Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents

Two practical and efficient approaches have been implemented as alternative procedures for the synthesis of naftifine and novel diversely substituted analogues 16 and 20 in good to excellent yields, mediated by Mannich-type reactions as the key step of the processes. In these approaches, the γ-am...

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Autores principales:	Abonia, Rodrigo, Garay, Alexander, Castillo, Juan, Insuasty, Braulio, Quiroga, Jairo, Nogueras, Manuel, Cobo, Justo, Butassi, Estefanía, Zacchino, Susana
Formato:	article artículo publishedVersion
Lenguaje:	Inglés
Publicado:	MDPI 2020
Materias:	Benzylamines Propiophenones gamma-Aminoalcohols Mannich-type Reaction Allylamines Naftifine Analogues Antifungal Activity
Acceso en línea:	http://hdl.handle.net/2133/19507 http://hdl.handle.net/2133/19507
Aporte de:	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario

id	I15-R121-2133-19507
record_format	dspace
institution	Universidad Nacional de Rosario
institution_str	I-15
repository_str	R-121
collection	Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR)
language	Inglés
orig_language_str_mv	eng
topic	Benzylamines Propiophenones gamma-Aminoalcohols Mannich-type Reaction Allylamines Naftifine Analogues Antifungal Activity
spellingShingle	Benzylamines Propiophenones gamma-Aminoalcohols Mannich-type Reaction Allylamines Naftifine Analogues Antifungal Activity Abonia, Rodrigo Garay, Alexander Castillo, Juan Insuasty, Braulio Quiroga, Jairo Nogueras, Manuel Cobo, Justo Butassi, Estefanía Zacchino, Susana Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
topic_facet	Benzylamines Propiophenones gamma-Aminoalcohols Mannich-type Reaction Allylamines Naftifine Analogues Antifungal Activity
description	Two practical and efficient approaches have been implemented as alternative procedures for the synthesis of naftifine and novel diversely substituted analogues 16 and 20 in good to excellent yields, mediated by Mannich-type reactions as the key step of the processes. In these approaches, the γ-aminoalcohols 15 and 19 were obtained as the key intermediates and their subsequent dehydration catalyzed either by Brønsted acids like H2SO4 and HCl or Lewis acid like AlCl3, respectively, led to naftifine, along with the target allylamines 16 and 20. The antifungal assay results showed that intermediates 18 (bearing both a β-aminoketo- and N-methyl functionalities in their structures) and products 20 were the most active. Particularly, structures 18b, 18c, and the allylamine 20c showed the lowest MIC values, in the 0.5–7.8 µg/mL range, against the dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes. Interesting enough, compound 18b bearing a 4-Br as the substituent of the phenyl ring, also displayed high activity against Candida albicans and Cryptococcus neoformans with MIC80 = 7.8 µg/mL, being fungicide rather than fungistatic with a relevant MFC value = 15.6 µg/mL against C. neoformans.
format	article artículo publishedVersion
author	Abonia, Rodrigo Garay, Alexander Castillo, Juan Insuasty, Braulio Quiroga, Jairo Nogueras, Manuel Cobo, Justo Butassi, Estefanía Zacchino, Susana
author_facet	Abonia, Rodrigo Garay, Alexander Castillo, Juan Insuasty, Braulio Quiroga, Jairo Nogueras, Manuel Cobo, Justo Butassi, Estefanía Zacchino, Susana
author_sort	Abonia, Rodrigo
title	Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
title_short	Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
title_full	Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
title_fullStr	Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
title_full_unstemmed	Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
title_sort	design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
publisher	MDPI
publishDate	2020
url	http://hdl.handle.net/2133/19507 http://hdl.handle.net/2133/19507
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bdutipo_str	Repositorios
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Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents

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