Synthesis, antifungal activity and QSAR of some novel carboxylic acid amides.
Molecules
; 20(3): 4071-87, 2015 Mar 04.
Article
in En
| MEDLINE
| ID: mdl-25749678
ABSTRACT
A series of novel aromatic carboxylic acid amides were synthesized and tested for their activities against six phytopathogenic fungi by an in vitro mycelia growth inhibition assay. Most of them displayed moderate to good activity. Among them N-(2-(1H-indazol-1-yl)phenyl)-2-(trifluoromethyl)benzamide (3c) exhibited the highest antifungal activity against Pythium aphanidermatum (EC50 = 16.75 µg/mL) and Rhizoctonia solani (EC50 = 19.19 µg/mL), compared to the reference compound boscalid with EC50 values of 10.68 and 14.47 µg/mL, respectively. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were employed to develop a three-dimensional quantitative structure-activity relationship model for the activity of the compounds. In the molecular docking, a fluorine atom and the carbonyl oxygen atom of 3c formed hydrogen bonds toward the hydroxyl hydrogens of TYR58 and TRP173.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Pythium
/
Rhizoctonia
/
Benzamides
/
Mycelium
/
Amides
/
Indazoles
/
Antifungal Agents
Language:
En
Journal:
Molecules
Journal subject:
BIOLOGIA
Year:
2015
Type:
Article
Affiliation country:
China