Isosteric ribavirin analogues: Synthesis and antiviral activities

Nikolay I Zhurilo; Mikhail V Chudinov; Andrey V Matveev; Olga S Smirnova; Irina D Konstantinova; Anatoly I Miroshnikov; Alexander N Prutkov; Lyubov E Grebenkina; Natalya V Pulkova; Vitaly I Shvets

doi:10.1016/j.bmcl.2017.11.029

Isosteric ribavirin analogues: Synthesis and antiviral activities

Bioorg Med Chem Lett. 2018 Jan 1;28(1):11-14. doi: 10.1016/j.bmcl.2017.11.029. Epub 2017 Nov 15.

Affiliations

¹ Lomonosov Institute of Fine Chemical Tehnologies, Moscow Technological University, Vernadskogo Pr. 78, 119454 Moscow, Russia.
² Lomonosov Institute of Fine Chemical Tehnologies, Moscow Technological University, Vernadskogo Pr. 78, 119454 Moscow, Russia. Electronic address: mikle@irims.ru.
³ Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya St. 16/10, 117997 GSP, Moscow B-437, Russia.
⁴ Moscow Politechnical University, Bolshaya Semenovskaya Str., 38, 107023 Moscow, Russia.

PMID: 29173944
DOI: 10.1016/j.bmcl.2017.11.029

Abstract

The novel isosteric ribavirin analogues were synthesized by two different ways. Some of them showed significant antiviral action against hepatitis C virus (HCV), herpes simplex (HCV-1) and influenza A virus comparable to that of ribavirin itself. The data obtained confirm the proposed theory of the ribavirin possible antiviral activity mechanism related with bioisosterism.

Keywords: Antivirals; Isosterism; Nucleoside analogues; Ribavirin.

MeSH terms

Animals
Antiviral Agents / chemical synthesis*
Antiviral Agents / chemistry
Antiviral Agents / pharmacology
Cell Survival / drug effects
Chlorocebus aethiops
Hepacivirus / drug effects
Herpesvirus 1, Human / drug effects
Humans
Influenza A virus / drug effects
Ribavirin / analogs & derivatives*
Ribavirin / chemical synthesis
Ribavirin / pharmacology
Vero Cells

Substances

Antiviral Agents
Ribavirin