Design, synthesis, and cytotoxic activity of Michael acceptors and enol esters in the benzo[b]acronycine series

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 8, 2005, Pages 919-922

  Doan Thi Mai, Huong ^a   Gaslonde, Thomas ^a   Michel, Sylvie ^a   Koch, Michel ^a   Tillequin, François ^a   Bailly, Christian ^b   David Cordonnier, Marie Hélène ^b   Pfeiffer, Bruno ^c   Léonce, Stéphane ^c   Pierré, Alain ^c  

^a UNIVERSITÉ PARIS DESCARTES   (France)

^b INSERM   (France)

^c INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

Acronycine; benzo b acronycine; Cytotoxicity

Indexed keywords

1,2 DIACETOXY 6 METHOXY 3,3,14 TRIMETHYL 1,2,3,14 TETRAHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 ACETOXY 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 ACETYL 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 BENZOYL 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 BUTYROXY 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 2 BUTYRYL 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; 6 METHOXY 3,3,14 TRIMETHYL 3,14 DIHYDRO 7H BENZO[B]PYRANO[3,2 H]ACRIDIN 7 ONE; ACRONINE; ALUMINUM CHLORIDE; DNA; HYDROCHLORIC ACID; S 23906 1; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DNA PURIFICATION; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; IC 50; LEUKEMIA L 1210; MOUSE; NONHUMAN;

EID: 24944511944     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.53.919     Document Type: Article

References (18)

1. Hughes G. K., Lahey F. N., Price J. R., Nature (London), 162, 223-224 (1948).
2. Macdonald P. L., Robertson A. V., Aust. J. Chem., 19, 275-281 (1966).
3. Tillequin F., Michel S., Skaltsounis A.-L., "Alkaloids: Chemical and Biological Perspectives," Vol. 12, ed. by Pelletier S. W., Elsevier, New York, 1998, pp. 1-102.
4. Svoboda G. H., Lloydia, 29, 206-224 (1966).
5. Svoboda G. H., Poore G. A., Simpson P. J., Boder G. B., J. Pharm. Sci., 55, 758-768 (1966).
6. Scarffe J. H., Beaumont A. R., Gowther D., Cancer Treat. Rep., 67, 93-94 (1983).
7. Brum-Bousquet M., Mitaku S., Skaltsounis A.-L., Tillequin F., Koch M., Planta Med., 54, 470-471 (1988).
8. Elomri A., Mitaku S., Michel S., Skaltsounis A.-L., Tillequin F., Koch M., Pierré A., Guilbaud N., Léonce S., Kraus-Berthier L., Rolland Y., Atassi Gh., J. Med. Chem., 39, 4762-4766 (1996).
9. Costes N., Le Deit H., Michel S., Tillequin F., Koch M., Pfeiffer B., Renard P., Léonce S., Guilbaud N., Kraus-Berthier L., Pierré A., Atassi Gh., J. Med. Chem., 43, 2395-2402 (2000).
10. Guilbaud N., Léonce S., Tillequin F., Koch M., Hickman J. A., Pierré A., Anti Cancer Drugs, 13, 445-449 (2002).
11. David-Cordonnier M.-H., Laine W., Lansiaux A., Kouach M., Briand G., Pierré A., Hickman J. A., Bailly C., Biochemistry, 41, 9911-9920 (2002).
12. Doan Thi Mai H., Gaslonde T., Michel S., Tillequin F., Koch M., Bongui J.-B., Elomri A., Seguin E., Pfeiffer B., Renard P., David-Cordonnier M.-H., Laine W., Bailly C., Kraus-Berthier L., Léonce S., Hickman J. A., Pierré A., J. Med. Chem., 46, 3072-3082 (2003).
13. David-Cordonnier M.-H., Laine W., Joubert A., Tardy C., Goossens J.-F., Kouach M., Briand G., Doan Thi Mai H., Michel S., Tillequin F., Koch M., Léonce S., Pierré A., Bailly C., Eur. J. Biochem., 270, 2848-2859 (2003).
14. David-Cordonnier M.-H., Laine W., Kouach M., Briand G., Vezin H., Gaslonde T., Michel S., Doan Thi Mai H., Tillequin F., Koch M., Léonce S., Pierré A., Bailly C., Bioorg. Med. Chem., 12, 23-29 (2004).
15. Michel S., Seguin E., Tillequin F., Curr. Med. Chem., 9, 1689-1700 (2002).
16. Shieh H. L., Pezzuto G. M., Cordell G. A., Chem.-Biol. Interact., 81, 35-55 (1992).
17. Elomri A., Skaltsounis A.-L., Michel S., Tillequin F., Koch M., Rolland Y., Pierré A., Atassi Gh., Chem. Pharm. Bull., 44, 2165-2168 (1996).
18. Pierré A., Kraus-Berthier L., Atassi Gh., Cros S., Poupon M. F., Lavielle G., Berlion M., Bizarri J. P., Cancer Res., 51, 2312-2318 (1991).