Structure-Activity Relationships of N-benzylsalicylamides for Inhibition of Photosynthetic Electron Transport

ISSN: 1875-6638 (Online)
ISSN: 1573-4064 (Print)

Volume 11, 8 Issues, 2015

Download PDF Flyer

Medicinal Chemistry

Aims & ScopeAbstracted/Indexed in

Submit Abstracts Online Submit Manuscripts Online

Honorary Life Fellow
Kings College
University of Cambridge

View Full Editorial Board

Subscribe Purchase Articles Order Reprints

Current: 1.387
5 - Year: 1.379

Structure-Activity Relationships of N-benzylsalicylamides for Inhibition of Photosynthetic Electron Transport

Author(s): Katarina Kralova, Milan Perina, Karel Waisser and Josef Jampilek

Affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic


Inhibition of photosynthetic electron transport (PET) in spinach chloroplasts by sixty-one ring-substituted N-benzylsalicylamides was investigated. The inhibitory potency of compounds expressed by IC50 value varied from 2.0 to 425.3 mol/L. Several of the evaluated compounds can be considered as effective PET inhibitors; these include N-(3,4-dichlorobenzyl)-2-hydroxy-5-nitrobenzamide (IC50 = 2.0 mol/L), 3,5-dibromo-N-(3,4-dichlorobenzyl)-2-hydroxybenzamide (IC50 = 2.3 mol/L) and 3,5-dibromo-N-(4-chlorobenzyl)-2-hydroxybenzamide (IC50 = 2.6 mol/L), which had activity comparable with the standard Diuron (IC50 = 1.9 mol/L). The PET inhibiting activity increased approximately linearly with increasing lipophilicity of the compounds as well as with the increasing sum of Hammett  constants of substituents on the acyl (R1 = H, 5-OCH3, 5-CH3, 5-Cl, 5-Br, 5-NO2, 4-OCH3, 4-Cl, 3,5-Cl and 3,5-Br) and benzylamide fragments (R2 = H, 4-OCH3, 4-CH3, 4-F, 4-Cl and 3,4-Cl). Based on evaluated structure-PET inhibiting activity relationships (QSAR) it was confirmed that the inhibitory activity of the compounds depends on lipophilicity (log P or distributive parameters 1 and 2 of individual substituents) and electronic properties of substituents on acyl (1) and benzylamide fragments (2), the contribution of 1 being more significant than that of 2

Purchase Online Order Reprints Order Eprints Rights and Permissions


Article Details

Volume: 10
First Page: 1
Page Count: 1
DOI: 10.2174/1573406410666140815125004

Related Journals

Webmaster Contact: Copyright © 2015 Bentham Science