Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

• Published in: ChemistrySelect (Weinheim) 2024-04, Vol.9 (14), p.n/a
• Main Authors: Laboud, Yara N., Zahran, Doaa, Hassaneen, Hamdi M, Elwahy, Ahmed H. M., Saleh, Fatma M.
• Format: Article
• Language: English
• Subjects: 4- Bis (2-carbamothioyl)hydrazine; Antibacterial evaluation; Bis-2-(methylthiocarbonothioyl)hydrazine; Thiadiazoles; Thiazoles; Thieno[2,3-b]thiophene
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202400045

The reaction of bis‐2‐(methylthiocarbonothioyl)hydrazone with the appropriate hydrazonoyl halides in 1,4‐dioxane in the presence of triethylamine at reflux yielded a novel series of bis(1,3,4‐thiadiazoles) linked to a thieno[2,3‐b]thiophene core. The reaction of the appropriate α‐ketohydrazonoyl halides or α‐haloketones with the corresponding bis(2‐carbamothioylhydrazone) in ethanol at reflux in the presence of a few drops of triethylamine produced good yields of novel bis‐thiazoles linked to the thieno[2,3‐b]thiophene core as novel hybrid molecules. Elemental analyses and spectral data were used to determine the structures of the novel compounds. The antibacterial activity of newly synthesized compounds was evaluated. The MIC determination using resazurin was studied for the most reactive compounds. The pharmacokinetic properties were evaluated by in silico ADMET analysis. The current work focuses on the synthesis of bis‐thiazoles and bis(1,3,4‐thiadiazoles), both coupled to a thieno[2,3‐b]thiophene core as unique hybrid molecules. The bactericidal properties of newly synthesized compounds were assessed. The findings indicated that compound 13a is by far the most effective, and it has the potential to be employed in the future as a promising candidate for treating bacterial infections