RESUMEN
In this article we present the synthesis, characterization, and in vitro biological and biochemical activities of new chalcogenozidovudine derivatives as antioxidant (inhibition of TBARS in brain membranes and thiol peroxidase-like activity) as well as antitumoral agents in bladder carcinoma 5637. A prominent response was obtained for the selected chalcogenonucleosides, showing effective antioxidant and antitumoral activities.
Asunto(s)
Antineoplásicos/química , Antioxidantes/química , Calcógenos/química , Neoplasias de la Vejiga Urinaria/tratamiento farmacológico , Zidovudina/química , Animales , Antineoplásicos/síntesis química , Antineoplásicos/farmacología , Antioxidantes/síntesis química , Antioxidantes/farmacología , Apoptosis/efectos de los fármacos , Línea Celular Tumoral , Calcógenos/síntesis química , Calcógenos/farmacología , Humanos , Masculino , Ratas Wistar , Sustancias Reactivas al Ácido Tiobarbitúrico/metabolismo , Vejiga Urinaria/efectos de los fármacos , Vejiga Urinaria/metabolismo , Vejiga Urinaria/patología , Neoplasias de la Vejiga Urinaria/metabolismo , Neoplasias de la Vejiga Urinaria/patología , Zidovudina/síntesis química , Zidovudina/farmacologíaRESUMEN
Ultrasonic irradiation was used in the synthesis of a series of novel 1,2,4-triazolo[1,5-a]pyrimidines. The products were synthetized from the cyclocondensation reaction of 1,1,1-trifluoro-4-metoxy-3-alken-2-one [CF3C(O)CHC(R)OMe, where R=Ph, 4-F-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH3-C6H4, 4-CH3O-C6H4, Thien-2-yl, Biphen-4-yl] or ß-enaminones [RC(O)CHCHNMe2, where R=Ph, 4-F-C6H4, 4-Br-C6H4, 4-I-C6H4, 4-CH3-C6H4, 4-CH3O-C6H4, 4-NO2-C6H4, Thien-2-yl, Biphen-4-yl, Naphth-2-yl, Pyrrol-2-yl, CCl3] with 5-amino-1,2,4-triazole in acetic acid at 99°C with 5-17 min of ultrasound irradiation. This methodology has shown several advantages, such as shorter reaction times, mild conditions, high regioselectivity, and excellent yields, when compared with conventional thermal heating (oil bath).
Asunto(s)
Pirimidinas/síntesis química , Triazoles/síntesis química , Ultrasonido , Técnicas de Química Sintética , Pirimidinas/química , Triazoles/químicaRESUMEN
Pyrazolo[1,5-a]pyrimidines were synthesized via the ultrasonic sonochemical method using the cyclocondensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones [CF3C(O)CH=C(R)(OMe) - where R=Me, Bu, i-Bu, Ph, 4-Me-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, naphth-2-yl and biphen-4-yl] - with 3-amino-5-methyl-1H-pyrazole in the presence of EtOH for 5 min. This methodology has several advantages, for example, it is a simple procedure, it has an easy work-up, mild conditions, short reaction times (5 min) and produces satisfactory yields (61-98%).