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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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Springer US
2015
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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. |
format | Online Article Text |
id | pubmed-4491105 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Springer US |
record_format | MEDLINE/PubMed |
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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