SYNTHESIS AND PROPERTIES OF IMIDATION PRODUCTS OF MONOSUBSTITUTED AND DISUBSTITUTED NAPHTHALIC ANHYDRIDES WITH P-AMINOBENZOIC ACID

4-Monosubstituted and 4,5-disubstituted halogeno- and nitro- N-(4-carboxyphenylnaphthalimides) were synthesized by imidation of the corresponding 4-monosubstituted and 4,5-disubstituted naphthalic anhydrides with para-aminobenzoic acid using acetic acid as solvent with 75-85% yields. 4-Amino-N- (4-carboxyphenyl)naphthalimide and 4,5-diamino-N-(4-carboxyphenyl)naphthalimide were obtained by reduction of corresponding nitrosubstituted N-(4-carboxyphenyl)naphthalimides using sodium dithionite as reducing agent in mixed ethanol-water solvent. The completion of reaction was monitored by thin layer chromatography with disappearance of the spot of the corresponding starting naphthalic anhydride. Starting 4-monosubstituted and 4,5-disubstituted naphthalic anhydrides were obtained by oxidation of corresponding substituted acenaphthenes with sodium dichromate in acetic acid. The synthesized N-carboxyphenylnaphthalimides with chlorine and bromine in positions 4 or 4 and 5 are yellow crystal substances with blue fluorescence; 4-nitro- and 4,5-dinitro-N-carboxyphenylnaphthalimides are orange crystal substances without fluorescence; 4-amino-, 4-dimethylamino and 4,5-diamino-N-carboxyphenylnaphthalimides are orange crystal substances with orange fluorescence. The structure of all the synthesized products was confirmed by IR and NMR 1H spectroscopy. The results of computer screening of the synthesized compounds using the PASS Online Internet service confirm a wide range of biological activity of N-carboxyphenylnaphthalimides, which makes them promising substances for further biological testing.