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

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

Journal

Molecular Diversity
ISSN: 1381-1991 , E-ISSN: 1573-501X

Output data

Year: 2020, Volume: 24, Number: 1, Pages: 61-67 Pages count : 7 DOI: 10.1007/s11030-019-09932-9

Tags

(+)-Camphoric acid; Single-stage synthesis; Alkaloid analogues; Influenza virus; Antiviral activity; Antivirals

Authors

Chernyshov Vladimir V. ^1,2 , Yarovaya Olga I. ^1,2 , Fadeev Dmitry S. ¹ , Gatilov Yuriy V. ^1,2 , Esaulkova Yana L. ³ , Muryleva Anna S. ³ , Sinegubova Katherina O. ³ , Zarubaev Vladimir V. ³ , Salakhutdinov Nariman F. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Lavrentjev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia
3	(Данные Web of science) Pasteur Inst Epidemiol & Microbiol, 14 Mira Str, St Petersburg 197101, Russia

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 degrees 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. [GRAPHICS] .

Chernyshov V.V. , Yarovaya O.I. , Fadeev D.S. , Gatilov Y.V. , Esaulkova Y.L. , Muryleva A.S. , Sinegubova K.O. , Zarubaev V.V. , Salakhutdinov N.F.
Single-stage synthesis of heterocyclic alkaloid-like compounds from (+)-camphoric acid and their antiviral activity

Molecular Diversity. 2020. V.24. N1. P.61-67. DOI: 10.1007/s11030-019-09932-9 WOS Scopus РИНЦ

Full text from publisher

Published online:	Feb 28, 2019
Published print:	Feb 1, 2020

Web of science	WOS:000515169600006
Scopus	2-s2.0-85062589474
Elibrary	43207415
OpenAlex	W2920138896