Synthesis and anticancer activity of thiosubstituted purines

New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vit...

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Autores principales: Kowalska, Alicja, Latocha, Małgorzata, Pluta, Krystian
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer US 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4491105/
https://www.ncbi.nlm.nih.gov/pubmed/26167104
http://dx.doi.org/10.1007/s00044-015-1364-2
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author Kowalska, Alicja
Latocha, Małgorzata
Pluta, Krystian
author_facet Kowalska, Alicja
Latocha, Małgorzata
Pluta, Krystian
author_sort Kowalska, Alicja
collection PubMed
description New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vitro against three cell lines: glioblastoma SNB-19, melanoma C-32, and human ductal breast epithelial tumor T47D. 2-Chloro-7-methyl-6-pyrrolidinobutynylthiopurine (5b) was the most potent compound against SBN-19 and C-32 cell lines with the activity similar to cisplatin (EC(50) = 5.00 and 7.58 μg/ml, respectively). The dialkylaminoalkylthio derivatives (4b, 4c, 4e, and 4f) showed good activity against SBN-19 cell line (EC(50) < 10 μg/ml). The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines. The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines. All studied thiopurines were less toxic than cisplatin. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00044-015-1364-2) contains supplementary material, which is available to authorized users.
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spelling pubmed-44911052015-07-08 Synthesis and anticancer activity of thiosubstituted purines Kowalska, Alicja Latocha, Małgorzata Pluta, Krystian Med Chem Res Original Research New thiopurines with the propargylthio, pyrrolidinobutynylthio, sulfenamide, and sulfonamide groups in the pyrimidine ring were synthesized. The anticancer activity of these compounds and previously obtained 2- or 6-substituted azathioprine analogs and dialkylaminoalkylthiopurines were tested in vitro against three cell lines: glioblastoma SNB-19, melanoma C-32, and human ductal breast epithelial tumor T47D. 2-Chloro-7-methyl-6-pyrrolidinobutynylthiopurine (5b) was the most potent compound against SBN-19 and C-32 cell lines with the activity similar to cisplatin (EC(50) = 5.00 and 7.58 μg/ml, respectively). The dialkylaminoalkylthio derivatives (4b, 4c, 4e, and 4f) showed good activity against SBN-19 cell line (EC(50) < 10 μg/ml). The azathioprine analogs (2a, 2b, and 3a) were more active than azathioprine against SBN-19 and C-32 cell lines. The sulfenamide and sulfonamide derivatives of purine were very weak active against tested cell lines. All studied thiopurines were less toxic than cisplatin. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00044-015-1364-2) contains supplementary material, which is available to authorized users. Springer US 2015-03-25 2015 /pmc/articles/PMC4491105/ /pubmed/26167104 http://dx.doi.org/10.1007/s00044-015-1364-2 Text en © The Author(s) 2015 https://creativecommons.org/licenses/by/4.0/ Open AccessThis article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and the source are credited.
spellingShingle Original Research
Kowalska, Alicja
Latocha, Małgorzata
Pluta, Krystian
Synthesis and anticancer activity of thiosubstituted purines
title Synthesis and anticancer activity of thiosubstituted purines
title_full Synthesis and anticancer activity of thiosubstituted purines
title_fullStr Synthesis and anticancer activity of thiosubstituted purines
title_full_unstemmed Synthesis and anticancer activity of thiosubstituted purines
title_short Synthesis and anticancer activity of thiosubstituted purines
title_sort synthesis and anticancer activity of thiosubstituted purines
topic Original Research
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4491105/
https://www.ncbi.nlm.nih.gov/pubmed/26167104
http://dx.doi.org/10.1007/s00044-015-1364-2
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