Substituted 4-acylpyrazoles and 4-acylpyrazolones: Synthesis and multidrug resistance-modulating activity

Journal of Medicinal Chemistry

Volumn 41, Issue 21, 1998, Pages 4001-4011

  Chiba, Peter ^a   Holzer, Wolfgang ^a   Landau, Marion ^a   Bechmann, Gerhard ^a   Lorenz, Karin ^a   Plagens, Brigitte ^a   Hitzler, Manuela ^a   Richter, Elisabeth ^a   Ecker, Gerhard ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 BIS(ALLYLAMINO) 6 [4 [[2,2 BIS(4 FLUOROPHENYL)ETHYL]AMINO]PIPERIDINO] 1,3,5 TRIAZINE; AMIODARONE; DEXNIGULDIPINE; PROPAFENONE; PYRAZOLONE DERIVATIVE; VERAPAMIL;

ANIMAL CELL; ARTICLE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MULTIDRUG RESISTANCE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; BIOLOGICAL TRANSPORT; DAUNORUBICIN; DRUG RESISTANCE, MULTIPLE; DRUG RESISTANCE, NEOPLASM; FLUORESCENT DYES; HUMANS; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MICE; P-GLYCOPROTEIN; PYRAZOLES; REGRESSION ANALYSIS; RHODAMINE 123; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 0032497637     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980121y     Document Type: Article

References (44)

1. De Vita, V. T., Jr, The Problem of Resistance; Keynote Address. In Drug Resistance: Mechanisms and Reversal; Mihich, E., Ed.; John Libbey CIC: Roma, Milano, London, Paris, New York, 1990.
2. Dano, K. Active Outward Transport of Daunomycin in Resistant Ehrlich Ascites Tumour Cells. Biochim. Biophys. Acta 1973, 323, 466-483.
3. Bosch, I.; Croop, J. P-Glycoprotein Multidrug Resistance and Cancer. Biochim. Biophys. Acta 1996, 1288, F37-F54.
4. Bradley, G.; Juranka, P. F.; Ling, V. Mechanism of Multidrug Resistance. Biochim. Biophys. Acta 1988, 948, 87-128.
5. Ford, J. M. Experimental Reversal of P-glycoprotein Mediated Multidrug Resistance by Pharmacological Chemosensitizers. Eur. J. Cancer 1996, 32A, 991-1001.
6. Tsuruo, T.; Iida, H.; Tsukagoshi, S.; Sakurai, Y. Overcoming of Vincristine Resistance in P 388 Leukemia In Vivo and In Vitro through Enhanced Cytotoxicity of Vincristine and Vinblastine by Verapamil, Cancer Res. 1981, 41, 1967-1972.
7. Boer, R.; Gekeler, V. Chemosensitizers in Tumor Therapy: New Compounds Promise Better Efficacy. Drugs Future 1995, 20, 499-509.
8. Chauffert, B.; Martin, M.; Hamman, A.; Michel, M. F.; Martin, F. Amiodaron-Induced Enhancement of Doxorubicin and 4′-Deoxydoxorubicin Cytotoxicity to Rat Colon Cancer Cells In Vitro and In Vivo. Cancer Res. 1986, 46, 825-830.
9. Yang, C. P.; DePinho, S. H.; Greenberger, L. M.; Arceci, R. J-; Horwitz, S. B. Progesterone Interacts With P-glycoprotein in Multidrug-Resistant Cells and in the Endometrium of Gravid Uterus. J. Biol. Chem. 1989, 264, 782-788.
10. Twentyman, P. R. Cyclosporins as Drug Resistance Modifiers. Biochem. Pharmacol, 1992, 43, 109-117.
11. Ford, J. M.; Prozialeck, W. C.; Hait, W. N. Structural Features Determining Activity of Phenothiazines and Related Drugs for Inhibition of Cell Growth and Reversal of Multidrug Resistance. Mol. Pharmacol. 1989, 55, 105-115.
12. Ford, J. M.; Bruggemann, E. P.; Pastan, I.; Gottesman, M. M.; Hait, W. N. Cellular and Biochemical Characterization of Thioxanthenes for Reversal of Multidrug Resistance in Human and Murine Cell Lines, Cancer Res, 1990, 50, 1748-1756.
13. Dhainaut, A.; Regnier, G.; Atassi, G.; Pierre, A.; Leonce, S.; Kraus-Berthier, L.; Prost, J. F. New Triazine Derivatives as Potent Modulators of Multi-Drug Resistance. J. Med. Chem. 1992, 55, 2481-2496.
14. Dodic, N.; Dumaitre, B.; Daugan, A.; Pianetti, P. Synthesis and Activity Against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides. J. Med. Chem. 1995, 38, 2418-2426.
15. Ecker, G.; Chiba, P. Recent Developments in Overcoming Tumour Cell Multi-Drug Resistance. Exp. Opin. Ther. Patents 1997, 7, 589-599.
16. Chiba, P.; Burghofer, S.; Richter, E.; Teil, B.; Moser, A.; Ecker, G. Synthesis, Pharmacologie Activity and Structure-Activity-Relationships of a Series of Propafenone-Related Modulators of Multi-Drug-Resistance. J. Med. Chem. 1995, 38, 2789-2793.
17. Chiba, P.; Ecker, G.; Schmid, D.; Drach, J.; Tell, B.; Gekeler, V. Structural Requirements for Activity of Propafenone Type Modulators in PGP-Mediated Multidrug Resistance. Mol. Pharmacol. 1996, 49, 1122-1130.
18. Elguero, J.; Marzin, C.; Katritzky, A. R.; Linda, P. The Tautomerism of Heterocycles. In Advances in Heterocyclic Chemistry, Supplement 1; Katritzky, A. R., Boulten, A. J., Eds.; Academic Press: New York, San Francisco, London, 1976; pp 313-336 and references therein.
19. Schofield, K.; Grimmett, M. R.; Keene, B. T. R Heteroaromatic Nitrogen Compounds: The Azotes; Cambridge University Press: Cambridge, 1976; pp 85-91 and references therein.
20. Holzer, W.; Plagens, B. On the Methylation of Pyrazolones. Sci. Pharm. 1996, 64, 455-462.
21. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AMI: A New General Purpose Quantum Mechanical Molecular Mode). J. Am. Chem, Soc, 1985, 107, 3902-3909. AMPAC 5.0, 1994; Semichem, 12715 W. 66th Terrace, Shawnee, KS 66216.
22. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AMI: A New General Purpose Quantum Mechanical Molecular Mode). J. Am. Chem, Soc, 1985, 107, 3902-3909. AMPAC 5.0, 1994; Semichem, 12715 W. 66th Terrace, Shawnee, KS 66216.
23. Holzer, W.; Plagens, B.; Lorenz, K. Alkylation of Pyrazolones via the Mitsunobu Reaction. Heterocycles 1997, 45, 309-314.
24. Patt, S. L.; Shoolery, J. N. Attached Proton Test for Carbon-13 NMR. J. Magn. Reson. 1982, 46, 535-539.
25. Neuhaus, D.; Williamson, M. P. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH Publishers: New York, Weinheim, Cambridge, 1989; pp 211-252.
26. Bax, A.; Freeman, R. Investigation of Complex Networks of Spin-Spin Coupling by Two-Dimensional NMR. J. Magn. Reson. 1981, 44, 542-561.
27. Bax, A.; Subramanian, S. Sensitivity-Enhanced Two-Dimensional Heteronuclear Shift Correlation NMR Spectroscopy. J. Magn. Reson, 1986, 67, 565-569.
28. 1H NMR Spectra by Selective Excitation of Experimental Subspectra. J. Am. Chem. Soc. 1985, 107, 7197-7198.
29. Sarkar, S. K.; Bax, A. A Simple and Sensitive One-Dimensional NMR Technique for Correlation of Proton and Carbon Chemical Shifts. J. Magn, Reson. 1085, 62, 109-112.
30. 13C couplings. J. Magn. Reson. 1984, 57, 314-318.
31. Ghose, A. K.; Pritchett, A.; Grippen, G. M. Atomic Physicochemical Parameters for Three-Dimensional Structure Directed Quantitative Structure-Activity Relationships III: Modeling Hydrophobic Interactions. J. Comput. Chem. 1988, 9, 80-90.
32. P. Baricic, M. Mackov, distributed by Milan Hudecek, P. Horova 18, 841 07 Bratislava, Slowakia.
33. O. A. Raevsky, V. Y. Grigor'ev, Institute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Moscow Region, Russia.
34. Tripos GmbH, Munich, Germany; 1997.
35. Gekeler, V.; Frese, G.; Noller, A.; Handgretinger, R.; Wilisch, A.; Schmidt, H.; Muller, D.; Dopfer, R.; Klingbiel, T.; Diddens, H.; Probst, H.; Niethammer, D. Mdr1/P-glycoprotein, Topoisomerase and Glutathione S-transferase Gene Expression in Primary and Relapsed State Adult and Childhood Leukemias. Er. J. Cancer 1992, 66, 507-517.
36. Ecker, G.; Chiba, P.; Hitzler, M.; Schmid, D.; Visser, K.; Cordes, H. P.; Csöllei, J.; Seydel, J. K.; Schaper, K.-J. Structure-Activity Relationship Studies on Benzofurane Analogues of Propafenone-Type Modulators of Tumor Cell Multidrug Resistance. J. Med. Chem. 1996, 39, 4767-4774.
37. Kubinyi, H. QSAR: Hansch Analysis and Related Approaches. In Methods and Principles in Medicinal Chemistry; Mannhold, R., Krogsgaard-Larsen, P., Timmermann, H., Eds.; Verlag Chemie: Weinheim, 1993; Vol. 1, pp 21-53.
38. Sarenko, A. S.; Kvitko, I. Y.; Efros, L. S. Heterocyclic Analogues of Xanthones II. C-Acylation of 5-Pyrazolones and Synthesis of Chromono[3,2-d]pyrazoles. Chem. Heterocycl. Compd. (Engl. Transl.) 1972, 8, 722-727.
39. Jensen, B. S. The Synthesis of 1-Phenyl-3-methyl-4-acyl-pyrazolones-5. Acta Chem. Scand. 1959, 13, 1668-1670.
40. Avar, L.; Hofer, K.; Preiswerk, M. Stabilizing Organic Materials Employing Pyrazole Compounds and Stabilized Compositions Thereof. U.S. Patent 4,008,200, Feb 15, 1977.
41. Lakkis, M.; Lakkis, Z.; Goetz-Grandmont, G. J.; Brunette, J.-P. Extraction of Cobalt(II) With Mixtures of 4-Acyl-pyrazol-5-ols and Aliquat 336 in Toluene: Effect of the Pyrazolol Substituants. Monatsh. Chem. 1991, 122, 9-15.
42. Gekeler, V.; Weger, S.; Probst, H. Mdr1/P-glycoprotein Gene Segments Analyzed from Various Human Leukemic Cell Lines Exhibiting Different Multidrug Resistance Profiles. Biochem, Biophys. Res. Commun. 1990, 169, 796-802.
43. Pastan, I.; Gottesman, M. M.; Ueda, K.; Lovelace, E.; Rutherford, A. V.; Willington, M. C. A Retrovirus Carrying an mdr1 cDNA Confers Multidrug Resistance and Polarized Expression of P-glycoprotein in MDCK Cells, Proc, Natl Acad. Sci. U.S.A. 1988, 85, 4486-4490.
44. Gilboa, E.; Eglitis, M. A.; Kantoff, P. W.; Anderson, F. Transfer and Expression of Cloned Genes Using Retroviral Vectors. Biotechniques 1986, 4, 504-512. JM980121Y