Implications of N-capped urea/thiourea and C-capped 3-(1-piperazinyl)-1,2-benzisothiazole with bridging Gly-Val/Phe-Gly-Val-Pro as therapeutic targets
A series of urea/thiourea derivatives were synthesized by using peptides conjugated to 3-(1-piperazinyl)-1,2-benzisothiazole and their structure was characterized by analytical and spectral (1H, 13C NMR and Mass) methods. These compounds were screened for antimicrobial and antiglycating activity as...
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Veröffentlicht in: | European journal of medicinal chemistry 2014-11, Vol.87, p.657-661 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | A series of urea/thiourea derivatives were synthesized by using peptides conjugated to 3-(1-piperazinyl)-1,2-benzisothiazole and their structure was characterized by analytical and spectral (1H, 13C NMR and Mass) methods. These compounds were screened for antimicrobial and antiglycating activity as well as urease and H+/K+-ATPase inhibition. Preliminary structure-activity relationship studies revealed that the compounds possessing fluoro moiety were excellent antimicrobial agents. Furthermore, for other biological activities methoxy substituent was found to be the most active particularly upon substitution at para position.
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•Pentamers conjugates derived ureas and thioureas.•Bioisosteric replacement of O in urea analogue by S showed enhanced bioactivity.•Derivatives containing fluoro were more potent antimicrobials.•Methoxy substituent proved to be active for antiglycation, urease inhibition and H+/K+-ATPase inhibition. |
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ISSN: | 0223-5234 1768-3254 |
DOI: | 10.1016/j.ejmech.2014.09.098 |