Design, synthesis, herbicidal activity and CoMFA of aryl-formyl piperidinone HPPD inhibitors.
Pestic Biochem Physiol
; 174: 104811, 2021 May.
Article
en En
| MEDLINE
| ID: mdl-33838713
ABSTRACT
Isoxazole, nicotinic acid and benzoic acid are important components in many natural products and useful synthons to build macrostructures having valuable biological activities. In continuation of our effort to discover 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) inhibitors and search for active fragments from natural products, a series of substituted aryl-formyl piperidinone derivatives with natural product fragments was rationally designed, synthesized and tested for their herbicidal activity. Compound I-9 was considered the most effective candidate with an IC50 value of 0.260 µM. The molecular docking results showed that the triketone group of compound I-9 forms a bidentate complex with a metal ion, and the benzene ring interacted with Phe424 and Phe381 via π-π stacking, which was similar to the mechanisms of mesotrione. The present work indicates that compound I-9 may serve as a potential lead compound for further development of green HPPD inhibitors.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Herbicidas
Idioma:
En
Revista:
Pestic Biochem Physiol
Año:
2021
Tipo del documento:
Article
País de afiliación:
China