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Int. J. Mol. Sci. 2014, 15(6), 10908-10925; doi:10.3390/ijms150610908
Article

Synthesis and Antioxidant Activity Evaluation of New Compounds from Hydrazinecarbothioamide and 1,2,4-Triazole Class Containing Diarylsulfone and 2,4-Difluorophenyl Moieties

1,* , 1,†
,
2,†
,
3,†
,
4,†
 and
1,†
1 Organic Chemistry Department, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania 2 Pharmaceutical Technology Department, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania 3 General and Inorganic Chemistry Department, Faculty of Pharmacy, "Carol Davila" University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania 4 Nenitescu" Institute of Organic Chemistry, Romanian Academy, 202B Splaiul Independenţei, 060023 Bucharest, Romania These authors contributed equally to this work.
* Author to whom correspondence should be addressed.
Received: 15 April 2014 / Revised: 7 June 2014 / Accepted: 10 June 2014 / Published: 17 June 2014
(This article belongs to the Special Issue Molecular Science for Drug Development and Biomedicine)
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Abstract

In the present investigation, new hydrazinecarbothioamides 46 were synthesized by reaction of 4-(4-X-phenylsulfonyl)benzoic acids hydrazides (X= H, Cl, Br) 13 with 2,4-difluorophenyl isothiocyanate and further these were treated with sodium hydroxide to obtain 1,2,4-triazole-3-thione derivatives 79. The reaction of 79 with α-halogenated ketones, in basic media, afforded new S-alkylated derivatives 1015. 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 46 showed excellent antioxidant activity and 1,2,4-triazole-3-thiones 79 showed good antioxidant activity using the DPPH method.
Keywords: hydrazinecarbothioamide; 1,2,4-triazole-3-thione; cyclization; alkylation; antioxidant activity, diarylsulfone, 2,4-difluorophenyl moiety hydrazinecarbothioamide; 1,2,4-triazole-3-thione; cyclization; alkylation; antioxidant activity, diarylsulfone, 2,4-difluorophenyl moiety
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Barbuceanu, S.-F.; Ilies, D.C.; Saramet, G.; Uivarosi, V.; Draghici, C.; Radulescu, V. Synthesis and Antioxidant Activity Evaluation of New Compounds from Hydrazinecarbothioamide and 1,2,4-Triazole Class Containing Diarylsulfone and 2,4-Difluorophenyl Moieties. Int. J. Mol. Sci. 2014, 15, 10908-10925.

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