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

• 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
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/S0223-5234(99)80061-0

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.