New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities
New thieno[2,3-b]pyridine clubbed various thiazole ring systems were synthesized by the reaction of 2-(1-(3-amino-4,6-dimethylthieno[2,3-b]pyridin-2-yl)ethylidene)hydrazine-1-carbothioamide with chloroacetone, phenacyl chloride, and chloroacetic acid. The molecular modeling of the synthesized compou...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2023-11-01
|
| Series: | Arabian Journal of Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535223006883 |
| _version_ | 1797657911396139008 |
|---|---|
| author | Noof A. Alenazi Haifa Alharbi Ahmad Fawzi Qarah Amerah Alsoliemy Matokah M. Abualnaja Alaa Karkashan Basma Abbas Nashwa M. El-Metwaly |
| author_facet | Noof A. Alenazi Haifa Alharbi Ahmad Fawzi Qarah Amerah Alsoliemy Matokah M. Abualnaja Alaa Karkashan Basma Abbas Nashwa M. El-Metwaly |
| author_sort | Noof A. Alenazi |
| collection | DOAJ |
| description | New thieno[2,3-b]pyridine clubbed various thiazole ring systems were synthesized by the reaction of 2-(1-(3-amino-4,6-dimethylthieno[2,3-b]pyridin-2-yl)ethylidene)hydrazine-1-carbothioamide with chloroacetone, phenacyl chloride, and chloroacetic acid. The molecular modeling of the synthesized compounds using DFT/B3LYP methodology revealed that all have a low HOMO and LUMO energies, −4.85 - −5.52 and −2.79 - −3.62, respectively, where the compound 10 has the highest values. The targeting thienopyridine analogues with various thiazole moieties 3–10 was assessed in order to create new antimicrobial agents and compared with ampicillin, gentamicin and miconazole as reference antibacterial and antifungal drugs. Compounds 8–10 exhibited potent antimicrobial activity against Gram positive S. aureus, Gram Gram negative E. coli bacteria, and C. albicans (antifungal), with IC50 (18.9 ± 0.63––24.3 ± 0.74 µg/mL), (14.2 ± 0.41––19.5 ± 0.64 µg/mL), and (19.2 ± 0.58–––23.4 ± 0.65 µg/mL), respectively. Furthermore, Molecular docking stimulation on MOE program was applied to expect the effect and interactions of the newly thienopyridine analogues and E. coli DNA gyrase B as it expressed by PDB ID: 1AJ6. |
| first_indexed | 2024-03-11T17:51:22Z |
| format | Article |
| id | doaj.art-d2a80805737f4720aabb7d6d7665587c |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-03-11T17:51:22Z |
| publishDate | 2023-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-d2a80805737f4720aabb7d6d7665587c2023-10-18T04:30:38ZengElsevierArabian Journal of Chemistry1878-53522023-11-011611105226New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activitiesNoof A. Alenazi0Haifa Alharbi1Ahmad Fawzi Qarah2Amerah Alsoliemy3Matokah M. Abualnaja4Alaa Karkashan5Basma Abbas6Nashwa M. El-Metwaly7Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam bin Abdulaziz University, Al-Kharj 11942, Saudi ArabiaDepartment of Chemistry, College of Science, Northern Border University, Saudi ArabiaDepartment of Chemistry, College of Science, Taibah University, Madinah, P. O. Box 344, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi ArabiaDepartment of biology, College of Sciences, University of Jeddah, Jeddah 21959, Saudi ArabiaDepartment of biology, College of Sciences, University of Jeddah, Jeddah 21959, Saudi ArabiaDepartment of Chemistry, Faculty of Applied Sciences, Umm Al-Qura University, Makkah, Saudi Arabia; Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria Street 35516, Egypt; Corresponding author.New thieno[2,3-b]pyridine clubbed various thiazole ring systems were synthesized by the reaction of 2-(1-(3-amino-4,6-dimethylthieno[2,3-b]pyridin-2-yl)ethylidene)hydrazine-1-carbothioamide with chloroacetone, phenacyl chloride, and chloroacetic acid. The molecular modeling of the synthesized compounds using DFT/B3LYP methodology revealed that all have a low HOMO and LUMO energies, −4.85 - −5.52 and −2.79 - −3.62, respectively, where the compound 10 has the highest values. The targeting thienopyridine analogues with various thiazole moieties 3–10 was assessed in order to create new antimicrobial agents and compared with ampicillin, gentamicin and miconazole as reference antibacterial and antifungal drugs. Compounds 8–10 exhibited potent antimicrobial activity against Gram positive S. aureus, Gram Gram negative E. coli bacteria, and C. albicans (antifungal), with IC50 (18.9 ± 0.63––24.3 ± 0.74 µg/mL), (14.2 ± 0.41––19.5 ± 0.64 µg/mL), and (19.2 ± 0.58–––23.4 ± 0.65 µg/mL), respectively. Furthermore, Molecular docking stimulation on MOE program was applied to expect the effect and interactions of the newly thienopyridine analogues and E. coli DNA gyrase B as it expressed by PDB ID: 1AJ6.http://www.sciencedirect.com/science/article/pii/S1878535223006883Thieno[2,3-b]pyridineChloroacetoneFukui’s indicesS. aureusPDB ID: 1AJ6 |
| spellingShingle | Noof A. Alenazi Haifa Alharbi Ahmad Fawzi Qarah Amerah Alsoliemy Matokah M. Abualnaja Alaa Karkashan Basma Abbas Nashwa M. El-Metwaly New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities Arabian Journal of Chemistry Thieno[2,3-b]pyridine Chloroacetone Fukui’s indices S. aureus PDB ID: 1AJ6 |
| title | New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities |
| title_full | New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities |
| title_fullStr | New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities |
| title_full_unstemmed | New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities |
| title_short | New thieno[2,3-b]pyridine-based compounds: Synthesis, molecular modelling, antibacterial and antifungal activities |
| title_sort | new thieno 2 3 b pyridine based compounds synthesis molecular modelling antibacterial and antifungal activities |
| topic | Thieno[2,3-b]pyridine Chloroacetone Fukui’s indices S. aureus PDB ID: 1AJ6 |
| url | http://www.sciencedirect.com/science/article/pii/S1878535223006883 |
| work_keys_str_mv | AT noofaalenazi newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT haifaalharbi newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT ahmadfawziqarah newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT amerahalsoliemy newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT matokahmabualnaja newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT alaakarkashan newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT basmaabbas newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities AT nashwamelmetwaly newthieno23bpyridinebasedcompoundssynthesismolecularmodellingantibacterialandantifungalactivities |