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Eur J Med Chem. 2015 Nov 13;105:263-73. doi: 10.1016/j.ejmech.2015.10.010. Epub 2015 Oct 22.

Discovery of a new class of antiviral compounds: camphor imine derivatives.

Author information

1
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090, Novosibirsk, Russia; Novosibirsk State University, Pirogova St. 2, 630090, Novosibirsk, Russia.
2
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090, Novosibirsk, Russia; Novosibirsk State University, Pirogova St. 2, 630090, Novosibirsk, Russia. Electronic address: ooo@nioch.nsc.ru.
3
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090, Novosibirsk, Russia.
4
Novosibirsk State University, Pirogova St. 2, 630090, Novosibirsk, Russia.
5
Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376, St. Petersburg, Russia. Electronic address: zarubaev@influenza.spb.ru.
6
Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376, St. Petersburg, Russia.

Abstract

A new class of compounds featuring a camphor moiety has been discovered that exhibits potent inhibitory activity against influenza A(H1N1)pdm09 and A(H5N1) viruses. The synthesized compounds were characterized by spectroscopic analysis; in addition the structures of compound 2 and 14 were elucidated by the X-ray diffraction technique. Structure-activity relationship studies have been conducted to identify the 1,7,7-trimethylbicyclo[2.2.1]heptanes2-ylidene group as the key functional group responsible for the observed antiviral activity. The most potent antiviral compound is imine 2 with therapeutic index more than 500.

KEYWORDS:

Antiviral; Cage compounds; Camphor derivatives; Influenza

PMID:
26498572
DOI:
10.1016/j.ejmech.2015.10.010
[Indexed for MEDLINE]

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