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New thiosemicarbazides and 1,2,4-triazolethiones derived from 2-(ethylsulfanyl) benzohydrazide as potent antioxidants

Nazarbahjat N 1 , Nordin N 1 , Abdullah Z 2 , Abdulla MA 3 , Yehye WA 4 , Halim SN 5 Show all authors , Kee CH 6 , Ariffin A 7

Affiliations 

  • 1 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. nnazarbahjat@yahoo.com
  • 2 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. zana@um.edu.my
  • 3 Department of Biomedical Science, Faculty of Medicine, University of Malaya, 50603 Kuala Lumpur, Malaysia. ammeen@um.edu.my
  • 4 Nanotechnology & Catalysis Research Centre (NANOCAT), University of Malaya, Block 3A, Institute of Postgraduate Studies Building, 50603 Kuala Lumpur, Malaysia. wdabdoub@um.edu.my
  • 5 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. nadiahhalim@um.edu.my
  • 6 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. chkee@um.edu.my
  • 7 Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia. azhar70@um.edu.my
Molecules, 2014;19(8):11520-37.
PMID: 25093989 DOI: 10.3390/molecules190811520

Abstract

New thiosemicarbazide derivatives 2-6 were synthesised by reacting 2-(ethylsulfanyl)benzohydrazide with various aryl isothiocyanates. The cyclisation of compounds 2-6 under reflux conditions in a basic medium (aqueous NaOH, 4 N) yielded compounds 7-11 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).

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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