Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity.

Autor: Chernyshov VV; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk, Russia, 630090. vladimir.chernyshov2012@yandex.ru.; Novosibirsk State University, Pirogova St. 2, Novosibirsk, Russia, 630090. vladimir.chernyshov2012@yandex.ru., Yarovaya OI; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk, Russia, 630090.; Novosibirsk State University, Pirogova St. 2, Novosibirsk, Russia, 630090., Fadeev DS; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk, Russia, 630090., Gatilov YV; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk, Russia, 630090.; Novosibirsk State University, Pirogova St. 2, Novosibirsk, Russia, 630090., Esaulkova YL; Pasteur Institute of Epidemiology and Microbiology, 14 Mira Str., St. Petersburg, Russia, 197101., Muryleva AS; Pasteur Institute of Epidemiology and Microbiology, 14 Mira Str., St. Petersburg, Russia, 197101., Sinegubova KO; Pasteur Institute of Epidemiology and Microbiology, 14 Mira Str., St. Petersburg, Russia, 197101., Zarubaev VV; Pasteur Institute of Epidemiology and Microbiology, 14 Mira Str., St. Petersburg, Russia, 197101., Salakhutdinov NF; N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, Novosibirsk, Russia, 630090.; Novosibirsk State University, Pirogova St. 2, Novosibirsk, Russia, 630090.
Jazyk: angličtina
Zdroj: Molecular diversity [Mol Divers] 2020 Feb; Vol. 24 (1), pp. 61-67. Date of Electronic Publication: 2019 Feb 28.
DOI: 10.1007/s11030-019-09932-9
Abstrakt: An effective technique for one-stage synthesis of new polycyclic nitrogen-containing compounds has been developed. The procedure involves refluxing mixtures of camphoric acid with aliphatic or aromatic diamine without catalysts. In cases where the starting amine has a low boiling point (less than 200 °C), phenol is used as a solvent, as it is the most optimal one for obtaining products with good yields. It has been shown that the use of Lewis acids as catalysts reduces the yield of the reaction products. A set of compounds have been synthesized, which can be attributed to synthetic analogues of alkaloids. In vitro screening for activity influenza virus A was carried out for the obtained compounds. The synthesized quinazoline-like agent 14 has inhibitory activity against different strains of influenza viruses.
Databáze: MEDLINE
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