Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.
The synthesis and antirhinovirus activity of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine (4 and 5) are reported. The structural assignments of 4 and 5 are based upon 13C NMR spectra of both isomers and also X-ray analysis of 5. The anti-isomer 5 was more potent than the syn-isomer 4 when compared as an inhibitor of rhinovirus multiplication in vitro. Both isomers inhibited multiplication of 15 different serotypes of rhinovirus.
D000998:Antiviral Agents / Q000138:chemical synthesis*; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010091:Oximes; D012229:Rhinovirus / Q000187:drug effects*; D013237:Stereoisomerism; D013449:Sulfonamides; D010948:Viral Plaque Assay; D014776:Virus Cultivation; D014779:Virus Replication / Q000187:drug effects*; D014961:X-Ray Diffraction
D000998:Antiviral Agents; D001562:Benzimidazoles; D010091:Oximes; D013449:Sulfonamides; C021595:viroxime