Synthesis and anti-influenza virus activity of dihydrofuran-fused perhydrophenanthrenes with a benzyloxy-type side-chain

Novel dihydrofuran-fused tetracyclic compounds (2) with a benzyl-type ether side-chain were found to exhibit potent anti-influenza virus activity comparable to the previously reported derivative 1. As one of our ongoing research project concerning development of a novel anti-influenza virus agent, d...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2010-02, Vol.18 (4), p.1477-1481
Main Authors: Matsuya, Yuji, Suzuki, Nozomi, Kobayashi, Shin-ya, Miyahara, Tatsuro, Ochiai, Hiroshi, Nemoto, Hideo
Format: Article
Language:English
Subjects:
Animals
Anti-influenza agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Antiviral Agents - chemical synthesis
Antiviral Agents - chemistry
Antiviral Agents - pharmacology
Biological and medical sciences
Cells, Cultured
Coupling reaction
Dogs
Furans - chemistry
Influenza A Virus, H3N2 Subtype - drug effects
Influenza A Virus, H3N2 Subtype - growth & development
Magnetic Resonance Spectroscopy
Mass Spectrometry
Medical sciences
Perhydrophenanthrenes
Pharmacology. Drug treatments
Phenanthrenes - chemical synthesis
Phenanthrenes - chemistry
Phenanthrenes - pharmacology
Spectroscopy, Fourier Transform Infrared
Synthesis
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Summary:Novel dihydrofuran-fused tetracyclic compounds (2) with a benzyl-type ether side-chain were found to exhibit potent anti-influenza virus activity comparable to the previously reported derivative 1. As one of our ongoing research project concerning development of a novel anti-influenza virus agent, dihydrofuran-fused perhydrophenanthrenes were derivatized by means of Williamson ether synthesis and Suzuki–Miyaura cross coupling reactions. Newly synthesized compounds were subjected to evaluation of anti-influenza virus activity using influenza A/Aichi/2/68 (H3N2 subtype) virus strain by a plaque titration method. These investigations revealed that incorporation of benzyl-type ether substituents was effective for exerting the inhibition activity of influenza virus proliferation.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2010.01.014