Synthesis and selected immunological properties of substituted quino[3,2-b]benzo[1,4]thiazines

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 444-456

  Jeleń, Małgorzata ^a   Pluta, Krystian ^a   Zimecki, Michał ^b   Morak Młodawska, Beata ^a   Artym, Jolanta ^b   Kociȩba, Maja ^b  

^a MEDICAL UNIVERSITY OF SILESIA   (Poland)

^b INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

Author keywords

Anticancer activity; Antiproliferative activity; Azaphenothiazines; Phenothiazines; Thiazine ring formation

Indexed keywords

6 (1 METHYL 2 PIPERIDYLETHYL) 9 CHLOROQUINOBENZOTHIAZINE; 6 (1 METHYL 2 PIPERIDYLETHYL) 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 (1 METHYL 2 PIPERIDYLETHYL)QUINOBENZOTHIAZINE; 6 (1 PIPERIDYLETHYL) 9 CHLOROQUINOBENZOTHIAZINE; 6 (1 PIPERIDYLETHYL) 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 (1 PIPERIDYLETHYL)QUINOBENZOTHIAZINE; 6 (1 PYRROLIDYLETHYL) 9 CHLOROQUINOBENZOTHIAZINE; 6 (1 PYRROLIDYLETHYL)METHYLTHIOQUINOBENZOTHIAZINE; 6 (1 PYRROLIDYLETHYL)QUINOBENZOTHIAZINE; 6 (2 DIETHYLAMINOETHYL) 9 CHLOROQUINOBENZOTHIAZINE; 6 (2 DIETHYLAMINOETHYL) 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 (2 DIETHYLAMINOETHYL)QUINOBENZOTHIAZINE; 6 (3 DIMETHYLAMINO 2 METHYLPROPYL) 9 CHLOROQUINOBENZO; 6 (3 DIMETHYLAMINO 2 METHYLPROPYL) 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 (3 DIMETHYLAMINO 2 METHYLPROPYL)QUINOBENZOTHIAZINE; 6 (3 DIMETHYLAMINOPROPYL) 9 CHLOROQUINOBENZOTHIAZINE; 6 (3 DIMETHYLAMINOPROPYL) 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 (3 DIMETHYLAMINOPROPYL)QUINOBENZOTHIAZINE; 6 ACETYLAMINOBUTYL 9 CHLOROQUINOBENZOTHIAZINE; 6 CHLOROETHYLUREIDOBUTYL 9 METHYLTHIOQUINOBENZOTHIAZINE; 6 CHLOROETHYLUREIDOPROPYL 9 CHLOROQUINOBENZOTHIAZINE; 6 PHTHALIMIDOBUTYLQUINOBENZOTHIAZINE; 6 PHTHALIMIDOPROPYLQUINOBENZOTHIAZINE; 9 CHLORO 6 PHTHALIMIDOBUTYLQUINOBENZOTHIAZINE; 9 CHLORO 6 PHTHALIMIDOPROPYLQUINOBENZOTHIAZINE; 9 METHYLTHIO 6 PHTHALIMIDOPROPYLQUINOBENZOTHIAZIN; ANTINEOPLASTIC AGENT; CISPLATIN; THIAZINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBODY DEPENDENT CELLULAR CYTOTOXICITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION; COLON CANCER; COMPETITIVE INHIBITION; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; PERIPHERAL BLOOD MONONUCLEAR CELL; PHARMACOPHORE; SKIN CARCINOMA; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ANIMALS; CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LEUKOCYTES, MONONUCLEAR; LIPOPOLYSACCHARIDES; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PHYTOHEMAGGLUTININS; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84875017901     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.023     Document Type: Article

References (32)

1. R.R. Gupta, and M. Kumar Synthesis, properties and reactions of phenothiazines R.R. Gupta, Phenothiazines and 1,4-Benzothiazines-Chemical and Biological Aspects 1988 Elsevier 1 161
2. N. Motohashi, M. Kawase, S. Saito, and H. Sakagami Antitumor potential and possible targets of phenothiazine-related compounds Curr. Drug Targets 1 2000 237 245
3. N. Motohashi, M. Kawase, K. Satoh, and H. Sakagami Cytotoxic potential of phenothiazines Curr. Drug Targets 7 2006 1055 1066
4. K. Pluta, B. Morak-Młodawska, and M. Jelenacute Recent progress in biological activities of synthesized phenothiazines Eur. J. Med. Chem. 46 2011 3179 3189
5. J.J. Aaron, M.D. Gaye Seye, S. Trajkovska, and N. Motohashi Bioactive Phenothiazines and Benzo[a]phenothiazines: spectroscopic studies and biological and biomedical properties and applications Top. Heterocycl. Chem. 16 2009 153 231 Springer-Verlag, Berlin
6. A. Dasgupta, S.G. Dastridara, Y. Shirataki, and N. Motohashi Antibacterial activity of artificial phenothiazines and isoflavones from plants Top. Heterocycl. Chem. 15 2008 67 132 Springer-Verlag, Berlin
7. K. Pluta, B. Morak-Młodawska, and M. Jelenacute Synthesis and properties of diaza-, triaza- and tetraazaphenothiazines J. Heterocycl. Chem. 46 2009 355 391
8. A. Hilgeroth, A. Molnar, J. Molnar, and B. Voigt Correlation of calculated molecular orbital energies of some phenothiazine compounds with MDR reversal properties Eur. J. Med. Chem. 41 2006 548 551
9. Y.S. Sadandam, M.M. Shetty, and A. Bhaskar Rao 10H-Phenothiazines: a new class of enzyme inhibitors for inflammatory diseases Eur. J. Med. Chem. 44 2009 197 202
10. V.K. Tandon, H.K. Maurya, A. Tripathi, G.B. Shiva Keshava, P.K. Shukla, P. Srivastava, and D. Panda 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: synthesis and biological evaluation as potential antiproliferative and antifungal agents Eur. J. Med. Chem. 44 2009 1086 1092
11. K. Pluta, A. Maślankiewicz, and M. Szmielew N, N-Dialkylaminoalkylsubstituted quinobenzo[1,4]thiazines and diquino[1,4] thiazines Phosphorus Sulfur Silicon 159 2000 79 86
12. B. Morak, and K. Pluta Synthesis of novel dipyrido-1,4-thiazines Heterocycles 71 2007 1347 1361
13. M. Nowak, K. Pluta, K. Suwińska, and L. Straver Synthesis of new pentacyclic diquinothiazines J. Heterocycl. Chem. 44 2007 543 550
14. M. Jeleń, and K. Pluta Synthesis of 6-aminoalkyldiquino-1,4- thiazines and their acyl and sulfonyl derivatives Heterocycles 75 2008 859 870
15. B. Morak-Młodawska, K. Suwińska, K. Pluta, and M. Jeleń 10-(3′-Nitro-4′-pyridyl)-1,8-diazaphenothiazine as the double Smiles rearrangement J. Mol. Struct. 1015 2012 94 98
16. K. Pluta, M. Jeleń, B. Morak-Młodawska, M. Zimecki, J. Artym, and M. Kociȩba Anticancer activity of newly synthesized azaphenothiazines in NCI's anticancer screening Pharmacol. Rep. 62 2010 319 332
17. M. Zimecki, J. Artym, M. Kociȩba, K. Pluta, B. Morak-Młodawska, and M. Jeleń Immunosupressive activities of newly synthesized azaphenothiazines in human and mouse models Cell. Mol. Biol. Lett. 14 2009 622 635
18. A. Ziȩba, A. Maślankiewicz, and K. Suwińska 1-Alkyl-4-(arylamino)quinobenzothiazinium-3-thiolates and 7-alkyl-12H-quino[3,4- b]-1,4-benzothiazinium salts Eur. J. Org. Chem. 2000 2947 2953
19. A. Ziȩba, A. Sochanik, A. Szurko, M. Rams, A. Mrozek, and P. Cmoch Synthesis and in vitro antiproliferative activity of 5-alkyl-12H-quino[3,4-b] benzothiazinium salts Eur. J. Med. Chem. 45 2010 4733 4739
20. M. Kumar, K. Sharma, R.M. Samarth, and A. Kumar Synthesis and antioxidant activity of quinolinobenzothiazinones Eur. J. Med. Chem. 45 2010 4467 4472
21. M. Jeleń, and K. Pluta Synthesis of quinobenzo-1,4-thiazines from diquino-1,4-dithiin and 2,2′-dichloro-3,3′-diquinolinyl disulfide Heterocycles 78 2009 2325 2336
22. B.A. Dreikorn, F.E. Elsasser, and G.P. Jourdan Reaction of thionyl chloride with 3,4-dihydro-2(1H)-quinolone J. Org. Chem. 44 1979 877 880
23. M. Nowak, K. Pluta, and K. Suwińska Synthesis of novel heteropentacenes containing nitrogen, sulfur and oxygen or selenium New J. Chem. 26 2002 1216 1220
24. M. Jeleń, K. Suwińska, C. Besnard, K. Pluta, and B. Morak-Młodawska The structures of 8- and 10-trifluoromethylquino[3,2-b] benzo[1,4]thiazines and their benzyl derivatives Heterocycles 85 2012 2281 2290
25. M. Jeleń, K. Suwińska, K. Pluta, and B. Morak-Młodawska N-[4-(chloroquino[3,2-b]benzo[1,4]thiazin-6-yl)butyl] acetamide Acta Cystallogr. E68 2012 o3324 o3325
26. G.E. Umbach, S.E. Singletary, B. Tomasovic, G. Spitzer, V. Hug, and B. Drevinko Dose-survival curves of cis-platinum, melphalan, and velban in human granulocyte/macrophage progenitor cells Int. J. Cell. Cloning 2 1984 335 340
27. X. Yao, K. Panichpisal, N. Kurtzman, and K. Nugent Cisplatin nephrotoxicity: a review Am. J. Med. Sci. 334 2007 115 124
28. N. Motohashi, T. Kurihara, H. Sakagami, D. Szabo, K. Csuri, and J. Molnár Chemical structure and tumor type specificity of "half-mustard type" phenothiazines Anticancer Res. 19 1999 1859 1864
29. S. Nagy, G. Argyelan, J. Molnár, M. Kawase, and N. Motohashi Antitumor activity of phenothiazine-related compounds Anticancer Res. 16 1996 1915 1918
30. H. Sakagami, H. Takahashi, H. Yoshida, M. Yamamura, K. Fukuchi, K. Gomi, N. Motohashi, and M. Takeda Induction of DNA fragmentation in human Myelogenous Leukaemic cell lines by phenothiazine-related compounds Anticancer Res. 15 1995 2533 2540
31. M.B. Hansen, S.E. Nielsen, and K. Berg Reexamination and further development of a precise and rapid dye method for measuring cell growth/cell kill J. Immunol. Methods 119 1989 203 210
32. T. Espevik, and J. Nissen-Meyer A highly sensitive cell line WEHI 164 clone 13, for measuring cytotoxic factor/tumor necrosis factor from human monocytes J. Immunol. Methods 95 1986 99 103