Synthesis and in vitro antitumor activity of ring C and D-substituted phenanthrolin-7-one derivatives, analogues of the marine pyridoacridine alkaloids ascididemin and meridine

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 15, 2004, Pages 3987-3994

  Delfourne, Evelyne ^a,d   Kiss, Robert ^b   Le Corre, Laurent ^a   Dujols, Frederic ^a   Bastide, Jean ^a   Collignon, Françoise ^c   Lesur, Brigitte ^c   Frydman, Armand ^c   Darro, Francis ^c,e  

^a UNIVERSITÉ DE PERPIGNAN   (France)

^b UNIVERSITÉ LIBRE DE BRUXELLES   (Belgium)

^c Cephalon France   (France)

^d Universite Toulouse III Paul Sabatier   (France)

^e Unibioscreen SA   (Belgium)

Author keywords

Ascididemin; Marine alkaloids; Meridine; Pyridoacridine

Indexed keywords

2 PHENYL 7H PYRIDO[4,3,2 DE][1,10]PHENANTHROLIN 7 ONE; 2 STYRYL 7H PYRIDO[4,3,2 DE][1,10]PHENANTHROLIN 7 ONE; 3 ACETOXYMETHYL 7H PYRIDO[4,3,2 DE][1,10]PHENANTHROLIN 7 ONE; 3 ACETOXYMETHYL 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 (1' PIPERIDINO) 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 [(2' METHOXYETHYL)(2'',2'',2'' TRIFLUOROETHYL)AMINO] 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 [BIS(2' CHLOROETHYL)AMINO] 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 AMINO 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 BIS(2' METHOXYETHYLAMINO) 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 BROMO 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 BUTOXY 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 CHLORO 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 DIMETHYLAMINO 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; 4 HYDROXY 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN ONE; 5 CHLORO 7H PYRIDO[4,3,2 DE]PHENANTHROLIN 7 ONE; 5 DIMETHYLAMINO 7H PYRIDO[4,3,2 DE][1,7]PHENANTHROLIN 7 ONE; ACRIDINE DERIVATIVE; ALKALOID DERIVATIVE; ANTINEOPLASTIC AGENT; ASCIDIDEMIN; HYDRAZONE DERIVATIVE; MERIDINE; PHENANTHROLINE DERIVATIVE; PYRIDOACRIDINE; QUINOLINE 5,8 DIONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DIELS ALDER REACTION; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; SUBSTITUTION REACTION;

ACRIDINES; ALKALOIDS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CELL LINE, TUMOR; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; MOLECULAR STRUCTURE; PHENANTHROLINES; QUINOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

BETULACEAE;

EID: 3042793405     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.06.006     Document Type: Article

References (13)

1. Alvarez M., Joule J. Synthesis of Pyridoacridines. Heterocycles. 34:1992;2385-2405
2. Molinski T.F. Marine Pyridoacridine Alkaloids: Structure, Synthesis, and Biological Chemistry. Chem. Rev. 93:1993;1825-1838
3. Ding Q., Chichak K., Lown J.W. Current Med. Chem. 6:1999;1-27
4. Delfourne E., Bastide J. Med. Res. Rev. 23:2003;234-252
5. Delfourne E., Darro F., Bontemps-Subielos N., Decaestecker C., Bastide J., Frydman A., Kiss R. Synthesis and Characterization of the Antitumor Activities of Analogues of Meridine, a Marine Pyridoacridine Alkaloid. J. Med. Chem. 44:2001;3275-3282
6. Delfourne E., Darro F., Portefaix P., Galaup C., Bayssade S., Bouteille A., Le Corre L., Bastide J., Collignon F., Lesur F., Frydman A., Kiss R. Synthesis and In Vitro Antitumor Activity of Novel Ring D Analogues of the Marine Pyridoacridine Ascididemin: Structure-Activity Relationship. J. Med. Chem. 45:2002;3765-3771
7. Delfourne E., Kiss R., Le Corre L., Dujols F., Bastide J., Collignon F., Lesur B., Frydman A., Darro F. Synthesis and In Vitro Antitumor Activity of Phenanthroline-7-one Derivatives, Analogues of the Marine Pyridoacridine Alkaloids Ascididemin and Meridine: Structure-Activity Relationship. J. Med. Chem. 46:2003;3536-3545
8. Bracher F. Total Synthesis of the Pentacyclic Alkaloid Ascididemin. Heterocycles. 29:1989;2093-2095
9. Lindsay B.S., Barrows L.R., Copp B.R. Structural Requirement for Biological Activity of the Marine Alkaloid Ascididemin. Bioorg. Med. Chem. Lett. 5:1995;739-742
10. Weinstein J.N., Kohn K.W., Grever M.R., Viswanadhan V.N., Rubinstein L.V., Monks A.P., Scudiero D.A., Welch L., Koutsoukos A.D., Chiausa A.J., Paull K.D. Neural Computing in Cancer Drug Development: Predicting Mechanism of Action. Science. 258:1992;447-449
11. Dowd P., Weber W. Preparation and Diels-Alder Reactions of (1E)-1, 3-dimethoxybutadiene. J. Org. Chem. 47:1982;4774-4777
12. Pauwels O., Kiss R., Pasteels J.L., Atassi G. Characterization of Alkylating Versus Intercalating Anticancer Drug-Induced Effects on Cell Survival, Cell Cycle Kinetic and Morphonuclear Pattern of Three Neoplastic Cell Lines Growing In Vitro. Pharm. Res. 12:1995;1011-1018
13. Camby I., Salmon I., Danguy A., Pasteels J.L., Brotchi J., Martinez J., Kiss R. Influence of Gastrin on Human Astrocytic Tumor Cell Proliferation. J. Natl. Cancer Inst. 88:1996;594-600