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

✍ Scribed by Ibrahim A. I. Ali; Iman A. Al-Masoudi; Bahjat Saeed; Najim A. Al-Masoudi; Palo La Colla

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: English
• Weight: 122 KB
• Volume: 16
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20082

✦ Synopsis

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 N~2~H~4~ċ__H__~2~O 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. Heteroatom Chem 16:148–222, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20082