4-Aminoquinolines Bearing a 1,3-Benzodioxole Moiety: Synthesis and Biological Evaluation as Potential Antifungal Agents.
Chem Biodivers
; 18(5): e2100106, 2021 May.
Article
em En
| MEDLINE
| ID: mdl-33759356
ABSTRACT
In search of new environmentally friendly and effective antifungal agents, a series of 4-aminoquinolines bearing a 1,3-benzodioxole moiety were prepared and their structures were fully elucidated by spectroscopic analyses. The antifungal activities of all the target compounds against five phytopathogenic fungi were evaluated inâ
vitro. The results revealed that most of the newly synthesized compounds exhibited obvious inhibitory activities at the concentration of 50â
µg/mL. Among them, 6-(furan-2-yl)-N-(4-methylphenyl)-2H-[1,3]dioxolo[4,5-g]quinolin-8-amine hydrochloride (7m) displayed more promising antifungal potency with EC50 values of 10.3 and 14.0â
µg/mL against C. lunata and A. alternate, respectively. Particularly, the EC50 value of 7m against C. lunata was 7.3-fold as potent as the standard azoxystrobin. There were some significant morphological alterations in the mycelia of C. lunata when treated with 7m at 50â
µg/mL. Additionally, the preliminary structure-activity relationships (SARs) were also discussed. Thus, this study suggests that 4-aminoquinolines bearing a 1,3-benzodioxole moiety are interesting scaffolds for the development of novel antifungal agents.
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Base de dados:
MEDLINE
Assunto principal:
Dioxóis
/
Fungos
/
Aminoquinolinas
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Antifúngicos
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article