Investigating biological activity spectrum for novel quinoline analogues

Abstract

The lack of the wide spectrum of biological data is an important obstacle preventing the efficient molecular design. Quinoline derivatives are known to exhibit a variety of biological effects. In the current publication, we tested a series of novel quinoline analogues for their photosynthesis-inhibiting activity (the inhibition of photosynthetic electron transport in spinach chloroplasts (Spinacia oleracea L.) and the reduction of chlorophyll content in Chlorella vulgaris Beij.). Moreover, antiproliferative activity was measured using SK-N-MC neuroepithelioma cell line. We described the structure-activity relationships (SAR) between the chemical structure and biological effects of the synthesized compounds. We also measured the lipophilicity of the novel compounds by means of the RP-HPLC and illustrate the relationships between the RP-HPLC retention parameter logK (the logarithm of capacity factor K) and logP data calculated by available programs.

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.…”

Dissociation Constants of some Quinoline Derivatives in Mixed Solvent Mixture

“…In continuation with our previous work, in the present paper dissociation constants of some derivatives of quinoline have been studied. Literature survey shows that various quinoline derivatives are known to have broad spectrum of biological activities [4][5][6], such as antifungal [7], antibacterial [8], antioxidant [9], antiparasitic [9], antimicrobial [10], anti tubercular [11], anticytoxic [12], antiinflammatory [13,14], antiviral [15], antiparasitic [15] etc. Some other pharmacological activities of these derivatives have also been reported by some workers [16][17][18].…”

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.).…”