Preparation, spectroscopic, X-ray crystallographic, DFT, antimicrobial and ADMET studies of N-[(4-flourophenyl)sulfanyl]phthalimide.

N-[(4-Fluorophenyl)sulfanyl]phthalimide (C14H8FNO2S, FP) was synthesized and characterized using X-ray crystallography. It was then investigated via quantum chemical analysis using the density functional theory (DFT) approach, as well as spectrochemically using FT-IR and 1H and 13C NMR spectroscopy, and elemental analysis. The observed and stimulated spectra are in very good agreement for the DFT method. The in vitro antimicrobial activity of FP against three Gram-positive bacteria, three Gram-negative bacteria and two fungi were determined using the serial dilution method, and FP showed the highest antibacterial activity against E. coli, with a MIC of 128 µg ml-1. Druglikeness, ADME (absorption, distribution, metabolism and excretion) and toxicology studies were carried out to theoretically examine the drug properties of FP.

Inhibitory effects of sulfenimides on human and bovine carbonic anhydrase enzymes.

A series of sulfenimide derivatives (1a-i) were investigated as inhibitors of human (hCA-I, hCA-II) and bovine (bCA) carbonic anhydrase enzymes. The compounds were synthesised by the reaction of substituted thiophenols with phthalimide by means of an effective, simple and eco-friendly method and the structures were confirmed by IR, 1H NMR, 13C NMR, MS and elemental analysis. All derivatives except for the methyl derivative (1b) exhibited effective inhibitory action at low micromolar concentrations on human isoforms, but only four derivatives (1e, 1f, 1h, 1i) inhibited the bovine enzyme. The bromo derivative (1f) was found to be strongest inhibitor of all three enzymes with KI values of 0.023, 0.044 and 20.57 µM for hCA-I, hCA-II and bCA, respectively. Results of our study will make valuable contributions to carbonic anhydrase inhibition studies for further investigations since inhibitors of this enzyme are important molecules for medicinal chemistry.