Acta Pharm.
57 (2007) 379-393
Original research paper
Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives
YASEEN A. AL-SOUD, NAJIM A. AL-MASOUDI, HAMED GH. HASSAN, ERIK DE CLERCQ and CHRISTOPHE PANNECOUQUE
Najim.Al-Masoudi@gmx.de
Department
of Chemistry, College of Science, University of Al al-Bayt,
Al-Mafraq, Jordan
Fachbereich Chemie,
Universität Konstanz, Postfach 5560, D-78457 Konstanz, Germany (formerly)
College of Science, Department
of Chemistry, University of Sulaimany, Iraq
Rega
Institute for Medical Research, Katholieke Universiteit Leuven, B-3000 Leuven,
Belgium
Accepted
July 27, 2007
A series of 2-alkylthio-1-[4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)-piperazin-1-yl]ethanones (3-9) and
alkyl-[4-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)-piperazin-1-yl)ketones (11-20) as well as the indole analogue 22
were synthesized from 4-nitro-5-piperazinyl imidazole
derivative 1, with the aim to
develop new non-nucleoside reverse transcriptase inhibitors (NNRTIs). The newly synthesized compounds were assayed
against HIV-1 and HIV-2 in MT-4 cells. Compound 2 showed inhibition of HIV-1 (EC50 0.45 µg mL-1) and HIV-2 (0.50 µg mL-1), while 9
showed inhibition of HIV-1 (EC50 2.48 µg mL-1, SI = 4).
Keywords: anti-HIV activity, 4-nitroimidazoles,
NNRTIs, piperazine