Abstract
In order to examine bioactivities, simple amino acid derivatives mainly of DL-phenylalanine were prepared. N-Alkyl or N-aralkyl derivatives of DL-phenylalanine (1-11), DL-alanine (12-13), and DL-leucine (14) were synthesized by two routes ; (a) via Schiff bases prepared from amino acids and carbonyl compounds, and (b) direct reductive alkylation of the amino acids with sodium cyanoborohydride. N-Acetyl- and N-benzoxycarbonyl-phenylalanines were coupled with various amines by the mixed anhydride procedure to give the corresponding amides (15-24). Some of the N-benzoxycarbonyl derivatives were hydrogenolyzed to produce free amino acid amides (25-27). 4-Nitro-(28), 4-amino-(29), and 4-(4-dimethylaminophenyl) azo (30-31) derivatives of phenylalanine were synthesized. N-Phthaloylamino acids were condensed with hydrazobenzene to yield diphenylhydrazides (32-33). Compound 32 was converted to free aminoacyldiphenylhydrazide (48). N-Diphenylacetamino acids (34-40) were prepared by the usual technique using diphenylacetyl chloride. Some cyclized derivatives of the amino acids (41-47) were also prepared. Biological tests, including antibacterial, and the action on central nervous, circulation, muscular systems, etc., of these compounds were examined, but none of them showed much activity.
