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Molecules 2014, 19(8), 11520-11537; doi:10.3390/molecules190811520

New Thiosemicarbazides and 1,2,4-Triazolethiones Derived from 2-(Ethylsulfanyl) Benzohydrazide as Potent Antioxidants

1
Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia
2
Department of Biomedical Science, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia
3
Department of Medical Analysis, College of Health and Medical Technologies, P.O.10047, Baghdad, Iraq
4
Section for Co-Curriculum Courses, External Faculty Electives & TITAS (SKET), University of Malaya, 50603 Kuala Lumpur, Malaysia
5
Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, 50603 Kuala Lumpur, Malaysia
*
Author to whom correspondence should be addressed.
Received: 25 June 2014 / Revised: 21 July 2014 / Accepted: 24 July 2014 / Published: 4 August 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [1552 KB, uploaded 4 August 2014]   |  

Abstract

New thiosemicarbazide derivatives 26 were synthesised by reacting 2-(ethylsulfanyl)benzohydrazide with various aryl isothiocyanates. The cyclisation of compounds 26 under reflux conditions in a basic medium (aqueous NaOH, 4 N) yielded compounds 711 that contain a 1,2,4-triazole ring. All of the synthesised compounds were screened for their antioxidant activities. Compounds 2, 3, and 7 showed better radical scavenging in a 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay, with IC50 values of 1.08, 0.22, and 0.74 µg/mL, respectively, compared to gallic acid (IC50, 1.2 µg/mL). Compound 3 also showed superior results in a ferric reducing antioxidant power (FRAP) assay (3054 µM/100 g) compared to those of ascorbic acid (1207 µM/100 g). View Full-Text
Keywords: thiosemicarbazide derivatives; 1,2,4-triazoles; thioethers; X-ray structure determination; antioxidant activity thiosemicarbazide derivatives; 1,2,4-triazoles; thioethers; X-ray structure determination; antioxidant activity
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Nazarbahjat, N.; Nordin, N.; Abdullah, Z.; Abdulla, M.A.; Yehye, W.A.; Halim, S.N.A.; Kee, C.H.; Ariffin, A. New Thiosemicarbazides and 1,2,4-Triazolethiones Derived from 2-(Ethylsulfanyl) Benzohydrazide as Potent Antioxidants. Molecules 2014, 19, 11520-11537.

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