3-Aminomethyl derivatives of 4,11-dihydroxynaphtho[2,3-f]indole-5,10-dione for circumvention of anticancer drug resistance

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 6, 2005, Pages 2285-2291

  Shchekotikhin, Andrey E ^a   Shtil, Alexander A ^b   Luzikov, Yuri N ^a   Bobrysheva, Tatyana V ^c   Buyanov, Vladimir N ^c   Preobrazhenskaya, Maria N ^a  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

^b N N BLOKHIN RUSSIAN CANCER RESEARCH CENTER   (Russian Federation)

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

Author keywords

Circumvention of anticancer drug resistance; Mannich reaction; Naphthoindolediones

Indexed keywords

3 [(4 BENZYL 1 PIPERAZINYL)METHYL] 4,11 DIHYDROXY 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 3 [[(2 AMINOETHYL)AMINO]METHYL] 4,11 DIHYDROXY 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 3 [[4 (2 ACETOXYETHYL) 1 PIPERAZINYL]METHYL] 4,11 DIHYDROXY 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 (1 PIPERAZINYLMETHYL) 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 (1H IMIDAZOL 1 YLMETHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 [(1 HOMOPIPERAZINYL)METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 [(4 METHYL 1 HOMOPIPERAZINYL)METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 [(4 METHYL 1 PIPERAZINYL)METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 [(DIMETHYLAMINO)METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE IODOMETHYLATE; 4,11 DIHYDROXY 3 [(QUINUCLIDIN 3 YLAMINO)METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; 4,11 DIHYDROXY 3 [[4 (2 HYDROXYETHYL) 1 PIPERAZINYL]METHYL] 1H NAPHTHO[2,3 F]INDOLE 5,10 DIONE; ANTINEOPLASTIC AGENT; DIAMINE; DOXORUBICIN; GLYCOPROTEIN P; INDOLE DERIVATIVE; NAPHTHOL DERIVATIVE; PIPERAZINE; PROTEIN P53; QUINUCLIDINE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL; CANCER CELL CULTURE; CANCER CENTER; COLON CARCINOMA; CONCENTRATION (PARAMETERS); CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; DRUG TRANSPORT; HUMAN; HUMAN CELL; LEUKEMIA CELL; MANNICH REACTION; PROTEIN EXPRESSION; PROTEIN VARIANT; TRANSAMINATION;

EID: 13844322497     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.12.044     Document Type: Article

References (21)

1. W.A. Denny Expert Opin. Emerg. Drugs 9 2004 109
2. A.E. Shchekotikhin, V.N. Buyanov, and M.N. Preobrazhenskaya Bioorg. Med. Chem. 32 2004 3923
3. A.E. Shchekotikhin, E.P. Baberkina, K.F. Turchin, V.N. Buyanov, and N.N. Suvorov Khim. Geterotsikl. Soedin. 8 2001 1030
4. Chem. Heterocycl. Compd. (Engl. Ed.) 37 2001 944
5. B. Sarkadi, C. Ozvegy-Laczka, K. Nemet, and A. Varadi FEBS Lett. 567 1 2004 116
6. H. Glavinas, P. Krajcsi, J. Cserepes, and B. Sarkadi Curr. Drug Delivery 1 2004 27
7. S.W. Lowe, H.E. Ruley, T. Jacks, and D.E. Housman Cell 74 6 1993 957
8. W. Henry, and E. Leete J. Am. Chem. Soc. 79 19 1957 5254
9. E.-S. Afsah, and A. Jackson J. Chem. Soc., Perkin Trans. 1 8 1984 1929
10. F. Yamada, K. Kobayashi, and A. Shimuzu Heterocycles 36 1993 2783
11. A. Monks, D.A. Scudiero, G.S. Johnson, K.D. Paull, and E.A. Sausville Anti-Cancer Drug Des. 12 1997 533
12. M.R. Boyd, and K.D. Paull Drug Dev. Res. 34 1995 91
13. A. Neubauer, M. He, C.A. Schmidt, D. Huhn, and E.T. Liu Leukemia 7 1993 593
14. S. Danhauser-Riedl, M. Warmuth, B.J. Druker, B. Emmerich, and M. Hallek Cancer Res. 56 1996 3589
15. R.U. Janicke, M.L. Sprengart, M.R. Wati, and A.G. Porter J. Biol. Chem. 273 1998 9357
16. V.J. Bykov, N. Issaeva, A. Shilov, M. Hultcrantz, E. Pugacheva, P. Chumakov, J. Bergman, K.G. Wiman, and G. Selivanova Nat. Med. 8 3 2002 282
17. V.J. Bykov, G. Selivanova, and K.G. Wiman Eur. J. Cancer 39 13 2003 1828
18. E.B. Mechetner, B. Schott, B.S. Morse, W.D. Stein, T. Druley, K.A. Davis, T. Tsuruo, and I.B. Roninson Proc. Natl. Acad. Sci. U.S.A. 94 1997 12908
19. F. Bunz, A. Dutriaux, C. Lengauer, T. Waldman, S. Zhou, J.P. Brown, J.M. Sedivy, K.W. Kinzler, and B. Vogelstein Science 282 5393 1998 1497
20. T. Mossman J. Immunol. Methods 65 1983 55
21. T.A. Sidorova, A. Nigmatov, E.S. Kakpakova, A.A. Stavrovskaya, G.K. Gerassimova, A.A. Shtil, and E.P. Serebryakov J. Med. Chem. 21 2002 5330