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Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues
New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic d-galactosyl or d-xylosyl sugar moieties in addition to their per-O-acetylated derivatives were synthesized. Heterocyclization of the formed sugar hydrazones afforded the...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024276/ https://www.ncbi.nlm.nih.gov/pubmed/31963649 http://dx.doi.org/10.3390/molecules25020399 |
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author | Basiony, Ebtesam A. Hassan, Allam A. Al-Amshany, Zahra M. Abd-Rabou, Ahmed A. Abdel-Rahman, Adel A.-H. Hassan, Nasser A. El-Sayed, Wael A. |
author_facet | Basiony, Ebtesam A. Hassan, Allam A. Al-Amshany, Zahra M. Abd-Rabou, Ahmed A. Abdel-Rahman, Adel A.-H. Hassan, Nasser A. El-Sayed, Wael A. |
author_sort | Basiony, Ebtesam A. |
collection | PubMed |
description | New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic d-galactosyl or d-xylosyl sugar moieties in addition to their per-O-acetylated derivatives were synthesized. Heterocyclization of the formed sugar hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the cyclization process. The cytotoxic activity of the synthesized compounds was studied against human breast cancer MCF7 and MDA-MB-231 cell lines as well as human colorectal cancer HCT 116 and Caco-2 cell lines. High activities were revealed by compounds 1, 8, 10, 11, and 13 against Caco-2 and MCF7 cells in addition to moderate activities exhibited by other compounds against HCT116 or MDA-MB-231 cells. |
format | Online Article Text |
id | pubmed-7024276 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-70242762020-03-11 Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues Basiony, Ebtesam A. Hassan, Allam A. Al-Amshany, Zahra M. Abd-Rabou, Ahmed A. Abdel-Rahman, Adel A.-H. Hassan, Nasser A. El-Sayed, Wael A. Molecules Article New thienyl- or chlorophenyl-substituted thiazolopyrimidine derivatives and their derived sugar hydrazones incorporating acyclic d-galactosyl or d-xylosyl sugar moieties in addition to their per-O-acetylated derivatives were synthesized. Heterocyclization of the formed sugar hydrazones afforded the derived acyclic nucleoside analogues possessing the 1,3,4-oxadiazoline as modified nucleobase via acetylation followed by the cyclization process. The cytotoxic activity of the synthesized compounds was studied against human breast cancer MCF7 and MDA-MB-231 cell lines as well as human colorectal cancer HCT 116 and Caco-2 cell lines. High activities were revealed by compounds 1, 8, 10, 11, and 13 against Caco-2 and MCF7 cells in addition to moderate activities exhibited by other compounds against HCT116 or MDA-MB-231 cells. MDPI 2020-01-18 /pmc/articles/PMC7024276/ /pubmed/31963649 http://dx.doi.org/10.3390/molecules25020399 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Basiony, Ebtesam A. Hassan, Allam A. Al-Amshany, Zahra M. Abd-Rabou, Ahmed A. Abdel-Rahman, Adel A.-H. Hassan, Nasser A. El-Sayed, Wael A. Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title_full | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title_fullStr | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title_full_unstemmed | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title_short | Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues |
title_sort | synthesis and cytotoxic activity of new thiazolopyrimidine sugar hydrazones and their derived acyclic nucleoside analogues |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7024276/ https://www.ncbi.nlm.nih.gov/pubmed/31963649 http://dx.doi.org/10.3390/molecules25020399 |
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