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Synthesis and antiviral activity of new phenylimidazopyridines and N-benzylidenequinolinamines derived by molecular simplification of phenylimidazo[4,5-g]quinolines

Loddo, Roberta and Briguglio, Irene and Corona, Paola and Piras, Sandra and Loriga, Mario and Paglietti, Giuseppe and Carta, Antonio and Sanna, Giuseppina and Giliberti, Gabriele and Ibba, Cristina and Farci, Pamela and La Colla, Paolo (2014) Synthesis and antiviral activity of new phenylimidazopyridines and N-benzylidenequinolinamines derived by molecular simplification of phenylimidazo[4,5-g]quinolines. European Journal of Medicinal Chemistry, Vol. 84 , p. 8-16. ISSN 0223-5234. Article.

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DOI: 10.1016/j.ejmech.2014.07.011


Continuing our program of research concerning the antiviral activity of a wide series of new angular and linear azolo bicyclic and tricyclic derivatives, now we have simplified and modified the 4-chloro-2-(4-nitrophenyl)-3H-imidazo[4,5-g]quinoline 1, which previously resulted the most active derivative, through either the elimination of the central ring or the opening of the imidazole ring, obtaining various imidazopyridines and Nbenzylidenequinolinamines respectively.

Title compounds were tested in cell-based assays for cytotoxicity and antiviral activity against representatives of two DNA virus families as wells as against representatives of RNA virus families containing single-stranded, either positive-sense (ssRNA+) or negative-sense (ssRNA), and double-stranded genomes (dsRNA). Some imidazo[4,5-b]pyridines emerged as new derivatives endowed with antiviral activity against Vaccinia Virus (VV) at concentrations ranging from 2 to 16 μM. In particular, compound 2b demonstrate to be about 10 times more potent than Cidofovir, used as reference drug. Similarly, the imidazo[4,5-c]pyridines and N-benzylidenequinolinamines derivatives resulted active against Bovine Viral Diarrhoea virus (BVDV), at concentrations ranging from 1.2 to 28 μM. Above all compounds 1, 3a and 3f showed an EC50 of the same order of magnitude of the reference drug, the 2′-C-methyl-guanosine. Moreover, several N-benzylidenequinolinamines showed an interesting activity against Respiratory Syncytial Virus (RSV) at concentrations between 12 and 26 μM.

Item Type:Article
ID Code:9996
Uncontrolled Keywords:Phenylimidazopiridines, N-benzylidenequinolinamines, antiviral activity, Bovine viral diarrhoea virus (BVDV), Vaccinia virus (VV), Respiratory syncytial virus (RSV), Coxsackie virus type B5 (CVB-5), Herpes simplex virus type 1 (HSV-1)
Subjects:Area 03 - Scienze chimiche > CHIM/08 Chimica farmaceutica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Elsevier Masson
Deposited On:01 Aug 2014 09:21

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