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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-...

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Autores principales: Hassanzadeh, Farshid, Sadeghi-aliabadi, Hojjat, Nikooei, Shadan, Jafari, Elham, Vaseghi, Golnaz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Wolters Kluwer - Medknow 2019
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.
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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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