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1.
Bioorg Med Chem Lett ; 22(1): 149-53, 2012 Jan 01.
Artículo en Inglés | MEDLINE | ID: mdl-22153344

RESUMEN

A series of novel phenylmethylene bis-isoxazolo[4,5-b]azepine derivatives (10) have been synthesized from 3-methyl-4-nitro-5-styrylisoxazoles 6. The reaction of 6 with 3,5-dimethyl-4-nitroisoxazole (7) in piperidine afforded the Michael type adducts 8, which on treatment with different substituted chalcones in the presence of piperidine gave the Michael adducts 9. Compounds 9 underwent reductive cyclization on treatment with SnCl(2)-MeOH to afford the title compounds 10. Structure of these compounds was established on the basis of IR, (1)H NMR, (13)C NMR and Mass spectral data. The title compounds 10a-j were evaluated for in vitro and in vivo anticancer activity. Compound 10j exhibited good anticancer activity as that of standard drug Cisplatin.


Asunto(s)
Antineoplásicos/farmacología , Azepinas/farmacología , Química Farmacéutica/métodos , Animales , Azepinas/química , Línea Celular Tumoral , Cisplatino/farmacología , Diseño de Fármacos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Técnicas In Vitro , Concentración 50 Inhibidora , Isoxazoles/química , Espectroscopía de Resonancia Magnética/métodos , Espectrometría de Masas/métodos , Metanol/química , Ratones , Modelos Químicos , Neoplasias/tratamiento farmacológico , Espectrofotometría Infrarroja/métodos , Sales de Tetrazolio/farmacología , Tiazoles/farmacología
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