Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives

Journal of Medicinal Chemistry

Volumn 45, Issue 21, 2002, Pages 4689-4694

  Chen, Yeh Long ^a   Lu, Chih Ming ^a   Chen, I Li ^a   Tsao, Lo Ti ^b   Wang, Jih Pyang ^b  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

9 ANILINOACRIDINE DERIVATIVE; 9 PHENOXYACRIDINE DERIVATIVE; ACRIDINE DERIVATIVE; BETA GLUCURONIDASE; LYSOSOME ENZYME; MEPACRINE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOTOXICITY; DRUG SYNTHESIS; IC 50; MACROPHAGE; MAST CELL DEGRANULATION; MICROGLIA; NEUTROPHIL; NONHUMAN; RAT;

ACRIDINES; AMSACRINE; ANILINE COMPOUNDS; ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTINEOPLASTIC AGENTS; CELL DEGRANULATION; CELLS, CULTURED; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MACROPHAGES; MAST CELLS; MICE; NEUTROPHILS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0037057563     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020102v     Document Type: Article

References (34)

1. Schwartz, L. B.; Austen, K. F. Structural and Function of the Chemical Mediators of Mast Cells. Prog. Allergy 1984, 34, 217-235.
2. Menninger, H.; Putzier, R.; Mohr, W.; Weissinghage, D.; Tillmann, K. Granulocyte Elastase at the Site of Cartilage Erosion by Rheumatoid Synovial Tissue. J. Rheumatol. 1980, 39, 145-156.
3. Hyers, T. M.; Fowler, A. A. Adult Respiratory Distress Syndrome: Causes, Morbidity, and Mortality. Fed. Proc., Fed. Am. Soc. Exp. Biol. 1986, 45, 25-29.
4. Solbach, W.; Moll, H.; Rollinghoff, M. Lymphocytes Play the Music but the Macrophage Calls the Tune. Immunol. Today 1991, 12, 4-6.
5. Beutler, G.; Cerami, A. Tumor Necrosis Factor, Cachexia, Shock, and Inflammation: A Common Mediator. Annu. Rev. Biochem. 1988, 57, 505-518.
6. Gehrman, J.; Mastsumoto, Y.; Kreutzberg, G. W. Microglia: Intrinsic Immunoeffector Cell of the Brain. Brain Res. Rev. 1995, 20, 269-287.
7. McGeer, P. L.; McGeer, E. G. The Inflammatory Response System of Brain: Implications for Therapy of Alzheimer and Other Neurodegenerative Disease. Brain Res. Rev. 1995, 21, 195-218.
8. Wakelin, L. P. G.; Adams, A.; Denny, W. A. Kinetic Studies of the Binding of Acridinecarboxamide Topoisomerase Poisons to DNA: Implications for Mode of Binding of Ligands with Uncharged Chromophores. J. Med. Chem. 2002, 45, 894-910.
9. Bailly, C.; Denny, W. A.; Mellor, L. E.; Wakelin, L. P. G.; Waring, M. J. Sequence Specificity of the Binding of 9-Aminoacridine-carboxamide and Amsacrine-4-carboxamide to DNA Studied by DNase-I Footprinting. Biochemistry 1992, 31, 3514-3524.
10. Gamage, S. A.; Tepsiri, N.; Wilairat, P.; Wojcik, S. J.; Figgitt, D. P.; Ralph, R. K.; Denny, W. A. Synthesis and In Vitro Evaluation of 9-Anilino-3,6-diaminoacridines Active against a Multidrug-Resistant Strain of Malaria Parasite Plasmodium Falciparum. J. Med. Chem. 1994, 37, 1486-1494.
11. McConnaughie, A. W.; Jenkins, T. C. Novel Acridine-triazenes as Prototype Combilexins: Synthesis, DNA Binding and Biological Activity. J. Med. Chem. 1995, 38, 3488-3501.
12. Gamage, S. A.; Figgitt, D. P.; Wojcik, S. J.; Ralph, R. K.; Ransijn, A.; Mauel, J.; Yardley, V.; Snowdon, D.; Croft, S. L.; Denny, W. A. Structure-Activity Relationships for the Antileishmanial and Antitrypanosomal Activities of 1′-Substituted 9-Anilinoacridines. J. Med. Chem. 1997, 40, 2634-2642.
13. Amellal, M.; Landry, Y. Lanthaides Are Transported by Ionophore A23187 and Mimic Calcium in the Histamine Secretion Process. Br. J. Pharmacol. 1983, 80, 365-370.
14. Chakravarty, N.; Nielsen, E. H. Histamine Release From Saponin-Permeabilized Rat Mast Cells by Calcium. Agents Actions 1986, 18, 65-67.
15. Yu, N.; Maciejewski-Lenoir, D.; Bloom, F. E.; Magistretti, P. J. Tumor Necrosis Nactor-alpha and Interleukin-1 Alpha Enhance Glucose Utilization by Astrocytes: Involvement of Phospholipase A2. Mol. Pharmacol. 1995, 48, 550-558.
16. 2-Arachidonate Metabolism System. Life Sci. 1997, 61, 557-566.
17. Denny, W. A.; Cain, B. F.; Hansch, G. J.; Panthananickal, A.; Leo, A. Potential Antitumor Agents. 36. Quanitative Relationships between Experimental Antitumor Activity, Toxicity, and Structure for the General Class of 9-Anilinoacridine Antitumor Agents. J. Med. Chem. 1982, 25, 276-300.
18. Atwell, G. J.; Cain, B. F.; Seelye, R. N. Potential Antitumor Agents. 12. 9-Anilinoacridine. J. Med. Chem. 1972, 15, 611-615.
19. Zwelling, L. A.; Michaels, S.; Erickson, L. C.; Ungerleider, R. S.; Nichols, M.; Kohn, K. W. Protein-Associated Deoxyribonucleic Acid Strand Breaks in L1210 Cells Treated with the Deoxyribonucleic Acid Intercalating Agents 4Κ-(9Acridinylamino)methane-sulfon-m-anisidide and Adriamycin. Biochemistry 1981, 20, 6553-6563.
20. Bonse, S.; Santelli-Rouvier, C.; Barbe, J.; Krauth-Siegel, R. L. Inhibition of Trypanosoma Cruzi Trypanothione Reductase by Acridines: Kinetic Studies and Structure-Activity Relationships. J. Med. Chem. 1999, 42, 5448-5454.
21. Baker, B. R.; Johnson, M. A. Irreversible Enzyme Inhibititors. CXI. Candidate Active-Site-Directed Irreversible Inhibitors of Dihydrofolic Reductase Derived from 4,6-Diamino-1,2-dihydro1-phenyl-s-triazines. J. Heterocycl. Chem. 1967, 4, 507-510.
22. Hu, M. K. Synthesis and In-vitro Anticancer Evaluation of Bis Tacrine Congeners. J. Pharm. Pharmacol. 2001, 53, 83-88.
23. Douglas, W. W. Histamine and 5-Hydroxytryptamine (Serotonin) and Their Anatgonists. In The Pharmacological Basis of Therapeutics; Gilman, A. G., et al., Eds.; Pergamon Press: New York, 1980; pp 609-646.
24. Baggiolini, M. Phagocyte Activation and Its Modulation by Drugs. In Handbook of Inflammation; Glynn, J. E., et al., Eds.; Elsevier Press: Amsterdam, 1985; Vol. 5, pp 117-135.
25. Smith, R. J.; Bowman, B. J.; Iden, S. S. Effects of Trifluoperazine on Human Neutrophil Function. Immunology 1981, 44, 677-684.
26. Ochs, D. L.; Reed, P. W. Inhibition of the Neutrophil Oxidative Burst and Degranulation by Phenothiazines. Biochem. Biophys. Res. Commun. 1981, 102, 958-962.
27. Han, J.; Thompson, P.; Beutler, B. Dexamethasone and Pentoxifylline Inhibit Endotoxin-Induced Cachectin/Tumor Necrosis Factor Synthesis at Separate Points in the Signaling Pathway. J. Exp. Med. 1990, 172, 391-394.
28. Monks, A.; Scuderio, D.; Skehan, P.; Shoemaker, R.; Paull, K.; Vistica, D.; Hose, C.; Langlay, J.; Cronise, P.; Vaigro-Wolff, A.; Gray-Goodrich, M.; Campbell, H.; Mayo, J.; Boyd, M. Feasibility of a High-Flux Anticancer Drug Screen Using a Diverse Panel of Cultured Human Tumor Cell Lines. J. Natl. Cancer Inst. 1991, 83, 757-766.
29. 2 Receptor Antagonist, Is Due to Mast Cell Degranulation. Eur. J. Pharmacol. 1989, 161, 143-149.
30. Barrett, A. J. In Lysosomes. A Laboratory Handbook; Dingle, J. T., Ed.; Elsevier Press: Amsterdam, 1972; pp 118-120.
31. Håkanson, R.; Rönnberg, A. L. Improved Fluorometric Assay of Histamine. Anal. Biochem. 1974, 60, 560-567.
32. Wang, J. P.; Raung, S. L.; Kuo, Y. H.; Teng, C. M. Daphnoretin-Induced Respiratory Burst in Neutrophils Is, Probably, Mainly through Protein Kinase C Activation. Eur. J. Pharmacol. 1995, 288, 341-348.
33. Absolom, D. R. Basic Methods for the Study of Phagocytosis. Methods Enzymol. 1986, 132, 92-179.
34. Corradin, S. B.; Manuel, J.; Donini, S. D.; Quattrocchi, E.; Ricciardi-Castagnoli, P. Inducible Nitric Oxide Synthase Activity of Cloned Murine Microglial Cells. Glia 1993, 7, 255-262.