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Molecules 2015, 20(2), 2555-2575; doi:10.3390/molecules20022555

Synthesis and Antioxidant Activity of Polyhydroxylated trans-Restricted 2-Arylcinnamic Acids

1
Faculty of Chemistry and Pharmacy, University of Sofia "St. Kliment. Ohridski", 1, James Bourchier Blvd., Sofia 1164, Bulgaria
2
Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Science, Acad. G. Bonchev Str. Bl. 9, Sofia 1113, Bulgaria
*
Author to whom correspondence should be addressed.
Academic Editor: D. Hadjipavlou-Litina
Received: 30 October 2014 / Accepted: 26 January 2015 / Published: 2 February 2015
(This article belongs to the Special Issue Cinnamic Acids Hybrids with Biological Interest)
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Abstract

A series of sixteen polyhydroxylated trans-restricted 2-arylcinnamic acid analogues 3ap were synthesized through a one-pot reaction between homophthalic anhydrides and various aromatic aldehydes, followed by treatment with BBr3. The structure of the newly synthesized compounds was confirmed by spectroscopic methods and the configuration around the double bond was unequivocally estimated by means of gated decoupling 13C-NMR spectra. It was shown that the trans-cinnamic acid fragment incorporated into the target compounds’ structure ensures the cis-configuration of the stilbene backbone and prevents further isomerization along the carbon–carbon double bond. The antioxidant activity of compounds 3ap was measured against 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl (OH) and superoxide (O2) radicals. The results obtained showed that the tested compounds possess higher activities than natural antioxidants such as protocatechuic acid, caffeic acid and gallic acid. Moreover, it was shown that a combination of two different and independently acting fragments of well-known pharmacological profiles into one covalently bonded hybrid molecule evoke a synergistic effect resulting in higher than expected activity. To rationalize the apparent antioxidant activity and to establish the mechanism of action, a SAR analysis and DFT quantum chemical computations were also performed. View Full-Text
Keywords: homophthalic anhydride; ROS; antioxidants; phenolic acids; hybrid molecules; synergy homophthalic anhydride; ROS; antioxidants; phenolic acids; hybrid molecules; synergy
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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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MDPI and ACS Style

Miliovsky, M.; Svinyarov, I.; Prokopova, E.; Batovska, D.; Stoyanov, S.; Bogdanov, M.G. Synthesis and Antioxidant Activity of Polyhydroxylated trans-Restricted 2-Arylcinnamic Acids. Molecules 2015, 20, 2555-2575.

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