ÓÄÊ 576.89
DOI 10.33861/2071-8020-2025-3-33-35
Original Empirical Research
Demidov O.P., Avakyan E.K., Pobedinskaya D.Yu., Ermolenko A.P., Svyatogorova A.E., Gritsay A.Yu.
Abstract. Based on direct oxidative SNH arylamination of methyl triflate salt of 1-methyl-6-nitroquinoline and 5-nitroisoquinoline in anhydrous dimethyl sulfoxide, previously unstudied imines of 1-methyl-6-nitroquinoline and, in the case of 5-nitroisoquinoline, the corresponding nitro- and nitroso compounds were obtained. The approach we developed is based on the addition of pre-generated anilide anions to the corresponding substrates, and does not require any participation of good leaving groups or the use of catalysts based on heavy metals. Diarylamines based on 5-nitrosoisoquinoline were subjected to intramolecular heterocyclization under various conditions, leading to condensed isoquinoline derivatives - pyrido[4,3-a]phenazines. Another synthetic modification of nitroso derivatives of isoquinoline allowed us to obtain N-oxides of 6-arylamino-5-nitroisoquinoline. The reaction was carried out by treating the corresponding nitroso derivatives with m-chloroperbenzoic acid at room temperature. A study of biological activity was performed for all the obtained products. Antibacterial, fungistatic and protistocidal activities were studied. The conducted study of the biological activity of the obtained products showed the absence of a fungistatic effect. Nevertheless, unsubstituted pyrido[4,3-a]phenazine showed moderate protistocidal activity, which was compared with the activity of fundazole. Interestingly, the presence of a substituent in position 10 leads to a complete absence of its manifestation. All compounds demonstrated noticeable bacteriostatic activity, reaching approximately 60% of the activity of furazolidone (used as a standard, along with ciprofloxacin to assess the antibacterial activity). The highest activity was found in the bromo-substituted N-oxide of 5-nitro-6-arylaminoisoquinoline 8. The moderate antibacterial activity of all presented quinoline/isoquinoline compounds is noteworthy, which makes the search for effective antibacterial drugs among similar structures a promising area of research.
Keywords: quinoline, isoquinoline, pyrido[4,3-a]phenazine, antibacterial activity, antiprotozoal activity, fungistatic activity.
Author affiliation:
Avakyan Elena K., Ph.D. in Chemistry, Senior Scientific Researcher of the Science Department of the North Caucasus Federal University; 1, Pushkina st., Stavropol; phone: 8-962-4126620; e-mail: awackyan.elena2015@yandex.ru.
Pobedinskaya Diana Yu., Ph.D. in Chemistry, Junior Scientific Researcher of the Science Department of the North Caucasus Federal University; 1, Pushkina st., Stavropol; phone: 8-961-4713665; e-mail: pobedinskayad@mail.ru.
Ermolenko Artem P., postgraduate student of the North Caucasus Federal University; 1, Pushkina st., Stavropol; phone: 8-919-7338386; e-mail: artem.p.ermolenko@gmail.com.
Gritsay Anna Yu., Junior Scientific Researcher of the creative team for the study of infectious pathology of animals of the North Caucasus Zonal Research Veterinary Institute - branch of the Federal Rostov Agrarian Scientific Center; 0, Rostovskoe hgw., Novocherkassk, Rostov region, 346421; phone: 8-908-5102689; e-mail: tkhim.sintez@yandex.ru.
Svyatogorova Aleksandra E., Ph.D. in Agriculture, Leading Scientific Researcher of the creative team for the chemical synthesis of new medicinal compounds, Academic Secretary of the North Caucasus Zonal Research Veterinary Institute - branch of the Federal Rostov Agrarian Scientific Center; 0, Rostovskoe hgw., Novocherkassk, Rostov region, 346421; phone: 8-988-9525755; e-mail: sviatogorova.a@yandex.ru.
Responsible for correspondence with the editorial board: Demidov Oleg P., D.Sc. in Chemistry, Associate Professor, Chief Scientific Researcher of the Department of Science of the North Caucasus Federal University; 1, Pushkina st., Stavropol; phone: 8-988-7612680; e-mail: odemidov@gmail.com.
Author’s Contribution:
Demidov O.P.: conceptualization, project administration, validation, writing -review & editing.
Avakyan E.K.: data curation, funding acquisition, resources, supervision, writing - 35 original draft preparation.
Ermolenko A.P.: investigation.
Pobedinskaya D.Yu. methodology.
Svyatogorova A.E.: formal analysis, investigation, visualization.
Gritsai A.Yu.: investigation, visualization.
Conflict of Interest Statement: the authors declare no conflict of interest.
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