Synthesis and evaluation of the antifungal activity of aromatic hydrazones

Acylhydrazones have been studied since 1850, they are important compounds for drug design due to their extensive biological activity. The compounds were synthesized by a nucleophilic addition reaction to the carbonyl group; six derivatives were obtained using 2,4-dinitrophenylhydra...

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Main Authors:	de la Cruz Argüello, Boris Ezequiel, Gálvez Cardoza, Bessy Evelyn, Díaz Crespín, Guillermo, Morán Rodríguez, Amy Elieth
Format:	Online
Language:	spa
Published:	Universidad Pedagógica y Tecnológica de Colombia - UPTC 2022
Subjects:	Aspergillus niger Candida albicans substituted benzhydrols substituted benzophenones hydrazine bencidroles sustituidos benzofenonas sustituidas hidrazonas
Online Access:	https://revistas.uptc.edu.co/index.php/ingenieria_sogamoso/article/view/15016
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author	de la Cruz Argüello, Boris Ezequiel Gálvez Cardoza, Bessy Evelyn Díaz Crespín, Guillermo Morán Rodríguez, Amy Elieth
author_facet	de la Cruz Argüello, Boris Ezequiel Gálvez Cardoza, Bessy Evelyn Díaz Crespín, Guillermo Morán Rodríguez, Amy Elieth
author_sort	de la Cruz Argüello, Boris Ezequiel
collection	OJS
description	Acylhydrazones have been studied since 1850, they are important compounds for drug design due to their extensive biological activity. The compounds were synthesized by a nucleophilic addition reaction to the carbonyl group; six derivatives were obtained using 2,4-dinitrophenylhydrazine (2,4-DNPH) and ketones: fluorenone, benzophenone and substituted benzophenones; Good yields have been obtained in all cases, the best percentage corresponds to compound (7), with 67% and the lowest to compound (10) with a yield of 29%. Principles number two and five of green chemistry were applied during the development of the synthesis. In addition, the production methodology used was a modification of the procedure described in the knowledge base. The substituted benzophenones were obtained by oxidation of the respective alcohols, so that it was obtained benzophenones and fluoenone; In this method, sodium hypochlorite is used as an oxidation agent and tetrabutyl ammonium bromide as a phase transfer medium in an aqueous medium. The molecules were characterized by proton nuclear magnetic resonance (1H-NMR) and attenuated total reflectance infrared spectroscopy (IR-ATR) among other spectroscopic techniques. Biological activity was evaluated by using the Kirby-Bauer method, in order to determine the sensitivity of an organism to antibiotics or antifungals. The results show that the substituted hydrazones (9 and 10) presented a higher inhibitory activity against Candida albicans and Aspergillus niger compared to 1% cycloheximide, but considerably less effective than ketoconazole compounds used as control.
format	Online
id	oai:oai.revistas.uptc.edu.co:article-15016
institution	Revista Ingeniería, Investigación y Desarrollo
language	spa
publishDate	2022
publisher	Universidad Pedagógica y Tecnológica de Colombia - UPTC
record_format	ojs
spelling	oai:oai.revistas.uptc.edu.co:article-150162023-06-25T18:59:23Z Synthesis and evaluation of the antifungal activity of aromatic hydrazones SÍNTESIS Y EVALUACIÓN DE LA ACTIVIDAD ANTIFUNGICA DE HIDRAZONAS AROMÁTICAS de la Cruz Argüello, Boris Ezequiel Gálvez Cardoza, Bessy Evelyn Díaz Crespín, Guillermo Morán Rodríguez, Amy Elieth Aspergillus niger Candida albicans substituted benzhydrols substituted benzophenones hydrazine Aspergillus niger Candida albicans bencidroles sustituidos benzofenonas sustituidas hidrazonas Acylhydrazones have been studied since 1850, they are important compounds for drug design due to their extensive biological activity. The compounds were synthesized by a nucleophilic addition reaction to the carbonyl group; six derivatives were obtained using 2,4-dinitrophenylhydrazine (2,4-DNPH) and ketones: fluorenone, benzophenone and substituted benzophenones; Good yields have been obtained in all cases, the best percentage corresponds to compound (7), with 67% and the lowest to compound (10) with a yield of 29%. Principles number two and five of green chemistry were applied during the development of the synthesis. In addition, the production methodology used was a modification of the procedure described in the knowledge base. The substituted benzophenones were obtained by oxidation of the respective alcohols, so that it was obtained benzophenones and fluoenone; In this method, sodium hypochlorite is used as an oxidation agent and tetrabutyl ammonium bromide as a phase transfer medium in an aqueous medium. The molecules were characterized by proton nuclear magnetic resonance (1H-NMR) and attenuated total reflectance infrared spectroscopy (IR-ATR) among other spectroscopic techniques. Biological activity was evaluated by using the Kirby-Bauer method, in order to determine the sensitivity of an organism to antibiotics or antifungals. The results show that the substituted hydrazones (9 and 10) presented a higher inhibitory activity against Candida albicans and Aspergillus niger compared to 1% cycloheximide, but considerably less effective than ketoconazole compounds used as control. Las acilhidrazonas se han estudiado desde 1850, son compuestos importantes para el diseño de fármacos por su amplia actividad biológica, entre ellas. Los compuestos fueron sintetizados mediante una reacción de adición nucleofílica al grupo carbonilo; se obtuvieron seis derivados empleando la 2,4-dinitrofenilhidracina (2,4-DNPH) y las cetonas: fluorenona, benzofenona y benzofenonas sustituidas; en todos los casos se han alcanzado buenos rendimientos, el mejor porcentaje corresponde al compuesto (7), con un 67% y el más bajo al compuesto (10) con un rendimiento de 29%. En el desarrollo de la síntesis se aplicaron los principios número dos y cinco de química verde. Además, la metodología de obtención usada fue una modificación del procedimiento descrito en la literatura. Las benzofenonas sustituidas fueron obtenidas mediante la oxidación de los respectivos alcoholes para la obtención de las benzofenonas y fluoenona; en este método se emplea hipoclorito de sodio como agente de oxidación y bromuro de tetrabutil amonio como medio de transferencia de fase en medio acuoso. Las moléculas se caracterizaron por resonancia magnética nuclear de protón (RMN-1H) y espectroscopia de infrarroja de reflectancia total atenuada (IR-ATR) entre otras técnicas espectroscópicas. La evaluación de la actividad biológica se realizó mediante el método Kirby-Bauer, empleado para determinar la sensibilidad de un organismo frente a antibióticos o antifúngicos. Los resultados muestran que las hidrazonas sustituidas (9) y (10) presentaron una actividad inhibitoria mayor frente Candida albicans y Aspergillus niger en comparación con cicloheximida al 1%, pero considerablemente son menos efectivo que ketoconazol compuestos utilizados como control. Universidad Pedagógica y Tecnológica de Colombia - UPTC 2022-09-29 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf https://revistas.uptc.edu.co/index.php/ingenieria_sogamoso/article/view/15016 10.19053/1900771X.v22.n2.2022.15016 Ingeniería Investigación y Desarrollo; Vol. 22 No. 2 (2022): Julio - Diciembre; 6-15 Ingeniería Investigación y Desarrollo; Vol. 22 Núm. 2 (2022): Julio - Diciembre; 6-15 2422-4324 1900-771X spa https://revistas.uptc.edu.co/index.php/ingenieria_sogamoso/article/view/15016/12231
spellingShingle	Aspergillus niger Candida albicans substituted benzhydrols substituted benzophenones hydrazine Aspergillus niger Candida albicans bencidroles sustituidos benzofenonas sustituidas hidrazonas de la Cruz Argüello, Boris Ezequiel Gálvez Cardoza, Bessy Evelyn Díaz Crespín, Guillermo Morán Rodríguez, Amy Elieth Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title	Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title_alt	SÍNTESIS Y EVALUACIÓN DE LA ACTIVIDAD ANTIFUNGICA DE HIDRAZONAS AROMÁTICAS
title_full	Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title_fullStr	Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title_full_unstemmed	Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title_short	Synthesis and evaluation of the antifungal activity of aromatic hydrazones
title_sort	synthesis and evaluation of the antifungal activity of aromatic hydrazones
topic	Aspergillus niger Candida albicans substituted benzhydrols substituted benzophenones hydrazine Aspergillus niger Candida albicans bencidroles sustituidos benzofenonas sustituidas hidrazonas
topic_facet	Aspergillus niger Candida albicans substituted benzhydrols substituted benzophenones hydrazine Aspergillus niger Candida albicans bencidroles sustituidos benzofenonas sustituidas hidrazonas
url	https://revistas.uptc.edu.co/index.php/ingenieria_sogamoso/article/view/15016
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