Nitroimidazoles part 2. Synthesis, antiviral and antitumor activity of new 4-nitroimidazoles

Chemistry and Biodiversity

Volumn 3, Issue 5, 2006, Pages 515-526

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

^a UNIVERSITY OF KONSTANZ   (Germany)

^b AL AL BAYT UNIVERSITY   (Jordan)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d NONE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

(1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)[BIS(2 CHLOROETHYL)]AMINE; 1 (4 CHLOROBENZYL) 2 METHYL 5 NITRO 5 (PYRROLIDIN 1 YL) 1H IMIDAZOLE; 1 [1 (4 CHLOROBENZYL) 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL] 4 METHYLPIPERAZINE; 1 [[1 (4 CHLOROBENZYL) 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL]AMINO] 1 DEOXY DEXTRO MANNITOL; 1 BENZYL 2 ETHYL 4 NITRO 5 [(4 NITROPHENYL)SULFANYL] 1H IMIDAZOLE; 1 BENZYL 2 ETHYL 5 [(NAPHTHALEN 1 YL)SULFANYL] 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 (BENZYLSULFANYL 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 (BENZYLSULFONYL) 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 [(4 BROMOPHENYL)SULFANYL] 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 [(4 CHLOROBENZYL)SULFANYL] 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 [(4 CHLOROPHENYL)SULFANYL] 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL 5 [(4 CHLOROPHENYL)SULFONYL] 2 ETHYL 4 NITRO 1H IMIDAZOLE; 1 BENZYL N [2 [(2,3,5,6 DI O ISOPROPYLIDENE ALPHA DEXTRO MANNOFURANOS 1 YL)OXY]ETHYL] 2 METHYL 4 NITRO 1H IMIDAZOL 5 AMINE; 2 [(1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)[BIS(2 HYDROXYETHYL)AMINO]ETHANOL; 2 [(1 BENZYL 2 METHYL 4 NITRO 1H IMIDAZOL 5 YL)AMINO]ETHANOL; 2 [[1 (4 CHLOROBENZYL) 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL]METHYLAMINO]ETHANOL; 2,3,4,5,6 PENTA O BENZYL 1 [[1 (4 CHLOROBENZYL) 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL]AMINO] 1 DEOXY DEXTRO MANNITOL; 4 (1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL)MORPHOLINE; 4 [1 (4 CHLOROBENZYL) 2 METHYL 4 NITRO 1H IMIDAZOL 5 YL]MORPHOLINE; 4 NITROIMIDAZOLE DERIVATIVE; 5 BROMO 1 BENZYL 2 ETHYL 4 NITRO 1H IMIDAZOLE; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; CAPRAVIRINE; EFAVIRENZ; METRONIDAZOLE; MISONIDAZOLE; N [1 (4 CHLOROBENZYL) 2 ETHYL 4 NITRO 1H IMIDAZOL 5 YL] N,N',N' TRIMETHYLETHANE 1,2 DIAMINE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROTECTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOMEGALOVIRUS; CYTOSTASIS; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; IN VITRO STUDY; LEUKEMIA CELL; MELANOMA CELL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; VACCINIA VIRUS; VARICELLA ZOSTER VIRUS; VESICULAR STOMATITIS VIRUS; VIRUS STRAIN;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CYTOMEGALOVIRUS; HEPACIVIRUS; HIV; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NITROIMIDAZOLES;

CYTOMEGALOVIRUS; HEPATITIS C VIRUS; HERPES; HUMAN HERPESVIRUS 3; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; VACCINIA VIRUS; VESICULAR STOMATITIS VIRUS;

EID: 33745050174     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.200690055     Document Type: Article

References (42)

1. a) Y. A. Al-Soud, N. A. Al-Masondi, Synth. Commun. 2005, 35, 2259
2. b) J. C. Eriks, H. van der Goot, G. G. Sterk, H. Timmerman. J. Med. Chem. 1992, 35, 3239.
3. R. C. Vollinger, J. P. de Konig, F. P. Jansen, R. Leurs, W. M. P. B. Menge, H. Timmerman, J. Med. Chem. 1994, 37, 332.
4. J. T. Koralainen, J. A. M. Christiaans, S. Kotisaari, J. T. Laitinen, P. T. Männistö, L. Tuomisto, J. Gynther, J. Med. Chem. 1999, 42, 1193.
5. S. C. Farsch, J. A. Nick, V. A. Fadok, D. L. Bratton, G. S. Worthen, P. M. Henson, J. Biol. Chem. 1998, 273, 8389.
6. T. F. Gallagher, G. L. Seibel, S. Kassis, J. T. Laydon, M. J. Blumenthal, J. C. Lee, S. M. Frier-Thompson, J. W. Abt, M. E. Soreson, J. M. Smietana, R. F. Hall, R. S. Garigipati, P. E. Bender, K. F. Erhard, A. J. Krog, G. A. Hofmann, P. L. Sheldrake, P. C. McDonnell, S. Kumar, P. R. Young, J. L. Adams, Bioorg. Med. Chem. 1997, 5, 49.
7. Y. Jiang, C. Chen, Z. Li, W. Guo, J. A. Gengner, J. Biol. Chem. 1996, 271, 17920.
8. Z. Li, Y. Jiang, R. J. Ulevitch, J. Han, Biochem. Biophys. Res. Commun. 1996, 228, 334.
9. J. L. Kummer, P. K. Rao, K. A. Heidenreich, J. Biol. Chem. 1997, 272, 20490.
10. J. C. Lee, J. T. Laydon, P. C. McDonnell, T. F. Gallagher, S. Kumar, D. Green, D. McNulty, M. J. Blumenthal, J. R. Heys, S. W. Landvatter, J. E. Strickler, P. R. Young, Nature 1994, 372, 739.
11. L. Salerno, V. Sorrenti, F. Guerrera, M. C. Sarva, M. A. Siracusa, C. D. Giacomo, A. Vanella, A. Pharmazie 1999, 54, 685.
12. S. C. Cherkofsky, T. R. Scarpe, German Offen. Pat. 2, 805, 166 (Chem. Abstr. 1979, 90, 23051q).
13. G. J. Atwell, J.-Y. Fan, K. Tan, W. A. Denny, J. Med. Chem. 1998, 41, 4744.
14. E. Winkelmann, W. Raether, A. Sinharay, Arzneim.-Forsch./Drug Res. 1978, 28, 351.
15. M. R. Grimmett, in 'Comprehensive Heterocyclic Chemistry', Eds. A. R. Katritzky, C. W. Rees, Pergamon Press, 1984, Vol. 4, p. 498.
16. M. E. Walts, R. H. Hodgkinss, D. S. Sehmi, M. Woodcock, Int. J. Radiat. Biol. 1980, 38, 673.
17. J. Morgenstern, R. Otto, S. Scheithaner, to Germ. (East) DD 260,062 (Chem. Abstr. 1989, 110, 231634r).
18. J. L. Skibba, D. D. Beal, K. K. Whitnable, Cancer Res. 1970, 30, 147.
19. J. E. Biskupiak, J. R. Grierson, J. S. Rasey, G. V. Martin, K. A. Krohn, J. Med. Chem. 1991, 34, 2165.
20. J. Bartroli, M. Alguero, E. Boncompte, J. Forn, Arzneim. Forsch. 1992, 42, 832.
21. I. Saji, K. Tamoto, H. Yamazaki, H. Aqui, Heterocycles 1981, 15, 943.
22. W. J. Ross, W. B. Jamieson, M. C. McCowen, J. Med. Chem. 1973, 16, 347.
23. T. Fujiwara, A. Sato, M. El-Farrash, S. Miki, K. Kabe, Y. Isaka, M. Kodama, Y. M. Wu, L. B. Chen, H. Harada, H. Sugimoto, M. Hatanaka, Y. Hinuma, Antimicrob. Agents. Chemother 1998, 42, 1340.
24. P. M. Kochergin, L. A. Reznichenko, R. N. Gireva, E. V. Aleksandrova, Chem. Heterocycl. Compd. 1998, 34, 1142.
25. P. M. Kochergin, S. G. Vereniki, Chem. Heterocycl. Compd. 1965, 1, 522.
26. S. Kulkarni, M. R. Grimmett, L. R. Hanton, J. Simpson, Aust. J. Chem. 1987, 40, 1399.
27. A. K. S. B. Rao, C. G. Rao, B. B. Sigh, Synth. Commun. 1994, 24, 341.
28. I. Wolska, T. Borowiak, S. Sobiak, Pol. J. Chem. 1994, 68, 1831.
29. S. Sobiak, Pol. J. Chem. 1998, 72, 78.
30. R. N. Gireva, G. A. Aleshina, L. A. Reznichenko, G. V. Zykina, Pharm. Chem. J. 1977, 11, 1336 (Chem. Abstr 1977, 88, 106470u).
31. P. Melloni, W. Logemann, I. De Carneri, Arzneim. Forsch. 1975, 25, 9; (Carlo Erba, S. P. A.) Ger. Offen. 2149825 (Chem. Abstr. 1972, 77, 48462u).
32. H. Simon, H. Lettau, H. Schubert, A. Jumar, Ger. (East) Patent DD 70886 (Chem. Abstr. 1970, 73, 98954u).
33. L. Zaprutko, M. Gajdzinski, W. Michalska, K. Pit Kilwicz, K. Lutomski, Z. Lukaszewski, U. Wrzeciono, Pharmazie 1989, 44, 817.
34. A. K. S. B. Rao, C. G. Rao, B. B. Singh, J. Org. Chem. 1992, 57, 3240.
35. J. D. Albright, D. B. Moran, J. Heterocycl. Chem. 1986, 23, 913.
36. E. R. de Labriola, V. Deulofue, J. Org. Chem. 1947, 12, 726.
37. I. A. I. Ali, E. S. H. El-Ashry, R. R. Schmidt, Eur. J. Org Chem 2003, 4121, refs. cit. therein.
38. I. A. I. Ali, E. S. H. El-Ashry, R. R. Schmidt, Tetrahedron 2004, 60, 4773, refs. cit. therein.
39. S. D. Young, S. F. Britcher, L. O. Tran, L. S. Payne, W. C. Lumma, T. A. Lyle, J. R. Huff, P. S. Anderson, D. B. Olsen, S. S. Carroll, D. J. Pettibone, J. A. Obrien, R. G. Ball, S. K. Balani, J. H. Lin, I. W. Chen, W. A. Schleif, V. V. Sardana, W. J. Long, V. W. Byrnes, E. A. Emini, Antimicrob. Agents Chemother. 1995, 39, 2602.
40. A. Monks, D. Scudiero, P. Skenan, R. Shoemaker, K. Paull, D. Vistica, C. Hose, J. Lengely, P. Cronsie, A. Vaigro-Wolf, M. Gray-Goodrich, H. Campell, J. Mayo, M. R. Boyd, J. Natl. Cancer Inst. 1991, 83, 757.
41. M. Boyd, K. Paull, Drug Dev. Res. 1995, 34, 91.
42. M. R. Grever, S. A. Schepartz, B. A. Chabner, Seminar Oncol. 1992, 19, 622.