International Journal of Molecular Sciences 2014-01-01

Synthesis and antioxidant activity evaluation of new compounds from hydrazinecarbothioamide and 1,2,4-triazole class containing diarylsulfone and 2,4-difluorophenyl moieties.

Stefania-Felicia Barbuceanu, Diana Carolina Ilies, Gabriel Saramet, Valentina Uivarosi, Constantin Draghici, Valeria Radulescu

Index: Int. J. Mol. Sci. 15(6) , 10908-25, (2014)

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Abstract

In the present investigation, new hydrazinecarbothioamides 4-6 were synthesized by reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X=H, Cl, Br) 1-3 with 2,4-difluorophenyl isothiocyanate and further these were treated with sodium hydroxide to obtain 1,2,4-triazole-3-thione derivatives 7-9. The reaction of 7-9 with α-halogenated ketones, in basic media, afforded new S-alkylated derivatives 10-15. The structures of the synthesized compounds have been established on the basis of 1H-NMR, 13C-NMR, IR, mass spectral studies and elemental analysis. The antioxidant activity of all compounds has been screened. Hydrazinecarbothioamides 4-6 showed excellent antioxidant activity and 1,2,4-triazole-3-thiones 7-9 showed good antioxidant activity using the DPPH method.