Synthesis, molecular modelling and docking studies of new thieno[2,3-b:4,5-b′] dipyridine compounds as antimicrobial agents
| Autor: | Noof A. Alenazi, Ahmad Fawzi Qarah, Mansoor Alsahag, Haifa Alharbi, Abrar Bayazeed, Salhah D. Al-Qahtani, Nashwa M. El-Metwaly |
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| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: | |
| Zdroj: | Arabian Journal of Chemistry, Vol 16, Iss 7, Pp 104839- (2023) |
| Druh dokumentu: | article |
| ISSN: | 1878-5352 97042447 |
| DOI: | 10.1016/j.arabjc.2023.104839 |
| Popis: | A series of substituted thieno[2,3-b:4,5-b′]dipyridine compounds were synthesized based on the reactions of 2-acetyl-3-aminothieno[2,3-b]pyridine derivative 1 with 1,3-bifunctional reagents (malononitrile, cyanoacetamide, acetylacetone, ethyl acetoacetate) and/or DMF-DMA. The frontier molecular orbitals of the produced derivatives were obtained from DFT/B3LYP calculations to investigate their structural and energetic properties. The data revealed that they had a low energy gap (ΔEH-L), 2.32–3.39 eV, where compounds 3 and 6 displayed the smallest and greatest values, respectively. Meanwhile, the antibacterial activity of synthesized thieno[2,3-b:4,5-b′]dipyridine analogues was tested against four bacterial strains. Derivatives 2, 3, 5 and 8 exhibited good activity against Gram-positive bacteria rather than Gram-negative comparable to the ampicillin drug reference. Also, thienodipyridine analogues 2, 3, 5 and 8 displayed good activity in general, but against Gram-positive rather than Gram-negative bacteria. Meanwhile, the SAR of the synthesized analogues was discussed to describe the effect of their substituents on both two Gram-positive bacteria (S. aureus and B. subtilis) and two Gram-negative bacteria (S. typhimurium and E. coli). Also, the molecular docking estimation was applied on these hybrids to inspect their binding interactions toward the E. coli DNA gyrase B active site (PDB code: 1AJ6). |
| Databáze: | Directory of Open Access Journals |
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