Author | Ferreira, Maria de Lourdes G. | |
Author | Pinheiro, Luiz C. S. | |
Author | Santos Filho, Osvaldo A. | |
Author | Peçanha, Marta D. S. | |
Author | Sacramento, Carolina Q. | |
Author | Machado, Viviane | |
Author | Ferreira, Vitor F. | |
Author | Souza, Thiago Moreno L. | |
Author | Boechat, Núbia | |
Access date | 2017-01-12T13:54:07Z | |
Available date | 2017-01-12T13:54:07Z | |
Document date | 2014 | |
Citation | FERREIRA, Maria de Lourdes G. et al. Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs. Med Chem Res, v. 23, p.1501–1511, 2014. | pt_BR |
ISSN | 1054-2523 | pt_BR |
URI | https://www.arca.fiocruz.br/handle/icict/16819 | |
Language | eng | pt_BR |
Publisher | Springer Verlag | pt_BR |
Rights | restricted access | pt_BR |
Subject in Portuguese | Antivirais | pt_BR |
Subject in Portuguese | Vírus da Influenza A | pt_BR |
Subject in Portuguese | Ribavirina | pt_BR |
Subject in Portuguese | DNA Polimerase Dirigida por RNA | pt_BR |
Title | Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs | pt_BR |
Type | Article | pt_BR |
DOI | 10.1007/s00044-013-0762-6 | |
Abstract | Ribavirin is a broad antiviral compound with
demonstrated activity against herpes simplex virus (HSV),
human immunodeficiency virus HIV-1, influenza virus,
respiratory syncytial virus, and hepatitis C virus, among
other viruses. However, routine clinical use of ribavirin is
limited because this compound is considerably cytotoxic.
Herein, we describe the design, synthesis, and antiviral
activity of new nucleoside ribavirin analogs based on the
following: (1) ring bioisosterism of a 1,2,4-triazole for a
1,2,3-triazole; (2) amide group exchange for other substituents,
such as c-propyl, methyl carboxylate, or trifluoromethyl
groups; and (3) the ribofuranose remained linked
to the triazole ring. Compounds 5a–c were obtained with
yields of 65–36 % and tested against Influenza A and HSV-
1 replication as well as reverse transcriptase (RT) from
human immunodeficiency virus type 1 (HIV-1 RT). Compound
5b (R = CO2CH3) was the most effective analog,
with IC50 values 14 and 3.8 lM for Influenza A and HIV-1
RT, respectively. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Tecnologia em Fármacos— Farmanguinhos. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Tecnologia em Fármacos— Farmanguinhos. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Tecnologia em Fármacos— Farmanguinhos. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Tecnologia em Fármacos— Farmanguinhos. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Vírus Respiratório. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Vírus Respiratório. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Universidade Federal Fluminense. Instituto de Química. Departamento de Química Orgânica.Niterói, RJ, Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Vírus Respiratório. Rio de Janeiro, RJ. Brasil. | pt_BR |
Affilliation | Fundação Oswaldo Cruz. Instituto Tecnologia em Fármacos— Farmanguinhos. Rio de Janeiro, RJ. Brasil. | pt_BR |
Subject | Antiviral | pt_BR |
Subject | Influenza A | pt_BR |
Subject | Ribavirin | pt_BR |
Subject | Reverse transcriptase | pt_BR |
Subject | 1,2,3-Triazole | pt_BR |
e-ISSN | 1554-8120 | |
Embargo date | 2030-01-01 | |