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Paper | Regular issue | Vol 71, No. 7, 2007, pp.1577-1587
Published online, 24th April, 2007
DOI: 10.3987/COM-07-11052
Synthesis, Characterization, and Biological Activities of New Benzofuran Derivatives

Kifah S. M. Salih, Mikdad T. Ayoub, Haythem A. Saadeh, Najim A. Al-Masoudi, and Mohammad S. Mubarak*

*Chemistry Department, Faculty of Science, University of Jordan, Amman 11942, Jordan

Abstract

A number of new benzofuran derivatives, ethyl 3-[(alkylamino)methyl]-6-methoxy-1-benzofuran-2-carboxylates (5a-i), were obtained via the reaction between ethyl 3-(bromomethyl)-6-methoxy-1-benzofuran-2-carboxylate (3) and amines or amino acid ethyl esters. In addition, 1,4-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)-methyl]piperazine (9), (2E)-N,N’-diethyl-N,N’-bis[(6-methoxy-1-benzofuran-3-yl-2-carboxylate)-methyl]but-2-ene-1,4-diamine (10) and 1,2-bis[(ethyl 6-methoxy-1-benzofuran-3-yl-2-carboxylate)methyl]-1,2-dimethylhydrazine (11) were also obtained from the reaction of 3 with diamines. Their in vitro anti-HIV-1 (strain IIIB) and HIV-2 (strain ROD) activities of the synthesized compounds in human T-lymphocyte were tested; ethyl 3-bromomethyl-6-methoxycoumarlate displayed an ability to inhibit HIV-1 and HIV-2 replication in cell culture at non-toxic concentrations.