Synthesis and biological evaluation of 2-hydroxy-3-[amino]benzoates

A series of twenty substituted 2-hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(alkoxycarbonyl)amino]benzoates were prepared and characterized. As similar compounds have been described as potential antimycobacterials, primary in vitro screening of the synthesized carbamates was also performed against t...

Full description

Saved in:
Bibliographic Details
Published inTheScientificWorld Vol. 13
Main Authors Tengler, Jan, Kapusova, Iva, Pesko, Matus, Govender, Rodney, Keltosova, Stanislava, Mokry, Petr, Kollar, Peter, O'Mahony, Jim, Coffey, Aidan, Kralova, Katarina, Jampuek, Josef
Format Journal Article
LanguageEnglish
Published Hindawi Limited 01.01.2013
Subjects
Amino compounds
Benzoates
Chemical properties
Chemical synthesis
Composition
Methods
Production processes
Online AccessGet full text

Cover

More Information
Summary:A series of twenty substituted 2-hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(alkoxycarbonyl)amino]benzoates were prepared and characterized. As similar compounds have been described as potential antimycobacterials, primary in vitro screening of the synthesized carbamates was also performed against two mycobacterial species. 2-Hydroxy-3-[2-(2,6-dimethoxyphenoxy)ethylamino]propyl 4-(butoxycarbonylamino)benzoate hydrochloride, 2-hydroxy-3-[2-(4-methoxyphenoxy)ethylamino]-propyl 4- (butoxycarbonylamino)benzoate hydrochloride, and 2-hydroxy-3-[2-(2-methoxyphenoxy)ethylamino]-propyl 4-(butoxycarbonylamino)benzoate hydrochloride showed higher activity against M. avium subsp. paratuberculosis and M. intracellulare than the standards ciprofloxacin, isoniazid, or pyrazinamide. Cytotoxicity assay of effective compounds was performed using the human monocytic leukaemia THP-1 cell line. Compounds with predicted amphiphilic properties were also tested for their effects on the rate of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. All butyl derivatives significantly stimulated the rate of PET, indicating that the compounds can induce conformational changes in thylakoid membranes resulting in an increase of their permeability and so causing uncoupling of phosphorylation from electron transport.
ISSN:1537-744X
1537-744X
DOI:10.1155/2013/274570