Synthesis, biological evaluation, and molecular modeling of novel thioacridone derivatives related to the anticancer alkaloid acronycine

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 3, 2005, Pages 689-698

  Dheyongera, James P ^a   Geldenhuys, Werner J ^a   Dekker, Theodor G ^b   Van Der Schyf, Cornelis J ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

^b TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER   (United States)

Author keywords

Acronycine; Bathochromic shift; DNA intercalation; Docking; QSAR; Thioacridones

Indexed keywords

1 (2 DIMETHYLAMINOETHYLAMINO) 10 METHYL 9(10H) THIOACRIDONE; 1 (2 DIMETHYLAMINOETHYLAMINO) 4 CHLORO 10 METHYL 9(10H) THIOACRIDONE; 1 (2 DIMETHYLAMINOETHYLAMINO) 4 CHLORO 9(10H) THIOACRIDONE; 1 (2 DIMETHYLAMINOETHYLAMINO) 4,10 DIMETHYL 9(10H) THIOACRIDONE; 1 (2 DIMETHYLAMINOETHYLAMINO) 9(10H) THIOACRIDONE; 1 BIS(2 CHLOROETHYL)AMINO 4 CHLORO 9(10H) THIOACRIDONE; 1 BIS(2 CHLOROETHYL)AMINO 4 METHYL 9(10H) THIOACRIDONE; 1 BIS(2 CHLOROETHYL)AMINO 9(10H) THIOACRIDONE; 1 CHLORO 10 METHYLTHIOACRIDONE; 1 CHLORO 4 METHYL 9(10H) THIOACRIDONE; 1 CHLORO 4,10 METHYLTHIOACRIDONE; 1 CHLORO 9(10H) THIOACRIDONE; 1,4 DICHLORO 10 METHYLTHIOACRIDONE; 1,4 DICHLORO 9(10H) THIOACRIDONE; ACRIDONE DERIVATIVE; ACRONINE; AMSACRINE; ANTINEOPLASTIC AGENT; DNA; INTERCALATING AGENT; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL LINE; COMPARATIVE STUDY; COMPLEX FORMATION; CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; DNA BINDING; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INFRARED SPECTROSCOPY; LINEAR REGRESSION ANALYSIS; MOLECULAR MODEL; PHYSICAL CHEMISTRY; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ACRIDINES; ACRONINE; ANTINEOPLASTIC AGENTS, PHYTOGENIC; DNA; HL-60 CELLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 11844269189     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.10.051     Document Type: Article

References (18)

1. G.K. Hughes, F.N. Lahey, J.R. Price, and L.J. Webb Nature 162 1948 223 224
2. G.H. Svoboda, G.A. Poore, P.J. Simpson, and G.B. Border J. Pharm. Sci. 55 1966 758 768
3. R.T. Dorr, J.D. Liddil, D.D. Von Hoff, M. Soble, and C.K. Osborne Cancer Res. 49 1989 340 344
4. F. Tillequin Ann. Pharm. Fr. 60 2002 246 252
5. J. Schneider, E.L. Evans, E. Grunberg, and R.I. Fryer J. Med. Chem. 15 1972 266 270
6. N. Costes, A. Elomri, H. Dufat, S. Michel, E. Seguin, M. Koch, F. Tillequin, B. Pfeiffer, P. Renard, S. Leonce, and A. Pierre Oncol. Res. 13 2003 191 197
7. R. Miri, K. Javidnia, B. Hemmateenejad, A. Azarpira, and Z. Amirghofran Bioorg. Med. Chem. 12 2004 2529 2536
8. U. Pindur, M. Haber, and K. Sattler J. Chem. Edu. 1993 263 272
9. A. Elomri, S. Mitaku, S. Michel, A.L. Skaltsounis, F. Tillequin, M. Koch, A. Pierre, N. Guilbaud, S. Leonce, L. Kraus-Berthier, Y. Rolland, and G. Atassi J. Med. Chem. 39 1996 4762 4766
10. R.R. Smolders, J. Hanuise, R. Coomans, V. Proietto, N. Voglet, and A. Waefelaer Synthesis 1982 493 494
11. K. Lehmstedt, and K. Schrader Ber. Dtsch. Chem. Ges. 70 1937 838 849
12. H.B. Nisbet J. Chem. Soc. 1933 1372 1373
13. B.F. Cain, B.C. Baguley, and W.A. Denny J. Med. Chem. 21 1978 656 668
14. T.L. Su, T.C. Chou, J.Y. Kim, J.T. Huang, G. Ciszewska, W.Y. Ren, G.M. Otter, F.M. Sirotnak, and K.A. Watanabe J. Med. Chem. 38 1995 3226 3235
15. M.J. Waring Eur. J. Cancer 12 1976 995 1001
16. J.C. Double, and J.R. Brown J. Pharm. Pharmacol. 27 1975 502 507
17. sybyl® 6.9.1 Tripos Inc., 1699 South Hanley Rd., St. Louis, Missouri, 63144, USA
18. ChemDraw® 8 CambridgeSoft Corporation, 100 Cambridge Park Drive, Cambridge, MA 02140, USA