New thioether-ester crown ethers have been synthesized starting from dithiodibenzoyl chloride and different β,β -dihydroxydithioethers. The synthetic compounds were screened for their antibacterial and antifungal activity on Klebsiella pneumoniae, Staphilococcus aureus, Pseudomanas aeruginosa and Candida albicans. The macrocyclic thioether-esters 6a-i were effective inhibitors against Klebsiella pneumoniae with MIC value in the range of 25-400 μg/mL. The qualitative structure activity relationship (QSAR) calculations (Moriguchi octanol-water partition coefficient (logP), polar surface area (PSA), hydrophilic factor (Hy), Ghose-Crippen molar refractivity (MR), unsaturation index (Ui) and 99 descriptors of WHIM-3D/QSAR (weighted holistic invariant molecular) of thioether compounds 6a-j were also studied. The results confirm the capability of the proposed approach to give predictive models for MIC values of K. pneumoniae. The structures of the synthetic compounds were confirmed by elemental analysis, 1H NMR and MS spectral studies.

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