Amino acid derivatives, part 2: Synthesis, antiviral, and antitumor activity of simple protected amino acids functionalized at N‐terminus with naphthalene side chain

Coupling of various acylated amino acid derivatives with (naphthalen‐2‐lyloxy)acetic acid (3) in the presence of 1‐hydroxy‐benzoteriazole (HOBt) and DCC afforded the new amides 6–12. Alternatively, the latter compounds were prepared from reaction of the corresponding hydrazide 5, via the azide‐coupling method, with the acylated amino acid derivatives. Treatment of 6, 10–12 with N2H4ċH2O afforded the hydrazides 13–16, respectively, as key intermediates for the synthesis of peptide derivatives. Reaction of 12, as a acceptor, with the glycosyl‐trichloroimidate 18, as donors in the presence of TMSOTf gave the new glycoside 19. The new compounds were evaluated for their anti‐HIV‐1, antibovine viral diarrhea virus (BVDV), and antitumor activity.