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New 6-Phenylimidazo[2,1-b]thiazole Derivatives: Synthesis and Antifungal Activity

Neue 6-Phenylimidazo[2,1-b]thiazolderivate: Synthese und fungistatische Aktivität

Monatshefte für Chemie / Chemical Monthly volume 130, pages 1399–1407 (1999)Cite this article

Summary.

 New benzylidene-(6-phenylimidazo[2,1-b]thiazol-3-yl)-acetic acid hydrazides, 4-alkyl-1-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetyl)-3-thiosemicarbazides, 2-aryl-3-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetamido)-4-thiazolidinones, and 3-alkyl-2-(((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinones were synthesized from 6-phenylimidazo[2,1-b]thiazole-3-acetic acid hydrazide and evaluated for antifungal activity against three dermatophyte strains using ketoconazole as standard. Several of them were found as effective as the standard against Trichophyton rubrum and Microsporum audounii (MIC=6 μg/cm3), whereas the activity of N-benzylidene-(6-phenylimidazo[2,1-b]-thiazol-3-yl)-acetic acid hydrazide against M. audounii was superior to the standard (MIC=3 μg/cm3). 2-(4-Methylphenyl)-3-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetamido)-4-thiazolidinone and 2-(4-chlorophenyl)-3-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetamido)-4-thiazolidinone showed the highest activity against Trichophyton mentagrophytes var. erinacei NCPF-375 (MIC=3 μg/cm3).

Zusammenfassung.

 Ausgehend von 6-Phenylimidazo[2,1-b]-thiazol-3-essigsäurehydrazid wurden neue Benzyliden-(6-phenylimidazo-[2,1-b]-thiazol-3-yl)-essigsäurehydrazide, 4-Alkyl-1-((6-phenylimidazo[2,1-b])thiazol-3-yl)-acetyl)-3-thiosemicarbazide, 2-Aryl-3-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetamido)-4-thiazolidinone und 3-Alkyl-2-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetyl)-hydrazono)-4-thiazolidinone dargestellt und hinsichtlich ihrer fungistatischen Aktivität untersucht. Einige der Verbindungen erwiesen sich als aktiv gegen Trichophyton rubrum und Microsporum audounii (MIC=6 μg/cm3). Es stellte sich heraus, daß N-benzyliden-(6-phenylimidazo[2,1-b]-thiazol-3-yl)-essigsäurehydrazide gegen M. audounii aktiver als die Standardsubstanz Ketokonazol ist (MIC=3 μg/cm3). 2-(4-Methylphenyl)-3-((6-phenylimidazo[2,1-b])thiazol-3-yl)-acetamido)-4-thiazolidinon und 2-(4-Chlorophenyl)-3-((6-phenylimidazo[2,1-b]thiazol-3-yl)-acetamido)-4-thiazolidinon zeigen die größte Aktivität gegen Trichophyton mentagrophytes var. erinacei NCPF-375 (MIC=3 μg/cm3).

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Authors and Affiliations

  1.  Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Istanbul, TR-34452 Beyazit, Istanbul, Turkey, TR

    Guültaze Çapan, Nuray Ulusoy & Nedime Ergenç

  2.  Department of Microbiology, Istanbul Faculty of Medicine, TR-34390 Istanbul, Turkey, TR

    Muammer Kiraz

Authors
  1. Guültaze Çapan
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  2. Nuray Ulusoy
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  3. Nedime Ergenç
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  4. Muammer Kiraz
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Received January 7, 1999. Accepted (revised) March 8, 1999

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Çapan, G., Ulusoy, N., Ergenç, N. et al. New 6-Phenylimidazo[2,1-b]thiazole Derivatives: Synthesis and Antifungal Activity. Monatshefte fuer Chemie 130, 1399–1407 (1999). https://doi.org/10.1007/PL00010200

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  • DOI: https://doi.org/10.1007/PL00010200

  • Keywords. Imidazo[2
  • 1-b]thiazole; Benzylidenehydrazides; Thiosemicarbazides; 4-Thiazolidinones; Antifungal activity.