E. S. Izmest’ev

Asymmetric synthesis of new optically active sulfinamides of menthane series and their derivatives

Asymmetric syntheses were performed of neomenthanesulfinamide in the yield of 60% and de 74%, of neomenthanesulfinaldimines and N-substituted neomenthanesulfinamides in 22–80 and 40–90% yields respectively.

Synthesis and membranoprotective properties of new disulfides with monoterpene and carbohydrate fragments

A cooxidation of carbohydrate and terpene thiols gives mixtures of disulfides containing 51—90% of the unsymmetric product. Membranoprotective and antioxidant properties of obtained unsymmetric and symmetric disulfides were evaluated based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes, as well as the accumulation of secondary products of the peroxy oxidation of lipids and the oxidation of hemoglobin.

Synthesis and reduction of new sulfinimines with isobornane structure

Synthesis of sulfenimines proceeding from isobornanethiol with yields up to 78% was performed. They were oxidized to diastereomeric isobornylsulfinimines and the latter were reduced to N-substituted isobornylsulfinamides in high yields.

The synthesis and membrane protective properties of sulfanyl imines derived from neomenthane and isobornane thiols

Neomenthane and isobornane thiol-derived sulfanyl imines were prepared in yields of up to 85%. On the basis of the capacity of the sulfanyl imines obtained to inhibit the H2H2- and AAPH-induced erythrocyte hemolysis and impede the accumulation of secondary products of lipid peroxidation and hemoglobin oxidation, they were shown to display membrane protective and antioxidant properties.

SYNTHESIS OF SEVERAL OPTICALLY ACTIVE MENTHANE DISULFIDES AND THIOSULFINATES

Symmetric and asymmetric disulfides were synthesized from mixtures of menthyl- and neomenthylthiols and were oxidized asymmetrically. Dineomenthyldisulfide, dimenthyldisulfide, and menthylneomenthyldisulfide were synthesized in yields of 47–48%, 24–25, and 29–55, respectively. Pure diastereomeric dimenthyl-, dineomenthyl-, and menthylneomenthylthiosulfinates were synthesized in yields of 85–90% and de up to 30%.

Synthesis and antitubercular activity of first glucuronosyl phosphates and amidophosphates containing polymethylene chains

Novel phosphorylated glycolipids based on glucuronic acid have been synthesized and shown to inhibit M. Tuberculosis H37Rv in vitro at a minimum inhibitory concentration of 12.5 μg/mL.

Synthesis and oxidation of thioglicosides underlain by neomenthanethiol, D-glucose, and D-fructose

Synthesis of sulfides proceeding from neomenthanethiol, 1,2-O-isopropylidene-α-D-glucofuranose and 2,3:4,5-di-O-isopropylidene-β-D-fructopyranose was performed to get 65 and 54% yield respectively. Oxidation of the sulfides afforded diastereomeric sulfoxides in the yields from 40 to 53%, and diastereomeric excess (de) up to 36%. After removing the isopropylidene protection from 1-deoxy-1-[(1S,2S,5R)-2-isopropyl-5-methylcyclohexylsulfanyl]-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose a water-soluble sulfide was obtained.

New N-substituted sulfinamides of neomenthane series

A reaction of neomenthanethiol with ammonia and N-chlorosuccinimide with subsequent addition of aromatic aldehydes leads to chiral N-arylideneneomenthylsulfenimines, whose oxidation at the sulfur atom gives N-arylideneneomenthylsulfinimines. The reactions of N-arylideneneomenthylsulfinimines with lithium aluminum hydride or Grignard reagents proceed at the imine fragment and lead to the corresponding N-benzylneomenthylsulfinamides.

Synthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides

Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H2O2-induced hemolysis of erythrocytes and retard the oxyhemoglobin oxidation.

Synthesis and oxidation of sulfides based on caryophyllene oxide and phenylmethanethiol

Lewis acid-catalyzed reaction of (–)-caryophyllene oxide with phenylmethanethiol gave sulfides with clovane and caryophyllane structure which were oxidized to the corresponding sulfoxides and sulfones in 74 and 84% yield, respectively.