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Z. Naturforsch. 2012, 67b, 925 – 934
doi:10.5560/ZNB.2012-0185
Nitroimidazoles Part 8. Synthesis and Anti-HIV Activity of New 4-Nitroimidazole Derivatives Using the Suzuki Cross-Coupling Reaction
Yaseen A. Al-Soud1, Najim A. Al-Masoudi2, Hossam H. Al-Suod1, and Christophe Pannecouque3
1 Department of Chemistry, College of Science, University of Al al-Bayt, Al-Mafraq, Jordan
2 Department of Chemistry, College of Science, University of Basrah, Basrah, Iraq
3 Rega Institute for Medical Research, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium
Reprint requests to Prof. Dr. N. A. Al-Masoudi. E-mail: najim.al-masoudi@gmx.de or Prof. Dr. Y. A. Al-Soud. E-mail: alsoud@aabu.edu.jo
Received July 7, 2012 / published online September 20, 2012
The development of new HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating structures of increased potency. To this end, a series of 1-(1-benzyl-2-ethyl-4-nitro-1H-imidazol-5-yl)-4-(1,1′-biaryl)-4-yl-piperazine derivatives (6al) was synthesized via the Suzuki coupling reaction. Analogously, coupling of the acid derivative 5, prepared from 4, with various amino acid methyl esters in the presence of HOBt/DCC reagents afforded the benzamide derivatives 811. The newly synthesized compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. All compounds are inactive, except compound 6f which showed inhibition of HIV-1 with EC50 = 2.60 μg mL−1 with a selectivity index (SI) of 9.
Key words: Anti-HIV Activity, Nitroimidazoles, NNRTIs, Piperazine Derivatives, Suzuki Cross-Coupling Reaction
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