Amino acid derivatives,part 3: New peptide and glycopeptide derivatives conjugated naphthalene. Synthesis,antitumor, anti‐HIV,and BVDV evaluation

A series of peptide derivatives conjugated naphthalene residue 11–25 , the glycoside 27 as well as the 7‐glycoside 30 , and the 2‐(2‐hydroxy‐3‐(N‐benzyl‐N‐isopropylamino)propoxy)naphthalene bearing methionine 31 were synthesized. The new compounds were evaluated in vitro for cytotoxicity against HIV‐1 and bovine viral diarrhea virus (BVDV), where 31 showed remarkable activity against HIV‐1. The cytotoxicity, in vitro, of 11–25 and 27 was assayed against a panel of tumor cell lines consisting of CD4 human T‐cells containing an integrated T‐leukemia virus type 1 (HTLV‐1), CD4 human acute T‐lympho‐ blastic leukemia, splenic B‐lympho‐blastoid cells, acute B‐lymphoblastic leukemia, mela‐noma, breast adenocarcinoma, lung squamous carcinoma, hepatocellular carcinoma, prostate carcinoma, foreskin fibroblasts, and lung fibroblasts. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:576–585, 2005; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20149