Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

4,5-Dihydropyrrolo [1,2-a]quinoxalines are interesting druggable scaffolds, with multifaceted biological properties, including anticancer properties targeting the G protein-coupled estrogen receptor 1 (GPER). In this work, the synthesis and preliminary antiproliferative activity of a small set of ne...

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Autores principales:	Gabriele Carullo, Sarah Mazzotta, Francesca Giordano, Francesca Aiello
Formato:	article
Lenguaje:	EN
Publicado:	Hindawi Limited 2021
Materias:	Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/c247b818aed04d14b72b6dcce73ac2ae
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spelling	oai:doaj.org-article:c247b818aed04d14b72b6dcce73ac2ae2021-11-08T02:36:57ZGreen Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells2090-907110.1155/2021/5596816https://doaj.org/article/c247b818aed04d14b72b6dcce73ac2ae2021-01-01T00:00:00Zhttp://dx.doi.org/10.1155/2021/5596816https://doaj.org/toc/2090-90714,5-Dihydropyrrolo [1,2-a]quinoxalines are interesting druggable scaffolds, with multifaceted biological properties, including anticancer properties targeting the G protein-coupled estrogen receptor 1 (GPER). In this work, the synthesis and preliminary antiproliferative activity of a small set of new 4,5-dihydropyrrolo[1,2-a]quinoxalines (18-20) and pyrrolo[1,2-a]quinoxalines (21, 22) has been reported, inspired by known antiproliferative agents (G-1, G-15, and G-36). The synthesis of the pyrroloquinoxalinic core was employed following the Pictet–Spengler reaction, using the surfactant p-dodecylbenzene sulphonic acid (p-DBSA), as catalyst. It demonstrated efficiency in the catalysis of the 4-phenylpyrrole [1,2-a] quinoxaline type compound formation in mild solvents such as water, ethanol, and hydroalcoholic solutions. In addition, the reactions proceeded in a short time (between 15 and 120 minutes) at room temperature and with high yields. The in vitro MTT assays showed that the presence of isopropyl groups furnished promising antiproliferative compounds. Although, the acetyl group provided also antiproliferative effects, breaking down its responsibility in the GPER transactivation. Nevertheless, it is possible to conclude that the 4,5-dihydropyrrolo[1,2-a]quinoxalines remain a feasible scaffold to develop anticancer agents against GPER-expressing cells.Gabriele CarulloSarah MazzottaFrancesca GiordanoFrancesca AielloHindawi LimitedarticleChemistryQD1-999ENJournal of Chemistry, Vol 2021 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Chemistry QD1-999
spellingShingle	Chemistry QD1-999 Gabriele Carullo Sarah Mazzotta Francesca Giordano Francesca Aiello Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
description	4,5-Dihydropyrrolo [1,2-a]quinoxalines are interesting druggable scaffolds, with multifaceted biological properties, including anticancer properties targeting the G protein-coupled estrogen receptor 1 (GPER). In this work, the synthesis and preliminary antiproliferative activity of a small set of new 4,5-dihydropyrrolo[1,2-a]quinoxalines (18-20) and pyrrolo[1,2-a]quinoxalines (21, 22) has been reported, inspired by known antiproliferative agents (G-1, G-15, and G-36). The synthesis of the pyrroloquinoxalinic core was employed following the Pictet–Spengler reaction, using the surfactant p-dodecylbenzene sulphonic acid (p-DBSA), as catalyst. It demonstrated efficiency in the catalysis of the 4-phenylpyrrole [1,2-a] quinoxaline type compound formation in mild solvents such as water, ethanol, and hydroalcoholic solutions. In addition, the reactions proceeded in a short time (between 15 and 120 minutes) at room temperature and with high yields. The in vitro MTT assays showed that the presence of isopropyl groups furnished promising antiproliferative compounds. Although, the acetyl group provided also antiproliferative effects, breaking down its responsibility in the GPER transactivation. Nevertheless, it is possible to conclude that the 4,5-dihydropyrrolo[1,2-a]quinoxalines remain a feasible scaffold to develop anticancer agents against GPER-expressing cells.
format	article
author	Gabriele Carullo Sarah Mazzotta Francesca Giordano Francesca Aiello
author_facet	Gabriele Carullo Sarah Mazzotta Francesca Giordano Francesca Aiello
author_sort	Gabriele Carullo
title	Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
title_short	Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
title_full	Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
title_fullStr	Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
title_full_unstemmed	Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells
title_sort	green synthesis of new pyrrolo [1,2-a] quinoxalines as antiproliferative agents in gper-expressing breast cancer cells
publisher	Hindawi Limited
publishDate	2021
url	https://doaj.org/article/c247b818aed04d14b72b6dcce73ac2ae
work_keys_str_mv	AT gabrielecarullo greensynthesisofnewpyrrolo12aquinoxalinesasantiproliferativeagentsingperexpressingbreastcancercells AT sarahmazzotta greensynthesisofnewpyrrolo12aquinoxalinesasantiproliferativeagentsingperexpressingbreastcancercells AT francescagiordano greensynthesisofnewpyrrolo12aquinoxalinesasantiproliferativeagentsingperexpressingbreastcancercells AT francescaaiello greensynthesisofnewpyrrolo12aquinoxalinesasantiproliferativeagentsingperexpressingbreastcancercells
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Green Synthesis of New Pyrrolo [1,2-a] quinoxalines as Antiproliferative Agents in GPER-expressing Breast Cancer Cells

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