Literature DB >> 8071937

Synthesis and antiviral activity evaluation of some aminoadamantane derivatives.

N Kolocouris1, G B Foscolos, A Kolocouris, P Marakos, N Pouli, G Fytas, S Ikeda, E De Clercq.   

Abstract

The synthesis of some spiro[cyclopropane-1,2'-adamantan]-2-amines and methanamines and some spiro[pyrrolidine-2,2'-adamantanes] is described. The title compounds were evaluated against a wide range of viruses (influenza A, influenza B, parainfluenza 3, RSV, HSV-1, TK- HSV-1, HSV-2, vaccinia, vesicular stomatitis, polio 1, coxsackie B4, sindbis, semliki forest, Reo 1, HIV-1, and HIV-2), and some of them (compounds 6b, 6c, 9a, 16a, 16b, and 17) inhibited the cytopathicity of influenza A virus at a concentration significantly lower than that of amantadine and also significantly lower than the concentrations at which they proved cytotoxic to the host cells. None of the new aminoadamantane derivatives was active against influenza B virus or any of the other viruses tested, which points to their specificity as anti-influenza A virus agents.

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Year:  1994        PMID: 8071937     DOI: 10.1021/jm00044a010

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  25 in total

1.  Influence of an additional amino group on the potency of aminoadamantanes against influenza virus A. II - Synthesis of spiropiperazines and in vitro activity against influenza A H3N2 virus.

Authors:  Christos Fytas; Antonios Kolocouris; George Fytas; Grigoris Zoidis; Charalampos Valmas; Christopher F Basler
Journal:  Bioorg Chem       Date:  2010-09-21       Impact factor: 5.275

2.  Affinity of Rimantadine Enantiomers against Influenza A/M2 Protein Revisited.

Authors:  Antonios Drakopoulos; Christina Tzitzoglaki; Chulong Ma; Kathrin Freudenberger; Anja Hoffmann; Yanmei Hu; Günter Gauglitz; Michaela Schmidtke; Jun Wang; Antonios Kolocouris
Journal:  ACS Med Chem Lett       Date:  2017-01-27       Impact factor: 4.345

Review 3.  The lipophilic bullet hits the targets: medicinal chemistry of adamantane derivatives.

Authors:  Lukas Wanka; Khalid Iqbal; Peter R Schreiner
Journal:  Chem Rev       Date:  2013-02-25       Impact factor: 60.622

4.  Molecular dynamics modeling the synthetic and biological polymers interactions pre-studied via docking: anchors modified polyanions interference with the HIV-1 fusion mediator.

Authors:  Vladimir B Tsvetkov; Alexander V Serbin
Journal:  J Comput Aided Mol Des       Date:  2014-05-27       Impact factor: 3.686

5.  A novel view of modelling interactions between synthetic and biological polymers via docking.

Authors:  Vladimir B Tsvetkov; Alexander V Serbin
Journal:  J Comput Aided Mol Des       Date:  2012-12-13       Impact factor: 3.686

6.  Exploring the size limit of templates for inhibitors of the M2 ion channel of influenza A virus.

Authors:  María D Duque; Chunlong Ma; Eva Torres; Jun Wang; Lieve Naesens; Jordi Juárez-Jiménez; Pelayo Camps; F Javier Luque; William F DeGrado; Robert A Lamb; Lawrence H Pinto; Santiago Vázquez
Journal:  J Med Chem       Date:  2011-04-05       Impact factor: 7.446

7.  Unraveling the Binding, Proton Blockage, and Inhibition of Influenza M2 WT and S31N by Rimantadine Variants.

Authors:  Antonios Drakopoulos; Christina Tzitzoglaki; Kelly McGuire; Anja Hoffmann; Athina Konstantinidi; Dimitrios Kolokouris; Chunlong Ma; Kathrin Freudenberger; Johanna Hutterer; Günter Gauglitz; Jun Wang; Michaela Schmidtke; David D Busath; Antonios Kolocouris
Journal:  ACS Med Chem Lett       Date:  2018-01-29       Impact factor: 4.345

8.  Ethyl 2-[(N-meth-oxy-N-methyl-carbamo-yl)meth-yl]-1-(phenyl-sulfon-yl)-1H-indole-3-carboxyl-ate.

Authors:  G Chakkaravarthi; V Dhayalan; A K Mohanakrishnan; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-21

9.  Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus.

Authors:  Jun Wang; Sarah D Cady; Victoria Balannik; Lawrence H Pinto; William F DeGrado; Mei Hong
Journal:  J Am Chem Soc       Date:  2009-06-17       Impact factor: 15.419

Review 10.  Potential for the Repurposing of Adamantane Antivirals for COVID-19.

Authors:  Roger F Butterworth
Journal:  Drugs R D       Date:  2021-06-21
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