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Structure-Activity Relationships of 2-Benzylsulfanylbenzothiazoles: Synthesis and Selective Antimycobacterial Properties

[ Vol. 8 , Issue. 2 ]

Author(s):

Vera Klimesova, Jan Koci, Karel Palat, Jirina Stolarikova, Hans-Martin Dahse and Ute Mollmann   Pages 281 - 292 ( 12 )

Abstract:


A set of 2-benzylsulfanyl derivatives of benzothiazole was synthesized and evaluated for antimicrobial and cytotoxic activities. The biological screening on antimicrobial activity against a panel of Gram-positive and Gramnegative bacteria, yeasts and fungi identified benzylsulfanyl derivatives of benzothiazole as selective inhibitors of mycobacteria. The lead compounds in the set, dinitro derivatives exhibited significant activity against sensitive and multidrug-resistant strains of M. tuberculosis and low cytotoxicity. The QSAR study indicated that the antituberculotic activity is connected with LUMO and HOMO energies. The lower lipophilicity and the increased size of the molecule contribute to antituberculotic activity. Thus, dinitrobenzylsulfanyl derivatives of benzothiazole represent promising smallmolecule synthetic antimycobacterials.

Dedicated to Professor Dr. Karel Waisser on the occasion of his 75th birthday.

Keywords:

Benzothiazole, Mycobacterium tuberculosis, multidrug-resistant M. tuberculosis, antimicrobial activity, cytotoxicity, Sidoova, alkyl chains, benzylsulfanyl, pharmaceuticals

Affiliation:

Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Heyrovskeho 1203, Hradec Kralove, 500 05, Czech Republic.



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