The synthetic access to 2-sec-amino-4H-3,1-benzothiazin-4-ones 2 was explored. Compounds 2 were available from methyl 2-thioureidobenzoates 1, 2-thioureidobenzoic acids 3, and novel 2-thioureidobenzamides 6, respectively, under different conditions. 2-Alkylthio-4H-3,1-benzothiazin-4-ones 5 have been prepared from anthranilic acid following a two step route. Both, benzothiazinones 2 and 5 underwent ring cleavage reactions to produce thioureas 1 and 6, respectively. Twelve benzothiazinones were evaluated as inhibitors against a panel of eight proteases and esterases to identify one selective inhibitor of human cathepsin L, 2b, and one selective inhibitor of human leukocyte elastase, 5i. © 2009 by the authors; licensee Molecular Diversity Preservation International.
CITATION STYLE
Häcker, H. G., Grundmann, F., Lohr, F., Ottersbach, P. A., Zhou, J., Schnakenburg, G., & Gütschow, M. (2009). 2-Amino- and 2-alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, interconversion and enzyme inhibitory activities. Molecules, 14(1), 378–402. https://doi.org/10.3390/molecules14010378
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