Synthesis of 1-(ω-aminoalkyl)naphthoindolediones with antiproliferative properties

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 14, 2004, Pages 3923-3930

  Shchekotikhin, Andrey E ^a   Buyanov, Vladimir N ^b   Preobrazhenskaya, Maria N ^a  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

^b MENDELEEV UNIVERSITY OF CHEMICAL TECHNOLOGY OF RUSSIA   (Russian Federation)

Author keywords

Cytotoxicity; N Alkylation; Naphthoindolediones; O Demethylation

Indexed keywords

1 [4 [BIS(2 CHLOROETHYL)AMINO]BUTYL] 4,11 DIHYDROXY 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 1 [4 [BIS(2 HYDROXYETHYL)AMINO]BUTYL] 4,11 DIHYDROXY 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [2 (1 PIPERIDINYL)ETHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [2 [4 (2 HYDROXYETHYL) 1 PIPERAZINYL]ETHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 (1 PIPERIDINYL)BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 (4 HYDROXY 1 PIPERIDINYL)BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 (4 MORPHOLINYL)BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 (DIMETHYLAMINO)BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 [[2 HYDROXY 1 (HYDROXYMETHYL) 1 METHYLETHYL]AMINO]BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 [[2 HYDROXY 1,1 BIS(HYDROXYMETHYL)ETHYL]AMINO]BUTYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 1 [4 [[2 HYDROXY 1,1 BIS(HYDROXYMETHYL)ETHYL]AMINO]PROPYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; ANTINEOPLASTIC AGENT; DOXORUBICIN; INDOLE DERIVATIVE; MITOXANTRONE; UNCLASSIFIED DRUG;

ARTICLE; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; IC 50; MULTIDRUG RESISTANCE;

ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; NAPHTHOLS; SPECTRUM ANALYSIS;

EID: 2942711477     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.04.042     Document Type: Article

References (29)

1. Monneret C. Eur. J. Med. Chem. 36:2001;483
2. Koeller J., Eble M. Clin. Pharmacol. 7:1988;574
3. Gewirtz D.A. Biochim. Pharmacol. 57:1999;727
4. Kenada M., Kitamara T., Ymasaky K., Nakamura S. J. Antibiot. 43:1990;1623
5. Ding W., Williams D.R., Northcote P., Siegel M.M., Tsao R., Asucroft J., Morton G.O., Alluri M., Abbanai D., Maiese W.M., Ellestad G.A. J. Antibiot. 47:1994;1250
6. Abe N., Nakakita Y., Nakamura N., Enoki N., Uchida H., Takeo S., Munkata M. J. Antibiot. 46:1993;1672
7. Larue L., Rivalle C., Muzard G., Paolletti C., Bisagni E., Paolletti J. J. Med. Chem. 31:1988;1951
8. Knubel G., Larsen L., Moore R.E., Levine I.A., Patterson G.M.L. J. Antibiot. 43:1990;1236
9. Tabor M.W., Coasts E., Sainsbury M., Shertzer H.G. Witmer C.M., Jollow D.D., Kalf G.F., Kocsis J.J., Sipes I.G. Biological Reactive Intermediate. Vol. IV:1991;833 Plenum, New York
10. Shchekotikhin A.E., Baberkina E.P., Buyanov V.N., Avramenko G.V., Turchin K.F., Suvorov N.N. Khim. Geterotsikl. Soedin. 8:1996;1053
11. Chem. Heterocycl. Comp. (Eng.). 32:1996;902
12. Henry D.V. Cancer Chemother. Rep. Prt. II. 4:1974;5
13. Jolles, G.; Maral, R.; Messer, M. In International Congress on Chemotherapy, Proc. London, 1976; p 1
14. Denny W.A. Anti-Cancer Drug Des. 4:1989;241
15. Baguley B.C. Anti-Cancer Drug Des. 6:1991;1
16. Guillonneau C., Pierre A., Charton Y., Guilbaud N., Kraus-Berthier L., Leonce S., Michel A., Bisagni E., Atassi G. J. Med. Chem. 42:1999;2191
17. Nguyen C.H., Bisagni E., Pepin O., Pierre A., De Cointet P. J. Med. Chem. 30:1987;1642
18. Atwell G.J., Rewcastle G.W., Baguley B.C., Denny W.A. J. Med. Chem. 30:1987;664
19. Zunino F., Gasazza A.M., Pratesi G. Biochem. Pharmacol. 30:1981;1856
20. Shchekotikhin A.E., Baberkina E.P., Turchin K.F., Buyanov V.N., Suvorov N.N. Khim. Geterotsikl. Soedin. 8:2001;1030
21. Chem. Heterocycl. Comp. (Eng.). 37:2001;944
22. Yadav J.S., Subra Reddy B.V., Madan Ch., Riaz Hashim S. Chem. Lett. 2000;738
23. Deo M.D., Marcantoni E., Torregiany E. J. Org. Chem. 31:2000;1951
24. Shchekotikhin A.E., Baberkina E.P., Turchin K.F., Buyanov V.N., Suvorov N.N. Khim. Geterotsikl. Soedin. 11:2000;1491
25. Chem. Heterocycl. Comp. (Eng.). 36:2000;1284
26. Monks A., Scudiero D.A., Johnson G.S., Paull K.D., Sausville E.A. Anti-Cancer Drug Des. 12:1997;533
27. Boyd M.R., Paull K.D. Drug Dev. Res. 34:1995;91
28. Houlbrook S., Harris A.L., Carmichael J., Stratford I.J. Anticancer Res. 16:1996;1603
29. Cytotoxic properties were studied in Rega Institute of Medical Research of the Catholic University of Leuven (Belgium) (Prof. Jan Balzarini)