Studies on propafenone-type modulators of multidrug resistance VI. Synthesis and pharmacological activity of compounds with varied spacer length between the central aromatic ring and the nitrogen atom

Farmaco

Volumn 53, Issue 5, 1998, Pages 357-364

  Chiba, Peter ^a   Annibali, Danilo ^a   Hitzler, Manuela ^a   Richter, Elisabeth ^a   Ecker, Gerhard ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Modulators; Multidrug resistance; P glycoprotein; Propafenone; Structure activity relationship

Indexed keywords

ALIPHATIC AMINE; DAUNORUBICIN; GLYCOPROTEIN P; GLYCOPROTEIN P INHIBITOR; HYDROCINNAMIC ACID DERIVATIVE; PROPAFENONE; PROPAFENONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; DRUG TRANSPORT; HUMAN; HUMAN CELL; LIPOPHILICITY; MULTIDRUG RESISTANCE; STRUCTURE ACTIVITY RELATION; T LYMPHOBLAST;

EID: 0032580718     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(98)00035-4     Document Type: Article

References (16)

1. [1] P.R. Twentyman, Multidrug resistance: strategies for circumvention, Drug News Persp. 6 (1993) 647-654.
2. [2] S.E. Kane, Multidrug resistance of cancer cells, Adv. Drug Res. 28 (1996) 182-252.
3. [3] J.A. Kellen, Multidrug Resistance, in: J.A. Kellen (Ed.), Reversal of Multidrug Resistance in Cancer; CRC Press, Boca Raton, FL, 1994, pp. 1-19.
4. [4] J.M. Ford, W.N. Hait, Pharmacology of drugs that alter multidrug resistance in cancer, Pharmacol. Rev. 42 ( 1990) 155-199.
5. [5] G. Ecker, P. Chiba, Recent developments in overcoming tumour cell multi-drug resistance, Exp. Opin. Ther. Patents 7 (1997) 589-599.
6. [6] G. Ecker, P. Chiba, Structure-activity-relationship studies on modulators of the multidrug transporter P-glycoprotein - an overview. Wien. Klin. Wochenschr. 107 (1995) 681-686.
7. [7] G. Ecker, P. Chiba, M. Hitzler, D. Schmid, K. Visser, H.P. Cordes, J. Csöllei, J.K. Seydel, K.J. Schaper, Structure-activity relationship studies on benzofurane analogs of propafenone-type modulators of tumor cell multidrug resistance, J. Med. Chem. 39 (1996) 4767-4774.
8. [8] P. Chiba, M. Hitzler, E. Richter, M. Huber, C. Tmej, E. Giovagnoni, G. Ecker, Studies on propafenone-type modulators of multidrug resistance, III. Variations on the nitrogen. Quant. Struct. Activity Relat. 16 (1997) 361-366.
9. [9] L. Turbanti, G.F. Di Paco, Nuovi dialchilamino e ciclometilen-aminoalcossi-β-fenilpropiofenoni ad azione coronarodilatatrice ed antispastica (Novel dialkylamino- and cyclomethyleneaminoalkoxy-β-phenylpropiophenones with coronardilating and antispastic activity), Farmaco Ed. Sci. 17 (1962) 651-659.
10. [10] L. Turbanti, C.S. Tauro, G. Garzelli, Alcuni nuovi dialchilamino-e ciclometilenaminoalcossi-β-fenilpropiofenoni ad azione coronarodilatatrice ed antispastica (A series of novel dialkylamino- and cyclomethyleneaminoalkoxy-β-phenylpropiophenones with coronardilating and antispastic activity), Farmaco Ed. Sci. 18 (1963) 149-169.
11. [11] V. Gekeler, G. Frese, A. Noller, R. Handgretinger, A. Wilisch, H. Schmidt, C. Muller, R. Dopfer, T. Klingbiel, H. Diddens, H. Probst, D. Niethammer, Mdr1/P-glycoprotein, topoisomerase and glutathione-S-transferase gene expression in primary and relapsed state adult and childhood leukemias, Br. J. Cancer 66 (1992) 507-517.
12. [12] P. Baricic, M. Mackov, MOLGEN, distributed by Milan Hudecek, P. Horova 18, 841 07 Bratislava, Slovakia.
13. [13] S. Prets, A. Jungreithmair, P. Chiba, G. Ecker, Comparison of different methods for estimation of propafenone-type modulators of multidrug resistance, Sci. Pharm. 64 (1996) 627-636.
14. [14] P. Chiba, S. Rebitzer, E. Richter, M. Hitzler, G. Ecker, Synthesis and pharmacological activity of the stereoisomeres of GP88, a propafenone-type modulator of multidrug resistance, Bioorg. Med. Chem. Lett. 8 (1998) 829-832.
15. [15] N. Dodic, B. Dumaitre, A. Daugan, P. Pianetti, Synthesis and activity against multidrug resistance in Chinese hamster ovary cells of new acridone-4-carboxamides, J. Med. Chem. 38 (1995) 2418-2426.
16. [16] E.A. Coats, M. Wiese, H.-L. Chi, H.P. Cordes, J.K. Seydel, Computer modelling and NMR studies of interactions between phospholipids and benzylamines. Quant. Struct. Activity Relat. 11 (1992) 364-369.