Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties

A novel pyrazolo-enaminones, bipyrazoles and bipyrazolopyridines from 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)butane-1,3-dione and 4-methyl-2-phenyl-2H-pyrazolo[3,4-b]pyridine-3,6(3aH,7H)-dione have been synthesized by assisted heating with microwave radiation without any catalyst. The pyridi...

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Autores principales:	Soufiane Akhramez, Asmaa Oumessaoud, Achraf Hibot, Soumaya Talbi, Salha Hamri, El Mostafa Ketatni, Hajiba Ouchetto, Abderrafia Hafid, Houda Ayad, Noureddine El Abbadi, Chorouk Zanane, Hassan Latrache, Mostafa Khouili, Maria Dolors Pujol
Formato:	article
Lenguaje:	EN
Publicado:	Elsevier 2022
Materias:	Intramolecular cyclization Pyrazolo-enaminones Bipyrazolopyridines Antioxidant activity Antibacterial activity Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/7d4157b49fc640e0857f4fce91b10738
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spelling	oai:doaj.org-article:7d4157b49fc640e0857f4fce91b107382021-11-16T04:09:28ZSynthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties1878-535210.1016/j.arabjc.2021.103527https://doaj.org/article/7d4157b49fc640e0857f4fce91b107382022-01-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S1878535221005426https://doaj.org/toc/1878-5352A novel pyrazolo-enaminones, bipyrazoles and bipyrazolopyridines from 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)butane-1,3-dione and 4-methyl-2-phenyl-2H-pyrazolo[3,4-b]pyridine-3,6(3aH,7H)-dione have been synthesized by assisted heating with microwave radiation without any catalyst. The pyridine and pyrazole ring formation has been developed from easily accessible enamino keto esters by formylation followed by intramolecular cyclization. The general applicability for the synthesis of the important pyrazolo-enaminones, bipyrazoles and pyrazolo-pyridines heterocycles was attributed to simplicity of operation, synthesis without catalyst, energy efficiency (shorter reaction time under microwave irradiation), good yields, more environmentally friendly and more cost-effective procedure. The antioxidant activity of new heterocyclic compounds was evaluated by free radical scavenging by DPPH assay. Several of these compounds showed good activity against both Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria.Soufiane AkhramezAsmaa OumessaoudAchraf HibotSoumaya TalbiSalha HamriEl Mostafa KetatniHajiba OuchettoAbderrafia HafidHouda AyadNoureddine El AbbadiChorouk ZananeHassan LatracheMostafa KhouiliMaria Dolors PujolElsevierarticleIntramolecular cyclizationPyrazolo-enaminonesBipyrazolopyridinesAntioxidant activityAntibacterial activityChemistryQD1-999ENArabian Journal of Chemistry, Vol 15, Iss 1, Pp 103527- (2022)
institution	DOAJ
collection	DOAJ
language	EN
topic	Intramolecular cyclization Pyrazolo-enaminones Bipyrazolopyridines Antioxidant activity Antibacterial activity Chemistry QD1-999
spellingShingle	Intramolecular cyclization Pyrazolo-enaminones Bipyrazolopyridines Antioxidant activity Antibacterial activity Chemistry QD1-999 Soufiane Akhramez Asmaa Oumessaoud Achraf Hibot Soumaya Talbi Salha Hamri El Mostafa Ketatni Hajiba Ouchetto Abderrafia Hafid Houda Ayad Noureddine El Abbadi Chorouk Zanane Hassan Latrache Mostafa Khouili Maria Dolors Pujol Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
description	A novel pyrazolo-enaminones, bipyrazoles and bipyrazolopyridines from 1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)butane-1,3-dione and 4-methyl-2-phenyl-2H-pyrazolo[3,4-b]pyridine-3,6(3aH,7H)-dione have been synthesized by assisted heating with microwave radiation without any catalyst. The pyridine and pyrazole ring formation has been developed from easily accessible enamino keto esters by formylation followed by intramolecular cyclization. The general applicability for the synthesis of the important pyrazolo-enaminones, bipyrazoles and pyrazolo-pyridines heterocycles was attributed to simplicity of operation, synthesis without catalyst, energy efficiency (shorter reaction time under microwave irradiation), good yields, more environmentally friendly and more cost-effective procedure. The antioxidant activity of new heterocyclic compounds was evaluated by free radical scavenging by DPPH assay. Several of these compounds showed good activity against both Gram-positive (S. aureus) and Gram-negative (E. coli) bacteria.
format	article
author	Soufiane Akhramez Asmaa Oumessaoud Achraf Hibot Soumaya Talbi Salha Hamri El Mostafa Ketatni Hajiba Ouchetto Abderrafia Hafid Houda Ayad Noureddine El Abbadi Chorouk Zanane Hassan Latrache Mostafa Khouili Maria Dolors Pujol
author_facet	Soufiane Akhramez Asmaa Oumessaoud Achraf Hibot Soumaya Talbi Salha Hamri El Mostafa Ketatni Hajiba Ouchetto Abderrafia Hafid Houda Ayad Noureddine El Abbadi Chorouk Zanane Hassan Latrache Mostafa Khouili Maria Dolors Pujol
author_sort	Soufiane Akhramez
title	Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
title_short	Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
title_full	Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
title_fullStr	Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
title_full_unstemmed	Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
title_sort	synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties
publisher	Elsevier
publishDate	2022
url	https://doaj.org/article/7d4157b49fc640e0857f4fce91b10738
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Synthesis of pyrazolo-enaminones, bipyrazoles and pyrazolopyrimidines and evaluation of antioxidant and antimicrobial properties

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