Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

• Type: Article in International Scientific Journal
• Date: 2011

Authors

menezes, jose c. j. m. d. s. (Author) Other; kamat, shrivallabh p. (Author) Other; cavaleiro, jose a. s. (Author) Other; gaspar, alexandra (Author) Other; garrido, jorge (Author) Other; borges, fernanda (Author) FCUP

Journal

Title: European Journal of Medicinal Chemistry

Vol. 46

Pages: 773-777

ISSN: 0223-5234

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 90 Citations

Scopus - 96 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Physical sciences > Chemistry > Applied chemistry > Pharmaceutical chemistry

Other information

Authenticus ID: P-002-VBM

DOI: 10.1016/j.ejmech.2010.12.016

Abstract (EN): Long chain alkyl hydroxycinnamates (8-21) were synthesized from the corresponding half esters of malonic acid (5-7) and benzaldehyde derivatives by Knoevenagel condensation. The total antioxidant capacity of these hydroxycinnamyl esters was evaluated using DPPH and ABTS assays. The observed antioxidant activity was highest for esters of caffeic acid followed by sinapic esters and ferulic esters. The parameters for drug-likeness of these hydroxycinnamyl esters were also evaluated according to the Lipinski's 'rule-of-five'. All the ester derivatives were found to violate one of the Lipinski's parameters (cLogP >5), even though they have been found to be soluble in protic solvents. The predictive topological polar surface area (TPSA) data allow concluding that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these novel lipophilic compounds as potential antioxidants for tackling oxidative processes. (C) 2010 Elsevier Masson SAS. All rights reserved.

Language: English

Type (Professor's evaluation): Scientific