Synthesis and selected immunological properties of 10-substituted 1,8-diazaphenothiazines

Medicinal Chemistry Research

Volumn 24, Issue 4, 2015, Pages 1408-1418

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

^a MEDICAL UNIVERSITY OF SILESIA   (Poland)

^b INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

Author keywords

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

Indexed keywords

EID: 84939898373     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-014-1220-9     Document Type: Article

References (30)

1. Aaron JJ, Gaye Seye MD, Trajkovska S, Motohashi N (2009) Bioactive Phenothiazines and Benzo[a]phenothiazines: spectroscopic studies and biological and biomedical properties and applications. Topics in Heterocyclic Chemistry, vol 16. Springer-Verlag, Berlin, pp 153-231
2. Dasgupta A, Dastridara SG, Shirataki Y, Motohashi N (2008) Antibacterial activity of artificial phenothiazines and isoflavones from plants. Topics in Heterocyclic Chemistry, vol 15. Springer-Verlag, Berlin, pp 67-132
3. Espevik T, Nissen-Meyer J (1986) A highly sensitive cell line WEHI 164 clone 13, for measuring cytotoxic factor/tumor necrosis factor from human monocytes. J Immunol Methods 95:99-103
4. Guadagni F, Ferroni P, Palmirotta R, Portarena I, Formica V, Roselli M (2007) Review. TNF/VEGF cross-talk in chronic inflammation-related cancer initiation and progression: an early target in anticancer therapeutic strategy. In Vivo 21:147-161
5. Gupta RR, Kumar M (1988) Synthesis, properties and reactions of phenothiazines. In: Gupta RR (ed) Phenothiazines and 1,4-benzothiazines: chemical and biological aspects. Elsevier, Amsterdam, pp 1-161
6. Hansen MB, Nielsen SE, Berg K (1989) Reexamination and further development of a precise and rapid dye method for measuring cell growth/cell kill. J Immunol Methods 119:203-210
7. Kopp E, Strell M (1962) Über 2,7-Diazaphenothiazin. Reaktionen in der pyridinreihe. Arch Pharm 295:99-107
8. Kopp E, Strell M, Janson R (1963) Verfahren zur Herstellung von 2,7-Diazaphenothiazinen. German Patent DE 1(147):235
9. Maki Y (1957) Sulfur-containing pyridine derivatives. Smiles rearrangement in pyridine derivatives and synthesis of azaphenothiazine derivatives. Yakugaku Zasshi 77:485-490
10. Morak B, Pluta K (2007) Synthesis of novel dipyrido-1,4-thiazines. Heterocycles 71:1347-1361
11. Morak B, Pluta K, Suwinska K (2002) Unexpected simple route to novel dipyrido-1,4-thiazines. Heterocycl Commun 8:331-334
12. Morak-Młodawska B, Pluta K, Matralis AN, Kourounakis AP (2010) Antioxidant activity of newly synthesized 2,7-diazaphenothiazines. Archiv Pharm Chem Life Sci 343:268-273
13. Morak-Młodawska B, Suwińska K, Pluta K, Jeleń M (2012) 10-(3′Nitro-4′pyridyl)-1,8-diazaphenothiazine as the double Smiles rearrangement. J Mol Struct 1015:94-98
14. Motohashi N, Kawase M, Saito S, Sakagami H (2000) Antitumor potential and possible targets of phenothiazine-related compounds. Curr Drug Targets 1:237-245
15. Motohashi N, Kawase M, Satoh K, Sakagami H (2006) Cytotoxic potential of phenothiazines. Curr Drug Targets 7:1055-1066
16. Okafor C (1967) Studies in the heterocyclic series. A novel diazaphenothiazine system. J Org Chem 32:2006-2007
17. Pluta K, Jeleń M, Morak-Młodawska B, Zimecki M, Artym J, Kocięba M (2010) Anticancer activity of newly synthesized azaphenothiazines in NCI's anticancer screening. Pharmacol Rep 62:319-332
18. Pluta K, Morak-Młodawska B, Jeleń M (2009) Synthesis and properties of diaza-, triaza- and tetraazaphenothiazines. J Heterocycl Chem 46:355-391
19. Pluta K, Morak-Młodawska B, Jeleń M (2011) Recent progress in biological activities of synthesized phenothiazines. Eur J Med Chem 46:3179-3189
20. Rath S (1957) Dimethylaminopropyl-dipyridothiazane. US Patent 2,789,978
21. Rodig OR, Collier RE, Schlatzer RK (1966) Pyridine chemistry. Further studies on the Smiles rearrangement of the 3-amino-2,2′dipyridyl sulfide system. The synthesis of some 1,6-diazaphenothiazines. J Med Chem 9:116-120
22. Sadandam YS, Shetty MM, Bhaskar Rao A (2009) 10H-Phenothiazines: a new class of enzyme inhibitors for inflammatory diseases. Eur J Med Chem 44:197-202
23. Silberg IA, Cormos G, Oniciu DC (2006) Retrosynthetic approach to the synthesis of phenothiazines. In Advances in heterocyclic chemistry; Katritzky AR (ed.), Elsevier, New York, vol 90, pp 205-237, and Biological evaluation as potential antiproliferative and antifungal agents. Eur J Med Chem 44:1086-1092
24. Takahashi T, Maki Y (1958a) Smiles rearrangement in pyridine derivatives and synthesis of benzopyrido- and dipyridothiazine derivatives. Yakugaku Zasshi 78:417-421
25. Takahashi T, Maki Y (1958b) Sulfur-containing pyridine derivatives. Smiles rearrangement of pyridine derivatives and synthesis of benzopyrido- and dipyrido-1,4-thiazine derivatives. Chem Pharm Bull 6:369-373
26. Tandon VK, Maurya HK, Tripathi A, Shiva Keshava GB, Shukla PK, Srivastava P, Panda D (2009) 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: synthesis. Eur J Med Chem 44(3):1086-1092
27. Umbach GE, Singletary SE, Tomasovic B, Spitzer G, Hug V, Drevinko B (1984) Dose-survival curves of cis-platinum, melphalan, and velban in human granulocyte/macrophage progenitor cells. Int J Cell Cloning 2:335-340
28. Wajant H (2009) The role of TNF in cancer. Results Probl Cell Differ 49:1-15
29. Yao X, Panichpisal K, Kurtzman N, Nugent K (2007) Cisplatin nephrotoxicity: a review. Am J Med Sci 334:12-115
30. Zimecki M, Artym J, Kocięba M, Pluta K, Morak-Młodawska B, Jeleń M (2009) Immunosupressive activities of newly synthesized azaphenothiazines in human and mouse models. Cell Mol Biol Lett 14:622-635