SYNTHESIS AND CONFORMATIONAL STUDY OF TRIAZOLYLCYCLOHEXANOLS AND TRANS-2-(AZAARYLSULFANYL)-CYCLOHEXANOLS

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH-range in which a switch can occur. The pH-induced switch of conformation can be monitored by 1H NMR.In this work, structurally similar trans-2-(azaarylsulfanyl)-cyclohexanol derivatives (Scheme 1) and trans-2-triazolylcyclohexanol derivatives (Scheme 2) have been explored for the first time as compounds with a potential for the analogous pH-induced conformational switch. The azaarylsulfanyl groups showed selective conformational flexibility while the triazolyl group showed a strong preference for the equatorial position. Further, conformational studies were done on a series of trans-2-triazolylcyclohexanols and triazolycyclohexanes to determine the previously unknown conformational energy of the triazolyl group.In addition, a series of carbasugar analogues based on trans-2-(1,2,3-triazolyl)-cyclohexanol moiety was synthesized and tested for activity (inhibition or activation) towards fungal glycosidases from Aspergillus and Penicillium sp due to the growing use of triazoles in the pharmaceutical industry

SYNTHESIS AND CONFORMATIONAL STUDY OF TRIAZOLYLCYCLOHEXANOLS AND TRANS-2-(AZAARYLSULFANYL)-CYCLOHEXANOLS

Amino-cyclohexanol derivatives have been successful models for pH-triggered conformational switches. By changing the groups on the amine nitrogen, these models provide a wide pH-range in which a switch can occur. The pH-induced switch of conformation can be monitored by 1H NMR.In this work, structurally similar trans-2-(azaarylsulfanyl)-cyclohexanol derivatives (Scheme 1) and trans-2-triazolylcyclohexanol derivatives (Scheme 2) have been explored for the first time as compounds with a potential for the analogous pH-induced conformational switch. The azaarylsulfanyl groups showed selective conformational flexibility while the triazolyl group showed a strong preference for the equatorial position. Further, conformational studies were done on a series of trans-2-triazolylcyclohexanols and triazolycyclohexanes to determine the previously unknown conformational energy of the triazolyl group.In addition, a series of carbasugar analogues based on trans-2-(1,2,3-triazolyl)-cyclohexanol moiety was synthesized and tested for activity (inhibition or activation) towards fungal glycosidases from Aspergillus and Penicillium sp due to the growing use of triazoles in the pharmaceutical industry

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential inhibitors for fungal glycosidases

A series of carbasugars based on trans-2-(1,2,3-triazolyl)-cyclohexanol moiety was synthesized for the first time by a “click reaction” of the corresponding azides and alkynes, and tested for the inhibitory activity towards fungal glycosidases from Aspergillus and Penicillium sp

Exploration of trans-2-(1,2,3-triazolyl)-cyclohexanols as potential inhibitors for fungal glycosidases

A series of carbasugars based on trans-2-(1,2,3-triazolyl)-cyclohexanol moiety was synthesized for the first time by a “click reaction” of the corresponding azides and alkynes, and tested for the inhibitory activity towards fungal glycosidases from Aspergillus and Penicillium sp