Antiviral Research, volume 81, issue 1, pages 56-63

New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3

Schmidtke Michaela

Schmidtke Michaela ¹

Wutzler Peter

Wutzler P. ¹

Zieger Romy ¹

Riabova Olga B ²

Makarov Vadim A

Makarov Vadim A. ²

Hide authors affiliations Show authors affiliations: 2 affiliations

Institute of Virology and Antiviral Therapy, Friedrich Schiller University, Hans Knoell Street 2, D-07745 Jena, Germany. |

Laboratory of Biochemistry of Stresses in Microorganisms, RAS Institute of Biochemistry, Leninsky prospekt, 33, Building 2, Moscow 119071, Russia |

Publication type: Journal Article

Publication date: 2009-01-01

Elsevier

Journal: Antiviral Research

Quartile SCImago

Quartile WOS

Impact factor: 7.6

ISSN: 01663542, 18729096

DOI: 10.1016/j.antiviral.2008.09.002

Copy DOI

Pharmacology

Virology

Abstract

Amino acid 1092 (AA1092) in capsid protein 1 of coxsackievirus B3 (CVB3) is located in close vicinity to the central phenoxy group of capsid binders (i.e. pleconaril). Whereas isoleucine is associated with drug susceptibility, leucine and methionine confer resistance to pleconaril. In the present study, novel analogues with different substitutions in the central phenoxy group were synthesized to study their influence on anti-CVB3 activity with the aim to overcome pleconaril resistance. Two [(biphenyloxy)propyl]isoxazoles and pleconaril were synthesized without methyl groups in the central phenoxy ring using Suzuki coupling reaction and tested for antiviral activity against the pleconaril-resistant CVB3 Nancy. Furthermore, pleconaril with 3-methyl, 3-methoxy, 3-bromine, 2,3-dimethyl in the central ring as well as the external rings in meta position were synthesized for structure-activity relationship analysis with CVB3 variants containing leucine, methionine or isoleucine at position 1092, other coxsackieviruses B (CVB) as well as several rhinoviruses. The results demonstrate a high impact of substituents in the central ring of capsid inhibitors for anti-enteroviral activity. Pleconaril resistance of CVB3 based on Leu1092 or Met1092 was overcome by unsubstituted analogues or by monosubstitution with 3-methyl as well as 3-bromine in the central phenyl. The 3-bromine derivative inhibited a broad spectrum of CVB and rhinoviruses.

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Citations by journals

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Antiviral Research	Antiviral Research, 4, 9.52% Antiviral Research 4 publications, 9.52%
European Journal of Medicinal Chemistry	European Journal of Medicinal Chemistry, 2, 4.76% European Journal of Medicinal Chemistry 2 publications, 4.76%
Bioorganic and Medicinal Chemistry Letters	Bioorganic and Medicinal Chemistry Letters, 2, 4.76% Bioorganic and Medicinal Chemistry Letters 2 publications, 4.76%
Russian Journal of Infection and Immunity	Russian Journal of Infection and Immunity, 2, 4.76% Russian Journal of Infection and Immunity 2 publications, 4.76%
Life	Life, 1, 2.38% Life 1 publication, 2.38%
Current Organic Synthesis	Current Organic Synthesis, 1, 2.38% Current Organic Synthesis 1 publication, 2.38%
Journal of Pediatric Hematology/Oncology	Journal of Pediatric Hematology/Oncology, 1, 2.38% Journal of Pediatric Hematology/Oncology 1 publication, 2.38%
Future Medicinal Chemistry	Future Medicinal Chemistry, 1, 2.38% Future Medicinal Chemistry 1 publication, 2.38%
Molecules	Molecules, 1, 2.38% Molecules 1 publication, 2.38%
Microorganisms	Microorganisms, 1, 2.38% Microorganisms 1 publication, 2.38%
Frontiers in Molecular Neuroscience	Frontiers in Molecular Neuroscience, 1, 2.38% Frontiers in Molecular Neuroscience 1 publication, 2.38%
Archives of Virology	Archives of Virology, 1, 2.38% Archives of Virology 1 publication, 2.38%
Russian Chemical Bulletin	Russian Chemical Bulletin, 1, 2.38% Russian Chemical Bulletin 1 publication, 2.38%
Monatshefte fur Chemie	Monatshefte fur Chemie, 1, 2.38% Monatshefte fur Chemie 1 publication, 2.38%
Virology	Virology, 1, 2.38% Virology 1 publication, 2.38%
Bioorganic and Medicinal Chemistry	Bioorganic and Medicinal Chemistry, 1, 2.38% Bioorganic and Medicinal Chemistry 1 publication, 2.38%
Journal of Molecular Structure	Journal of Molecular Structure, 1, 2.38% Journal of Molecular Structure 1 publication, 2.38%
Ultrasonics Sonochemistry	Ultrasonics Sonochemistry, 1, 2.38% Ultrasonics Sonochemistry 1 publication, 2.38%
International Journal of Antimicrobial Agents	International Journal of Antimicrobial Agents, 1, 2.38% International Journal of Antimicrobial Agents 1 publication, 2.38%
Acta Pharmaceutica Sinica B	Acta Pharmaceutica Sinica B, 1, 2.38% Acta Pharmaceutica Sinica B 1 publication, 2.38%
ChemMedChem	ChemMedChem, 1, 2.38% ChemMedChem 1 publication, 2.38%
Medicinal Research Reviews	Medicinal Research Reviews, 1, 2.38% Medicinal Research Reviews 1 publication, 2.38%
Nanoscale	Nanoscale, 1, 2.38% Nanoscale 1 publication, 2.38%
Expert Review of Anti-Infective Therapy	Expert Review of Anti-Infective Therapy, 1, 2.38% Expert Review of Anti-Infective Therapy 1 publication, 2.38%
Pathogens and Global Health	Pathogens and Global Health, 1, 2.38% Pathogens and Global Health 1 publication, 2.38%
Journal of Enzyme Inhibition and Medicinal Chemistry	Journal of Enzyme Inhibition and Medicinal Chemistry, 1, 2.38% Journal of Enzyme Inhibition and Medicinal Chemistry 1 publication, 2.38%
Research Results in Pharmacology	Research Results in Pharmacology, 1, 2.38% Research Results in Pharmacology 1 publication, 2.38%
Pathogens and Disease	Pathogens and Disease, 1, 2.38% Pathogens and Disease 1 publication, 2.38%
Journal of Virology	Journal of Virology, 1, 2.38% Journal of Virology 1 publication, 2.38%
Proceedings of the National Academy of Sciences of the United States of America	Proceedings of the National Academy of Sciences of the United States of America, 1, 2.38% Proceedings of the National Academy of Sciences of the United States of America 1 publication, 2.38%

	1 2 3 4

Citations by publishers

	2 4 6 8 10 12 14
Elsevier	Elsevier, 14, 33.33% Elsevier 14 publications, 33.33%
Taylor & Francis	Taylor & Francis, 5, 11.9% Taylor & Francis 5 publications, 11.9%
Springer Nature	Springer Nature, 4, 9.52% Springer Nature 4 publications, 9.52%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 3, 7.14% Multidisciplinary Digital Publishing Institute (MDPI) 3 publications, 7.14%
Wiley	Wiley, 3, 7.14% Wiley 3 publications, 7.14%
Saint Petersburg Pasteur Institute	Saint Petersburg Pasteur Institute, 2, 4.76% Saint Petersburg Pasteur Institute 2 publications, 4.76%
Bentham Science	Bentham Science, 1, 2.38% Bentham Science 1 publication, 2.38%
Wolters Kluwer Health	Wolters Kluwer Health, 1, 2.38% Wolters Kluwer Health 1 publication, 2.38%
Future Medicine	Future Medicine, 1, 2.38% Future Medicine 1 publication, 2.38%
Frontiers Media S.A.	Frontiers Media S.A., 1, 2.38% Frontiers Media S.A. 1 publication, 2.38%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 1, 2.38% Royal Society of Chemistry (RSC) 1 publication, 2.38%
Belgorod National Research University	Belgorod National Research University, 1, 2.38% Belgorod National Research University 1 publication, 2.38%
Oxford University Press	Oxford University Press, 1, 2.38% Oxford University Press 1 publication, 2.38%
American Society for Microbiology	American Society for Microbiology, 1, 2.38% American Society for Microbiology 1 publication, 2.38%
Proceedings of the National Academy of Sciences (PNAS)	Proceedings of the National Academy of Sciences (PNAS), 1, 2.38% Proceedings of the National Academy of Sciences (PNAS) 1 publication, 2.38%
Universita Palackeho Olomouc	Universita Palackeho Olomouc, 1, 2.38% Universita Palackeho Olomouc 1 publication, 2.38%
Electrochemical Science Group, University of Belgrade	Electrochemical Science Group, University of Belgrade, 1, 2.38% Electrochemical Science Group, University of Belgrade 1 publication, 2.38%
	2 4 6 8 10 12 14

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Schmidtke M. et al. New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3 // Antiviral Research. 2009. Vol. 81. No. 1. pp. 56-63.

GOST all authors (up to 50) Copy

Schmidtke M., Schmidtke M., Wutzler P., Wutzler P., Zieger R., Riabova O. B., Makarov V. A., Makarov V. A. New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3 // Antiviral Research. 2009. Vol. 81. No. 1. pp. 56-63.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/j.antiviral.2008.09.002

UR - https://doi.org/10.1016%2Fj.antiviral.2008.09.002

TI - New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3

T2 - Antiviral Research

AU - Schmidtke, Michaela

AU - Wutzler, Peter

AU - Zieger, Romy

AU - Riabova, Olga B

AU - Makarov, Vadim A

AU - Schmidtke, Michaela

AU - Wutzler, P.

AU - Makarov, Vadim A.

PY - 2009

DA - 2009/01/01 00:00:00

PB - Elsevier

SP - 56-63

IS - 1

VL - 81

SN - 0166-3542

SN - 1872-9096

ER -

BibTex |

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@article{2009_Schmidtke,

author = {Michaela Schmidtke and Peter Wutzler and Romy Zieger and Olga B Riabova and Vadim A Makarov and Michaela Schmidtke and P. Wutzler and Vadim A. Makarov},

title = {New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3},

journal = {Antiviral Research},

year = {2009},

volume = {81},

publisher = {Elsevier},

month = {jan},

url = {https://doi.org/10.1016%2Fj.antiviral.2008.09.002},

number = {1},

pages = {56--63},

doi = {10.1016/j.antiviral.2008.09.002}

}

MLA

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MLA Copy

Schmidtke, Michaela, et al. “New pleconaril and [(biphenyloxy)propyl]isoxazole derivatives with substitutions in the central ring exhibit antiviral activity against pleconaril-resistant coxsackievirus B3.” Antiviral Research, vol. 81, no. 1, Jan. 2009, pp. 56-63. https://doi.org/10.1016%2Fj.antiviral.2008.09.002.

Found error?

Publisher

Elsevier

Journal

Antiviral Research

Quartile SCImago

Quartile WOS

Impact factor

7.6

ISSN

01663542 (Print)
18729096 (Electronic)

Labs

Laboratory of Biomedical Chemistry

Profiles

Makarov, Vadim Albertovich