title: Nitroimidazoles. V. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives.
abstract: 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 newly non-nucleoside reverse transcriptase inhibitors (NNRTIs). The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compound 4 showed inhibition of HIV-1 (EC50 0.45 microg mL-1) and HIV-2 (0.50 microg mL-1), while 11 showed inhibition of HIV-1 (EC50 2.48 microg mL-1, SI = 4).
authors.affiliation: Department of Chemistry, College of Science, University of Al al-Bayt Al-Mafraq, Jordan.
authors.forename: Yaseen A
authors.initials: YA
authors.lastname: Al-Soud
authors.forename: Najim A
authors.initials: NA
authors.lastname: Al-Masoudi
authors.forename: Hamed Gh
authors.initials: HG
authors.lastname: Hassan
authors.forename: Erik
authors.initials: E
authors.lastname: De Clercq
authors.forename: Christophe
authors.initials: C
authors.lastname: Pannecouque
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D004305:Dose-Response Relationship, Drug; D024921:Drug Resistance, Multiple, Viral; D054303:HIV Reverse Transcriptase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D015497:HIV-1 / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development; D015498:HIV-2 / Q000187:drug effects* / Q000201:enzymology / Q000254:growth & development; D006801:Humans; D015394:Molecular Structure; D009593:Nitroimidazoles / Q000138:chemical synthesis / Q000494:pharmacology; D018894:Reverse Transcriptase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D009593:Nitroimidazoles; D018894:Reverse Transcriptase Inhibitors; C514824:reverse transcriptase, Human immunodeficiency virus 1; C072416:reverse transcriptase, Human immunodeficiency virus 2; D054303:HIV Reverse Transcriptase