Synthesis and activity of substituted 2-phenylquinolin-4-amines, antagonists of immunostimulatory CpG-oligodeoxynucleotides.

doi:10.1021/JM020374Y

Paper

Synthesis and activity of substituted 2-phenylquinolin-4-amines, antagonists of immunostimulatory CpG-oligodeoxynucleotides.

Published Mar 27, 2003 · L. Strekowski,, Martial Say, M. Henary

Journal of medicinal chemistry

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48

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Abstract

Fifty-seven 2-phenylquinolines substituted at the phenyl group and C4 of the quinoline were synthesized and analyzed for inhibition of the immunostimulatory effect of oligodeoxynucleotides with a CpG-motif. The Fujita-Ban variant of the classical Free-Wilson analysis gave a highly significant correlation for a series of 48 relatively small molecules demonstrating that (i) the partial contributions of substituents to biological activity (EC(50)) are additive and (ii) assuming similar bioavailability for all quinolines studied, the larger molecules cannot be accommodated within a still unknown biological receptor. The results suggest interaction of a basic antagonist molecule with weakly acidic groups in the antagonist-receptor complex. N-[2-(Dimethylamino)ethyl]-2-[4-(4-methylpiperazino)phenyl]quinolin-4-amine (50) is the most effective antagonist found in this study (EC(50) = 0.76 nM).

In Vitro Study

Study Snapshot

Substituted 2-phenylquinolines effectively inhibit the immunostimulatory effect of CpG-oligodeoxynucleotides, with N-[2-(Dimethylamino)ethyl]-2-[4-(4-methylpiperazino)phenyl

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and activity of substituted 2-phenylquinolin-4-amines, antagonists of immunostimulatory CpG-oligodeoxynucleotides.

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References

Citations

4-Aminoquinoline as a privileged scaffold for the design of leishmanicidal agents: structure–property relationships and key biological targets

4-aminoquinoline scaffolds offer potential for designing safe and effective leishmanicidal agents by targeting key aspects of parasite survival.

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This study developed a mild, efficient, and practical protocol for preparing 2-sulfonylquinolines through deoxygenative C2-H sulfonylation of quinoline N-oxides with readily available RSO2Cl, exhibiting wide substrate scope and functional group tolerance.

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This study developed an organocatalytic Csp2-O amination of quinolin-4(1H)-ones with 3-alkynyl-3-hydroxyisoindolinones, enabling the direct asymmetric synthesis of Csp2-N atropisomers.

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This metal-free method efficiently synthesizes fluorescent -carboline C1 substituted pyrido(2,3-c)carbazole derivatives with excellent luminescent properties and up to 60% quantum yield.

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This study demonstrates a novel electrochemical method for synthesizing sulfonylated electron-deficient heteroarenes/arenes at room temperature, with excellent regioselectivity.

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