Title
Synthesis and anti-tubercular activity of <tex>$N^{2}$</tex>-arylbenzo[g]isoquinoline-5,10-dione-3-iminium bromides Synthesis and anti-tubercular activity of <tex>$N^{2}$</tex>-arylbenzo[g]isoquinoline-5,10-dione-3-iminium bromides
Author
Faculty/Department
Faculty of Sciences. Chemistry
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
Cambridge ,
Subject
Chemistry
Source (journal)
Organic and biomolecular chemistry. - Cambridge, 2003, currens
Volume/pages
14(2016) :6 , p. 2041-2051
ISSN
1477-0520
ISI
000369601600018
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
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.
E-info
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Full text (open access)
https://repository.uantwerpen.be/docman/irua/4eb1a6/131635.pdf
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