2,4-Diamino-9H-pyrimido[4,5-b]indol-5-ols: Synthesis, in vitro cytotoxic activity, and QSAR investigations

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 21, 2006, Pages 7282-7292

  Dotzauer, Bernd ^a   Grünert, Renate ^b   Bednarski, Patrick J ^b   Lanig, Harald ^a   Landwehr, Jens ^a   Troschütz, Reinhard ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY MEDICINE GREIFSWALD   (Germany)

Author keywords

Cytotoxicity; Ellipticine analogues; Nenitzescu reaction; QSAR

Indexed keywords

2 AMINO 4 (4 METHYLPIPERAZIN 1 YL) 9H PYRIMIDO[4,5 B]INDOL-6-OL; 2 AMINO 4 DIETHYLAMINO 9H PYRIMIDO[4,5 B]INDO 6 OL; 2 AMINO 4 DIMETHYLAMINO 9H PYRIMIDO[4,5 B]INDOLE; 2 AMINO 4 METHOXY 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2 AMINO 4 MORPHOLIN 4 YL 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2 AMINO 4 PYRROLIDIN 1 YL 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 BIS(4 METHYLPIPERAZIN 1 YL) 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 BIS(DIETHYLAMINO) 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 BIS(DIMETHYLAMINO) 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 DIAMINO 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 DIMORPHOLIN 4 YL 9H PYRIMIDO[4,5 B]INDOL 6 OL; 2,4 DIPYRROLIDIN 1 YL 9H PYRIMIDO[4,5 B]INDOL 6 OL; 4 AMINO 2 (4 METHYLPIPERAZIN 1 YL) 9H PYRIMIDO[4,5 B]INDOL 6 OL; 4 AMINO 2 DIETHYLAMINO 9H PYRIMIDO[4,5 B]INDOL 6 OL; 4 AMINO 2 DIMETHYLAMINO 9H PYRIMIDO[4,5 B]INDOL 6 OL; 4 AMINO 2 MORPHOLIN 4 YL 9H PYRIMIDO[4,5 B]INDOL 6 OL; 4 AMINO 2 PYRROLIDIN 1 9H PYRIMIDO[4,5 B]INDOL 6 OL; 6 METHOXY 2 PYRROLIDIN 1 YL 9H PYRIMIDO[4,5 B]INDOL 4 AMINE; 7 AMINO 9 (4 METHYLPIPERAZIN 1 YL) 11H BENZO[G]PYRIMIDO[4,5 B]INDOL 5 OL; 7 AMINO 9 (MORPHOLIN 4 YL) 11H BENZO[G]PYRIMIDO[4,5 B]INDOL 5 OL; 7 AMINO 9 PYRROLIDIN 1 YL 11H BENZO[G]PYRIMIDO[4,5 B]INDOL 5 OL; 7 AMINO 9 PYRROLIDIN 1 YL 11H PYRIMIDO[50,40:4,5] PYRROLO[2,3 F]QUINOLIN 5 OL; 7 AMINO 9 PYRROLIDIN 1 YL 11H PYRIMIDO[50,40:4,5] PYRROLO[2,3 F]QUINOXALIN 5 OL; 7,9 DIAMINO 11H BENZO[G]PYRIMIDO[4,5 B]INDOL 5 OL; 9 AMINO 7 (MORPHOLIN 4 YL) 11H BENZO[G]PYRIMIDO[4,5 B]INDOL 5 OL; CISPLATIN; CYTOTOXIC AGENT; ELLIPTICINE; INDOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PYRIMIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SPECTROPHOTOMETRY, INFRARED;

EID: 33748750231     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.06.051     Document Type: Article

References (25)

1. Dalton L.K., Demerac S., Elmes B.C., Loder J.W., Swan J.M., and Teitei T. Aust. J. Chem. 20 (1967) 2715
2. Guillonneau C., Pierre A., Charton Y., Guilbaud N., Kraus-Bertier L., Leonce S., Bisagni E., and Atassi G. J. Med. Chem. 42 (1999) 2191
3. Garbett N.C., and Graves D.E. Curr. Med. Chem. 4 (2004) 149
4. Schönfeld F., and Troschütz R. Heterocycles 55 (2001) 1679
5. Wollein G., and Troschütz R. J. Heterocycl. Chem. 39 (2002) 1195
6. Bisagni E., Ngyen C.H., Pierre A., Pepin O., De Cointel P., and Gros P. J. Med. Chem. 31 (1988) 398
7. Bisagni E., Ducrocq C., Lhoste J.-M., Rivalle C., and Civier A. J. Chem. Soc., Perkin Trans. 1 (1979) 1706
8. Lowinger, T.; Shimazaki, M.; Sato, H.; Tanaka; K.; Tsuno, N.; Marx, K.; Yamamoto, M.; Urbans, K.; Ganther, F.; Okogami, H.; Nakashima, K.; Takeshita, K.; Bacon, K.; Komura, H.; Yoshida, N. PTC Int. Appl. WO 03/037898, 2003..
9. Traxler P.M., Furet P., Mett H., Buchdunger E., Meyer T., and Lydon N. J. Med. Chem. 39 (1996) 2285
10. Bundy G.L., Ayer D.E., Banitt L.S., Belonga K.L., Mizsak S.A., Palmer J.R., Tustin J.M., Chin J.E., Hall E.D., Linsemann K.L., Scherch H.M., Sun F.F., Yonkers P.A., Larson P.G., Lin J.M., Padbury G.E., Aaron C.S., and Mayo J.K. J. Med. Chem. 38 (1995) 4161
11. Hall E.D., Andrus P.K., Smith S.L., Fleck T.J., Scherch H.M., Lutzke B.S., Sawada G.A., Althaus J.S., von Voightlander P.F., Padbury G.E., Larson P.G., Palmer J.R., and Bundy G.L. J. Pharmacol. Exp. Ther. 281 (1997) 895
12. Allen, G. R. In Organic Reactions Reactants; Wiley: New York, 1973; Vol. 33, p 20.
13. Granik V.G., Lyubchanskaya V.M., and Mukhanova T.T. Khim. Farm. Zh. 27 (1993) 37
14. Pharm. Chem. J. (1993) 413
15. Dotzauer B., and Troschütz R. Synlett (2004) 1039
16. Troschütz R., and Anders E. Arch. Pharm. (Weinheim) 325 (1992) 341
17. Barret R., and Daundon M. Tetrahedron Lett. 34 (1990) 4871
18. Bock H., Dickmann P., and Herrmann H.-F. Z. Naturforsch. B 46 (1991) 326
19. Landwehr J., and Troschütz R. Synthesis 14 (2005) 2414
20. Saczewski F., Reszka P., Gdaniec M., Grünert R., and Bednarski P.J. J. Med. Chem. 47 (2004) 3438
21. Rinke K., Grünert R., and Bednarski P.J. Pharmazie 56 (2001) 763
22. Rauhut, G.; Alex, A.; Chandrasekhar, J.; Steinke, T.; Sauer, W.; Beck, B.; Hutter, M.; Gedeck, P.; Clark, T. VAMP 7, 1997, Accelrys, Cambridge, UK (formally Oxford Molecular Ltd.).
23. Dewar M.J.S., Zoebisch E.G., Healy E.F., and Stewart J.J.P. J. Am. Chem. Soc. 107 (1985) 3902-3909
24. Beck B., Clark T., and Glen R.C. J. Comput. Chem. 18 (1997) 744-756
25. TSAR 3.3, 2000, Accelrys, Cambridge, UK (formally Oxford Molecular Ltd.).