Collect. Czech. Chem. Commun.
1993, 58, 191-196
https://doi.org/10.1135/cccc19930191
Relations between Structure and Antituberculotic Activity of 4-Alkoxybenzoic Acids
Karel Waissera, Jiří Kuneša, Jiří Klimešb, Miroslav Polášekc and Želmíra Odlerovád
a Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 501 65 Hradec Králové, Czech Republic
b Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University, 501 65 Hradec Králové, Czech Republic
c Department of Analytical Chemistry, Faculty of Pharmacy, Charles University, 501 65 Hradec Králové, Czech Republic
d Institute of Preventive and Clinical Medicine, 833 01 Bratislava, Slovak Republic
Abstract
Antimycobacterial activity of a series of alkoxybenzoic acids including 4-methoxybenzoic acid (II), 4-ethoxybenzoic acid (III), 4-propoxybenzoic acid (IV), 4-butoxybenzoic acid (V), 4-pentoxybenzoic acid (VI), 4-allyloxybenzoic acid (IX), 4-isopropoxybenzoic acid (VII), 4-isobutoxybenzoic acid (VIII) and 4-benzyloxybenzoic acid (X) has been determined and found to increase with the lipophilicity of the compounds expressed by the corresponding HPLC capacity factors. Also determined were the pKa values of the compounds mentioned. The most active compound, 4-pentoxybenzoic acid (VI), is comparable with commercial antituberculotics when tested in vitro.
