Synthesis and antiviral activity of imidazo[1,2- a]pyridines

Imidazo[1,2- a]pyridines bearing a 3-(dithiolan-, dioxolan- or oxathiolan-2-yl) substituent were synthesized from the corresponding aldehydes. The dithiolanyl derivative 6a proved active against cytomegalovirus at an inhibitory concentration (IC 50) of 16 μM, whilethe oxathiolanyl compound 6c inhibi...

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Bibliographic Details
Published in:	European journal of medicinal chemistry Vol. 34; no. 3; pp. 271 - 274
Main Authors:	Lhassani, Mohammed, Chavignon, Olivier, Chezal, Jean-Michel, Teulade, Jean-Claude, Chapat, Jean-Pierre, Snoeck, Richard, Andrei, Graciela, Balzarini, Jan, De Clercq, Erik, Gueiffier, Alain
Format:	Journal Article
Language:	English
Published:	Oxford Elsevier Masson SAS 01-03-1999 Elsevier
Subjects:	Antibiotics. Antiinfectious agents. Antiparasitic agents antiviral activity Antiviral agents Biological and medical sciences cytomegalovirus imidazo[1,2- a]pyridine Medical sciences Pharmacology. Drug treatments respiratory syncytial virus thioacetal thioacetal imidazo[1,2- a]pyridine antiviral activity cytomegalovirus respiratory syncytial virus Human Oxygen sulfur heterocycle Human respiratory syncytial virus Pneumovirinae Angular nitrogen heterocycle Herpesviridae Thioacetal Betaherpesvirinae In vitro Hela cell line Thioaldehyde Paramyxoviridae Human cytomegalovirus Virus Mononegavirales Dithioacetal Sulfur heterocycle Cell line Structure activity relation Bicyclic compound Antiviral Pneumovirus Chemical synthesis
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Summary:	Imidazo[1,2- a]pyridines bearing a 3-(dithiolan-, dioxolan- or oxathiolan-2-yl) substituent were synthesized from the corresponding aldehydes. The dithiolanyl derivative 6a proved active against cytomegalovirus at an inhibitory concentration (IC 50) of 16 μM, whilethe oxathiolanyl compound 6c inhibited respiratory syncytial virus (IC 50: 58 μM). The thioacetal 7 was active against cytomegalovirus at an IC 50 of 3.1 μM. None of the compounds had anti-HIV activity and were not inhibitory against other RNA and DNA viruses evaluated. Compounds 6a,c and 7 had in vitro selectivity indexes (ratio cytostatic concentration/antivirally active concentration) ranging between 8 and 10.
ISSN:	0223-5234 1768-3254
DOI:	10.1016/S0223-5234(99)80061-0