Cytotoxic α-bromoacrylic derivatives of distamycin analogues modified at the amidino moiety

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 11, 2000, Pages 1273-1276

  Cozzi, Paolo ^a   Beria, Italo ^a   Caldarelli, Marina ^a   Geroni, Cristina ^a   Mongelli, Nicola ^a   Pennella, Giulia ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISTAMYCIN A DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARCINOMA CELL; CHEMICAL MODIFICATION; DRUG DESIGN; DRUG SYNTHESIS; HEMATOPOIETIC STEM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; OVARY CARCINOMA;

AMIDINES; ANIMALS; ANTINEOPLASTIC AGENTS; DISTAMYCINS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MICE; TUMOR CELLS, CULTURED;

EID: 0034608708     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00205-5     Document Type: Article

References (16)

1. See e.g., Pindur, U.; Fischer, G. Curr. Med. Chem. 1996, 3, 379 and references therein.
2. See e.g., Zunino, F.; Animati, F.; Capranico G. Current Pharmaceutical Design 1995, 1, 83 and references therein.
3. See e.g., (a) Lee, M.; Rhodes, A.L.; Wyatt, M.; Forrow, S.; Hartley, J.A. Anticancer Drug Design 1993, 8, 173
4. (b) Wyatt, M.D.; Garbiras, B.J.; Haskell, M.K.; Lee, M.; Souhami, R.L.; Hartley, J.A., Anticancer Drug Design 1994, 9, 511
5. (c) Wyatt, M.D.; Lee, M.; Hartley, J. A. Anticancer Drug Design 1997, 12, 49.
6. Brooks N., Hartley J.A., Simpson J.E., Wright S.R., Woo S., Centioni S., Fontaine M.D., McIntyre T.E., Lee M. Biorg. Med. Chem. 5:1997;1497.
7. Cozzi P., Beria I., Biasoli G., Caldarelli M., Capolongo L., Geroni C., Mongelli N. Biorg. Med. Chem. Lett. 7:1997;2979.
8. D'Alessio R., Geroni C., Biasoli G., Pesenti E., Grandi M., Mongelli N. Bioorg. Med. Chem. Lett. 4:1994;1467.
9. Marchini V., Cirò M., Gallinari F., Geroni C., Cozzi P., D'Incalci M., Broggini M. Br. J. Cancer. 80:1999;991.
10. Cozzi P., Beria I., Caldarelli M., Capolongo L., Geroni C., Mongelli N. Bioorg. Med. Chem. Lett. 10:2000;1269.
11. 6) are given. (Bruker AC200 spectrometer, δ in ppm, TMS as internal standard). (1): 7.94 (t, J=5.9 Hz, 1H); 7.3 (b.s., 1H); 6.8 (b.s., 1H); 3.3 (m, 2H); 2.30 (t, J=7.2 Hz, 2H). (2): 5 (b.s., 1H); 9.1 (b.s., 1H); 8.5 (b.s., 1H); 8.22 (t, J=5.9 Hz, 1H); 3.48 (m, 2H); 2.79 (s, 3H); 2.62 (m, 2H). (3): 9.2 (b.s., 2H); 8.33 (t, J=6.0 Hz, 1H); 3.44 (m, 2H); 3.00 (s, 3H); 2.79 (s, 3H); 2.73 (m, 2H). (4): 9.0 (b.s., 1H); 8.31 (t, J=5.8 Hz, 1H); 3.46 (m, 2H) 3,22 (s, 3H); 3.03 (b.s., 3H), 2.77 (t, J=6.5 Hz, 2H). (6): 8.10 (t, J=5.9 Hz, 1H); 7.56 (t, J=5.9, 1H); 7.2 (b.s., 4H); 3.30 (m, 4H). (7): 9.5 (b.s., 2H); 8.5 (b.s., 1H); 7.98 (t, J=5.9 Hz, 1H); 3.38 (m, 2H); 2,31 (m, 2H).(8): 8.3 (b.s., 2H); 8.1 (b.s., 1H); 3.4 (b.s., 2H); 2,6 (b.s., 2H). (9): 7.94 (t, J=5.9 Hz, 1H); 6.8 (b.s., 2H); 3.33 (m, 2H); 2.30 (t, J=7.2 Hz, 2H). (10): 8.36 (t, J=5.9 Hz, 1H); 3,42 (m, 2H); 2.75 (t, J=6.5 Hz, 2H).
12. Caldarelli M., Biasoli G., Cozzi P., Mongelli N. Tetrahedron Lett. 39:1998;3551.
13. Geroni C., Pesenti E., Tagliabue G., Ballinari D., Mongelli N., Broggini M., Erba E., D'Incalci M. Cancer Res. 53:1993;308.
14. See e.g. Lown, J. W. Chemtracts-Organic Chemistry 1993, 6, 205.
15. Ciomei, M.; Pastori, W.; Cozzi, P.; Geroni, C. Proceedings of AACR, Philadelphia 1999, 40 Abst.1490, 224.
16. Geroni, C.; Pennella, G.; Capolongo, L.; Moneta, D.; Rossi, R.; Farao, M.; Marchini, S.; Cozzi, P. Proceedings of AACR, San Francisco, 2000, in press.