Veskamide, enferamide, becatamide, and oretamide are phenolic amides whose analogues are found in plants. In this study, the four amides were prepared by chemical synthesis and their protective effects on H(2)O(2)-induced apoptosis in PC-12 cells were investigated. The syntheses were relatively simple and the yields were more than 43%. Using NMR spectroscopic methods, the chemical structures of veskamide, enferamide, becatamide, and oretamide were confirmed. The decreasing order of the protective effects on H(2)O(2)-induced apoptosis was becatamide>enferamide≥oretamide>veskamide. In fact, becatamide suppressed H(2)O(2)-induced mitochondrial membrane depolarization in a dose-dependent manner. At the concentration of 10 μM, becatamide maintained mitochondrial membrane depolarization at 16% compared to 51% in H(2)O(2)-treated PC-12 cells (P<0.05). Also, at the same concentration, becatamide inhibited H(2)O(2)-induced caspase-9 activation and caspase-independent chromatin condensation by 68% (P<0.05) and 73% (P<0.05), respectively. This is the first report about the chemical synthesis of becatamide and its potential biological activity to inhibit H(2)O(2)-induced apoptosis of PC-12 cells via protecting mitochondrial membrane integrity, thereby suppressing caspase-9 activation and chromatin condensation.