LC-MS/MS method for the determination of a semi-synthetic phenolic antioxidant 2,6-diisobornyl-4-methylphenol in rats after different administration routes.

IBP (2,6-diisobornyl-4-methylphenol) is a small drug molecule with antioxidant properties considered to be a promising neuro-, cardio-, and retinoprotective agent. In this study, a bioanalytical LC-MS/MS method for its determination in rat plasma was developed using 11H-indeno[1,2-b]quinoxalin-11-one oxime as an internal standard (IS). The analytes were extracted from plasma by liquid-liquid extraction technique using isopropyl alcohol:chloroform mixture (1:5, v/v) followed by evaporation and reconstitution of the residues in acetonitrile.

Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols.

The widespread presence of multidrug-resistant pathogenic microorganisms challenges the development of novel chemotype antimicrobials, insensitive to microbial tools of resistance. To date, various monoterpenoids have been shown as potential antimicrobials. Among many classes of molecules with antimicrobial activity, terpenes and terpenoids are an attractive basis for the design of antimicrobials because of their low toxicity and availability for various modifications.

Synthesis of Trifluoromethylated Monoterpene Amino Alcohols.

For the first time, monoterpene trifluoromethylated β-hydroxy-benzyl--oximes were synthesized in 81-95% yields by nucleophilic addition of the Ruppert-Prakash reagent (TMSCF) to the corresponding β-keto-benzyl--oximes based on (+)-nopinone, (-)-verbanone and (+)-camphoroquinone. Trifluoromethylation has been determined to entirely proceed chemo- and stereoselective at the C=O rather than C=N bond. Trifluoromethylated benzyl--oximes were reduced to the corresponding α-trifluoromethyl-β-amino alcohols in 82-88% yields.

Isobornylchalcones as Scaffold for the Synthesis of Diarylpyrazolines with Antioxidant Activity.

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.

Synthesis and Antioxidant Activity of Carane and Pinane Based Sulfenimines and Sulfinimines.

The synthesis of sulfenimines and sulfinimines has been carried out with 10-hydroxyisocamphylthiol. The configuration of the compounds has been deduced by methods of NMR, DFT calculations and X-ray diffraction analysis. The cytotoxic, antioxidant and membrane-protective activity of the synthesized compounds as well as of the previously obtained sulfenimines and sulfinimines based on 4-caranethiol have been determined.

Synthesis and Antioxidant Ability of Novel Derivatives Based on para-Coumaric Acid Containing Isobornyl Groups.

A series of novel esters and amides was synthesized on the basis of para-coumaric acid containing isobornyl groups in ortho-positions relative to the phenolic hydroxy group. Antioxidant properties of the obtained compounds were evaluated and compared on in vitro models: radical-scavenging ability, antioxidant activity on a substrate containing the lipids of animal brain, cytotoxicity of red blood cells, antioxidant and membrane-protective properties on the model of oxidative red blood cells hemolysis. Statistically significant relationship was established between the antioxidant activity of the studied compounds in model system containing animal lipids and the parameters reflecting their antioxidant properties on the model of H O -induced hemolysis of red blood cells.

Novel Aminomethyl Derivatives of 4-Methyl-2-prenylphenol: Synthesis and Antioxidant Properties.

4-Methyl-2-prenylphenol (1) was synthesized from para-cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models.

Caryophyllane Thiols, Vinyl Thioethers, Di- and Bis-Sulfides: Antioxidant and Membrane Protective Activities.

Caryophyllane thioterpenoids were synthesized in 23 - 81% yields. The antioxidant properties of the obtained compounds in various model systems were found. It was revealed that 4,5-epoxycaryophyll-9-ylmethanethiol has the greatest antioxidant activity.

Synthesis and membrane-protective activity of novel derivatives of α-mangostin at the C-4 position.

A series of new C-4-derivatives of α-mangostin has been synthesized with the use of Mannich reaction and alkylation with 4-bromomethyl-2,6-dialkylphenols. It has been shown on a model of H2O2-induced erythrocyte hemolysis that the Mannich bases containing morpholinomethyl and piperidinomethyl fragments differ from parent α-mangostin by their high antioxidant and membrane-protective activity.