Synthesis, characterization, and cytotoxic activity of some imides from galloyl hydrazide

A new series of amic acids [III]a-e and N-substituted-imides [IV]a-e containing a 1,2,4-triazole moiety were designed, synthesized, and evaluated for its antimicrobial activities and cytotoxic effects. The structural modifications at position 3 of the 4-amino-5-mercapto-4H-1,2,4-triazole ring (linked to a bioactive 3,4,5-trihydroxyphenyl moiety) were expected to give new 1,2,4-triazole derivatives with a wide spectrum of biological activities. FT-IR, 1H-NMR, 13C-NMR, and mass spectroscopic analyses were used for structure elucidation of these compounds. Furthermore, all the new compounds were investigated for the potential antibacterial activities against two types of bacteria: Staphylococcus aureus and Klebsiella pneumonia. Some of these target compounds showed good activity comparable to ampicillin (used as the reference antibiotic). Finally, the cytotoxic effects of compounds [III]d and [IV]d were assessed by using two cell lines (MCF7 and MDA-MB231) with increasing concentrations by the MTT assay. The results against both cell lines indicated the resistance to compound [III]d, however, the highest dose (40 μM) reduced the viability in both cell lines to nearly similar percentage (87.6% and 88.7%, respectively). The compound [IV]d was more effective than compound [III]d on both cell lines. In addition, MDA-MB231 was more sensitive than MCF7 to compound [IV]d (IC50 for MCF7 = 20 μM; IC50 for MDA-MB231 = 10 μM). The results of the biological evaluation of the antibacterial/cytotoxic activities of some Imides from galloyl hydrazide showed that compounds [III]d and [IV]d surprisingly exhibited very high and significant anticancer (mainly) and antibacterial activities, and they could be very promising lead and parent compounds for the design and synthesis of new drugs by further in vivo biological evaluations and structural modifications.