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Arzneimittelforschung 2000; 50(11): 1023-1027
DOI: 10.1055/s-0031-1300327
Antibiotics · Chemotherapeutics · Antiviral Drugs · Cytostatics
Editio Cantor Verlag Aulendorf (Germany)

Synthesis and Antimicrobial Activity of New 2-Phenylethynylbenzothiazoles and Related Salts

Peter Magdolen
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, (Slovakia)
,
Pavol Zahradník
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, (Slovakia)
,
Pavlína Foltínov
Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University, Bratislava, (Slovakia)
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Publication History

Publication Date:
27 December 2011 (online)

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Summary

New 2-phenylethynylbenzothiazoles were synthesized by coupling reaction between 2-iodoben-zothiazole and substituted phenylacetylenes under palladium catalysis. The modified Wittig reaction was used to prepare the substituted phenylacetylenes from corresponding benzaldehydes. 2-Phenylethynylbenzothiazoles were next quarternized with trimethyloxonium tetra-fluoroborate to 3-methylbenzothiazolium salts. Antimicrobial in vitro activities were determined for all new compounds.

Zusammenfassung

Synthese und Antimikrobielle Wirkung neuer 2-Phenylethinylbenzothiazole und ihrer Salze

Neue 2-Phenylethinylbenzothiazole wurden durch eine Kopplungsreaktion zwischen 2-Iodo-benzothiazol und substituierten Phenylacetylenen unter Palladium-Katalyse synthetisiert. Die Phenylacetylene wurden aus Benzaldehyden mittels modifizierter Wittig-Reaktion dargestellt. Die 2-Phenylethinylbenzothiazole wurden anschließend mit Trimethyloxoniumtetrafluorobo-rat zu 3-Methylbenzothiazolium-Salzen quarternisiert. Bei allen neuen Verbindungen wurde die antimikrobielle Wirkung in vitro bestimmt.

Key words

Benzothiazoles, antimicrobial activity, synthesis - Benzothiazolium salts, antimicrobial activity, synthesis