Synthesis and antifungal activity of the 2,2,5-tetrahydrofuran regioisomers of SCH 51048

Raymond G Lovey; Anil K Saksena; Viyyoor M Girijavallabhan; Paul Blundell; Henry Guzik; David Loebenberg; Raulo M Parmegiani; Anthony Cacciapuoti

doi:10.1016/s0960-894x(02)00282-2

Synthesis and antifungal activity of the 2,2,5-tetrahydrofuran regioisomers of SCH 51048

Bioorg Med Chem Lett. 2002 Jul 8;12(13):1739-42. doi: 10.1016/s0960-894x(02)00282-2.

Authors

Raymond G Lovey¹, Anil K Saksena, Viyyoor M Girijavallabhan, Paul Blundell, Henry Guzik, David Loebenberg, Raulo M Parmegiani, Anthony Cacciapuoti

Affiliation

¹ Department of Chemical Research, Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA. [email protected]

PMID: 12067550
DOI: 10.1016/s0960-894x(02)00282-2

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.

MeSH terms

Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology
Benzene / chemistry
Binding Sites
Furans / chemical synthesis*
Furans / chemistry
Furans / pharmacology
In Vitro Techniques
Microbial Sensitivity Tests
Oxygen / chemistry
Stereoisomerism
Structure-Activity Relationship
Triazoles / chemistry*
Triazoles / pharmacology

Substances

Antifungal Agents
Furans
SCH 51048
Triazoles
tetrahydrofuran
Benzene
Oxygen