Synthesis of methoxychalcone derivatives with isobornyl substituents

Попова, С. А.; Pavlova, Evgeniya V.; Chukicheva, I. Yu.

doi:10.24820/ark.5550190.p011.471

Cited by 2 publications

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“…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). The synthesis of chalcones 6a-k and 8a-k has been previously described [44,45]. Chalcones 6a-d and 8a-d were synthesized by KOH/MeOH condensation of compounds 3 and 4 with appropriate benzaldehydes, methoxychalcones 6e-k, 8e-k by condensation of compounds 3 and 4 with methoxy-substituted benzaldehydes 5e-k in the presence of sodium hydride in dimethylformamide.…”

Section: Resultsmentioning

confidence: 99%

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity

et al. 2021

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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.

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Section: Resultsmentioning

confidence: 99%