F. G. Kamaev

Membrane-active properties and antiradical activity of gossypol and its derivatives

A novel asymmetric gossypol derivative was synthesized. The antioxidant activity of gossypol and certain of its derivatives at the aldehyde groups and the interaction of these compounds with model membranes were studied. It was shown that the antiradical and membrane activities of the gossypol derivatives were determined by the structure of the substituent and that gossypol and its derivatives were partially localized in the lipid bilayer and possibly induced formation of a new interdigitating phase.

New gossypol imines

Information is given on new gossypol imines. The use of hydrazines as the imine components produces Schiff bases of gossypol existing in the benzoid form.

Azo-Derivatives of Gossypol and Its Imines

Azo-coupling of diazotized aromatic amines with gossypol and gossypolimines was studied. The physicochemical properties and interferon-inducing activity of the products were determined. It was found that the interferon-inducing activity depended on the reaction type, the position of functional groups (o-, m-, p-) in the added substituents, and the dose and contact time of the compounds with the cells.

Synthesis, Structure, and Membrane Activity of New Glycyrrhetic Acid Derivatives

Derivatives of 3-O-acetyl-18-βH-glycyrrhetic acid were synthesized. Their structures and membrane activities were studied.

Synthesis, structure, and action of some gossypol derivatives on the peroxidation of the lipids of biosubstrates

The synthesis has been effected of new gossypol derivatives using piperidino-and morpholinoethylamines. According to their PMR spectra, these substances exist in the keto-amine form. Their action on the peroxidation of lipids (POL) of various biosubstrates has been studied. Gossypol bis(piperinoethylimine) and bis(morpholinoethylimine) in concentrations of 1·10−7–5·10−6 mM exert a pronounced antioxidant action on human blood serum and rat brain synaptosomes. In the same concentrations, these substances suppressed the POL in enzymatic and nonenzymatic systems of the oxidation of rat liver microsomes.

1H NMR study on the solvent effect on imine-enamine tautomerism of the condensation product of gossypol with 4-aminoantipyrine

According to the 1H NMR data, the condensation product of gossypol with 4-aminoantipyrine in chloroform-d exists in the imine form, while in DMSO-d6, as the enamine tautomer. The condensation product of 2-hydroxynaphthalene-1-carbaldehyde with 4-aminoantipyrine has the imine tautomer structure in both solvents.

Synthesis and Interferon-Inducing Activity of Azo-Derivatives of Gossypol and Its Imines

New azo-derivatives of gossypol and its imines were described. Their physicochemical properties and data on their interferon-inducing activity were presented.

Investigation of the products of the oxidation of gossypol structure of gossindan

A new compound, which we have called gossindan, has been isolated from the products of the oxidation of gossypol by oxygen in an alkaline medium. The structure of gossindan has been established on the basis of a study of IR, mass, PMR, and13C NMR spectra and x-ray structural analysis as 6,6′-di-(2,7-dihydroxy-3-isopropyl-5-methylindan-1-one).

Imines of gossypol ethers

Imines of methyl ethers of gossypol have been synthesized for the first time, their structures have been shown, and their immunomodulating activities have been determined. The quinoid form of existence of the imines of the dimethyl ether and the benzoid form of the imine of the mexamethyl ether of gossypol have been shown.

Synthesis and structure of gossypol bisdiethylaminophenylimines and their antioxidant and anticholinesterase activities

The synthesis has been performed of gossypol gis-p- and-m-diethylaminophenylimines, which possess anticholinesterase activity, antioxidant action on rat brain synaptosome membranes, and an innibiting influence on the oxidase system of zymosan-activated macrophages.