Diaza- and triazachrysenes: Potent topoisomerase-targeting agents with exceptional antitumor activity against the human tumor xenograft, MDA-MB-435

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 22, 2002, Pages 3333-3336

  Ruchelman, Alexander L ^a,d   Singh, Sudhir K ^a   Wu, Xiaohua ^a,b   Ray, Abhijit ^a   Yang, Jin Ming ^b,c   Li, Tsai Kun ^c   Liu, Angela ^c   Liu, Leroy F ^b,c   LaVoie, Edmond J ^a,b  

^a RUTGERS UNIVERSITY   (United States)

^b RUTGERS CANCER INSTITUTE OF NEW JERSEY   (United States)

^c RUTGERS ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

^d RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,12 DIAZACHRYSEN 6 ONE; 5,6,11 TRIAZACHRYSEN 12 ONE; CAMPTOTHECIN; CHRYSENE DERIVATIVE; DNA; DNA TOPOISOMERASE; HYCAMPTIN; IRINOTECAN; RPMI8402; TOPOTECAN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; ENZYME INHIBITOR; HETEROCYCLIC COMPOUND;

ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN; CELL STRAIN MDA MB 435; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; MOUSE; NONHUMAN; NUDE MOUSE; PROTEIN TARGETING; TUMOR MODEL; TUMOR XENOGRAFT; ANIMAL; CANCER TRANSPLANTATION; CELL CULTURE; CELL DIVISION; DRUG ANTAGONISM; DRUG EFFECT; EXPERIMENTAL NEOPLASM; HUMAN; METABOLISM; SYNTHESIS; TREATMENT OUTCOME; XENOGRAFT;

MUS MUSCULUS; STAPHYLOCOCCUS PHAGE 3A;

ANIMALS; ANTINEOPLASTIC AGENTS; AZA COMPOUNDS; CELL DIVISION; CHRYSENES; DNA; DNA TOPOISOMERASES, TYPE I; ENZYME INHIBITORS; HUMANS; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; NEOPLASMS, EXPERIMENTAL; TRANSPLANTATION, HETEROLOGOUS; TREATMENT OUTCOME; TUMOR CELLS, CULTURED;

EID: 0037131728     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00737-0     Document Type: Article

References (32)

1. Wang J.C. Annu. Rev. Biochem. 54:1985;665.
2. Chen A.Y., Liu L.F. Annu. Rev. Pharmacol. Toxicol. 34:1994;191.
3. Li T.-K., Liu L.F. Annu. Rev. Pharmacol. Toxicol. 41:2001;53.
4. Hsiang Y., Lihou M., Liu L. Cancer Res. 49:1989;5077.
5. Wall J.G., Burris H.A., Von-Hoff D.D., Rodriquez G., Kneuper-Hall R., Shaffer D., O'Rourke T., Brown T., Weiss G., Clark G. Anti-Cancer Drugs. 3:1992;337.
6. Burke T.G., Mi Z. J. Med. Chem. 36:1993;2580.
7. Burke T.G., Mi Z. Anal. Biochem. 212:1993;285.
8. Hendricks C.B., Rowinsky E.K., Grochow L.B., Donehower R.C., Kaufmann S.H. Cancer Res. 42:1992;4719.
9. Schellens J.H., Maliepaard M., Scheper R.J., Scheffer G.L., Jonker J.W., Smit J.W., Beijnen J.H., Schinkel A.H. Ann. N.Y. Acad. Sci. 922:2000;188.
10. Yang C.H., Schneider E., Kuo M.L., Rocchi E., Chen Y.C. Biochem. Pharmacol. 60:2000;831.
11. Kim J.S., Gatto B., Yu C., Liu A., Liu L.F., LaVoie E.J. J. Med. Chem. 39:1996;992.
12. Sun Q., Gatto B., Yu C., Liu A., Liu L.F., LaVoie E.J. J. Med. Chem. 38:1995;3638.
13. Makhey D., Yu C., Liu A., Liu L.F., LaVoie E.J. Bioorg. Med. Chem. 8:2000;1171.
14. Janin Y.L., Croisy A., Riou J.-F., Bisagni E. J. Med. Chem. 36:1993;3686.
15. Makhey D., Gatto B., Yu C., Liu A., Liu L.F., LaVoie E.J. Med. Chem. Res. 5:1995;1.
16. Yamashita Y., Fujii N., Murakaya C., Ashizawa T., Okabe M., Nakano H. Biochemistry. 31:1992;12069.
17. Fujii N., Yamashita Y., Saitoh Y., Nakano H. J. Biol. Chem. 268:1993;13160.
18. Yamashita Y., Kawada S.-Z., Fujii N., Nakano H. Biochemistry. 30:1991;5838.
19. Jayaraman M., Fox B.M., Hollingshead M., Kohlhagen G., Pommier Y., Cushman M. J. Med. Chem. 45:2002;242.
20. Vicker N., Burgess L., Chuckowree I.S., Dodd R., Folkes A.J., Hardick D., Hancox T.C., Miller W., Milton J., Sohal S., Wang S., Wren S.P., Charlton P.A., Dangerfield W., Liddle C., Mistry P., Stewart A.J., Denny W.A. J. Med. Chem. 45:2002;721.
21. Harayama T., Akiyama T., Akamatsu H., Kawano K., Abe H., Takeuchi Y. Synthesis. 2001;444.
22. Gall-Istok K., Sterk L., Deak G. Acta Chim. Hungarica. 112:1983;241.
23. Schofield K., Simpson J.C.E. J. Chem. Soc. 1945;512.
24. Castle R.N., Kruse F.H. J. Org. Chem. 17:1952;1571.
25. Chapouland V.G., Plé N., Turck A., Quéguiner G. Tetrahedron. 56:2000;5499.
26. Wright G.C., Watson E.J., Ebetino F.F., Lougheed G., Stevenson B.F., Winterstein A., Bickerton R.K., Halliday R.P., Pals D.T. J. Med. Chem. 14:1971;1060.
27. Landquist J.K. J. Chem. Soc. 1951;1038.
28. Lowrie H.S. J. Med. Chem. 9:1966;670.
29. Lowrie, H. S. US Patent 3,265,693, 1966; Chem. Abstr. 1966, 65, 82316.
30. Kundu N.G., Khan M.W. Tetrahedron. 56:2000;4777.
31. 3 with TMS as internal standard): (3a) 2.33 (s, 6H), 3.04 (t, 2H, J=7.2 Hz), 4.07 (s, 3H), 4.14 (s, 3H), 4.64 (t, 2H, J=7.2 Hz), 6.18 (s, 2H), 7.47 (s, 1H), 7.68 (s, 1H), 7.89 (s, 2H), 9.37 (s, 1H); (3b) 1.95-1.98 (m, 9H), 2.77 (dd, 1H, J=12.0, 8.0 Hz), 3.21 (dd, 1H, J=12.0, 8.0 Hz), 4.06 (s, 3H), 4.13 (s, 3H), 4.84-4.92 (m, 1H), 6.17 (s, 2H), 7.46 (s, 1H), 7.66 (s, 1H), 7.77 (s, 1H), 7.87 (s, 1H), 9.35 (s, 1H); (3c) 1.80-2.21 (m, 4H), 3.63-3.82 (m, 2H), 4.07 (s, 3H), 4.14 (s, 3H), 4.52-4.84 (m, 3H), 6.18 (s, 2H), 7.48 (s, 1H), 7.70 (s, 1H), 7.90 (s, 1H), 8.04 (s, 1H), 9.39 (s, 1H); (4a) 2.42(s, 6H), 3.04 (t, 2H, J=7.2 Hz), 4.08 (s, 3H), 4.17 (s, 3H), 4.64 (t, 2H, J=7.2 Hz), 6.25 (s, 2H), 7.81 (s, 1H), 7.84 (s, 1H), 8.07 (s, 1H), 8.65 (s, 1H); (4b) 1.96-1.98 (m, 9H), 2.79 (dd, 1H, J=12.2, 7.2 Hz), 3.26 (dd, 1H, J=12.0, 7.8 Hz), 4.08 (s, 3H), 4.18 (s, 3H), 4.80-4.88 (m, 1H), 6.22 (s, 2H), 7.66 (s, 1H), 7.80 (s, 1H), 7.82 (s, 1H), 8.58 (s, 1H); (4c) 1.74-2.33 (m, 4H), 3.74-4.0 (m, 2H), 4.09 (s, 3H), 4.18 (s, 3H), 4.56-4.70 (m, 3H), 6.25 (s, 2H), 7.80 (s, 1H), 7.84 (s, 1H), 8.32 (s, 1H), 8.63 (s, 1H); (4d) 1.07 (t, J=7.4 Hz, 3H), 1.56 (m, 2H), 2.14 (m, 2H), 4.09 (s, 3H), 4.17 (s, 3H), 4.49 (m, 2H), 6.26 (s, 2H), 7.62 (s, 1H), 7.85 (s, 1H), 7.87 (s, 1H), 8.65 (s, 1H).
32. Dewar M.J.S., Zoebisch E.G., Healy E.F., Stewart J.J.P. J. Amer. Chem. Soc. 107:1985;3902.