{"database":"biostudies-literature","file_versions":[],"scores":{"citationCount":0,"reanalysisCount":0,"viewCount":40,"searchCount":0},"additional":{"omics_type":["Unknown"],"volume":["25(11)"],"submitter":["Morak-Mlodawska B"],"pubmed_abstract":["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 <i>N</i>-methylated product. Some 10-substituted 1,6-diazaphenothizines (<b>5</b>, <b>10</b>, <b>12</b>, <b>13</b>) 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."],"journal":["Medicinal chemistry research : an international journal for rapid communications on design and mechanisms of action of biologically active agents"],"pagination":["2425-2433"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5075014"],"repository":["biostudies-literature"],"pubmed_title":["Synthesis, spectroscopic characterization, and anticancer activity of new 10-substituted 1,6-diazaphenothiazines."],"pmcid":["PMC5075014"],"pubmed_authors":["Morak-Mlodawska B","Pluta K","Latocha M","Jelen M"],"view_count":["40"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis, spectroscopic characterization, and anticancer activity of new 10-substituted 1,6-diazaphenothiazines.","description":"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 <i>N</i>-methylated product. Some 10-substituted 1,6-diazaphenothizines (<b>5</b>, <b>10</b>, <b>12</b>, <b>13</b>) 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.","dates":{"release":"2016-01-01T00:00:00Z","publication":"2016","modification":"2024-11-20T14:16:38.638Z","creation":"2019-03-27T02:27:19Z"},"accession":"S-EPMC5075014","cross_references":{"pubmed":["27818603"],"doi":["10.1007/s00044-016-1646-3"]}}