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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.

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

New azo derivatives of gossypol are described. Their physicochemical properties are reported. The presence of hydroxyazo- and quinonhydrazo-tautomers is proposed.

The results are given of a study of the hydrolysis of alkyl- and heterylimines of gossypol at various pH values.

The results are given of a study of gossypol, its physiologically active derivatives, and their complexes with N-polyvinylpyrrolidone (M.m. 8000) in various media. It has been shown that the production of complexes permits the creation not only of water-soluble forms but also of more stable forms of the compounds.

The method of obtaining radioactively labeled14C-gossypol-acetic acid has been improved: from it have been synthesized14C-derivatives of gossypol and their complexes with N-polyvinylpyrrolidone. A comparative study has been made of the pharmacokinetics of batriden, megosin, and their water-soluble complexes.

It has beeen shown that water-soluble complexes of gossypol derivatives obtained by their immobilization on polyvinylpyrrolidone posses a lower membrane activity than the initial substances. The degree of interaction of the substances under investigation with biomembranes has been determined from the change in the intensity of the flourescence of I-anilinonaphthalene-8-sulfonic acid (ANS).

Information is given on the antiviral and interferon-inducing activities of gossypol and its derivatives.

This review of the literature and of the authors' own investigations is devoted to the biological activity of gossypol and its derivatives. Certain results of the structural—functional analysis of gossypol ethers and the products of its condensation with amines and CH-acids are discussed. The results of pharmacokinetic investigations of radioactively labeled samples of gossypol and its physiologically active derivatives are given.

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.

Samples of batriden (a drug based on gossypol) radioactively labeled with14C in different parts of the molecule have been synthesized. Pharmacokinetic investigations of the14C-batridens have enabled the mechanism of the action of the drug to be elucidated.

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.

The results are given of a comparative spectroscopic study of some gossypol derivatives and their complexes with N-polyvinylpyrrolidone.

In continuation of our search for physiologically active compounds among aromatic aldehyde derivatives, we synthesized the sodium salts of some arylideniminoethane sulfonic acids. Certain hydroxyalkyloxybenzaldehydes and naphthaldehydes were used for condensation with sodium B-aminoethyl sulfate. The resultant compounds are water-soluble brightly colored powderlike substances with poor solubility in organic solvents (Table i).

It has been shown on the basis of the results of a study of PMR spectra that, regardless of its source and method of purification, in weakly polar solvents gossypol exists predominantly in the aldehyde form.

1. By direct analysis of daughter ions, a study has been made of the paths of fragmentation of the molecular and fragment ions manifested in the mass spectra of arylidene derivatives of barbituric acid and 2-thioxy-4-thiazolidone. It has been shown that the fragmentation of these compounds proceeds through decomposition of the heterocyclic part and the substituents of the aryl part of the molecule. 2. It has been shown that the condensation of barbituric acid and 2-thioxy-4-thiazolidone with o-hydroxyaryl aldehydes proceeds with the formation of anomalous products, the structure of which has been established from an analysis of the spectral data.

Information is given on the immunosuppressive activity of a number of gossypol derivatives, and it is shown that practically all the compounds studied are immunotropic. The structural-functional relationship and the dose-dependent nature of the action of the substances obtained are shown.

A number of new Schiff's bases of gossypol with aromatic amines and sulfanilamide compounds has been obtained. It has been shown by UV and PMR spectroscopy and x-ray structural analysis that in some solvents they exist predominantly in the quinoid form. For dianilinegossypol (in the solid state) the quinoid structure has been demonstrated and two polymorphic modifications have been revealed by x-ray structural analysis.

1. The existence of a tautomeric equilibrium between the aldehyde and lactol forms gossypol has, for the first time, been demonstrated through NMR spectroscopy. In DMSO, gossypol exists primarily in the lactol form, and primarily in the aldehyde form in acids, bases, and inert solvents. 2. The method of preparation of the ethers of this compound determines the form of the product obtained.

The 5-arylidenebarbituric acids were obtained by a known method [i] and were colored substances, poorly soluble in normal organic solvents (see Table i). UV spectra for the 5arylidenebarbituric acids have, in addition to characteristic absorption for them in the range 245-255 nm, intensive absorption at 380-420 nm. A bathochromic shift to longer wave lengths in observed on increasing the conjugation chain through the aldehyde component.