Syntheses and biological activities of calix[4]resorcinarene derivatives modified by sulfonic acid and sulfonamides.

Functionalization of C-propyl-resorcinolcalix[4]arene (1a) and C-iso-butyl-resorcinolcalix[4]arene (1b) with sodium sulfite and formaldehyde solution gave two corresponding sulfonatomethylated calix[4]resorcinarenes 2a/b. Further modification of 2a/b with different primary amines afforded three calix[4]resorcinarene sulfonamides 3a/b and 4c. Antibacterial and antitumor tests were performed on the starting calix[4]resorcinarenes and their sulfonic acid and sulfonamide derivatives. 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. Of which compound 1b was the most effective against Escherichia coli with a MIC value of 6.25 mg mL; compound 2b was the most effective against Staphylococcus aureus with a MIC value of 3.12 mg mL-1. In terms of antitumor activity, calix[4]resorcinarenes and their derivatives showed 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 1b, and the survival rates of HepG2 and MDA-MB-321 were 28.66% and 65.39% in the presence of 40 μM 2b, respectively.