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Highly Lipophilic Benzoxazoles with Potential Antibacterial Activity
* 1 , 2 , 3 , 4
1  Department of Inorganic and Organic Chemistry, Faculty of Pharmacy Charles University, CZ – 500 05 Hradec Králové, Czech Republic
2  Georgetown University, Washington DC 20057-1227, USA
3  Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University, CZ – 500 05 Hradec Králové, Czech Republic
4  National Reference Laboratory for Mycobacterium Kansasii, Regional Institute of Hygiene, Ostrava, Czech Republic

Abstract: A series of lipophilic 5,7-di-tert-butylbenzoxazoles substituted in position 2 was prepared by the reaction of 3,5-di-tert-butyl-1,2-benzoquinone with amino acids and dipeptides carrying N-terminal glycine in medium yields. Dipeptides having other N-terminal amino acid undergo oxidative deamination. 5,7-Di-tert-butylbenzoxazoles have shown activity against Mycobacterium tuberculosis and some nontuberculous strains where Isoniazide has been inactive. Antifungal activity was mediocre.
Keywords: 3,5-di-tert-butyl-1,2-benzoquinone; 5,7-di-tert-butylbenzoxazoles; antimycobacterial activity; antifungal activity