Dedicated to Acad. Bogdan Kurtev on the occasion of his 100 th birth anniversary trans-5-Aminomethyl-1-benzyl-6-phenylpiperidin-2-one (2) was prepared in high yield via Mitsunobu methodology and acylated by means of N-protected α-amino acids glycine, L-tryptophan, L-phenylalanine and L-alanine to give new piperidinones with a peptide bond in the side chain to the piperidinone cycle. N-Deprotection was carried out and the side chain of the tryptophan derivative 4 was elongated to yield products

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... ontaining two peptide bonds in it. Mass spectra (EI and/or ESI) of most of the derivatives were taken and some fragmentation patterns were suggested. Tryptophan derivatives 3-5 have been described in a previous paper to possess antihistamine activity. In the present study four peptide derivatives have been tested for ACE inhibitory activity and compounds 13a,b and 14 have shown a weak ACE inhibitory activity.