Publication
Title
Synthesis of natural pyranonaphthoquinones and related antibiotic aza-analogues
Author
Abstract
Pentalongin, the active principle isolated from the roots of the Central East African medicinal plant Pentas longiflora, revealing the basic skeleton of 3,4-dehydropyranonaphthoquinones, was synthesized by ring-closing metathesis of a suitable precursor. Mollugin, together with the (+)-cis-dihydroxylated analogue and the tetracyclic isagarin have been isolated from P. longiflora as well as from other rubiaceous herbs, which are often used in Chinese folk medicine. Synthetic routes of these natural products are presented, as well as the first syntheses of the natural products 3-hydroxy- and 3-methoxymollugin. Although pyranonaphthoquinones represent a large class of natural products, reports of their naturally occurring 2-aza analogues, all of which have been isolated as 2-aza-anthraquinones, are scarce in the literature. Nevertheless, this class of compounds has been found to possess interesting antitumor, antifungal, and antibiotic properties. Therefore, several synthetic routes to new classes of 2-aza-anthraquinones were developed. In vitro testing of the obtained compounds for their activity against Mycobacterium tuberculosis showed promising results.
Language
English
Source (journal)
Pure and applied chemistry. - London
Publication
London : 2011
ISSN
0033-4545
Volume/pages
83:9(2011), p. 1651-1674
ISI
000298741900003
Full text (Publisher's DOI)
UAntwerpen
Faculty/Department
Research group
Publication type
Subject
Affiliation
Publications with a UAntwerp address
External links
Web of Science
Record
Identification
Creation 18.04.2012
Last edited 16.11.2017
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