Synthesis of quinoline/naphthalene-containing azaphenothiazines and their potent in vitro antioxidant properties

Medicinal Chemistry Research : an International Journal for Rapid Communications on Design and Mechanisms of Action of Biologically Active Agents
Małgorzata JeleńKrystian Pluta

Abstract

New tetracyclic and pentacyclic azaphenothiazines containing one or two quinoline rings instead of benzene rings were obtained in the original reactions of isomeric diquinodithiins, dichlorodiquinolinyl sulfides, and disulfide with aromatic amines. The type of ring fusion in the azaphenothiazine system was concluded from the (1)H NMR spectra. The obtained azaphenothiazines were evaluated in vitro for their antioxidant activity on rat hepatic microsomal membranes for protection of non-enzymatic lipid peroxidation promoted by the Fe(2+)/ascorbic acid redox system. Most compounds exhibited a very significant antioxidant activity with IC50 values between 1 and 23 μM. The degree of antioxidant activity depends on the lipophilicity and molecular size as well as the (non)substitution of the thiazine nitrogen atom and type of ring system fusion. It is the first time to our knowledge that azaphenothiazines are shown to exhibit such potent antioxidant activity.

References

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Citations

Apr 30, 2016·Biochemistry Research International·Godwill Azeh EngwaMarcellus Unaegbu
Nov 10, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Andrzej ZiębaDariusz Kuśmierz
May 9, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Jimena VaraCristina S Ortiz
Oct 27, 2018·European Journal of Medicinal Chemistry·Subhajit MakarSushil K Singh
Aug 29, 2021·Medicinal Research Reviews·Kritika LaxmikeshavNagula Shankaraiah

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Methods Mentioned

BETA
column chromatography

Software Mentioned

Spartan
CS Chem 3D Ultra

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