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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creator | Rhodes, Steven Short, Spencer Sharma, Sidhika Kaur, Ramneet Jha, Mukund |
description | 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. |
doi_str_mv | 10.1039/c9ob00500e |
format | Article |
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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.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob00500e</identifier><creationdate>2019-04</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Rhodes, Steven</creatorcontrib><creatorcontrib>Short, Spencer</creatorcontrib><creatorcontrib>Sharma, Sidhika</creatorcontrib><creatorcontrib>Kaur, Ramneet</creatorcontrib><creatorcontrib>Jha, Mukund</creatorcontrib><title>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</title><description>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
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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.</abstract><doi>10.1039/c9ob00500e</doi><tpages>7</tpages></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
title | 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 |
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