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Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety
BACKGROUND: 1,2,4-Triazole derivatives have received much attention due to their versatile biological properties including antibacterial, antifungal, anticonvulsant, antiinflammatory, anticancer, and antiproliferative properties. 1,2,4-Triazole nucleus has been incorporated into a wide variety of th...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Springer
2012
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490741/ https://www.ncbi.nlm.nih.gov/pubmed/22759342 http://dx.doi.org/10.1186/2191-2858-2-26 |
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author | Li, Xiang Li, Xue-Qiang Liu, He-Mei Zhou, Xue-Zhang Shao, Zhi-Hui |
author_facet | Li, Xiang Li, Xue-Qiang Liu, He-Mei Zhou, Xue-Zhang Shao, Zhi-Hui |
author_sort | Li, Xiang |
collection | PubMed |
description | BACKGROUND: 1,2,4-Triazole derivatives have received much attention due to their versatile biological properties including antibacterial, antifungal, anticonvulsant, antiinflammatory, anticancer, and antiproliferative properties. 1,2,4-Triazole nucleus has been incorporated into a wide variety of therapeutically interesting molecules to transform them into better drugs. Schiff bases of 1,2,4-triazoles have also been found to possess extensive biological activities. On the other hand, γ-substituted butenolide moiety represents a biological important entity that is present in numerous biologically active natural products. RESULTS: We have described herein the synthesis of 12 hybrid 1,2,4-triazole Schiff bases bearing γ-substituted butenolide moiety. These compounds were synthesized by utilizing the tandem asymmetric Michael addition/elimination reaction as the key step. All the new compounds were evaluated for their in vitro anticancer activity. CONCLUSIONS: Tandem asymmetric Michael addition/elimination approach has offered an easy access to new chiral 1,2,4-triazole compounds 7a-7l. All these chiral 1,2,4-triazole derivatives exhibited good anticancer activities towards Hela. Of all the tested compounds, the chiral compound 7l with an IC(50) of 1.8 μM was found to be the most active. |
format | Online Article Text |
id | pubmed-3490741 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | Springer |
record_format | MEDLINE/PubMed |
spelling | pubmed-34907412012-11-07 Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety Li, Xiang Li, Xue-Qiang Liu, He-Mei Zhou, Xue-Zhang Shao, Zhi-Hui Org Med Chem Lett Original Article BACKGROUND: 1,2,4-Triazole derivatives have received much attention due to their versatile biological properties including antibacterial, antifungal, anticonvulsant, antiinflammatory, anticancer, and antiproliferative properties. 1,2,4-Triazole nucleus has been incorporated into a wide variety of therapeutically interesting molecules to transform them into better drugs. Schiff bases of 1,2,4-triazoles have also been found to possess extensive biological activities. On the other hand, γ-substituted butenolide moiety represents a biological important entity that is present in numerous biologically active natural products. RESULTS: We have described herein the synthesis of 12 hybrid 1,2,4-triazole Schiff bases bearing γ-substituted butenolide moiety. These compounds were synthesized by utilizing the tandem asymmetric Michael addition/elimination reaction as the key step. All the new compounds were evaluated for their in vitro anticancer activity. CONCLUSIONS: Tandem asymmetric Michael addition/elimination approach has offered an easy access to new chiral 1,2,4-triazole compounds 7a-7l. All these chiral 1,2,4-triazole derivatives exhibited good anticancer activities towards Hela. Of all the tested compounds, the chiral compound 7l with an IC(50) of 1.8 μM was found to be the most active. Springer 2012-07-03 /pmc/articles/PMC3490741/ /pubmed/22759342 http://dx.doi.org/10.1186/2191-2858-2-26 Text en Copyright ©2012 Li et al.; licensee Springer. http://creativecommons.org/licenses/by/2.0 This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Original Article Li, Xiang Li, Xue-Qiang Liu, He-Mei Zhou, Xue-Zhang Shao, Zhi-Hui Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title | Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title_full | Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title_fullStr | Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title_full_unstemmed | Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title_short | Synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole Schiff bases bearing γ-butenolide moiety |
title_sort | synthesis and evaluation of antitumor activities of novel chiral 1,2,4-triazole schiff bases bearing γ-butenolide moiety |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490741/ https://www.ncbi.nlm.nih.gov/pubmed/22759342 http://dx.doi.org/10.1186/2191-2858-2-26 |
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