T. V. Goreva

Synthesis and biological activity of N-substituted tetrahydro-γ-carbolins bearing bis(dimethylamino)phenothiazine moiety

An approach for modification of biologically active N-substituted tetrahydro-γ-carbolines with bis(dimethylamino)phenothiazine moiety via the CsF-catalyzed reaction of γ-carbolines with 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]propenone was developed. Effects of the synthesized compounds on neuronal NMDA receptors were examined by radioligand binding assay.

Acylimines of hexafluoroacetone and methyl trifluoropyruvate in cyclocondensation with 2-aminothiazolines

Reactions of acylimines of hexafluoroacetone and methyl trifluoropyruvate with 2-aminothiazolines afforded fluorine-containing heterocycles of two structural types: 6,7-dihydro-2H-thiazolo[3,2-a][1,3,5]triazines and 2,3,5,6-tetrahydroimidazo[2,1-b]thiazoles.

Molecular design of multitarget neuroprotectors 3. Synthesis and bioactivity of tetrahydrocarbazole—aminoadamantane conjugates

A synthetic approach to the design of new multitarget neuroprotectors consisting in combination of the tetrahydrocarbazole and aminoadamantane pharmacophore fragments through a 2-hydroxypropylene spacer upon the reaction of 9-oxiranylmethyl-2,3,4,9-tetrahydro-1H-carbazoles and aminoadamantanes, which affords 1-(adamantan-1-ylamino)-3-(1,2,3,4-tetrahydrocarbazol-9-yl)-propan-2-ols, is proposed. The effect of the synthesized compounds on the neuronal NMDA receptors and the functional characteristics of rat liver mitochondria was studied.

Modification of biologically active amides and amines by fluoro-containing heterocycles 10. γ-Carbolines modified by 2-trifluoromethylimidazo-[1,2-a]pyridin-3-ylpropionamide fragments

An approach to the modification of biologically active γ-carbolines by the 2-trifluoromethylimidazo[1,2-a]pyridin-3-ylpropionamide fragments was suggested, which consisted of the reaction of N-methyl-N-(2-trifluoromethylimidazo[1,2-a]pyridin-3-yl)prop-2-enamides with γ-carbolines in the presence of catalytic amounts of cesium fluoride. Method of radioligand binding was used to study effects of the synthesized 3-(1,2,3,4-tetrahydro-5H-pyrido[4,3-b]-indol-5-yl)-N-methyl-N-[2-(trifluoromethyl)imidazo-[1,2-a]pyridin-3-yl]propanamides on the neuronal NMDA-receptors.

Acylimines of methyl trifluoropyruvate in cyclocondensation with C,N-bisnucleophiles

Reactions of acylimines of methyl trifluoropyruvate with C,N-bisnucleophiles gave fluoro-containing heterocycles including the 5-oxo-4,5-dihydro-1H-pyrrole fragment.

Molecular design of multitarget neuroprotectors 2. Synthesis and bioactivity of carbazole—γ-carboline conjugates

Earlier unknown conjugates of carbazoles and γ-carbolines were obtained by the reaction of 3,6-substituted 9-oxiranylmethylcarbazoles and 2,8-substituted 2,3,4,5-tetrahydro-1H-pyrido-[4,3]indoles. The effects of synthesized 1-(9H-carbazol-9-yl)-3-(1,2,3,4-tetrahydro-5H-pyrido-[4,3-b]indol-5-yl)propan-2-ones and their hydrochlorides on neuronal NMDA receptors, polymerization of tubulin to form microtubules, and functional characteristics of rat liver mitochondria were studied.

Molecular construction of multitarget neuroprotectors 1. Synthesis and biological activity of conjugates of substituted indoles and bis(dimethylamino)phenothiazine

Synthetic strategy to access new multitarget neuroprotectors by conjugation of pharma-cophoric indole and bis(dimethylamino)phenothiazine moieties via 1-oxopropylene spacer was developed. The transformation was achieved by the cesium fluoride-catalyzed reaction of cycloalkaneindoles with 1-propenone. Effect of the synthesized compounds on neuronal NMDA receptors was evaluated by radioligand binding assay.

N-substituted imines of methyl trif luoropyruvate in the synthesis of 5-amino-5-trifluoromethylhydantoins

Cyclocondensation of N-substituted imines of methyl trifluoropyruvate with monosubstituted ureas afforded novel 5-amino-5-trifluoromethylhydantoins.

Benzamidines in cyclocondensation with hexafluoroacetone and methyl trifluoropyruvate acyl- and ethoxycarbonylimines

The reactions of hexafluoroacetone and methyl trifluoropyruvate acyl- and ethoxycarbonylimines with benzamidines afford fluoro containing heterocycles of four structural types: dihydrotriazines, dihydrotriazinones, imidazoles, and imidazooxazoles.

Convenient method for the synthesis and some transformations of the lithium salt of bis(diethoxyphosphoryl)fluoromethane

A convenient method was developed for the synthesis of the lithium salt of 1,1-bis(diethoxyphosphoryl)fluoromethane from availableO,O-diethyl (chlorofluoromethyl)phosphonate, and some transformations of the resulting salt were studied.