Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity

1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH<sub>4</sub>CO<sub>2</sub>H-Pd/C is here demonstrated as a new system for the O-N reduction,...

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Autores principales:	Paola Marzullo, Sonya Vasto, Silvestre Buscemi, Andrea Pace, Domenico Nuzzo, Antonio Palumbo Piccionello
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	1,2,4-oxadiazole reduction quinazolin-4-one acylguanidine diacylguanidine ammonium formate Biology (General) QH301-705.5 Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/e64d262621b6435ab975ad4d9c74eaab
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spelling	oai:doaj.org-article:e64d262621b6435ab975ad4d9c74eaab2021-11-25T17:55:15ZAmmonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity10.3390/ijms2222123011422-00671661-6596https://doaj.org/article/e64d262621b6435ab975ad4d9c74eaab2021-11-01T00:00:00Zhttps://www.mdpi.com/1422-0067/22/22/12301https://doaj.org/toc/1661-6596https://doaj.org/toc/1422-00671,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH<sub>4</sub>CO<sub>2</sub>H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1<i>H</i>)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.Paola MarzulloSonya VastoSilvestre BuscemiAndrea PaceDomenico NuzzoAntonio Palumbo PiccionelloMDPI AGarticle1,2,4-oxadiazolereductionquinazolin-4-oneacylguanidinediacylguanidineammonium formateBiology (General)QH301-705.5ChemistryQD1-999ENInternational Journal of Molecular Sciences, Vol 22, Iss 12301, p 12301 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	1,2,4-oxadiazole reduction quinazolin-4-one acylguanidine diacylguanidine ammonium formate Biology (General) QH301-705.5 Chemistry QD1-999
spellingShingle	1,2,4-oxadiazole reduction quinazolin-4-one acylguanidine diacylguanidine ammonium formate Biology (General) QH301-705.5 Chemistry QD1-999 Paola Marzullo Sonya Vasto Silvestre Buscemi Andrea Pace Domenico Nuzzo Antonio Palumbo Piccionello Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
description	1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH<sub>4</sub>CO<sub>2</sub>H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2′-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1<i>H</i>)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.
format	article
author	Paola Marzullo Sonya Vasto Silvestre Buscemi Andrea Pace Domenico Nuzzo Antonio Palumbo Piccionello
author_facet	Paola Marzullo Sonya Vasto Silvestre Buscemi Andrea Pace Domenico Nuzzo Antonio Palumbo Piccionello
author_sort	Paola Marzullo
title	Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
title_short	Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
title_full	Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
title_fullStr	Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
title_full_unstemmed	Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
title_sort	ammonium formate-pd/c as a new reducing system for 1,2,4-oxadiazoles. synthesis of guanidine derivatives and reductive rearrangement to quinazolin-4-ones with potential anti-diabetic activity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/e64d262621b6435ab975ad4d9c74eaab
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Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity

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