Literature DB >> 12408716

Synthesis and biological activity of strongly fluorescent tricyclic analogues of acyclovir and ganciclovir.

Tomasz Goslinski1, Bozenna Golankiewicz, Erik De Clercq, Jan Balzarini.   

Abstract

In search of strongly fluorescent tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, several 6-[4-(acyloxy)phenyl], 6-[4-(acylamino)phenyl], and 6-[4-(phenoxycarbonyloxy)phenyl]-substituted TACV and TGCV analogues were synthesized and evaluated for their activity against herpes simplex virus types 1 and 2 in cell culture. All TACV and TGCV analogues showed strong fluorescence (quantum yield of 30-65% vs 2-aminopurine 100%). The 6-[4-(phenoxycarbonyloxy)phenyl]-substituted compounds 11 and 19 displayed the best combination of the fluorescence and antiviral potency.

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Year:  2002        PMID： 12408716     DOI： 10.1021/jm020827z

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


  7 in total

1.  Synthesis, antiviral activity, and stability of nucleoside analogs containing tricyclic bases.

Authors:  Franck Amblard; Emilie Fromentin; Mervi Detorio; Alexander Obikhod; Kimberly L Rapp; Tamara R McBrayer; Tony Whitaker; Steven J Coats; Raymond F Schinazi
Journal:  Eur J Med Chem       Date:  2009-04-08       Impact factor: 6.514

2.  Prevention of UVA-induced oxidative damage in human dermal fibroblasts by new UV filters, assessed using a novel in vitro experimental system.

Authors:  Francesca Brugè; Luca Tiano; Paola Astolfi; Monica Emanuelli; Elisabetta Damiani
Journal:  PLoS One       Date:  2014-01-07       Impact factor: 3.240

Review 3.  Base-Modified Nucleosides: Etheno Derivatives.

Authors:  Zofia Jahnz-Wechmann; Grzegorz R Framski; Piotr A Januszczyk; Jerzy Boryski
Journal:  Front Chem       Date:  2016-04-28       Impact factor: 5.221

4.  Tricyclic Derivative of Acyclovir and Its Esters in Relation to the Esters of Acyclovir Enzymatic Stability: Enzymatic Stability Study.

Authors:  Izabela Muszalska-Kolos; Monika A Lesniewska-Kowiel; Szymon Plewa; Agnieszka Klupczyńska
Journal:  Molecules       Date:  2020-05-05       Impact factor: 4.411

Review 5.  The next ten stories on antiviral drug discovery (part E): advents, advances, and adventures.

Authors:  Erik De Clercq
Journal:  Med Res Rev       Date:  2011-01       Impact factor: 12.944

6.  Synthesis and anti-HSV activity of tricyclic penciclovir and hydroxybutylguanine derivatives.

Authors:  Anber F Mohammed; Graciela Andrei; Alaa M Hayallah; Samia G Abdel-Moty; Robert Snoeck; Claire Simons
Journal:  Bioorg Med Chem       Date:  2019-02-02       Impact factor: 3.641

7.  Comparison of Aqueous and 1-Octanol Solubility as well as Liquid-Liquid Distribution of Acyclovir Derivatives and Their Complexes with Hydroxypropyl-β-Cyclodextrin.

Authors:  Małgorzata Koźbiał; Paweł Gierycz
Journal:  J Solution Chem       Date:  2013-04-26       Impact factor: 1.677
  7 in total

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