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Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids
Triazoles and quinazolinones are important heterocyclic structures with diverse biological properties including cytotoxic, antibacterial, antifungal and anticonvulsant activities. Due to valuable cytotoxic effects of both triazole and quinazoline derivatives, in this study a series of quinazolinone-...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Wolters Kluwer - Medknow
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6791177/ https://www.ncbi.nlm.nih.gov/pubmed/31620189 http://dx.doi.org/10.4103/1735-5362.253360 |
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author | Hassanzadeh, Farshid Sadeghi-aliabadi, Hojjat Nikooei, Shadan Jafari, Elham Vaseghi, Golnaz |
author_facet | Hassanzadeh, Farshid Sadeghi-aliabadi, Hojjat Nikooei, Shadan Jafari, Elham Vaseghi, Golnaz |
author_sort | Hassanzadeh, Farshid |
collection | PubMed |
description | Triazoles and quinazolinones are important heterocyclic structures with diverse biological properties including cytotoxic, antibacterial, antifungal and anticonvulsant activities. Due to valuable cytotoxic effects of both triazole and quinazoline derivatives, in this study a series of quinazolinone-triazole hybrids were synthesized in a multiple-step reaction procedure. 3-Amino-quinazolinone derivatives were treated with chloroacetyl chloride in the presence of dichloromethane/triethylamine to afford 2-chloro -N-(4-oxo-2- quinazolin3 (3H)-yl) acetamide derivatives. The reaction of resultants with 4-mehyl-4-H-1, 2, 4-triazole-3- thiol in dry acetone and potassium carbonate led to the formation of final products. Synthesized compounds were evaluated for their cytotoxic effects against MCF-7 and Hela cell lines using MTT colorimetric assay. Amongst tested compounds, 6a showed the highest cytotoxic activity against MCF7 cell line at all tested concentrations while compounds 6b and 6c indicated mild cytotoxic effects against Hela cell line at highest tested concentration reducing cell viability about 40%. The IC50 values of tested compounds revealed that the MCF-7 is more susceptible to the compound 6a. |
format | Online Article Text |
id | pubmed-6791177 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Wolters Kluwer - Medknow |
record_format | MEDLINE/PubMed |
spelling | pubmed-67911772019-10-16 Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids Hassanzadeh, Farshid Sadeghi-aliabadi, Hojjat Nikooei, Shadan Jafari, Elham Vaseghi, Golnaz Res Pharm Sci Original Article Triazoles and quinazolinones are important heterocyclic structures with diverse biological properties including cytotoxic, antibacterial, antifungal and anticonvulsant activities. Due to valuable cytotoxic effects of both triazole and quinazoline derivatives, in this study a series of quinazolinone-triazole hybrids were synthesized in a multiple-step reaction procedure. 3-Amino-quinazolinone derivatives were treated with chloroacetyl chloride in the presence of dichloromethane/triethylamine to afford 2-chloro -N-(4-oxo-2- quinazolin3 (3H)-yl) acetamide derivatives. The reaction of resultants with 4-mehyl-4-H-1, 2, 4-triazole-3- thiol in dry acetone and potassium carbonate led to the formation of final products. Synthesized compounds were evaluated for their cytotoxic effects against MCF-7 and Hela cell lines using MTT colorimetric assay. Amongst tested compounds, 6a showed the highest cytotoxic activity against MCF7 cell line at all tested concentrations while compounds 6b and 6c indicated mild cytotoxic effects against Hela cell line at highest tested concentration reducing cell viability about 40%. The IC50 values of tested compounds revealed that the MCF-7 is more susceptible to the compound 6a. Wolters Kluwer - Medknow 2019-03-08 /pmc/articles/PMC6791177/ /pubmed/31620189 http://dx.doi.org/10.4103/1735-5362.253360 Text en Copyright: © 2019 Research in Pharmaceutical Sciences http://creativecommons.org/licenses/by-nc-sa/4.0 This is an open access journal, and articles are distributed under the terms of the Creative Commons Attribution-NonCommercial-ShareAlike 4.0 License, which allows others to remix, tweak, and build upon the work non-commercially, as long as appropriate credit is given and the new creations are licensed under the identical terms. |
spellingShingle | Original Article Hassanzadeh, Farshid Sadeghi-aliabadi, Hojjat Nikooei, Shadan Jafari, Elham Vaseghi, Golnaz Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title | Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title_full | Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title_fullStr | Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title_full_unstemmed | Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title_short | Synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
title_sort | synthesis and cytotoxic evaluation of some derivatives of triazole-quinazolinone hybrids |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6791177/ https://www.ncbi.nlm.nih.gov/pubmed/31620189 http://dx.doi.org/10.4103/1735-5362.253360 |
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