Investigating biological activity spectrum for novel quinoline analogues 2: Hydroxyquinolinecarboxamides with photosynthesis-inhibiting activity

Photosynthetic Inhibitors

“…Details about the preparation of the mentioned compounds can be found in the cited references and will not be covered herein since this is not the focus of this book chapter. Several papers has been published in the last few years dealing with the synthesis of various aromatic nitrogenated compounds and their biological evaluation as photosynthetic inhibitors (Jampilek et al, 2009a,b;Musiol et al, 2007;Musiol et al, 2008;Musiol et al, 2010;Otevrel et al, 2010). The general structures and their associated most active compounds are presented in Figure 7 along with the IC 50 data.…”

“…Compounds lacking this functionality at the specified position were completely inactive. Considering the quinolines (31), no simple structure-activity relationship explaining the observed activity was found being the two most active derivatives (31a) and (31b) (Musiol et al, 2008). In a series of twelve ring-substituted 4-hydroxy-1H-quinolin-2-one derivatives (general structure 32), all of the compounds displayed very low inhibitory activity (IC 50 ranging from 126 to 925 mol L -1 ) on electron transport in photosynthesis from water to DCPIP (Jampilek et al, 2009a).…”

Preparation and Herbicidal Activity of Halogenated 8-Hydroxyquinoline-2-carboxanilides

“…In addition, according to the results reported recently, some quinoline derivatives and their analogues/isosteres also showed noteworthy herbicidal activities [7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Although at present approximately 20 mechanisms of action of herbicides are known [21], over 50% of commercially available herbicides act by reversible binding to photosystem II (PS II), a membrane-protein complex in the thylakoid membranes, which catalyses the oxidation of water and the reduction of plastoquinone [22], and thereby inhibit photosynthesis [23][24][25].…”

“…Although at present approximately 20 mechanisms of action of herbicides are known [21], over 50% of commercially available herbicides act by reversible binding to photosystem II (PS II), a membrane-protein complex in the thylakoid membranes, which catalyses the oxidation of water and the reduction of plastoquinone [22], and thereby inhibit photosynthesis [23][24][25]. Some organic compounds, possessing an amide (-NHCO-) group, e.g., substituted anilides [11,[15][16][17][18]20], or a wide variety of compounds containing the quinoline system [9,10,[12][13][14]19] were found to interact with tyrosine radicals Tyr Z and Tyr D (or their surroundings) which are situated in D 1 and D 2 proteins on the donor side of PS II. Due to this interaction, interruption of the photosynthetic electron transport occurs.…”

“…Due to this interaction, interruption of the photosynthetic electron transport occurs. In the context of the previously-described azanaphtalenes and their isosteres [7][8][9][10][11][12][13][14][15][16][17][18][19][20], new simple modifications of quinoline that can possess interesting biological activity were investigated. The compounds were tested for their photosynthesis-inhibiting activity -the inhibition of photosynthetic electron transport in spinach chloroplasts (Spinacia oleracea L.).…”