Literature DB >> 19195900

Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity.

Grigoris Zoidis1, Nicolas Kolocouris, Lieve Naesens, Erik De Clercq.   

Abstract

1-2 Annulated adamantane piperidines 4, 6, 16, 17, 19, 23 and 25 were synthesized and evaluated for anti-influenza A virus activity. The stereoelectronic requirements for optimal antiviral potency were investigated. Piperidine 23 proved to be the most active of the compounds tested against influenza A virus, being 3.5-fold more active than amantadine, equipotent to rimantadine and 15-fold more potent than ribavirin. It is noteworthy that piperidine 23 displayed one of the highest selectivity indexes (SI>732) among aminoadamantanes or other cage structure amines tested till now.

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Year:  2009        PMID： 19195900     DOI： 10.1016/j.bmc.2009.01.009

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  3 in total

Review 1.  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

2.  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

3.  Camphor-based symmetric diimines as inhibitors of influenza virus reproduction.

Authors:  Anastasiya S Sokolova; O Cyrilliclga I Yarovaya; Dina V Korchagina; Vladimir V Zarubaev; Tatiana S Tretiak; Pavel M Anfimov; Oleg I Kiselev; Nariman F Salakhutdinov
Journal:  Bioorg Med Chem       Date:  2014-03-01       Impact factor: 3.641
  3 in total

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