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

…, D Loebenberg, RM Parmegiani, A Cacciapuoti

Index: Lovey, Raymond G.; Saksena, Anil K.; Girijavallabhan, Viyyoor M.; Blundell, Paul; Guzik, Henry; Loebenberg, David; Parmegiani, Raulo M.; Cacciapuoti, Anthony Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 13 p. 1739 - 1742

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Citation Number: 5

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.