title: Synthesis and antifungal activity of the 2,2,5-tetrahydrofuran regioisomers of SCH 51048.
abstract: The four 2,2,5-regioisomer counterparts of SCH 51048 were synthesized and evaluated. As with the parent series, only the two cis isomers possessed any in vitro activity, and only the activity of the isomer with the R-configuration at the tetrahydrofuran 2-carbon was significant. The activity data suggests that oxygen at only one of the two possible ring positions benzylic to the difluorobenzene participates usefully in active site binding.
authors.affiliation: Department of Chemical Research, Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA. raymond.lovey@spcorp.com
authors.forename: Raymond G
authors.initials: RG
authors.lastname: Lovey
authors.forename: Anil K
authors.initials: AK
authors.lastname: Saksena
authors.forename: Viyyoor M
authors.initials: VM
authors.lastname: Girijavallabhan
authors.forename: Paul
authors.initials: P
authors.lastname: Blundell
authors.forename: Henry
authors.initials: H
authors.lastname: Guzik
authors.forename: David
authors.initials: D
authors.lastname: Loebenberg
authors.forename: Raulo M
authors.initials: RM
authors.lastname: Parmegiani
authors.forename: Anthony
authors.initials: A
authors.lastname: Cacciapuoti
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001554:Benzene / Q000737:chemistry; D001665:Binding Sites; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D008826:Microbial Sensitivity Tests; D010100:Oxygen / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D005663:Furans; C094161:SCH 51048; D014230:Triazoles; C018674:tetrahydrofuran; D001554:Benzene; D010100:Oxygen