Syntheses and Biological Activities of Calix[4]resorcinarene Derivatives Modified by Sulfonamides

Abstract

Calixarenes are a diverse class of macrocyclic compounds, and the calix[4]resorcinarenes studied in this paper are one of the special subgroups. The calix[4]resorcinarene derivatives with the introduction of sulfonic and sulfonamides groups at C-2 positions were synthesized and characterized by IR and 1H NMR spectroscopies. The compounds synthesized in the paper were used for antibacterial and antitumor tests. The results showed that in terms of antimicrobial activity calix[4]resorcinarenes and their derivatives showed bacteriostatic activity against both Escherichia coli and Staphylococcus aureus, with compound 4c being the most effective: the MIC value for E. coli was 6.25 mg/mL and for S. aureus was 1.56 mg/mL. In terms of antitumor activity, calix[4]resorcinarenes and their derivatives showed strong inhibitory effects on the three tumor cells selected for the experiment. Among them, the survival rate of A549 was 76.03% in the presence of 40 µM 1d, and the survival rates of HepG2 and MDA-MB-321 were 28.66% and 65.39% in the presence of 40 µM 2d, respectively.