Synthesis and preliminary biological evaluation of a compound library of triazolylcyclitols

Gonzalo Carrau; Carine C Drewes; Ana Lúcia B Shimada; Ana Bertucci; Sandra H P Farsky; Helio A Stefani; David Gonzalez

doi:10.1016/j.bmc.2013.04.084

Synthesis and preliminary biological evaluation of a compound library of triazolylcyclitols

Bioorg Med Chem. 2013 Jul 15;21(14):4225-32. doi: 10.1016/j.bmc.2013.04.084. Epub 2013 May 14.

Authors

Gonzalo Carrau¹, Carine C Drewes, Ana Lúcia B Shimada, Ana Bertucci, Sandra H P Farsky, Helio A Stefani, David Gonzalez

Affiliation

¹ Depto. de Química Orgánica, Facultad. de Química, Universidad de la República, UdelaR, Montevideo, Uruguay.

PMID: 23721916
DOI: 10.1016/j.bmc.2013.04.084

Abstract

A small library of compounds was prepared by a combination of toluene dioxygenase (TDO)-catalyzed enzymatic dihydroxylation and copper(I)-catalyzed Hüisgen cycloaddition. Some compounds were obtained by coupling an alkyne and a conduritol derivative, while more complex structures were obtained by a double Hüisgen reaction of a dialkyne and two molecules of the cyclitol. The compounds were fully characterized and subjected to preliminary biological screening.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry
Antifungal Agents / pharmacology
Cell Proliferation / drug effects
Cells, Cultured
Cyclitols / chemical synthesis*
Cyclitols / chemistry
Cyclitols / pharmacology*
Cycloaddition Reaction
Immunosuppressive Agents / chemical synthesis
Immunosuppressive Agents / chemistry
Immunosuppressive Agents / pharmacology
Male
Mice
Mice, Inbred C57BL
Molecular Structure
Small Molecule Libraries / chemical synthesis*
Small Molecule Libraries / chemistry
Small Molecule Libraries / pharmacology*
Triazoles / chemical synthesis
Triazoles / chemistry
Triazoles / pharmacology

Substances

Antifungal Agents
Cyclitols
Immunosuppressive Agents
Small Molecule Libraries
Triazoles