Phenazine-1-carboxamides: Structure-cytotoxicity relationships for 9-substituents and changes in the H-bonding pattern of the cationic side chain

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 4, 2006, Pages 1160-1168

  Gamage, Swarna A ^a   Rewcastle, Gordon W ^a   Baguley, Bruce C ^a   Charlton, Peter A ^b   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b Cantab Pharmaceuticals Ltd   (United Kingdom)

Author keywords

DNA binders; P glycoprotein; Phenazine 1 carboxamides; Polycyclic aromatic carboxamides

Indexed keywords

(3 DIMETHYLAMINO) N (9 METHYLPHENAZIN 1 YL)PROPANECARBOXAMIDE; 2 DIMETHYLAMINO N (8,9 BENZOPHENAZIN 1 YL)ETHANECARBOXAMIDE; 2 DIMETHYLAMINO N (9 METHYLPHENAZIN 1 YL)ETHANECARBOXAMIDE; 3 (MORPHOLINO) N (8,9 BENZOPHENAZIN 1 YL)PROPANECARBOXAMIDE; 3 (MORPHOLINO) N (9 METHYLPHENAZIN 1 YL)PROPANECARBOXAMIDE; 3 DIMETHYLAMINO N (8,9 BENZOPHENAZIN 1 YL)PROPANECARBOXAMIDE; 9 METHYL 1 ((3 DIMETHYLAMINO)PROPOXY)PHENAZINE; GLYCOPROTEIN P; N ((2 DIMETHYLAMINO)ETHYL) 9 METHYLPHENAZINE METHYL AMINE; N ((3 DIMETHYLAMINO)PROPYL) 8,9 BENZOPHENAZIN 1 AMINE; N ((3 DIMETHYLAMINO)PROPYL) 9 METHYLPHENAZIN 1 AMINE; N (2 (DIMETHYLAMINO)ETHYL) 9 (DIMETHYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (2 CHLORO)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (2 HYDROXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (2 METHOXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (2 METHYL)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (3 HYDROXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (3 METHOXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (4 HYDROXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N (4 METHOXY)PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 (N 1 NAPHTHYLAMINO)PHENAZINE 1 CARBOXAMIDE; N (2 (DIMETHYLAMINO)ETHYL) 9 PHENOXYPHENAZINE 1 CARBOXAMIDE; N (2 DIMETHYLAMINOETHYL) 9 (N PHENYLAMINO)PHENAZINE 1 CARBOXAMIDE; PHENAZINE 1 CARBOXAMIDE; PHENAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHROMATOPHORE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DNA BINDING; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOLECULAR MODEL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CATIONS; CELL LINE, TUMOR; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; METHYLATION; MICE; MOLECULAR STRUCTURE; PHENAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 30344477363     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.032     Document Type: Article

References (21)

1. F. Arcamone, F. Animati, G. Capranico, P. Lombardi, G. Pratesi, S. Manzini, R. Supino, and F. Zunino Pharmacol. Ther. 76 1997 117 124
2. H. Malonne, and G. Atassi Anti-Cancer Drugs 8 1997 811 822
3. R. Van Gijn, W.W. ten Bokkel Huinink, S. Rodenhuis, J.B. Vermorken, O. van Tellingen, H. Rosing, L.J.C. van Warmerdam, and J.H. Beijnen Anti-Cancer Drugs 10 1999 17 23
4. M.J.A. de Jonge, S. Kaye, J. Verweij, C. Brock, S. Reade, M. Scurr, L. van Doorn, C. Verheij, W. Loos, C. Brindley, P. Mistry, M. Cooper, and I. Judson Br. J. Cancer 91 2004 1459 1465
5. B.D. Palmer, G.W. Rewcastle, B.C. Baguley, and W.A. Denny J. Med. Chem. 31 1988 707 712
6. G.J. Atwell, B.C. Baguley, and W.A. Denny J. Med. Chem. 32 1989 396 401
7. M.R. McCrystal, B.D. Evans, V.J. Harvey, P.I. Thompson, D.J. Porter, and B.C. Baguley Cancer Chemother. Pharmacol. 44 1999 39 44
8. M. Bigioni, F. Zunino, and G. Capranico Nucleic Acids Res. 22 1994 2274 2281
9. I. Berger, L. Su, J.R. Spitzner, C. Kang, T.G. Burke, and A. Rich Nucleic Acids Res. 23 1995 4488 4494
10. A. Ettorre, M. Cirilli, and G. Ughetto Eur. J. Biochem. 258 1998 350 354
11. A.K. Todd, A. Adams, J.H. Thorpe, W.A. Denny, L.P.G. Wakelin, and C.J. Cardin J. Med. Chem. 42 1999 536 540
12. A. Adams, J.M. Guss, C.A. Collyer, W.A. Denny, and L.P.G. Wakelin Biochemistry 38 1999 9221 9233
13. G.W. Rewcastle, W.A. Denny, and B.C. Baguley J. Med. Chem. 30 1987 843 851
14. J.A. Spicer, S.A. Gamage, G.W. Rewcastle, G.J. Finlay, D.J.A. Bridewell, B.C. Baguley, and W.A. Denny J. Med. Chem. 43 2000 1350 1358
15. G.W. Rewcastle, and W.A. Denny Synth. Commun. 17 1987 1171 1179
16. R. Sharma, G.H. Voynov, T.V. Ovaska, and V.E. Marquez Synlett 1995 839 840
17. N. Vicker, L. Burgess, I.S. Chuckowree, R. Dodd, A.J. Folkes, D.J. Hardick, T.C. Hancox, W. Miller, J. Milton, S. Sohal, S. Wang, S.P. Wren, P.A. Charlton, W. Dangerfield, C. Liddle, P. Mistry, A.J. Stewart, and W.A. Denny J. Med. Chem. 45 2002 721 739
18. G.J. Finlay, K.M. Holdaway, and B.C. Baguley Oncol. Res. 6 1994 33 37
19. P. Mistry, A.J. Stewart, W. Dangerfield, S. Okiji, C. Liddle, D. Bootle, J.A. Plumb, D. Templeton, and P. Charlton Cancer Res. 61 2001 749 758
20. P. Skehan, R. Storeng, D. Scudeiro, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Broesch, S. Kenny, and M.R. Boyd J. Natl. Cancer Inst. 82 1990 1107 1112
21. E.S. Marshall, G.J. Finlay, J.H.L. Matthews, J.H.F. Shaw, J. Nixon, and B.C. Baguley J. Natl. Cancer Inst. 84 1992 340 345