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

Antiviral Chemistry and Chemotherapy

Volumn 18, Issue 4, 2007, Pages 191-200

  Al Masoudi, Najim A ^a,d   Al Soud, Yaseen A ^b   De Clercq, Erik ^c   Pannecouque, Christophe ^c  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b AL AL BAYT UNIVERSITY   (Jordan)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d NONE   (Germany)

Author keywords

Antiviral agent; Nitroimidazole; Synthesis

Indexed keywords

2 AMINO 1 [4 (BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]ETHANONE; 2 [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL]PHTHALIMIDE; 3 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YLTHIO) N [2 (4 (1 BENZYL 2 ETHYL 4 NITRO 1H 4,5 DIHYDRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL) 2 OXOETHYL]PROPANAMIDE; 3 [4 [1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL]PIPERAZIN 1 YL]PROPYL 1 AMINE; CAPRAVIRINE; EFAVIRENZ; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 2,4 DICHLOROBENZAMIDE; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 4 ACETAMIDOBENZENE SULPHONAMIDE; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 4 CHLOROBENZENE SULPHONAMIDE; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 4 METHOXYBENZAMIDE; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 4 METHYLBENZENE SULPHONAMIDE; N [2 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL] 2 OXOETHYL] 4 NITROBENZENE SULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL] 2 ETHOXYBENZAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL] 2,4 DICHLOROBENZAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL] 4 ACETAMIDOBENZENE SULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL] 4 CHLOROBENZENESULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL] 4 METHYLBENZENE SULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL]METHANESULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL]PHTHALIMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL]THIOPHENE 2 CARBOXAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPERAZIN 1 YL]PROPYL]TRICHLOROMETHANE SULPHONAMIDE; N [3 [4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)PIPRAZIN 1 YL]PROPYL] 4 NITROBENZENESULPHONAMIDE; NITROIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; NONHUMAN; PATHOGENICITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; VIRUS REPLICATION; VIRUS STRAIN;

EID: 34848844664     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632020701800403     Document Type: Article

References (34)

1. Adams GE, Clarke ED, Flockhart IR, Jacobs RS, Sehmi DS, Stratford IJ, Wardman P, Watt ME Patrick J, Wallace RG & Smithen CE (1979) Structure-activity relationships in the development of hypoxic cell radiosensitizers. I. Sensitization efficiency. International Journal of Radiation Biology 35:133-150.
2. Al-Masoudi NA, Al-Soud YA, Kalogerakis A, De Clercq E & Pannecouque C (2006a) Nitroimidazoles Part 2. Synthesis, antiviral and antitumor activity of new 4-nitroimidazoles Chemistry & Biodiversity 3:515-526.
3. Al-Soud YA & Al-Masoudi NA (2005) An unexpected reactivity during the cyclization of 3-(5-amino-3-benzyl-2-ethyl-3H-imidazole-4-ylsulfanyl)- propionic acid methyl ester. Synthetic Communications 35:2258-2264.
4. Al-Soud YA, Al-Masoudi NA, De Clercq E and Pannecouque C (2007a) Nitroimidazoles Part 4. Synthesis and anti-HIV activity of new 5-alkylsulfanyl and 5-(4′-arylsulfonyl) piperazinyl-4-nitroimidazole derivatives. Heteroatom Chemistry, 18:333-340.
5. Al-Soud YA, Al-Masoudi NA, Hassan HG, De Clercq E and Pannecouque C (2007b) Nitroimidazoles Part 5. Synthesis and anti-HIV evaluation of new 5-substituted piperazinyl-4-nitroimidazole derivatives. Acta Pharmaceutica, in press.
6. Al-Soud YA, Al-Sa'doni H, Amajaour HAS & Al-Masoudi NA (2006b) Nitroimidazoles, Part 3. Synthesis and anti-HIV activity of new N-alkyl 4-nitroimidazoles bearing benzothiazole and benzoxazole backbones. Zeitschrift für Naturforschung B 62b:523-528.
7. Barbara G, Scozzafava A, Mastrolorenzo A & Supuran CT (2005) Highly active antiretroviral therapy: current state of the art, new agents and their pharmacological interactions useful for improving therapeutic outcome. Current Pharmaceutical Design 11:1805-1843.
8. Bartroli J, Alguero M, Boncompte E & Forn J (1992) Synthesis and antifungal activity of a series of difluorotritylimidazoles. Arzneimittel-Forschung/Drugs Research 42:832-835.
9. Bergan T (1985) Antibacterial activity and pharmacokinetics of nitroimidazoles. A review. Scandinavian Journal of Infectious Diseases. Supplementum 46:64-71.
10. Biskupiak JE, Grierson JR, Rasey JS, Martin GV & Krohn KA (1991) Synthesis of an (iodovinyl)misonidazole derivative for hypoxia imaging. Journal of Medicinal Chemistry 34:2165-2168.
11. Breccia A, Cavalleri R & Adams GE (1982) Nitroimidazoles: Chemistry, Pharmacology and Clinical Application, vol. 42. New York: Plenum Press.
12. Buchel KH, Draber W, Regel E & Plempel M. (1972) Synthesis and properties of clotrimazole and other antimycotic 1-triphenylmethylimidazoles. Arzneimittelforschung 22:1260-1272.
13. Carmine AA, Brogden RN, Heel RC, Speight TM & Avery GS (1982) Tinidazole in anaerobic infections. Drugs 24:85-117.
14. Castelli M, Malagoli M, Lupo L, Roffia S, Paolucci F, Cermelli C, Zanca A & Baggio G (2000) Cytotoxicity and probable mechanism of action of sulphimidazole. Journal of Antimicrobial Chemotherapy 46:541-550.
15. Cosar C & Julou L (1959) The activity of 1-(2-hydroxyethyl)-2-methyl- 5-nitroimidazole (R. P. 8823) against experimental Trichomonas vaginalis infections. Annales de l'Institut Pasteur 96:238-241.
16. De Clercq E (2004a) Anti-HIV chemotherapy: current state of the art. Medical Chemical Research 13:439-478.
17. De Clercq E (2004b) Non-nucleoside reverse transcriptase inhibitors (NNRTIs): past, present, and future. Chemistry & Biodiversity 1:44-64.
18. De Clercq E (2005) Emerging anti-HIV drugs. Expert Opinion Emerging Drugs 10:241-273.
19. Freimuth WW (1996) Delavirdine mesylate, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor. Advances in Experimental of Medical Biology 394:279-289.
20. Fujiwara T, Sato A, El-Farrash M, Miki S, Kabe K, Isaka Y, Kodama M, Wu, YM, Chen LB, Harada H, Sugimoto H, Hatanaka M & Hinuma Y (1998) S-1153 Inhibits replication of known drug-resistant strains of human immunodeficiency virus type 1. Antimicrobial Agents and Chemotherapy 42:1340-1345.
21. Hof H & Stroder J (1986) Antibacterial activity of GO 10213, a nitroimidazole derivative. Antimicrobial Agents and Chemotherapy 29:953-954.
22. Imamichi T (2004) Action of Anti-HIV drugs and resistance: reverse transcriptase inhibitors and protease inhibitors. Current Pharmaceutical Design 10:4039-4053.
23. Koup RA, Merluzzi VJ & Hargrave KD, Adams J, Grozinger K, Eckner RJ and Sullivan JL (1991) Inhibition of human immunodeficiency virus type 1 (HIV-1) replication by the dipyridodiazepinone BI-RG-587. Journal of Infectious Diseases 163:966-970.
24. Pauwels R (2004) New non-nucleoside reverse transcriptase inhibitors (NNRTIs) in development for the treatment of HIV infections. Current Opinion in Pharmacology 4:437-446.
25. Pauwels R, Balzarini J, Baba M, Snoeck R, Schols D, Herdewijn P, Desmyter J & De Clercq E (1988) Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. Journal of Virological Methods 20:309-321.
26. Ren J, Nichols C, Bird LE, Fujiwara T, Sugimoto H, Stuart DI, Stammers DK (2000) Binding of the second generation nonnucleoside inhibitor S-1153 to HIV-1 reverse transcriptase involves extensive main chain hydrogen bonding. Journal of Biological Chemistry 275:14316-14320.
27. Romero DL, Morge RA, Biles C, Berrios-Pena TN, May PD, Palmer JP, Johnson PM, Smith HW, Busso M, Tan C-K, Voorman RL, Reusser F, Althaus IW, Downey KM, So AG, Resnick L, Tarpley WG & Aristoff PA (1994) Discovery, synthesis and bioactivity of bis (heteroaryl) piperazines (BHAPs): a novel class of non-nucleoide HIV-1 reverse transcriptase inhibitors. Journal of Medicinal Chemistry 37:999-1014.
28. Romero DL, Olmsted RA, Poel TJ, Morge RA, Biles C, Keiser BJ, Kopta LA, Friis JM, Hosley JD, Stefanski KJ, Wishka DG, Evans DB, Morris J, Stehle RG, Sharma SK, Yagi Y, Voorman RL, Adams WJ, Tarpley WG, Thomas RC (1996) Targeting delavirdine/atevirdine resistant HIV-1: identification of (alkylamino) piperidine-containing is(heteroaryl) piperazines as broad spectrum HIV-1 reverse transcriptase inhibitors. Journal of Medicinal Chemistry 39:3769-3789.
29. Ross WJ, Jamieson WB & McCowen MC (1972) Antiparasitic nitroimidazoles. 1. 2-Styryl-5-nitroimidazoles. Journal of Medicinal Chemistry 15:1035-1040.
30. Ross WJ, Jamieson WB & McCowen MC (1973) Antiparasitic nitroimidazoles. 3. Synthesis of 2-(4-carboxystyryl)-5-nitro-l-vinylimidazole and related compounds. Journal of Medicinal Chemistry 16:347-352.
31. Skibba JL, Beal DD & Whitnable KK (1970) N-Demethylation the antineoplastic agent4(5)-(3,3-dimethyl-l-triazeno)imidazole-5(4)-carboxamide by rats and man. Cancer Research 30:147-150.
32. Tally FP, Goldin BR, Sullivan N, Johnston J & Gorbach SL (1978) Antimicrobial activity of metronidazole in anaerobic bacteria. Antimicrobial Agents and Chemotherapy 13:460-465.
33. Wainberg MA, Sawyer JP, Montaner JS, Murphy RL, Kuritzkes DR & Raffi F (2005) Challenges for the clinical development of new nucleoside reverse transcriptase inhibitors for HIV infection. Antiviral Therapy 10:13-28.
34. Young SD, Britcher SF, Tran LO, Payne LS, Lumma WC, Lyle TA, Huff JR, Anderson PS, Olsen DB, Carroll SS, Pettibone DJ, Obrien JA, Ball RG, Balani SK, Lin JH, Chen IW, Schleif WA, Sardana W, Long WJ, Byrnes VW & Emini EA (1995) Novel, highly potent non-nucleoside inhibitor of the human immunodeficiency- virus type-1 reverse transcriptase. Antimicrobial Agents and Chemotherapy 9:2602-2605.