Designed synthetic pathway of stereoselective novel monocyclic cis‐bis‐β‐lactams including a 1,3,4‐thiadiazole‐2,5‐dithiol constituent: Antimicrobial activity, molecular docking

Abstract

AbstractA simple synthetic method has been developed for novel monocyclic bis‐β‐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 bis‐β‐lactam derivatives at C‐3 and C‐4 stereocenters was validated by 1H 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.