Publication
Title
Synthesis and anti-tubercular activity of $N^{2}$-arylbenzo[g]isoquinoline-5,10-dione-3-iminium bromides
Author
Abstract
 Tuberculosis has remained a challenge for medicinal chemists worldwide. In the framework of a collaborative program to identify and evaluate novel antitubercular candidate compounds, the biological properties of benzo[g]isoquinoline-5,10-diones have been found to be very promising. In this paper we have further expanded the library by incorporation of an amidinium moiety into the benzo[g] isoquinoline-5,10-dione scaffold. The presence of this functional group also increased the solubility of the quinones in polar solvents. To this purpose N-2-arylbenzo[g]isoquinoline-5,10-dione-3-iminium bromides were synthesized in a straightforward way by means of a reaction of anilines with 2-(bromomethyl)-3-(cyanomethyl)-1,4-dimethoxynaphthalene. Following the biological evaluation, N-2-(4-chlorophenyl)-5,10-dioxobenzo[g]isoquinoline-3(2H)-iminium bromide (MIC = 1.16 mu M, CC50 = 28.51 mu M, SI = 24.58) was selected as the most promising representative. Apart from the nano-molar anti-mycobacterial activity, the compound was able to target intracellular residing Mycobacterium tuberculosis and the susceptibility of a multi-drug-resistant strain towards the compound was confirmed.
Language
English
Source (journal)
Organic and biomolecular chemistry. - Cambridge, 2003, currens
Publication
Cambridge : 2016
ISSN
1477-0520 [print]
1477-0539 [online]
Volume/pages
14:6(2016), p. 2041-2051
ISI
000369601600018
Full text (Publisher's DOI)
Full text (open access)
UAntwerpen
 Faculty/Department Research group Publication type Subject Affiliation Publications with a UAntwerp address