highly lipophilic benzoxazoles with potential antibacterial activity高度亲脂性的苯并恶唑和潜在的抗菌活性.pdfVIP

Molecules 2005, 10, 783-793 molecules ISSN 1420-3049 Highly Lipophilic Benzoxazoles with Potential Antibacterial Activity Jarmila Vinšová 1,*, Václav Horák 2, Vladimír Buchta 3, Jarmila Kaustová 4 1 Department of Inorganic and Organic Chemistry, Faculty of Pharmacy Charles University, 500 05 Hradec Králové, The Czech Republic 2 Georgetown University, Washington DC 20057-1227, USA 3 Department of Biological and Medical Sciences, Faculty of Pharmacy, Charles University 4 National Reference Laboratory for Mycobacterium Kansasii, Regional Institute of Hygiene, Ostrava, The Czech Republic * Author to whom correspondence should be addressed; e-mail: vinsova@faf.cuni.cz, tel. (+420)-49- 5067343; fax (+420)-49-5514330; Received: 9 November 2004; in revised form: 4 March 2005 / Accepted: 10 March / Published: 31 August 2005 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. Keywords: 3,5-di-tert-Butyl-1,2-benzoquinone, 5,7-di-tert-butylbenzoxazoles, antimyco- bacterial activity, antifungal activity Introduction The objectives of this study were the preparation and biological testing of some highly lipophilic 2-substituted-5,7-di-tert-butyl-benzoxazoles. Such lipophi