Synthesis and In-silico Simulation of Some New Bis-thiazole Derivatives and Their Preliminary Antimicrobial Profile: Investigation of Hydrazonoyl Chloride Addition to Hydroxy-Functionalized Bis-carbazones

• Main Authors: Refaie M. Kassab, Sobhi M. Gomha, Sami A. Al-Hussain, Ahmed S. Abo Dena, Marwa M. Abdel-Aziz, Magdi E.A. Zaki, Zeinab A. Muhammad
• Format: Article
• Language: English
• Published: Elsevier 2021-11-01
• Series: Arabian Journal of Chemistry
• Subjects: Carbazone; Hydrazonoyl chlorides; Bis-thiazoles; Antimicrobial; DFT; In-silico studies
• Online Access: http://www.sciencedirect.com/science/article/pii/S1878535221004111

Two new series of bis-thiazoles 6a-f and bis-thiazolones 9a-d were prepared via reacting bis-thiosemicarbazone 3 with hydrazonoyl chloride derivatives 4a-f and 7a-d, respectively, in dioxane under basic conditions. Another group of bis-thiazole derivatives 12a-h was prepared by reacting bis-thiosemicarbazone 3 with each of phenacyl bromide derivatives 10a-h under a similar reaction protocol. A plausible mechanism was proposed. Structural elucidation of the new products was established using both elemental and spectrometric/spectroscopic analyses. Structural, electronic, and the pharmacological characteristics of the prepared molecules were investigated with DFT calculations. Antibacterial and antifungal activities of the new bis-thiazoles were screened and compared with vancomycin and amphotericin B as antimicrobial standards. Molecular docking studies on the promising candidate compounds, with the lowest minimum inhibitory concentrations (MIC), were performed with SAP2 of C. albicans and FabI of S. aureus and P. aeruginosa.