Efficient synthesis and anti-enteroviral activity of 9-arylpurines

Leire Aguado; María-Dolores Canela; Hendrik Jan Thibaut; Eva-María Priego; María-José Camarasa; Pieter Leyssen; Johan Neyts; María-Jesús Pérez-Pérez

doi:10.1016/j.ejmech.2012.01.022

Efficient synthesis and anti-enteroviral activity of 9-arylpurines

Leire Aguado, María-Dolores Canela, Hendrik Jan Thibaut, Eva-María Priego, María-José Camarasa, Pieter Leyssen, Johan Neyts, María-Jesús Pérez-Pérez

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC(50) values varying from 3 to 15 μM, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime.

Original language	English
Pages (from-to)	279-88
Number of pages	10
Journal	European Journal of Medicinal Chemistry
Volume	49
DOIs	https://doi.org/10.1016/j.ejmech.2012.01.022
Publication status	Published - 2012

Keywords

Animals
Antiviral Agents
Cell Line
Cercopithecus aethiops
Enterovirus B, Human
Enterovirus Infections
Halogenation
Humans
Microbial Sensitivity Tests
Microwaves
Models, Molecular
Oxazolidinones
Purines
Vero Cells

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10.1016/j.ejmech.2012.01.022

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title = "Efficient synthesis and anti-enteroviral activity of 9-arylpurines",

abstract = "To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC(50) values varying from 3 to 15 μM, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime.",

keywords = "Animals, Antiviral Agents, Cell Line, Cercopithecus aethiops, Enterovirus B, Human, Enterovirus Infections, Halogenation, Humans, Microbial Sensitivity Tests, Microwaves, Models, Molecular, Oxazolidinones, Purines, Vero Cells",

author = "Leire Aguado and Mar{\'i}a-Dolores Canela and Thibaut, {Hendrik Jan} and Eva-Mar{\'i}a Priego and Mar{\'i}a-Jos{\'e} Camarasa and Pieter Leyssen and Johan Neyts and Mar{\'i}a-Jes{\'u}s P{\'e}rez-P{\'e}rez",

year = "2012",

doi = "10.1016/j.ejmech.2012.01.022",

language = "English",

volume = "49",

pages = "279--88",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson SAS",

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TY - JOUR

T1 - Efficient synthesis and anti-enteroviral activity of 9-arylpurines

AU - Aguado, Leire

AU - Canela, María-Dolores

AU - Thibaut, Hendrik Jan

AU - Priego, Eva-María

AU - Camarasa, María-José

AU - Leyssen, Pieter

AU - Neyts, Johan

AU - Pérez-Pérez, María-Jesús

PY - 2012

Y1 - 2012

N2 - To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC(50) values varying from 3 to 15 μM, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime.

AB - To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC(50) values varying from 3 to 15 μM, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime.

KW - Animals

KW - Antiviral Agents

KW - Cell Line

KW - Cercopithecus aethiops

KW - Enterovirus B, Human

KW - Enterovirus Infections

KW - Halogenation

KW - Humans

KW - Microbial Sensitivity Tests

KW - Microwaves

KW - Models, Molecular

KW - Oxazolidinones

KW - Purines

KW - Vero Cells

U2 - 10.1016/j.ejmech.2012.01.022

DO - 10.1016/j.ejmech.2012.01.022

M3 - Article

C2 - 22305341

SN - 0223-5234

VL - 49

SP - 279

EP - 288

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

ER -

Efficient synthesis and anti-enteroviral activity of 9-arylpurines

Abstract

Keywords

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