Diastereoselective Synthesis and Antifungal Activity of Glycosyl Isoxazolines

Abstract

Glycosyl nitrile oxides, generated in situ by reaction of glycosyl oximes (3a, 3b, 4) with N‐chlorosuccinimide and DBU, on 1,3‐dipolar cycloaddition with substituted alkenes resulted in glycosyl isoxazolines (5, 7–28) in diastereoselective manner. The extent of diastereoselection varies with the nature of substituents both in sugar and alkenes. The compounds synthesized were screened in vitro against many fungi wherein two of the compounds (12, 23) showed significant inhibition against Sporothrix schenckii, Trychophyton mentagrophytes, and Cryptococcus neoformans with MIC of 12.5 and 6.25 µg/mL, respectively.

^#CDRI Communication No.6460.

Keywords:

• Cycloaddition
• Isoxazoline
• DBU
• Antifungal activity

Acknowledgments

Authors thank the director of CDRI, for his keen interest in the program; ICMR, New Delhi, for financial support; and RSIC staff for spectral data and analysis.

Notes

^#CDRI Communication No.6460.