Nitroimidazoles Part 6. Synthesis, structure and in vitro anti-HIV activity of new 5-substituted piperazinyl-4-nitroimidazole derivatives.

2-Amino-1-[4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)piperazin-1-yl]ethanone [6] was prepared from 1-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl) piperazine [3]. A series of new 2-oxoethyl-arylamide [9,10] and 2-oxoethyl-arylsulphonamide [11-14] derivatives were synthesized from [6] with the aim of developing new non-nucleoside reverse transcriptase inhibitors. Alternatively, the amine [17] was synthesized from [3] via the phthalimide derivative [16]. The arylsulphonamide derivatives [18-23] and the arylamide analogues [24-26] were synthesized from [17]. The compounds were evaluated for their anti-HIV-1 and anti-HIV-2 activity in MT-4 cells.