Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity

The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields,...

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Autores principales: Acosta, Paola, Butassi, Estefanía, Insuasty, Braulio, Ortiz, Alejandro, Abonia, Rodrigo, Zacchino, Susana, Quiroga, Jairo
Formato: article artículo publishedVersion
Lenguaje:Inglés
Publicado: MDPI 2020
Materias:
Antifungal Activity
Antitumoral Activity
Pyrazolonaphthyridines;
Microwave Irradiation
Candida albicans
Cryptococcus neoformans
Acceso en línea:http://hdl.handle.net/2133/19514
http://hdl.handle.net/2133/19514
Aporte de:
Repositorio Hipermedial de la Universidad Nacional de Rosario (UNR) de Universidad Nacional de Rosario
id I15-R121-2133-19514
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 Antifungal Activity
Antitumoral Activity
Pyrazolonaphthyridines;
Microwave Irradiation
Candida albicans
Cryptococcus neoformans
spellingShingle Antifungal Activity
Antitumoral Activity
Pyrazolonaphthyridines;
Microwave Irradiation
Candida albicans
Cryptococcus neoformans
Acosta, Paola
Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana
Quiroga, Jairo
Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
topic_facet Antifungal Activity
Antitumoral Activity
Pyrazolonaphthyridines;
Microwave Irradiation
Candida albicans
Cryptococcus neoformans
description The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.
format article
artículo
publishedVersion
author Acosta, Paola
Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana
Quiroga, Jairo
author_facet Acosta, Paola
Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana
Quiroga, Jairo
author_sort Acosta, Paola
title Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_short Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_full Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_fullStr Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_full_unstemmed Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_sort microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
publisher MDPI
publishDate 2020
url http://hdl.handle.net/2133/19514
http://hdl.handle.net/2133/19514
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