Cargando…

Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives

BACKGROUND: Homoisoflavonoids are naturally occurring compounds belong to flavonoid classes possessing various biological properties such as cytotoxicity. In this work, an efficient strategy for the synthesis of novel homoisoflavonoids, [1,3]dioxolo[4,5-g]chromen-8-ones, was developed and all compou...

Descripción completa

Detalles Bibliográficos
Autores principales: Alipour, Eskandar, Mousavi, Zinatsadat, Safaei, Zahra, Pordeli, Mahboobeh, Safavi, Maliheh, Firoozpour, Loghman, Mohammadhosseini, Negar, Saeedi, Mina, Ardestani, Sussan Kabudanian, Shafiee, Abbas, Foroumadi, Alireza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: BioMed Central 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4019946/
https://www.ncbi.nlm.nih.gov/pubmed/24887061
http://dx.doi.org/10.1186/2008-2231-22-41
_version_ 1782480239644901376
author Alipour, Eskandar
Mousavi, Zinatsadat
Safaei, Zahra
Pordeli, Mahboobeh
Safavi, Maliheh
Firoozpour, Loghman
Mohammadhosseini, Negar
Saeedi, Mina
Ardestani, Sussan Kabudanian
Shafiee, Abbas
Foroumadi, Alireza
author_facet Alipour, Eskandar
Mousavi, Zinatsadat
Safaei, Zahra
Pordeli, Mahboobeh
Safavi, Maliheh
Firoozpour, Loghman
Mohammadhosseini, Negar
Saeedi, Mina
Ardestani, Sussan Kabudanian
Shafiee, Abbas
Foroumadi, Alireza
author_sort Alipour, Eskandar
collection PubMed
description BACKGROUND: Homoisoflavonoids are naturally occurring compounds belong to flavonoid classes possessing various biological properties such as cytotoxicity. In this work, an efficient strategy for the synthesis of novel homoisoflavonoids, [1,3]dioxolo[4,5-g]chromen-8-ones, was developed and all compounds were evaluated for their cytotoxic activities on three breast cancer cell lines. METHODS: Our synthetic route started from benzo[d][1,3]dioxol-5-ol which was reacted with 3-bromopropanoic acid followed by the reaction of oxalyl chloride to afford 6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one. The aldol condensation of the later compound with aromatic aldehydes led to the formation of the title compounds. Five novel derivatives 4a-e were tested for their cytotoxic activity against three human breast cancer cell lines including MCF-7, T47D, and MDA-MB-231 using the MTT assay. RESULTS: Among the synthesized compounds, 7-benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4a) exhibited the highest activity against three cell lines. Also the analysis of acridine orange/ethidium bromide staining results revealed that 7-benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4a) and 7-(2-methoxybenzylidene)-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4b) induced apoptosis in T47D cell line. CONCLUSION: Finally, the effect of methoxy group on the cytotoxicity of compounds 4b-4d was investigated in and it was revealed that it did not improve the activity of [1,3]dioxolo[4,5-g]chromen-8-ones against MCF-7, T47D, and MDA-MB-231.
format Online
Article
Text
id pubmed-4019946
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher BioMed Central
record_format MEDLINE/PubMed
spelling pubmed-40199462014-05-15 Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives Alipour, Eskandar Mousavi, Zinatsadat Safaei, Zahra Pordeli, Mahboobeh Safavi, Maliheh Firoozpour, Loghman Mohammadhosseini, Negar Saeedi, Mina Ardestani, Sussan Kabudanian Shafiee, Abbas Foroumadi, Alireza Daru Research Article BACKGROUND: Homoisoflavonoids are naturally occurring compounds belong to flavonoid classes possessing various biological properties such as cytotoxicity. In this work, an efficient strategy for the synthesis of novel homoisoflavonoids, [1,3]dioxolo[4,5-g]chromen-8-ones, was developed and all compounds were evaluated for their cytotoxic activities on three breast cancer cell lines. METHODS: Our synthetic route started from benzo[d][1,3]dioxol-5-ol which was reacted with 3-bromopropanoic acid followed by the reaction of oxalyl chloride to afford 6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one. The aldol condensation of the later compound with aromatic aldehydes led to the formation of the title compounds. Five novel derivatives 4a-e were tested for their cytotoxic activity against three human breast cancer cell lines including MCF-7, T47D, and MDA-MB-231 using the MTT assay. RESULTS: Among the synthesized compounds, 7-benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4a) exhibited the highest activity against three cell lines. Also the analysis of acridine orange/ethidium bromide staining results revealed that 7-benzylidene-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4a) and 7-(2-methoxybenzylidene)-6,7-dihydro-8H-[1,3]dioxolo[4,5-g]chromen-8-one (4b) induced apoptosis in T47D cell line. CONCLUSION: Finally, the effect of methoxy group on the cytotoxicity of compounds 4b-4d was investigated in and it was revealed that it did not improve the activity of [1,3]dioxolo[4,5-g]chromen-8-ones against MCF-7, T47D, and MDA-MB-231. BioMed Central 2014-05-02 /pmc/articles/PMC4019946/ /pubmed/24887061 http://dx.doi.org/10.1186/2008-2231-22-41 Text en Copyright © 2014 Alipour et al.; licensee BioMed Central Ltd. 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 credited. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated.
spellingShingle Research Article
Alipour, Eskandar
Mousavi, Zinatsadat
Safaei, Zahra
Pordeli, Mahboobeh
Safavi, Maliheh
Firoozpour, Loghman
Mohammadhosseini, Negar
Saeedi, Mina
Ardestani, Sussan Kabudanian
Shafiee, Abbas
Foroumadi, Alireza
Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title_full Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title_fullStr Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title_full_unstemmed Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title_short Synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
title_sort synthesis and cytotoxic evaluation of some new[1,3]dioxolo[4,5-g]chromen-8-one derivatives
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4019946/
https://www.ncbi.nlm.nih.gov/pubmed/24887061
http://dx.doi.org/10.1186/2008-2231-22-41
work_keys_str_mv AT alipoureskandar synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT mousavizinatsadat synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT safaeizahra synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT pordelimahboobeh synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT safavimaliheh synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT firoozpourloghman synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT mohammadhosseininegar synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT saeedimina synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT ardestanisussankabudanian synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT shafieeabbas synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives
AT foroumadialireza synthesisandcytotoxicevaluationofsomenew13dioxolo45gchromen8onederivatives