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Molecules 2016, 21(2), 224; doi:10.3390/molecules21020224

Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study

1
Department of Chemistry, Faculty of Science, University of Malaya, Kuala Lumpur 50603, Malaysia
2
General Directorate of Curricula, Ministry of Education, Baghdad 3310, Iraq
3
Department of Molecular Medicine, Faculty of Medicine, University of Malaya, Kuala Lumpur 50603, Malaysia
*
Author to whom correspondence should be addressed.
Academic Editor: Richard A. Bunce
Received: 8 January 2016 / Revised: 4 February 2016 / Accepted: 5 February 2016 / Published: 17 February 2016
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [2349 KB, uploaded 17 February 2016]   |  

Abstract

A series of heterocyclic compounds bearing the well-known free radical scavenging 3,4,5-trimethoxybenzyloxy group, was synthesized. The key compound 4-(3,4,5-trimethoxybenzyl-oxy)benzohydrazide was converted into thiosemicarbazide derivatives, which were subsequently cyclized with NaOH to provide 1,2,4-triazole derivatives. Alternative treatment of the acid hydrazide with carbon disulfide in the presence of KOH led to the corresponding 1,3,4-oxadiazole and various alkylated derivatives. The newly synthesized compounds were purified and the structures of the products were elucidated and confirmed on the basis of their analytical and spectral data. Their antioxidant activities were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and Ferric Reducing Antioxidant Power (FRAP) assays. The thiosemicarbazide derivatives were highly active in both antioxidant assays with the lowest IC50 value for DPPH radical scavenging. Theoretical calculations based on density functional theory (DFT) were performed to understand the relative importance of NH, SH and CH hydrogens on the radical scavenging activities of these compounds. View Full-Text
Keywords: thiosemicarbazide; triazole; oxadiazole; antioxidant; hydrogen atom transfer; single electron transfer thiosemicarbazide; triazole; oxadiazole; antioxidant; hydrogen atom transfer; single electron transfer
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kareem, H.S.; Nordin, N.; Heidelberg, T.; Abdul-Aziz, A.; Ariffin, A. Conjugated Oligo-Aromatic Compounds Bearing a 3,4,5-Trimethoxy Moiety: Investigation of Their Antioxidant Activity Correlated with a DFT Study. Molecules 2016, 21, 224.

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