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

dc.creatorAbonia, Rodrigo
dc.creatorGaray, Alexander
dc.creatorCastillo, Juan
dc.creatorInsuasty, Braulio
dc.creatorQuiroga, Jairo
dc.creatorNogueras, Manuel
dc.creatorCobo, Justo
dc.creatorButassi, Estefanía
dc.creatorZacchino, Susana
dc.date2020-12-18T01:08:46Z
dc.date2020-12-18T01:08:46Z
dc.date2018-02-26
dc.date2020-12-18T01:08:46Z
dc.date2020-12-18T01:08:46Z
dc.date2018-02-26
dc.date.accessioned2022-10-14T19:59:40Z
dc.date.available2022-10-14T19:59:40Z
dc.identifier1420-3049
dc.identifierhttp://hdl.handle.net/2133/19507
dc.identifierhttp://hdl.handle.net/2133/19507
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/4293066
dc.descriptionTwo 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.
dc.descriptionFil: Abonia, Rodrigo. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.
dc.descriptionFil: Garay, Alexander. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.
dc.descriptionFil: Castillo, Juan. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.
dc.descriptionFil: Castillo, Juan. Universidad Pedagógica y Tecnológica de Colombia (UPTC). Facultad de Ciencias. Escuela de Ciencias Químicas; Colombia.
dc.descriptionFil: Insuasty, Braulio. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.
dc.descriptionFil: Quiroga, Jairo. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química. Grupo de Investigación de Compuestos Heterocíclicos (GICH); Colombia.
dc.descriptionFil: Nogueras, Manuel. Universidad de Jaen. Departamento de Química Inorgánica y Orgánica; España.
dc.descriptionFil: Cobo, Justo. Universidad de Jaen. Departamento de Química Inorgánica y Orgánica; España.
dc.descriptionFil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.
dc.descriptionFil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.
dc.formatapplication/pdf
dc.languageeng
dc.publisherMDPI
dc.relationhttps://doi.org/10.3390/molecules23030520
dc.relationhttps://www.mdpi.com/1420-3049/23/3/520
dc.rightshttps://creativecommons.org/licenses/by/4.0/
dc.rightsUniversidad Nacional de Rosario
dc.rightsAbonia, Rodrigo
dc.rightsGaray, Alexander
dc.rightsCastillo, Juan
dc.rightsInsuasty, Braulio
dc.rightsQuiroga, Jairo
dc.rightsNogueras, Manuel
dc.rightsCobo, Justo
dc.rightsButassi, Estefanía
dc.rightsZacchino, Susana
dc.rightsAttribution 4.0 International (CC BY 4.0)
dc.rightsopenAccess
dc.subjectBenzylamines
dc.subjectPropiophenones
dc.subjectgamma-Aminoalcohols
dc.subjectMannich-type Reaction
dc.subjectAllylamines
dc.subjectNaftifine Analogues
dc.subjectAntifungal Activity
dc.titleDesign of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents
dc.typearticle
dc.typeartículo
dc.typepublishedVersion


Este ítem pertenece a la siguiente institución