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Molecules 2017, 22(8), 1247; doi:10.3390/molecules22081247

Multifunctional Cinnamic Acid Derivatives

1
Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Health Sciences, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece
2
Department of Pharmaceutical Technology and Pharmaceutical Analysis, School of Pharmacy, University of Patras, Rio Patras 26504, Greece
*
Author to whom correspondence should be addressed.
Received: 9 June 2017 / Revised: 24 July 2017 / Accepted: 24 July 2017 / Published: 25 July 2017
(This article belongs to the Special Issue Polypharmacology and Multitarget Drug Discovery)
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Abstract

Our research to discover potential new multitarget agents led to the synthesis of 10 novel derivatives of cinnamic acids and propranolol, atenolol, 1-adamantanol, naphth-1-ol, and (benzylamino) ethan-1-ol. The synthesized molecules were evaluated as trypsin, lipoxygenase and lipid peroxidation inhibitors and for their cytotoxicity. Compound 2b derived from phenoxyphenyl cinnamic acid and propranolol showed the highest lipoxygenase (LOX) inhibition (IC50 = 6 μΜ) and antiproteolytic activity (IC50 = 0.425 μΜ). The conjugate 1a of simple cinnamic acid with propranolol showed the higher antiproteolytic activity (IC50 = 0.315 μΜ) and good LOX inhibitory activity (IC50 = 66 μΜ). Compounds 3a and 3b, derived from methoxylated caffeic acid present a promising combination of in vitro inhibitory and antioxidative activities. The S isomer of 2b also presented an interesting multitarget biological profile in vitro. Molecular docking studies point to the fact that the theoretical results for LOX-inhibitor binding are identical to those from preliminary in vitro study. View Full-Text
Keywords: cinnamic acids; multitarget; lipoxygenase inhibitors; antiproteolytic activity cinnamic acids; multitarget; lipoxygenase inhibitors; antiproteolytic activity
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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

Peperidou, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Voulgari, E.; Avgoustakis, K. Multifunctional Cinnamic Acid Derivatives. Molecules 2017, 22, 1247.

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