Design, synthesis, and in vitro antitumor activity of new 1,4-diarylimidazole-2-ones and their 2-thione analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 3, 2008, Pages 989-993

  Congiu, Cenzo ^a   Cocco, Maria Teresa ^a   Onnis, Valentina ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Antitumor activity; Imidazole derivatives

Indexed keywords

2 THIONE DERIVATIVE; ANTINEOPLASTIC AGENT; IMIDAZOLE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; HUMAN; HUMAN CELL; LEUKEMIA CELL;

ANTINEOPLASTIC AGENTS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IMIDAZOLES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIONES; TUMOR CELLS, CULTURED;

EID: 38749112183     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.12.023     Document Type: Article

References (27)

1. Pettit G.R., Cragg G.M., and Singh S.B. J. Nat. Prod. 50 (1987) 386
2. McGown A.T., and Fox B.W. Cancer Chemother. Pharmacol. 26 (1990) 79
3. Pettit G.R., Singh S.B., Hamel E., Lin C.M., Alberts D.S., and Garcia-Kendall D. Experientia 45 (1989) 209
4. Dorr R.T., Dvorakova K., Snead K., Alberts D.S., Salmon S.E., and Pettit G.R. Invest. New Drug 14 (1996) 131
5. Ohsumi K., Nakagawa R., Fukuda Y., Hatanaka T., Morinaga Y., Nihei Y., Ohishi K., Suga Y., Akiyama Y., and Tsuji T. J. Med. Chem. 41 (1998) 3022
6. Pettit G.R., Temple Jr. C., Narayanan V.L., Varma R., Simpson M.J., Boyd M.R., Rener G.A., and Bansal N.C. Anti-Cancer Drug Des. 10 (1995) 299
7. Chaplin D.J., Pettit G.R., and Hill S.A. Anticancer Res. 19 (1999) 189
8. Nabha S.M., Mohammad R.M., Wall N.R., Dutcher J.A., Salkini B.M., Pettit G.R., and Al Katib A.M. Anticancer Drugs 12 (2001) 57
9. West C.M., and Price P. Anticancer Drugs 15 (2004) 179
10. Pettit G.R., Rhodes M.R., Herald D.L., Chaplin D.J., Stratford M.R.L., Hamel E., Pettit R.K., Chapuis J.-C., and Oliva D. Anti-Cancer Drug Des. 13 (1998) 981
11. Nam N.H., Kim Y., You Y.-J., Hong D.-H., Ki H.-M., and Ahn B.-Z. Bioorg. Med. Chem. Lett. 11 (2001) 3073
12. Nam N.H. Curr. Med. Chem. 10 (2003) 1697 and references therein
13. Ohsumi K., Hatanaka T., Fujita K., Nakagawa R., Fukuda Y., Nihei Y., Suga Y., Morinaga Y., Akiyama Y., and Tsuji T. Bioorg. Med. Chem. Lett. 8 (1998) 3153
14. Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Bruce Credo R., Hui Y.-H., Marsh K., Warner R., Lee J.Y., Zielinski-Mozng N., Frost D., Rosenberg S.H., and Sham H.L. J. Med. Chem. 45 (2002) 1697
15. Edwards M.L., Stemerick D.M., and Sunkara P.S. J. Med. Chem. 33 (1990) 1948
16. Wu-Wong J.R., Alder J.D., Alder L., Burns D.J., Han E.K., Credo B., Tahir S.K., Dayton B.D., Ewing P.J., and Chiou W.J. Cancer Res. 61 (2001) 1486
17. Fang L., He Q., Hu Y., and Yang B. Cancer Chemother. Pharmacol. 59 (2007) 397
18. Hsieh H.P., Liou J.P., and Mahindroo N. Curr. Pharm. Des. 11 (2005) 1655
19. Li C., Lee M.H., and Sartorelli A.C. J. Med. Chem. 22 (1979) 1030
20. Devan B., and Rajagopalan K. Tetrahedron Lett. 35 (1994) 1585
21. Cortes S., Liao Z.-K., Watson D., and Kohn H. J. Med. Chem. 28 (1985) 601
22. 6) δ 3.79 (s, 3H), 3.94 (s, 6H), 7.25 (s, 2H Ar), 7.59 (d, J = 8.5 Hz, 2H, Ar), 7.72 (m, 2H, Ar + 1H, imidazolic), 11.21 (broad, 1H, NH).
23. Dodson R.M., and Ross F. J. Am. Chem. Soc. 72 (1950) 1478
24. Porretta G.C., Scalzo M., Artico M., Biava M., Panico S., and Simonetti N. Farmaco Ed. Sci. 40 (1985) 404
25. 6) δ 3.89 (s, 3H), 3.92 (s, 3H), 7.11 (d, J = 8.5 Hz, 1H Ar), 7.42 (d, J = 8.5 Hz, 1H Ar), 7.49 (s, 1H Ar), 7.71 (d, J = 8.5 Hz, 2H Ar), 7.88 (d, J = 8.5 Hz, 2H Ar), 7.92 (s, 1H, imidazolic), 13.01 (broad, 1H, NH).
26. Boyd M.R., and Paull K.D. Drug Dev. Res. 34 (1995) 91
27. Hadfield J.A., Ducki S., Hirst N., and McGown A.T. Prog. Cell Cycle Res. 5 (2003) 309