Abstract
Eleven new 2-styrylbenzothiazole-N-oxides have been prepared by aldol – type condensation reactions between 2-methylbenzothiazole–N-oxide and para-substituted benzaldehydes. Compounds with cyclic amino substituents showed typical push-pull molecule properties. Four compounds were tested against various bacterial strains as well as the protozoan Euglena gracilis as model microorganisms. Unlike previously prepared analogous benzothiazolium salts, only weak activity was recorded.
Highlights
Various benzothiazoles are known as industrial chemicals, dyes and drugs [1,2,3]
Molecules 2009, 14 substituent was changed to N-cyclic amino and the nitrogen in benzothiazole part of molecule was quaternized to the corresponding N-alkylbenzothiazolium salt, preferentially with allyl, propargyl or methyl halogenides [7]
2-methyl hydrogens, the most appropriate way to prepare the target styryl compounds consists of the aldol-type condensation of 2-methylbenzothiazole-N-oxide and a substituted benzaldehyde (Scheme 1)
Summary
Various benzothiazoles are known as industrial chemicals, dyes and drugs [1,2,3]. The biological activity of compounds with benzothiazole skeletons includes anticancer, antibacterial, antifungal and anthelmintic properties [4,5]. 2-methyl hydrogens, the most appropriate way to prepare the target styryl compounds consists of the aldol-type condensation of 2-methylbenzothiazole-N-oxide and a substituted benzaldehyde (Scheme 1).
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