Amino acid derivatives, part 4: synthesis and anti-HIV activity of new naphthalene derivatives.

A new series of 2-(naphthalen-2-yloxy)-N-[(aryl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl] acetamides 5a-f was synthesized from naphthalene-derived glycine derivative 2 via the hydrazinoacetamide analogs 4a-f. Alternatively, treatment of 4a with H(2)SO(4) afforded 2-(naphthalen-2-yloxy)-N-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)methyl) acetamide 6a. Alkylation or sulphonylation of 5a afforded the S-alkylated derivatives 7 and 8, respectively.