Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety

Novel 11-substituted 3,11-dihydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]-thiazole-2,5,10-triones 4a–i were synthesized in 75–90% yields via the hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with 1,4-naphthoquinone. The synthesized compounds were evaluated for their antineoplas...

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Autores principales: Atamanyuk, Dmytro, Zimenkovsky, Borys, Atamanyuk, Vasyl, Nektegayev, Ihor, Lesyk, Roman
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Österreichische Apotheker-Verlagsgesellschaft 2013
Materias:
Research Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3700073/
https://www.ncbi.nlm.nih.gov/pubmed/23833711
http://dx.doi.org/10.3797/scipharm.1301-13
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author Atamanyuk, Dmytro
Zimenkovsky, Borys
Atamanyuk, Vasyl
Nektegayev, Ihor
Lesyk, Roman
author_facet Atamanyuk, Dmytro
Zimenkovsky, Borys
Atamanyuk, Vasyl
Nektegayev, Ihor
Lesyk, Roman
author_sort Atamanyuk, Dmytro
collection PubMed
description Novel 11-substituted 3,11-dihydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]-thiazole-2,5,10-triones 4a–i were synthesized in 75–90% yields via the hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with 1,4-naphthoquinone. The synthesized compounds were evaluated for their antineoplastic and antimycobacterial activities. A moderate selectivity against melanoma cancer cells (GI(50) (UACC-257-melanoma) = 0.22 μM) was demonstrated for 4i, whereas derivatives 4a, 4c, 4g, and 4h showed promising antimycobacterial activity at a low toxicity level.
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spelling pubmed-37000732013-07-05 Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety Atamanyuk, Dmytro Zimenkovsky, Borys Atamanyuk, Vasyl Nektegayev, Ihor Lesyk, Roman Sci Pharm Research Article Novel 11-substituted 3,11-dihydro-2H-benzo[6,7]thiochromeno[2,3-d][1,3]-thiazole-2,5,10-triones 4a–i were synthesized in 75–90% yields via the hetero-Diels-Alder reaction of 5-arylidene-4-thioxo-2-thiazolidinones with 1,4-naphthoquinone. The synthesized compounds were evaluated for their antineoplastic and antimycobacterial activities. A moderate selectivity against melanoma cancer cells (GI(50) (UACC-257-melanoma) = 0.22 μM) was demonstrated for 4i, whereas derivatives 4a, 4c, 4g, and 4h showed promising antimycobacterial activity at a low toxicity level. Österreichische Apotheker-Verlagsgesellschaft 2013 2013-02-04 /pmc/articles/PMC3700073/ /pubmed/23833711 http://dx.doi.org/10.3797/scipharm.1301-13 Text en © 2013 Atamanyuk et al.; licensee Österreichische Apotheker-Verlagsgesellschaft m. b. H., Vienna, Austria. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Article
Atamanyuk, Dmytro
Zimenkovsky, Borys
Atamanyuk, Vasyl
Nektegayev, Ihor
Lesyk, Roman
Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title_full Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title_fullStr Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title_full_unstemmed Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title_short Synthesis and Biological Activity of New Thiopyrano[2,3-d]thiazoles Containing a Naphthoquinone Moiety
title_sort synthesis and biological activity of new thiopyrano[2,3-d]thiazoles containing a naphthoquinone moiety
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3700073/
https://www.ncbi.nlm.nih.gov/pubmed/23833711
http://dx.doi.org/10.3797/scipharm.1301-13
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