Synthesis, cytotoxic and antioxidant evaluations of amino derivatives from perezone

Abstract A series of eight amino derivatives ( 3a – h) from perezone 1 were prepared by nucleophilic addition of bioactive amines v.gr . melatonin, acetyl tryptamine, tryptophan and other amino acids esters (valine, leucine and methionine). Their structures were elucidated by spectroscopy data. The cytotoxic evaluation against four human tumor cell lines PC-3, K-562, HCT-15 and SKLU-1 was performed as well as the TBARS assay for antioxidant activity. The results suggest that 1 and its isomer 4 were highly active against all cell lines, 4 was twice as potent than 1 against PC-3 and HCT-15. The derivative 3a (IC 50  = 7.5 ± 0.3 μM) was more active than 1 against HCT-15 whereas 3h was selective against K-562 with IC 50  = 4.5 ± 0.4 μM. The TBARS assay has shown that 3c with IC 50  = 5.564 ± 0.24 μM is a potent antioxidant with superior effect comparing to α-tocopherol and moreover was more active than the precursor molecule 1 .