QSAR analysis of 1,4-dihydro-4-oxo-1-(2-thiazolyl)-1,8-naphthyridines with anticancer activity

European Journal of Medicinal Chemistry

Volumn 42, Issue 9, 2007, Pages 1184-1192

  Atanasova, Mariyana ^a   Ilieva, Sonia ^a   Galabov, Boris ^a  

^a UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHOXY 4 (METHYLAMINO)PYRROLIDIN 1 YL) 4 OXO 1 (THIAZOL 2 YL) 1,4 DIHYDRO 1,8 NAPHTHYRIDINE 3 CARBOXYLIC ACID; AG 7352; ETOPOSIDE; NAPHTHYRIDINE DERIVATIVE; SNS 595; SPC 595; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ATOM; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPUTER PROGRAM; CONTROLLED STUDY; ELECTRICITY; HUMAN; HUMAN CELL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; MODELS, MOLECULAR; NAPHTHYRIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34547764356     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2007.01.029     Document Type: Article

References (50)

1. Tomita K., Tsuzuki Y., Shibamori K., Tashima M., Kajikawa F., Sato Y., Kashimoto S., Chiba K., and Hino K. J. Med. Chem. 45 (2002) 5564-5575
2. Tsuzuki Y., Tomita K., Shibamori K., Sato Y., Kashimoto S., and Chiba K. J. Med. Chem. 47 (2004) 2097-2109
3. Tsuzuki Y., Tomita K., Sato Y., Shibamori K., Kashimoto S., and Chiba K. Bioorg. Med. Chem. Lett. 14 (2004) 3189-3193
4. Chu D.T.W., and Fernandes P.B. In: Testa B. (Ed). Advances in Drug Research vol. 21 (1991), Academic Press, New York 39-144
5. Hooper D.C. Drugs 58 Suppl. 2 (1999) 6-10
6. Berger J.M., Gamblin S.J., Harrison S.C., and Wang J.C. Nature 379 (1996) 225-232
7. Malonne H., and Atassi G. Anticancer Drugs. 8 (1997) 811-822
8. Burden D.A., and Osheroff N. Biochim. Biophys. Acta. 1400 (1998) 139-154
9. Yamashita Y., Ashizawa T., Morimoto M., Hosomi J., and Nakano H. Cancer Res. 52 (1992) 2818-2822
10. Suto M.J., Domagala J.M., Roland G.E., Maillour G.B., and Cohen M.A. J. Med. Chem. 35 (1992) 4745-4750
11. Hoshino K., Sato K., Akahane K., Yoshida A., Hayakawa I., Sato M., Une T., and Osada Y. Antimicrob. Agents Chemother. 35 (1991) 309-312
12. Hoshino K., Sato K., Une T., and Osada Y. Antimicrob. Agents Chemother. 33 (1989) 1816-1818
13. Chu D.T.W. Drugs Future 17 (1992) 1101-1109
14. Froelich-Ammon S.J., McGuirk P.R., Gootz T.D., Jefson M.R., and Osheroff N. Antimicrob. Agents Chemother. 37 (1993) 646-651
15. Kuo G.H., Eissenstat M.A., Wentland M.P., Robinson R.G., Klingbeil K.M., Danz D.W., and Coughlin S.A. Bioorg. Med. Chem. Lett. 5 (1995) 399-404
16. Wentland M.P., Aldous S.C., Gruett M.D., Perni R.B., Powles R.G., Danz D.W., Klingbeil K.M., Peverly A.D., Robinson R.G., Corbett T.H., Rake J.B., and Coughlin S.A. Bioorg. Med. Chem. Lett. 5 (1995) 405-410
17. Eissenstat M.A., Kuo G.H., Weaver J.D., Wentland M.P., Robinson R.G., Klingbeil K.M., Danz D.W., Corbett T.H., and Coughlin S.A. Bioorg. Med. Chem. Lett. 5 (1995) 1021-1026
18. Barrett J.F., Gootz T.D., McGuirk P.R., Farrell C.A., and Sokolowski S.A. Antimicrob. Agents Chemother. 33 (1989) 1697-1703
19. Robinson M.J., Martin B.A., Gootz T.D., McGuirk P.R., Moynihan M., Sutcliffe J.A., and Osheroff N. J. Biol. Chem. 266 (1991) 14585-14592
20. Robinson M.J., Martin B.A., Gootz T.D., Mcguirk P.R., and Osheroff N. Antimicrob. Agents Chemother. 36 (1992) 751-756
21. Elsea S.H., Osheroff N., and Nitissll J.L. J. Biol. Chem. 267 (1992) 13150-13153
22. Wentland M.P., Lesher G.Y., Reuman M., Gruett M.D., Singh B., Aldous S.C., Dorff P.H., Rake J.B., and Coughlin S.A. J. Med. Chem. 36 (1993) 2801-2809
23. Permana P.A., Snapka R.M., Shen L.L., Chu D.T.W., Clement J.J., and Plattner J.J. Biochemistry 33 (1994) 11333-11339
24. Chu D.T., Hallas R., Clement J.J., Alder J., McDonald E., and Plattner J.J. Drugs Exp. Clin. Res. 18 (1992) 275-282
25. Kuo S.C., Lee H.Z., Juang J.P., Lin Y.T., Wu T.S., Chang J.J., Lednicer D., Paull K.D., Lin C.M., Hamel E., and Lee K.H. J. Med. Chem. 36 (1993) 1146-1156
26. Li L., Wang H.K., Kuo S.C., Wu T.S., Lednicer D., Lin C.M., Hamel E., and Lee K.H. J. Med. Chem. 37 (1994) 1126-1135
27. Li L., Wang H.K., Kuo S.C., Wu T.S., Mauger A., Lin C.M., Hamel E., and Lee K.H. J. Med. Chem. 37 (1994) 3400-3407
28. Chen K., Kuo S.C., Mauger A., Lin C.M., Hamel E., and Lee K.H. J. Med. Chem. 40 (1997) 2266-2275
29. Ji Z., Wang K.H., Bastow K.F., Zhu X.K., Cho S.J., Cheng Y.C., and Lee K.L. Bioorg. Med. Chem. Lett. 7 (1997) 607-612
30. Chen K., Kuo S.C., Hsieh M.C., Mauger A., Lin C.M., Hamel E., and Lee K.H. J. Med. Chem. 40 (1997) 3049-3056
31. Xia Y., Yang Z.Y., Xia P., Bastow K.F., Tachibana Y., Kuo S.C., Hamel E., Hackl T., and Lee K.H. J. Med. Chem. 41 (1998) 1155-1162
32. Zhang S.X., Bastow K.F., Tachibana Y., Kuo S.C., Hamel E., Mauger A., Narayanan V.L., and Lee K.H. J. Med. Chem. 42 (1999) 4081-4087
33. Hour M.J., Huang L.J., Kuo S.C., Xia Y., Bastow K., Nakanishi Y., Hamel E., and Lee K.H. J. Med. Chem. 43 (2000) 4479-4487
34. Xia Y., Yang Z.Y., Hour M.J., Kuo S.C., Xia P., Bastow K.F., Nakanishi Y., Nampoothiri P., Hackl T., Hamel E., and Lee K.H. Bioorg. Med. Chem. Lett. 11 (2001) 1193-1196
35. Lai Y.Y., Huang L.J., Lee K.H., Xiao Z., Bastow K.F., Yamoric T., and Kuoa S.C. Bioorg. Med. Chem. 13 (2005) 265-275
36. El-Subbagh H.I., Abadi A.H., Al-Khawad I.E., and Al-Rashood K.A. Arch. Pharm. Pharm. Med. Chem. 101 (1999) 19-24
37. U. Hoch, J. Hyde, M.A. Nannini, M.J. Evanchik, C.E. Lawrence, M.R. Arkin, D.H. Walker, J.A. Silverman, 96th Annual American Association for Cancer Research Meeting (2005) Anaheim, CA, Abstract No 2277, http://sunesis.com/pdf/Sunesis_PDPoster_final.pdf.
38. J. Wright, J. Hyde, J.A. Silverman, D.H. Walker, M.R. Arkin, 97th Annual American Association for Cancer Research Meeting (2006), Washington D.C., Abstract No 2132, http://sunesis.com/pdf/poster1_04_06.pdf.
39. Advani R., Gordon M., Hurwitz H., Mendelson D., Wakelee H., Ebbinghaus S., Hoch U., Silverman J.A., Havrilla N., and Adelman D. J. Clin. Oncol. 23 (2005) 159S
40. J. Hyde, J. Wright, J.A. Silverman, D.H. Walker, M.R. Arkin, 96th Annual American Association for Cancer Research Meeting (2005) Anaheim, CA, Abstract No 2285, http://sunesis.com/pdf/Sunesis_apoptosisfinal.pdf.
41. Hoch U., Evanchik M.J., and Silverman J.A. Clin. Cancer Res. 11 (2005) 9154S
42. J. Hyde, J. Wright, N. Osheroff, J.A. Silverman, D.H. Walker, M.R. Arkin, 96th Annual American Association for Cancer Research Meeting (2005) Anaheim, CA, Abstract No 2293, http://sunesis.com/pdf/Sunesis_cellcyclefinal1.pdf.
43. J. Hyde, J. Wright, D.H. Walker, J.A. Silverman, M.R. Arkin, 97th Annual American Association for Cancer Research Meeting (2006) Washington D.C., Abstract No 2074, http://sunesis.com/pdf/poster2_04_06.pdf.
44. Chem-X, Chem-X was developed at Chemical Design Ltd. (now part of Accelrys), 2000.
45. Fujita T., and Ban T. J. Med. Chem. 14 (1971) 148-152
46. Free Jr. S.M., and Wilson J.W. J. Med. Chem. 7 (1964) 395-399
47. Muszynski I.C., Scapozza L., Kovar K.-A., and Folkers G. Quant. Struct. Act. Relat. 18 (1999) 342-353
48. Weifan Z., Srinivas E.G., Jin C.S., and Tropsha A. 215th ACS National Meeting, Comparative studies of 3D (CoMFA) and 2D QSAR methods, Book of Abstracts (1998), Am. Chem. Soc., Washington
49. U.C. Singh, P.K. Weiner, J. Caldwell, P.A. Kollman, AMBER Version 3, developed at the University of California at San Francisco, 1986.
50. Kubinyi H. Pharm. Acta Helv. 69 (1995) 259-269