RESUMEN
An elegant, efficient, and highly regioselective approach for the synthesis of novel methyl 5-amino-3-(methylthio)-1-differently substituted-1H-pyrazole-4-carboxylates is reported. The procedure involves the cyclocondensation of α-oxeketene S, S-dimethyl acetal building blocks with different alkyl, aryl, and heterocyclic acid hydrazides. The novel molecules were obtained in good yields and their identities confirmed by NMR and HRMS spectrometry.
Asunto(s)
Acetales/química , Etilenos/química , Hidrazinas/química , Cetonas/química , Nitrógeno/química , Pirazoles/química , Pirazoles/síntesis química , Técnicas de Química Sintética , EstereoisomerismoRESUMEN
In this study, the interaction between soy isoflavone genistein and asolectin liposomes was investigated by monitoring the effects of isoflavone on lipidic hydration, mobility, location and order. These properties were analyzed by the following techniques: horizontal attenuated total reflection Fourier transform infrared spectroscopy (HATR-FTIR), low-field (1)H nuclear magnetic resonance (NMR), high-field (31)P NMR, zeta potential, differential scanning calorimetry (DSC) and UV-vis spectroscopy. The antioxidant and antitumoral activities of the genistein liposomal system were also studied. The genistein saturation concentration in ASO liposomes corresponded to 484 µM. HATR-FTIR results indicated that genistein influences the dynamics of the lipidic phosphate, choline, carbonyl and acyl chain methylenes groups. At the lipid polar head, HATR-FTIR and (31)P NMR results showed that the isoflavone reduces the hydration degree of the phosphate group, as well as its mobility. Genistein ordered the lipid interfacial carbonyl group, as evidenced by the HATR-FTIR bandwidth analysis. This ordering effect was also observed in the lipidic hydrophobic region, by HATR-FTIR, NMR, DSC and turbidity responses. At the saturation concentration, liposome-loaded genistein inhibits the lipid peroxidation induced by hydroxyl radical in 90.9%. ASO liposome-loaded genistein at 100 µM decreased C6 glioma cell viability by 57% after 72 h of treatment. Results showed an increase of the genistein in vitro activities after its incorporation in liposomes. The data described in this work will contribute to a better understanding of the interaction between genistein and a natural-source membrane and of its influence on isoflavone biological activities. Furthermore, the antitumoral results showed that genistein-based liposomes, which contain natural-sourced lipids, may be promising as a drug delivery system to be used in the glioma therapy.
Asunto(s)
Antineoplásicos/farmacología , Antioxidantes/farmacología , Genisteína/farmacología , Liposomas/química , Fosfatidilcolinas/química , Antineoplásicos/administración & dosificación , Antineoplásicos/química , Antioxidantes/administración & dosificación , Antioxidantes/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Genisteína/administración & dosificación , Genisteína/química , Glioma/tratamiento farmacológico , Humanos , Peroxidación de Lípido/efectos de los fármacos , Espectroscopía de Resonancia MagnéticaRESUMEN
This work describes the ultrasound-assisted regeneration of aldehydes from oximes in ethanol and phosphoric acid as mediator of the reaction. The large scale regeneration of benzaldehyde was shown under similar conditions. The products were isolated in good yields after short reaction times under mild conditions.
Asunto(s)
Aldehídos/química , Oximas/química , Ultrasonido , Catálisis , Etanol/química , Ácidos Fosfóricos/químicaRESUMEN
A rapid and cleaner procedure for the synthesis of a series of 2-(3,5-diaryl-4,5-dihydro-1H-pyrazol-1-yl)-4-phenylthiazoles under ultrasonic irradiation in ethanol is described.
Asunto(s)
Tiazoles/síntesis química , Ultrasonido , Etanol/química , Tiazoles/químicaRESUMEN
An ultrasound-enhanced method has been developed for the synthesis of a variety of thioesters from benzoyl chlorides and 2-mercaptobenzoxa(thia)zoles. Applying this methodology, 14 compounds were synthesized in excellent yields.
RESUMEN
An ultrasound-assisted preparation of a series of novel 3,5-diaryl-4,5-dihydro-1H-pyrazole-1-carboximidamides that proceeds via the efficient reaction of chalcones with aminoguanidine hydrochloride under clean conditions is described.
Asunto(s)
Amidas/síntesis química , Amidas/efectos de la radiación , Chalconas/química , Chalconas/efectos de la radiación , Guanidinas/química , Guanidinas/efectos de la radiación , Sonicación/métodos , Dosis de RadiaciónRESUMEN
An efficient and green synthesis of thiocarbamoyl-3,5-diaryl-4,5-dihydro-1H-pyrazoles via the condensation of chalcones with thiosemicarbazide in ethanol and KOH under ultrasound irradiation is reported. The products were isolated in good yields after short reaction times.