Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
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
_version_ 1783498397969285120
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
work_keys_str_mv AT basionyebtesama synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT hassanallama synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT alamshanyzahram synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT abdrabouahmeda synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT abdelrahmanadelah synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT hassannassera synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues
AT elsayedwaela synthesisandcytotoxicactivityofnewthiazolopyrimidinesugarhydrazonesandtheirderivedacyclicnucleosideanalogues