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


ABSTRACT: 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.

SUBMITTER: Chernyshov VV 

PROVIDER: S-EPMC7223885 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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

Chernyshov Vladimir V VV   Yarovaya Olga I OI   Fadeev Dmitry S DS   Gatilov Yuriy V YV   Esaulkova Yana L YL   Muryleva Anna S AS   Sinegubova Katherina O KO   Zarubaev Vladimir V VV   Zarubaev Vladimir V VV   Salakhutdinov Nariman F NF  

Molecular diversity 20190228 1


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  ...[more]

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