Design, synthesis, and pharmacological evaluation of new neuroactive pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives with in vivo hypnotic and analgesic profile.
Bioorg Med Chem
; 14(3): 632-40, 2006 Feb 01.
Article
en En
| MEDLINE
| ID: mdl-16198114
ABSTRACT
The present study describes the synthesis and pharmacological profiles of four novel pyrazolo[3,4-b]pyrrolo[3,4-d]pyridine derivatives 2-5, which were structurally designed by using the sedative and analgesic drug zolpidem 1 as lead compound. The heterotricyclic system present in the target compounds 2-5 was constructed in good yields, exploiting a regioselective hetero Diels-Alder reaction of the key azabutadiene derivative 7 and functionalized N-phenylmaleimides 9-12. Additionally, we identified that 1-methyl-7-(4-nitrophenyl)-3-phenyl-3,6,7,8-tetrahydropyrazolo[3,4-b]pyrrolo[3,4-d]pyridine-6,8-dione derivative (LASSBio-873, 5) presented not only the most potent ability to promote sedation, which was similar to that induced by the standard benzodiazepine drug midazolam, but also potent central antinociceptive effect.
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Bases de datos:
MEDLINE
Asunto principal:
Piridinas
/
Analgésicos no Narcóticos
/
Hipnóticos y Sedantes
Idioma:
En
Revista:
Bioorg Med Chem
Año:
2006
Tipo del documento:
Article
País de afiliación:
Brasil