Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity
| Autor: | Dmitry S. Fadeev, Nariman F. Salakhutdinov, Yuriy V. Gatilov, Yana L Esaulkova, Vladimir V. Chernyshov, Olga I. Yarovaya, Katherina O Sinegubova, Anna S Muryleva, Vladimir V. Zarubaev |
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| Rok vydání: | 2019 |
| Předmět: |
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Molecular Molecular Conformation Chemistry Techniques Synthetic Microbial Sensitivity Tests Antiviral Agents Catalysis Single-stage synthesis Inorganic Chemistry Structure-Activity Relationship chemistry.chemical_compound Alkaloids Influenza A Virus H1N1 Subtype Alkaloid analogues Drug Discovery Organic chemistry Phenol Camphoric acid Lewis acids and bases Antiviral activity Physical and Theoretical Chemistry Molecular Biology (+)-Camphoric acid Dose-Response Relationship Drug Molecular Structure Chemistry Alkaloid Organic Chemistry General Medicine Antivirals Solvent Yield (chemistry) Original Article Amine gas treating Influenza virus Information Systems |
| Zdroj: | Molecular Diversity |
| ISSN: | 1573-501X 1381-1991 |
| DOI: | 10.1007/s11030-019-09932-9 |
| Popis: | 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. Graphical abstract Electronic supplementary material The online version of this article (10.1007/s11030-019-09932-9) contains supplementary material, which is available to authorized users. |
| Databáze: | OpenAIRE |
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