Il'chenko O. The Synthesis, chemical and biological activity of 2-thioxo-2,3-dihydro[1]-benzofuro[3,2-d]pyrimidin-4-ones and their 2-oxoanalogues

An effective method of synthesis of N'-anthranoyl-a-hydrazide of (±)-camphoric acid has been developed. 2-Substituted derivatives of quinazolin-4(3H)-one, 1,2,3,4-tetrahydroquinazolin-4-one and 2-oxo(thioxo)-1,2,3,4-tetrahydroquinazolin-4-one with the moiety of amide or imide 1,2,2-trimethylcyclopentan-1,3-dicarboxilic acid in the position 3 of heterocycle has been synthesized on the basic of this substance. The structure of synthesized compounds has been confirmed by IR-, NMR-, mass-spectra, alternative synthesis, the purity has been controled by TLC method. The sequence of formation of quinazolin-4(3H)-one and 3-azabicyclo[3.2.1]-octan-2,4-dion cycles closure during the synthesis of 1,8,8-trimethyl-3-(4-оxо-2-alkyl(aryl)-3,4-dihydroquinazolin-3-il)-3-azabicyclo[3.2.1]-octan-2,4-diones has been determined. For the first time the method of formation quinazolin-4(3H)-ones by the reaction anthranilamide with ?-diketones has been discovered. The hypoglycemic, diuretic, antimicrobic, anticoagulatic, hemostatic, anticonvulsive screening of the synthesized compounds has been conducted. The "structure - activity" relationship for these types of activities have been determined. According to the results of biological assay two low-toxic substances 3-[2-(2-(5-bromothiophene-2-yl)-2-oxoеthylthio)-4-oxo-3,4-dihydroquin-azo-lin-3-yl]-1,8,8-tri-me-thyl-3-azabicyclo[3.2.1]octan-2,4-dione (with hipoglicemic activity) and 3-[2-(2-(3-nitrophenyl)-2-oxoеthylthio)-4-oxo-3,4-dihydroquin-azo-lin-3-yl]-1,8,8-tri-me-thyl-3-azabicyclo[3.2.1]octan-2,4-dione (with high anticonvulsive activity) has been recommended for profound pharmacological study.