Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles. (2nd November 2016)

• Record Type: Journal Article
• Authors: Łączkowski, Krzysztof Z.; Biernasiuk, Anna; Baranowska-Łączkowska, Angelika; Zielińska, Sylwia; Sałat, Kinga; Furgała, Anna; Misiura, Konrad; Malm, Anna
• Is Part Of: Journal of enzyme inhibition and medicinal chemistry. Volume 31(2016:Apr.)Supplement 2
• Page Start: 24
• Page End: 39
• Publication Date: 2016-11-02
• Subjects: Anticonvulsant activity -- Candida spp. -- selenazole -- tetrahydro-4H-thiopyran-4-one -- thiazole; Enzyme inhibitors -- Periodicals; Enzyme Inhibitors -- periodicals; Biochemistry -- periodicals; 572.7
• DOI: 10.1080/14756366.2016.1186020
• Languages: English
• ISSNs: 1475-6366

Abstract

Abstract: Synthesis and investigation of antimicrobial activity of 22 novel thiazoles and selenazoles derived from dihydro- 2H -thiopyran-4( 3H )-one are presented. Additionally, anticonvulsant activity of six derivatives is examinated. Among the derivatives, compounds4a–f, 4i, 4k, 4 l, 4n, 4o–s and4v have very strong activity against Candida spp. with MIC = 1.95–15.62 μg/ml. In the case of compounds4a–f, 4i, 4k, 4 l, 4n, 4o, 4r and4s, the activity is very strong against some strains of Candida spp. isolated from clinical materials, with MIC = 0.98 to 15.62 μg/ml. Additionally, compounds4n-v are found to be active against Gram-positive bacteria with MIC = 7.81–62.5 μg/ml. The results of anticonvulsant screening reveal that compounds4a, 4b, 4m and4n demonstrate a statistically significant anticonvulsant activity in the pentylenetetrazole model, whereas compounds4a and4n showed protection in 6-Hz psychomotor seizure model. Noteworthy, none of these compounds impaired animals' motor skills in the rotarod test. We also performed quantum chemical calculation of interaction and binding energies in complex of4a with cyclodextrin.