Синтез та властивості продуктів імідування монозаміщених та дизаміщених нафталевих ангідридів пара-амінобензойною кислотою
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Дата
2021
Науковий керівник
Укладач
Редактор
Назва журналу
ISSN
E-ISSN
Назва тому
Видавець
Одеський національний університет імені І. І. Мечникова
Анотація
Синтезовані 4-монозаміщені та 4,5-дизаміщені N-(4-карбоксифенілнафталіміди)
імідуванням відповідних 4-монозаміщених та 4,5-дизаміщених нафталевих ангідридів
пара-амінобензойною кислотою з виходами 75–85%. Результати комп’ютерного
скринінгу синтезованих сполук з використанням інтернет-сервісу
PASS Online
підтверджують широкий спектр біологічної активності синтезованих сполук, що робить їх перспективними для подальшого біологічного тестування.
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 NMR1H 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.
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 NMR1H 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.
Опис
Ключові слова
аценафтен, нафталевий ангідрид, пара-амінобензойна кислота, нафталімід, імідування, acenaphthene, 1,8-naphthalic anhydride, p-aminobenzoic acid, 1,8-naphthalimide, imidation
Бібліографічний опис
Вісник Одеського національного університету = Odesa National University Herald