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

International Journal of Molecular Sciences

Stefania-Felicia Barbuceanu¹  Diana Carolina Ilies¹  Gabriel Saramet²  Valentina Uivarosi⁴  Constantin Draghici³ 

[1]Organic Chemistry Department, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania

[2] E-Mails:

[3]Pharmaceutical Technology Department, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania

[4] E-Mail:

[5]“C.D. Nenitescu” Institute of Organic Chemistry, Romanian Academy, 202B Splaiul Independenţei, 060023 Bucharest, Romania

[6] E-Mail:

[7]General and Inorganic Chemistry Department, Faculty of Pharmacy, “Carol Davila” University of Medicine and Pharmacy, 6 Traian Vuia, 020956 Bucharest, Romania

[8] E-Mail:

关键词: hydrazinecarbothioamide;    1;    2;    4-triazole-3-thione;    cyclization;    alkylation;    antioxidant activity;    diarylsulfone;    2;    4-difluorophenyl moiety;   

DOI  :  10.3390/ijms150610908

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2014 by the authors; licensee MDPI, Basel, Switzerland.