4bcba910beda830dac6c |
| institution | Kabale University |
| issn | 2054-5703 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | The Royal Society |
| record_format | Article |
| series | Royal Society Open Science |
| spelling | doaj-art-54b599b3b83f4bcba910beda830dac6c2025-01-29T00:06:33ZengThe Royal SocietyRoyal Society Open Science2054-57032025-01-0112110.1098/rsos.241411Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalconesFahmida Akhter0Sumita Saznin Marufa1S. M. Anyet Ullah Shohag2Hiroshi Nishino3Mohammad Sayed Alam4Md. Aminul Haque5Mohammad Mostafizur Rahman6Department of Chemistry, Jagannath University, Dhaka 1100, BangladeshDepartment of Chemistry, Jagannath University, Dhaka 1100, BangladeshDepartment of Chemical Engineering and Polymer Science, Shahjalal University of Science and Technology, Sylhet 3114, BangladeshDepartment of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kumamoto, JapanDepartment of Chemistry, Jagannath University, Dhaka 1100, BangladeshDepartment of Chemistry, Jagannath University, Dhaka 1100, BangladeshDepartment of Chemistry, Jagannath University, Dhaka 1100, BangladeshIn this study, three pyridine- and four thiophene-containing chalcone derivatives were synthesized via Claisen–Schmidt condensation reaction, where five derivatives were new. Different spectral analyses (IR, 1H NMR, HRMS) clarified the structures and these proposed compounds were screened for antimicrobial activity by the agar disc diffusion technique. Compound 1c was conspicuously active against most of the bacterial and fungal strains. It displayed higher activity against Bacillus cereus (22.3 ± 0.6 mm), Shigella sonnei (43.3 ± 0.6 mm) and Shigella boydii (34.0 ± 1.0 mm) compared to the standard ceftriaxone (20.3 ± 0.6 mm, 40.3 ± 0.6 mm and 25.7 ± 0.6 mm, respectively). In addition, the exhibited inhibition zone of compound 1c against all fungal strains was higher than that of the standard amphotericin B. All the newly synthesized derivatives satisfied the ADME properties, and no toxicological risks were found. All compounds were docked against three protein receptors with the range of binding affinity of −6.3 to −9.6 kcal mol−1. Molecular dynamics simulation was scrutinized further for compound 1c in three protein–ligand complexes where root mean square deviation and root mean square fluctuation data were below 2 Å, proposing its stability inside and minimal structural changes.https://royalsocietypublishing.org/doi/10.1098/rsos.241411chalconeantimicrobial activitiesADMETdockingmolecular dynamics |
| spellingShingle | Fahmida Akhter Sumita Saznin Marufa S. M. Anyet Ullah Shohag Hiroshi Nishino Mohammad Sayed Alam Md. Aminul Haque Mohammad Mostafizur Rahman Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones Royal Society Open Science chalcone antimicrobial activities ADMET docking molecular dynamics |
| title | Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones |
| title_full | Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones |
| title_fullStr | Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones |
| title_full_unstemmed | Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones |
| title_short | Synthesis, antimicrobial evaluation, ADMET prediction, molecular docking and dynamics studies of pyridine and thiophene moiety-containing chalcones |
| title_sort | synthesis antimicrobial evaluation admet prediction molecular docking and dynamics studies of pyridine and thiophene moiety containing chalcones |
| topic | chalcone antimicrobial activities ADMET docking molecular dynamics |
| url | https://royalsocietypublishing.org/doi/10.1098/rsos.241411 |
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