TY - JOUR
T1 - Ultrasound-Assisted Synthesis and Antioxidant Activity of 3-Selanyl-1 H-indole and 3-Selanylimidazo[1,2-a]pyridine Derivatives
AU - Vieira, Beatriz M.
AU - Thurow, Samuel
AU - da Costa, Monaliza
AU - Casaril, Angela M.
AU - Domingues, Micaela
AU - Schumacher, Ricardo F.
AU - Perin, Gelson
AU - Alves, Diego
AU - Savegnago, Lucielli
AU - Lenardão, Eder J.
N1 - Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/11
Y1 - 2017/11
N2 - A simple and rapid method for the selective synthesis of 3-(organylselanyl)-1 H-indoles and 3-(organylselanyl)imidazo[1,2-a]pyridines catalyzed by CuI/SeO2 under ultrasound irradiation was developed. This protocol employs a diverse range of 1 H-indoles or imidazo[1,2-a]pyridines and diorganyl diselenides to afford the corresponding products selectively in good to excellent yields. Moreover, the antioxidant activity of these compounds was evaluated by using a wide range of in vitro assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, ferric ion reducing antioxidant power (FRAP), and inhibition of reactive species formation in mice cortex. The bioassays revealed that both classes of the newly synthesized organoselenium compounds present antioxidant activity, with emphasis on the 3-(organylselanyl)-1 H-indoles. This pharmacological activity opens a wide range of biological applications where the reduction of oxidative stress is essential.
AB - A simple and rapid method for the selective synthesis of 3-(organylselanyl)-1 H-indoles and 3-(organylselanyl)imidazo[1,2-a]pyridines catalyzed by CuI/SeO2 under ultrasound irradiation was developed. This protocol employs a diverse range of 1 H-indoles or imidazo[1,2-a]pyridines and diorganyl diselenides to afford the corresponding products selectively in good to excellent yields. Moreover, the antioxidant activity of these compounds was evaluated by using a wide range of in vitro assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, ferric ion reducing antioxidant power (FRAP), and inhibition of reactive species formation in mice cortex. The bioassays revealed that both classes of the newly synthesized organoselenium compounds present antioxidant activity, with emphasis on the 3-(organylselanyl)-1 H-indoles. This pharmacological activity opens a wide range of biological applications where the reduction of oxidative stress is essential.
KW - 3-selanyl-1 H-indole
KW - 3-selanylimidazo[1,2-a]pyridine
KW - antioxidant activity
KW - organoselenium
KW - sonochemistry
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U2 - 10.1002/ajoc.201700339
DO - 10.1002/ajoc.201700339
M3 - Article
AN - SCOPUS:85029216598
SN - 2193-5807
VL - 6
SP - 1635
EP - 1646
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 11
ER -