Abstract
The pyrazoline ring is defined as a “privileged structure” in medicinal chemistry. A variety of pharmacological properties of pyrazolines is associated with the nature and position of various substituents, which is especially evident in diarylpyrazolines. Compounds with a chalcone fragment show a wide range of biological properties as well as high reactivity which is primarily due to the presence of an α, β-unsaturated carbonyl system. At the same time, bicyclic monoterpenoids deserve special attention as a source of a key structural block or as one of the pharmacophore components of biologically active molecules. A series of new diarylpyrazoline derivatives based on isobornylchalcones with different substitutes (MeO, Hal, NO2, N(Me)2) was synthesized. Antioxidant properties of the obtained compounds were comparatively evaluated using in vitro model Fe2+/ascorbate-initiated lipid peroxidation in the substrate containing brain lipids of laboratory mice. It was demonstrated that the combination of the electron-donating group in the para-position of ring B and OH-group in the ring A in the structure of chalcone fragment provides significant antioxidant activity of synthesized diarylpyrazoline derivatives.
Highlights
Lipid peroxidation (LPO) is a process initiated by free radicals attacking phospholipids or polyunsaturated fatty acids, which leads to the formation of various types of toxic oxidation products [1]
The initial racemic 1,3-dihydroxy-4-isobornylbenzene 1 was synthesized via the alkylation of resorcinol with camphene according to the known method [43] (Scheme 1)
Claisen–Schmidt condensation of isobornylacetophenone derivatives 3 and 4 with appropriately substituted benzaldehydes was carried out in order to synthesize a set of chalcone derivatives with dimethylamino, chloro, bromo, methoxy, and nitro B-ring substituents (Scheme 1)
Summary
Lipid peroxidation (LPO) is a process initiated by free radicals attacking phospholipids or polyunsaturated fatty acids, which leads to the formation of various types of toxic oxidation products [1]. The 3,4-dihydro-2Hbenz[e][1,3]oxazine derivative of 2-hydroxy-3-isobornyl-5-methylbenzaldehyde showed high membrane-protective activity on the model H2O2-induced hemolysis towards mammalian red blood cells [27] From this point of view, the synthesis of heterocyclic compounds based on the transformations of isobornylphenols and the study of their antioxidant activity is an interesting subject of research. The brain contains a relatively high degree of polyunsaturated fatty acids that are good substrates for peroxidation reactions [39,40] This approach is common for studies of antioxidant activity of food products, plant extracts, and chemical compounds promising for pharmacology.
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