FIELD: chemistry.
SUBSTANCE: invention relates to novel compounds of general formula 1 having anti-tuberculosis activity, and a method for production thereof. In general formula 1
R represents H, halogen, digalogen, R1 represents chlorophenyl, nitrophenyl, dichlorophenyl, cyclohexyl, X is O or S, compounds are selected from: N-(3-chlorophenyl)-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide, N-(2,3-dichlorophenyl)-4-(3-chlorophenyl) 6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide, N-(4-nitrophenyl) -4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide), N-(4-nitrophenyl)-6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide, N-(4-nitrophenyl)-4-(2,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide, N-cyclohexyl-4-(2,4-dichlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide. Method of producing compounds of formula 1 comprises a) mixing substituted acetoacetanilide, substituted aldehyde and urea, in molar ratio 1:1:1.5 in a solvent, preferably absolute ethanol; b) heating reaction mixture obtained at step (a), at temperature within range of 60-100 °C for a period of time in range of 4-8 hours; c) adding p-TSA (p-toluenesulphonic acid) to reaction mixture obtained at step (b), with subsequent boiling with reflux condenser at temperature within range of 60-100 °C for a period of time in range of 4-8 hours; d) cooling reaction mixture obtained at step (c), followed by separation of solid substances by filtration, flushing of alcohol.
EFFECT: disclosed compounds exhibit anti-tuberculosis activity towards mycobacteria, both in active phase and at rest, which increases efficiency of reducing rate of tuberculosis and allows to reduce morbidity and mortality from said disease.
9 cl, 1 dwg, 3 tbl, 27 ex
Формула 1 - Formula 1
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