A simple synthetic method has been developed for novel monocyclic bisβ-lactams including a 1,3,4-thiadiazole-2,5-thiol constituent via [2 + 2] cycloaddition reactions, that is, Staudinger reaction (ketene-imine) of acyl chloride and numerous aromatic imines. Easily available starting materials, an easy workup, a simple purification process, no column chromatography needed, and a great yield are specific features of this work. Spectroscopic methods revealed the confirmation of synthesized products. Products were easily purified through a simple crystallization technique. The stereochemistry of bisβ-lactam derivatives at C-3 and C-4 stereocenters was validated by 1 H NMR spectra. All synthesized products exhibited good antimicrobial activities against three Gram-positive bacteria Staphylococcus aureus, Bacillus anthracis, and Clostridium perfringens, and two Gram-negative bacteria Escherichia coli, Brucella abortus. The molecular docking studies were carried out with the target receptor from E. coli, S. aureus, B. anthracis, B. abortus, and C. perfringens of PDB ID: 3T88, 4Q7G, 3Q2O, 4WJM, and 6PV4, respectively, to obtain a moderate binding interaction.
Fifteen imine compounds were synthesized from the condensation of (Z)‐3‐(4‐bromophenyl)‐3‐(5‐methyl‐2‐thioxo‐1,3,4‐thiadiazol‐3(2H)‐yl) acrylaldehyde and various derivatives of primary amine, and their crystal structure was validated by single‐crystal XRD. Hirshfeld surface studies comprehensively explore intermolecular interactions in crystal packing. A state‐of‐the‐art dual computational strategy using quantum chemistry and molecular docking methodologies illuminates the molecular structure, electronic characteristics, and bioactivity of synthesized imines. Optimized and experimental molecule geometries were compared. By the agar well diffusion method, the synthesized imines were tested for antibacterial and antifungal activity against E. Coli, S. Aureus, A. Niger, and C. Albicans respectively. Based on their biofunctions synthesized imine derivatives were tested for their ability to inhibit E. Coli, C. Albicans, and ACE2. We observed that imine interaction energy values were excellent. We anticipate the current combination study using experiments and computational tools will attract the scientific community and inspire further in vitro and in vivo research.
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