Structure-activity and crystallographic analysis of benzophenone derivatives - The potential anticancer agents

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 1, 2003, Pages 101-105

  Hsieh, Hsing Pang ^a   Liou, Jing Ping ^a   Lin, Ying Ting ^a   Mahindroo, Neeraj ^a   Chang, Jang Yang ^a   Yang, Yung Ning ^a   Chern, Shuenn Shing ^b   Tan, Uan Kang ^c   Chang, Chun Wei ^a   Chen, Tung Wei ^a   Lin, Chi Hung ^d   Chang, Ying Ying ^a   Wang, Chiung Chiu ^a  

^a NATIONAL HEALTH RESEARCH INSTITUTES   (Taiwan)

^b INSTITUTE OF MOLECULAR BIOLOGY   (Taiwan)

^c TECHNOLOGY AND SCIENCE INSTITUTE OF NORTHERN TAIWAN   (Taiwan)

^d NATIONAL YANG MING UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; AVE 8063; BENZOPHENONE DERIVATIVE; COMBRETASTATIN A4; DRUG ANALOG; HYDROGEN; OXIGENE; PHENSTATIN; PROTON; UNCLASSIFIED DRUG; BIBENZYL DERIVATIVE; COMBRETASTATIN; STILBENE DERIVATIVE;

ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROGEN BOND; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; CELL CULTURE; CELL CYCLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; IC 50; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BENZOPHENONES; BIBENZYLS; CELL CYCLE; CRYSTALLOGRAPHY, X-RAY; DRUG RESISTANCE, MULTIPLE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 10744225059     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00850-8     Document Type: Article

References (29)

1. Pettit G.R., Cragg G.M., Singh S.B. J. Nat. Prod. 50:1987;386.
2. Li Q., Woods K.W., Claiborne A., Gwaltney S.L. II, Barr K.J., Liu G., Gehrke L., Credo R.B., Hui Y.H., Lee J., Warner R.B., Kovar P., Nukkala M.A., Zielinski N.A., Tahir S.K., Fitzgerald M., Kim K.H., Marsh K., Frost D., Ng S.C., Rosenberg S., Sham H.L. Bioorg. Med. Chem. Lett. 12:2002;465.
3. Horsman M.R., Murata R., Breidahl T., Nielsen F.U., Maxwell R.J., Stodkiled-Jorgensen H., Overgaard J. Adv. Exp. Med. Biol. 476:2000;311.
4. Tozer G.M., Prise V.E., Wilson J., Locke R.J., Vojnovic B., Stratford M.R., Dennis M.F., Chaplin D.J. Cancer Res. 59:1999;1626.
5. Pettit G.R., Temple C. Jr., Narayanan V.L., Varma R., Simpson M.J., Boyd M.R., Rener G.A., Bansal N. Anticancer Drug Des. 10:1995;299.
6. Lin C.M., Ho H.H., Pettit G.R., Hamel E. Biochemistry. 28:1989;6984.
7. Pettit G.R., Toki B., Herald D.L., Verdier-Pinard P., Boyd M.R., Hamel E., Pettit R.K. J. Med. Chem. 41:1998;1688.
8. Liou J.-P., Chang C.-W., Song J.-S., Yang Y.-N., Yeh C.-F., Tseng H.-Y., Lo Y.-K., Chang Y.-L., Chang C.-M., Hsieh H.-P. J. Med. Chem. 45:2002;2556.
9. (a) Ohsumi K., Hatanaka T., Fujita K., Nakagawa R., Fukuda Y., Nihei Y., Suga Y., Morinaga Y., Akiyama Y., Tsuji T. Bioorg. Med. Chem. Lett. 8:1998;3153.
10. (b) Wang L., Woods K.W., Li Q., Barr K.J., McCroskey R.W., Hannick S.M., Gherke L., Credo R.B., Hui Y.H., Marsh K., Warner R., Lee J.Y., Zielinski-Mozng N., Frost D., Rosenberg S.H., Sham H.L. J. Med. Chem. 45:2002;1697.
11. (c) Aleksandrzak K., McGown A.T., Hadfield J.A. Anticancer Drugs. 9:1998;545.
12. (d) Ohsumi K., Nakagawa R., Fukuda Y., Hatanaka T., Morinaga Y., Nihei Y., Ohishi K., Suga Y., Akiyama Y., Tsuji T. J. Med. Chem. 41:1998;3022
13. (e) Shirai R., Takayama H., Nishikawa A., Koiso Y., Hashimoto Y. Bioorg. Med. Chem. Lett. 8:1998;1997.
14. (f) Lawrence N.J., Rennison D., Woo M., McGown A.T., Hadfield J.A. Bioorg. Med. Chem. Lett. 11:2001;51
15. (g) Medina, J. C. 2002, WO9936391A1.
16. Nihei Y., Suga Y., Morinaga Y., Ohishi K., Okano A., Ohsumi K., Hatanaka T., Nakagawa R., Tsuji T., Akiyama Y., Saito S., Hori K., Sato Y., Tsuruo T. Jpn. J. Cancer Res. 90:1999;1016.
17. Pettit G.R., Grealish M.P., Herald D.L., Boyd M.R., Hamel E., Pettit R.K. J. Med. Chem. 43:2000;2731.
18. Pettit G.R., Singh S.B., Boyd M.R., Hamel E., Pettit R.K., Schmidt J.M., Hogan F. J. Med. Chem. 38:1995;1666.
19. Blokhin A.V., Yoo H.D., Geralds R.S., Nagle D.G., Gerwick W.H., Hamel E. Mol. Pharmacol. 48:1995;523.
20. Hamel E. Med. Res. Rev. 16:1996;207.
21. Lin C.M., Singh S.B., Chu P.S., Dempcy R.O., Schmidt J.M., Pettit G.R., Hamel E. Mol. Pharmacol. 34:1988;200.
22. 4: C, 59.73; H, 5.01; N, 4.35. Found: C, 59.32; H, 5.23; N, 4.17.
23. 5: C, 59.54; H, 4.68. Found: C, 59.32; H, 4.34.
24. Carmichael J., Degraff W.G., Gazdar A.F., Minna J.D., Mitchel J.B. Cancer Res. 47:1987;936.
25. Ferguson P.J., Fisher M.H., Stephenson J., Li D.H., Zhou B.S., Cheng Y.C. Cancer Res. 48:1988;5956.
26. Beidler D.R., Chang J.Y., Zhou B.S., Cheng Y.C. Cancer Res. 56:1996;345.
27. Chang J.Y., Liu J.F., Chung S.H., Liu T.W., Chen L.T. Cancer Res. 62:2002;3716.
28. Boquest A.C., Day B.N., Prather R.S. Biol. Reprod. 60:1999;1013.
29. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 189015 for compound 3 and 189016 for compound 5. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 (0)1223 336033 or e-mail: deposit @ccdc.cam.ac.uk ).