Highly lipophilic benzoxazoles with potential antibacterial activity

Jarmila Vinsová; Václav Horák; Vladimír Buchta; Jarmila Kaustová

doi:10.3390/10070783

Highly lipophilic benzoxazoles with potential antibacterial activity

Molecules. 2005 Aug 31;10(7):783-93. doi: 10.3390/10070783.

Authors

Jarmila Vinsová¹, Václav Horák, Vladimír Buchta, Jarmila Kaustová

Affiliation

¹ Department of Inorganic and Organic Chemistry, Faculty of Pharmacy Charles University, 500 05 Hradec Králové, The Czech Republic. vinsova@faf.cuni.cz

Abstract

A series of lipophilic 2-substituted 5,7-di-tert-butylbenzoxazoles was prepared in average yields by the reaction of 3,5-di-tert-butyl-1,2-benzoquinone with amino acids and dipeptides bearing N-terminal glycine. Dipeptides having other N-terminal amino acids undergo oxidative deamination. 5,7-Di-tert-butylbenzoxazoles have shown activity against Mycobacterium tuberculosis and some nontuberculous strains where isoniazid has been inactive. Antifungal activity was mediocre.

Publication types

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

MeSH terms

Anti-Bacterial Agents / pharmacology*
Antifungal Agents / pharmacology
Antitubercular Agents / pharmacology
Benzoxazoles / chemistry*
Benzoxazoles / pharmacology*
Isomerism
Isoniazid / pharmacology
Models, Molecular
Molecular Conformation
Mycobacterium tuberculosis / drug effects
Solubility
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Antifungal Agents
Antitubercular Agents
Benzoxazoles
Isoniazid