One-pot mild and efficient synthesis of [1,3]thiazino[3,2-a]indol-4-ones and their anti-proliferative activityElectronic supplementary information (ESI) available: Copies of NMR (1H & 13C) spectra of synthesized compounds 10, 17, and 19-34. See DOI: 10.1039/c9ob00500e
A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2- a ]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates in...
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Zusammenfassung: | A base mediated environmentally benign one-pot efficient methodology has been developed for the synthesis of [1,3]thiazino[3,2-
a
]indol-4-ones using indoline-2-thiones and propiolate esters in aqueous medium. The conjugate addition of thiones first results in ethyl (3-(indol-2-yl)thio)acrylates
in situ
, which subsequently undergoes intramolecular cyclization to produce indole-fused thiazin-4-ones in good to excellent yields. The cytotoxic screening of the synthesized compounds using MTT assay revealed the anti-proliferative nature of these frameworks against triple negative breast cancer cell lines with the highest activity emanating from 4
H
-[1,3]thiazino[3,2-
a
]indol-4-one and 8-methyl-2-propyl-4
H
-[1,3]thiazino[3,2-
a
]indol-4-one compounds.
One-pot synthesis of [1,3]thiazino[3,2-
a
]indol-4-one frameworks is developed in aqueous medium and the anti-proliferative activity of the synthesized compounds is evaluated against two triple negative breast cancer cell lines. |
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ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c9ob00500e |