Date of Award

2021

Document Type

Dissertation

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Pharmaceutical and Chemical Sciences

First Advisor

Vyacheslav V. Samoshin

First Committee Member

Liang Xue

Second Committee Member

Andreas Franz

Third Committee Member

Jerry Tsai

Fourth Committee Member

Sven Hackbusch

Abstract

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.

Pages

297

Included in

Chemistry Commons

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