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.
Al-Masoudi
Najim A
NA
Fachbereich Chemie, Universität Konstanz, Postfach 5560, D-78457 Konstanz, Germany. Najim.Al-Masoudi@gmx.de
Al-Soud
Yaseen A
YA
De Clercq
Erik
E
Pannecouque
Christophe
C
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D015497:HIV-1 / Q000187:drug effects*; D015498:HIV-2 / Q000187:drug effects*; D006801:Humans; D008214:Lymphocytes / Q000821:virology; D015394:Molecular Structure; D009593:Nitroimidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*
D019380:Anti-HIV Agents; D009593:Nitroimidazoles