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

Abstract

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 N2H4·H2O 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. © 2005 Wiley Periodicals, Inc.