SUBSTITUTED ETHYL ESTERS (E)-2-(5-AMINO-4-R1-3-OXO-2-(2-OXO-2-(P-TOLYL)ETHYLIDENE)-2,3-DIHYDRO-1H-PYRROL- 1-YL)-5,6,7,8-TETRAHYDRO-4H-CYCLOHEPTA[b]THIOPHENE-3-CARBOXYLIC ACID, WHICH HAS ANTICANCER ACTIVITY IN THE TREATMENT OF LUNG MELANOMA Russian patent published in 2023 - IPC C07D409/04 A61K31/4025 A61P35/00 

FIELD: organic; medicinal chemistry.

SUBSTANCE: new biologically active substances of the 5-amino-3-pyrrolinones class, namely to substituted ethyl esters (E)-2-(5-amino-4-R¹-3-oxo-2-(2-oxo-2-(p-tolyl)ethylidene)-2,3-dihydro-1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid 1 a,b, general formula:

,

which have anticancer activity in the treatment of lung melanoma, which allows their use in medicine as drugs with cytotoxic properties and low toxicity. Ethyl ester (E)-2-amino-4-oxo-5-(2-oxo-2-(p-tolyl)ethylidene)-1-(3-(ethoxycarbonyl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-2-yl)-4,5-dihydro-1H-pyrrole-3-carboxylic acid 1a and 2-(5-amino-3-oxo-2-(2-oxo-2) ethyl ester-(p-tolyl)ethylidene)-4-cyano-2,3-dihydro-1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid 1b is synthesized by reacting ethyl ester (E)-2-((2-oxo-5-(p-tolyl)furan-3(2H)-ylidene)amino)-5,6,7,8-tetrahydro-4H-cyclohepta[ b]thiophene-3-carboxylic acid with cyanoacetic acid ethyl ester for compounds 1a and malonodinitrile in the case of compound 1b in the presence of triethylamine, in anhydrous dioxane at 24° C 24 hours, followed by isolation of target products using known methods.

EFFECT: technical result is achieved by chemical synthesis and the use of substituted ethyl esters (E)-2-(5-amino-4-R¹-3-oxo-2-(2-oxo-2-(p-tolyl)ethylidene)-2,3-dihydro-1H-pyrrol-1-yl)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid 1 a,b, which have anticancer activity in the treatment of lung melanoma and low toxicity in relation to healthy tissues.

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