Synthesis, spectroscopic characterization, and anticancer activity of new 10-substituted 1,6-diazaphenothiazinesReportar como inadecuado

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Medicinal Chemistry Research

, Volume 25, Issue 11, pp 2425–2433

First Online: 04 August 2016Received: 06 July 2015Accepted: 04 July 2016


New phenothiazine derivatives as 10-substituted dipyridothiazines of the 1,6-diazaphenothiazine structure were obtained in the cyclization reaction of 3-amino-3′-nitro-2,2′-dipyridinyl sulfide and 3,3′-dinitro-2,2′-dipyridinyl disulfide, and in the reaction of 2-chloro-3-ntropyridine with sodium 3-amino-2-pyridinethiolate followed by various alkylation and arylation reactions. The reaction of the thiazine ring formation ran via the Smiles rearrangement of the S-N type. As the alkylation reactions could proceed at the thiazine, azine or both nitrogen atoms, the product structure elucidation was based on the 2D NMR Rotating-frame Overhauser Effect Spectroscopy, Correlated Spectroscopy, Heteronuclear Single Quantum Coherence, and Heteronuclear Multiple Bond Correlation spectra of the N-methylated product. Some 10-substituted 1,6-diazaphenothizines 5 , 10 , 12 , 13 were at least anticancer active against melanoma C-32 and breast cancer MCF-7 cell lines as a reference drug – cisplatin. The monoazaphenothiazine drug, prothipendyl, turned out to be less active than least 6 derivatives of the 1,6-diazaphenothiazine structure.

KeywordsPhenothiazines Dipyridothiazines NMR structure elucidation 2D NMR spectra The Smiles rearrangement Anticancer activity  Download fulltext PDF

Autor: Beata Morak-Młodawska - Krystian Pluta - Małgorzata Latocha - Małgorzata Jeleń


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