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Molecules 2009, 14(1), 378-402; doi:10.3390/molecules14010378
Article

2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

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Received: 26 November 2008; in revised form: 8 January 2009 / Accepted: 12 January 2009 / Published: 14 January 2009
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Abstract: 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.
Keywords: 4H-3; 1-Benzothiazin-4-ones; Heterocyclisation; Protease inhibition 4H-3; 1-Benzothiazin-4-ones; Heterocyclisation; Protease inhibition
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Häcker, H.-G.; Grundmann, F.; Lohr, F.; Ottersbach, P.A.; Zhou, J.; Schnakenburg, G.; Gütschow, M. 2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities. Molecules 2009, 14, 378-402.

AMA Style

Häcker H-G, Grundmann F, Lohr F, Ottersbach PA, Zhou J, Schnakenburg G, Gütschow M. 2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities. Molecules. 2009; 14(1):378-402.

Chicago/Turabian Style

Häcker, Hans-Georg; Grundmann, Florian; Lohr, Friederike; Ottersbach, Philipp A.; Zhou, Jing; Schnakenburg, Gregor; Gütschow, Michael. 2009. "2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities." Molecules 14, no. 1: 378-402.



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