Literature DB >> 24900429

Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds.

Eva Torres1, Roser Fernández1, Stéphanie Miquet1, Mercè Font-Bardia2, Evelien Vanderlinden3, Lieve Naesens3, Santiago Vázquez1.   

Abstract

The synthesis of several 2,2-dialkyladamantyl-1-amines through the combination of a Ritter reaction with a Wagner-Meerwein rearrangement from noradamantane alcohols is reported. Several of the novel amines displayed low micromolar activities against several H1N1 influenza virus strains, including the amantadine-resistant A/PuertoRico/8/34 strain. Most of the compounds did not show cytotoxicity for MDCK cells.

Entities:  

Keywords:  M2 channel; Ritter reaction; Wagner−Meerwein rearrangement; amantadine; influenza

Year:  2012        PMID： 24900429      PMCID： PMC4025864          DOI： 10.1021/ml300279b

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  17 in total

Review 1.  Amantadine and rimantadine for influenza A in adults.

Authors:  T Jefferson; V Demicheli; C Di Pietrantonj; D Rivetti
Journal:  Cochrane Database Syst Rev       Date:  2006-04-19

Review 2.  Antivirals targeting influenza A virus.

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Review 3.  Structural basis for proton conduction and inhibition by the influenza M2 protein.

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Review 4.  Resistance characteristics of influenza to amino-adamantyls.

Authors:  Peleg Astrahan; Isaiah T Arkin
Journal:  Biochim Biophys Acta       Date:  2010-06-27

5.  Synthesis of several halobisnoradamantane derivatives and their reactivity through the S(RN)1 mechanism.

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Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

Review 6.  Structural and dynamic mechanisms for the function and inhibition of the M2 proton channel from influenza A virus.

Authors:  Jun Wang; Jade Xiaoyan Qiu; Cinque Soto; William F DeGrado
Journal:  Curr Opin Struct Biol       Date:  2011-01-17       Impact factor: 6.809

7.  Surveillance of resistance to adamantanes among influenza A(H3N2) and A(H1N1) viruses isolated worldwide.

Authors:  Varough M Deyde; Xiyan Xu; Rick A Bright; Michael Shaw; Catherine B Smith; Ye Zhang; Yuelong Shu; Larisa V Gubareva; Nancy J Cox; Alexander I Klimov
Journal:  J Infect Dis       Date:  2007-06-07       Impact factor: 5.226

8.  Carbon tunneling in the ring expansion of noradamantylchlorocarbene.

Authors:  Robert A Moss; Ronald R Sauers; Robert S Sheridan; Jingzhi Tian; Peter S Zuev
Journal:  J Am Chem Soc       Date:  2004-08-25       Impact factor: 15.419

9.  Influenza virus M2 protein has ion channel activity.

Authors:  L H Pinto; L J Holsinger; R A Lamb
Journal:  Cell       Date:  1992-05-01       Impact factor: 41.582

10.  The molecular basis of the specific anti-influenza action of amantadine.

Authors:  A J Hay; A J Wolstenholme; J J Skehel; M H Smith
Journal:  EMBO J       Date:  1985-11       Impact factor: 11.598
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Authors:  Matias Rey-Carrizo; Eva Torres; Chunlong Ma; Marta Barniol-Xicota; Jun Wang; Yibing Wu; Lieve Naesens; William F DeGrado; Robert A Lamb; Lawrence H Pinto; Santiago Vázquez
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2.  Azapropellanes with anti-influenza a virus activity.

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3.  Binding and Proton Blockage by Amantadine Variants of the Influenza M2WT and M2S31N Explained.

Authors:  Christina Tzitzoglaki; Anna Wright; Kathrin Freudenberger; Anja Hoffmann; Ian Tietjen; Ioannis Stylianakis; Felix Kolarov; David Fedida; Michaela Schmidtke; Günter Gauglitz; Timothy A Cross; Antonios Kolocouris
Journal:  J Med Chem       Date:  2017-02-15       Impact factor: 8.039

4.  Investigation of a recent rise of dual amantadine-resistance mutations in the influenza A M2 sequence.

Authors:  Matthew G Durrant; Dennis L Eggett; David D Busath
Journal:  BMC Genet       Date:  2015-04-23       Impact factor: 2.797

5.  Aminoadamantanes with persistent in vitro efficacy against H1N1 (2009) influenza A.

Authors:  Antonios Kolocouris; Christina Tzitzoglaki; F Brent Johnson; Roland Zell; Anna K Wright; Timothy A Cross; Ian Tietjen; David Fedida; David D Busath
Journal:  J Med Chem       Date:  2014-05-15       Impact factor: 7.446

6.  Role of the viral hemagglutinin in the anti-influenza virus activity of newly synthesized polycyclic amine compounds.

Authors:  Eva Torres; María D Duque; Evelien Vanderlinden; Chunlong Ma; Lawrence H Pinto; Pelayo Camps; Mathy Froeyen; Santiago Vázquez; Lieve Naesens
Journal:  Antiviral Res       Date:  2013-06-22       Impact factor: 5.970

7.  Adamantane-Substituted Purines and Their β-Cyclodextrin Complexes: Synthesis and Biological Activity.

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Journal:  Int J Mol Sci       Date:  2021-11-24       Impact factor: 5.923

8.  Easily accessible polycyclic amines that inhibit the wild-type and amantadine-resistant mutants of the M2 channel of influenza A virus.

Authors:  Matias Rey-Carrizo; Marta Barniol-Xicota; Chunlong Ma; Marta Frigolé-Vivas; Eva Torres; Lieve Naesens; Salomé Llabrés; Jordi Juárez-Jiménez; Francisco J Luque; William F DeGrado; Robert A Lamb; Lawrence H Pinto; Santiago Vázquez
Journal:  J Med Chem       Date:  2014-06-30       Impact factor: 7.446
  8 in total

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