Synthesis, Pharmacologic Activity, and Structure-Activity Relationships of a Series of Propafenone-Related Modulators of Multidrug Resistance

Journal of Medicinal Chemistry

Volumn 38, Issue 14, 1995, Pages 2789-2793

  Chiba, Peter ^a   Burghofer, Sabine ^a   Richter, Elisabeth ^a   Tell, Barbara ^a   Moser, Andrea ^a   Ecker, Gerhard ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 [2 HYDROXY 3 [4 (2 METHYLPHENYL) 1 PIPERAZINYL]PROPOXY]PHENYL] 3 PHENYL 1 PROPANONE; 1 [2 [2 HYDROXY 3 [4 (4 METHOXYPHENYL) 1 PIPERAZINYL]PROPOXY]PHENYL] 3 PHENYL 1 PROPANONE; 1 [2 [3 [4 (4 FLUOROPHENYL) 1 PIPERAZINYL] 2 HYDROXYPROPOXY]PHENYL] 3 PHENYL 1 PROPANONE; CYTOSTATIC AGENT; DAUNORUBICIN; ETOPOSIDE; GLYCOPROTEIN P; PROPAFENONE; PROPAFENONE DERIVATIVE; UNCLASSIFIED DRUG; VERAPAMIL;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; DRUG UPTAKE; HUMAN; HUMAN CELL; LYMPHOBLASTOID CELL LINE; MULTIDRUG RESISTANCE; SENSITIZATION; STRUCTURE ACTIVITY RELATION; TUMOR CELL;

DAUNORUBICIN; DRUG RESISTANCE, MULTIPLE; DRUG SYNERGISM; ETOPOSIDE; HUMAN; MAGNETIC RESONANCE SPECTROSCOPY; PROPAFENONE; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; TUMOR CELLS, CULTURED;

EID: 0029009203     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00014a031     Document Type: Article

References (31)

1. Juliano, R. L.; Ling, V. A surface glycoprotein modulating drug permeability in Chinese hamster ovary cell mutants. Biochim. Biophys. Acta 1976, 455, 152-162.
2. Roninson, I. B.; Abelson, H.; Housman, D. E.; Howell, N.; Varshavsky, A. Amplification of specific DNA sequences correlates with multidrug resistance in Chinese hamster cells. Nature 1984, 309, 626-628.
3. Ueda, K.; Cornwell, M. M.; Gottesman, M. M.; Pastan, I.; Roninson, I. B.; Ling, V.; Riordan, J. R. The mdrl gene, responsible for multidrug resistance, codes for P-glycoprotein. Biochem. Biophys. Res. Commun. 1986, 141, 956-960.
4. Horio, M.; Gottesman, M. M.; Pastan, I. ATP-dependent transport of vinblastine in vesicels from human multidrug-resistant cells. Proc. Natl. Acad. Sci. U. SA. 1988, 85, 3580-3584.
5. Goldstein, L. J.; Gottesman, M. M.; Pastan, I. Expression of the MDR1 gene in human cancers. Cancer Treat. Res. 1991, 57, 101-119.
6. Goldstein, L. J.; Pastan, I.; Gottesman, M. M. Multidrug resistance in human cancer. Crit. Rev. Oncol. Hematol. 1992, 12, 243-253.
7. Bates, S. E.; Ching, Y. S.; Tsokos, M. Expression of mdr-1/P- glycoprotein in human neuroblastoma. Am. J. Pathol. 1991, 139, 305-315.
8. Borst, P. Genetic mechanisms of drug resistance. Rev. Oncol. 1991, 4, 87-105.
9. Tsuruo, T. Reversal of multidrug resistance by calcium channel blockers and other agents. In Molecular and cellular biology of multidrug resistance in tumor cells’, Ronisnon, I. B., Ed.; Plenum Publishing Corp.: London, 1991.
10. Ford, J. M.; Hait, W. N. Pharmacology of drugs that alter multidrug resistance in cancer. Pharmacol. Rev. 1990, 42, 155-199.
11. Miller, T. P.; Grogan, T. M.; Dalton, W. S.; et al. P-glycoprotein expression in malignant lymphoma and reversal of clinical drug resistance with chemotherapy plus high-dose verapamil. J. Clin. Oncol. 1991, 9, 17-24.
12. Chan, H. S. L.; DeBoer, G.; Koren, G.; Thiessen, J. J.; Thomer, P. S.; Giesbrecht, E.; Haddad, G.; Veijee, Z.; Ling, V.; Gallie, B. L. Cyclosporin A-modulated chemotherapy with focal therapy: a new approach to retinoblastoma. Proc. Am. Assoc. Cancer Res. 1994, 35, 359.
13. Twentyman, P. R. Cyclosporins as drug resistance modifiers. Biochem. Pharmacol. 1992, 43, 109-117.
14. Raderer, M.; Scheithauer, W. Clinical trials of agents that reverse multidrug resistance. A literature review. Cancer 1993, 72, 3553-3563.
15. Beck, W. T. Multidrug resistance and its circumvention. Eur. J. Cancer 1990, 26, 513-515.
16. Klopman, C.; Srivastava, S.; Kolosssvary, R. F.; Epand, R. F.; Ahmed, N.; Epand, R. M. Structure-activity study and design of multidrug resistant reversal compounds by a computer automated structure evaluation methodology. Cancer Res. 1992, 52, 4121-4129.
17. Ford, J. M.; Hait, W. N. Pharmacology of drugs that alter multidrug resistance in cancer. Pharmacol. Rev. 1990, 42, 155-199.
18. Chiba, P.; Ecker, G.; Tell, B.; Moser, A.; Schmid, D.; Drach, J. Modulation of PGP-mediated multidrug-resistance by propafenone analogs. Proc. Am. Assoc. Cancer Res. 1994, 35, 357.
19. Ecker, G.; Fleischhacker, W.; Chiba, P. Pharmakologisch wirk- same o-Acylaryloxypropanolamine mit tertiarem und quartarem Stickstoff. (Pharmacologically active o-Acylaryloxypropanol- amines with tertiary and quaternary nitrogen.) Austrian Patent Appl. 15A 963/93-1, May 17, 1993.
20. Ford, J. M.; Bruggemann, E. P.; Pastan, I.; Gottesman, M. M.; Hait, W. N. Cellular and biochemical characterization of thiox- anthenes for reversal of multidrug resistance in human and murine cell lines. Cancer Res. 1990, 50, 1748-1756.
21. Petrik, W.; Sachse, R. (Helopharm) Verfahren zur Herstellung neuer, therapeutisch wertvoller Derivate des 2′-Hydroxy-3- phenyl-propiophenons und deren Salze. (Therapeutically useful derivatives of 2′-hydroxy-3-phenylpropiophenones and their salts.) DE 2001431, Jan. 6, 1970
22. Petrik, W.; Sachse, R. Chem. Abstr. 1971, 75, 151538f.
23. Ecker, G.; Fleischhacker, W.; Noe, C. R. Ein Verfahren zur Synthese der Enantiomere von Propafenon. (A Method for the Synthesis of the Enantiomers of Propafenone.) Arch. Pharm. 1994, 327, 691-695.
24. Ecker, G.; Fleischhacker, W.; Noe, C. R. New Benzofurane-Type Antiarrhythmic Compounds Related to Propafenone. Heterocycles 1994, 38, 1247-1256.
25. Gekeler, V.; Weger, S.; Probst, H. MDRl/P-glycoprotein gene segments analyzed from various human leukemic cell lines exhibiting different multidrug resistance profiles. Biochem. Biophys. Res. Commun. 1990, 169, 796-802.
26. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
27. Kraupp, M.; Paskutti, B.; Schon, C.; Marz, R. Inhibition of purine nucleobase transport in human erythrocytes and cell lines by papaverine. Investigation of structure-activity relationship. Biochem. Pharmacol. 1994, 48, 41-47.
28. Franke, A.; Mueller, J.; Lietz, H.; Wiesdorff, W.; Hege, H.; Mueller, C.; Gries, J.; Lenke, D.; Von Philipsbom, G.; Raschack, M. (BASF) Aminopropanol derivatives of 2-hydroxy-/3-phenylpropiophenones and therapeutic agents containing them. Eur. Pat. Appl. EP 75. 207, Mar. 30, 1983
29. Franke, A.; Mueller, J.; Lietz, H.; Wiesdorff, W.; Hege, H.; Mueller, C.; Gries, J.; Lenke, D.; Von Philipsbom, G.; Raschack, M. Chem. Abstr. 1983, 99, 122033c.
30. Offermanns, H.; Poselt, K. (Deutsche Gold- und Silber-Scheide- anstalt) l-(2-Acylethyl)- and l-((acylamino) methyl)-4-(3, 4, 5-tri- methoxybenzoyl) piperazines and homologs. Ger. Offen. 2, 360, 545, June 12, 1974
31. Offermanns, H.; Poselt, K. Chem. Abstr. 1974, 81, 105570m.