2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities
| Autor: | Jing Zhou, Gregor Schnakenburg, Friederike Lohr, Florian Grundmann, Philipp A. Ottersbach, Hans-Georg Häcker, Michael Gütschow |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Proteases
Protease inhibition Stereochemistry Cathepsin L Pharmaceutical Science Cleavage (embryo) Benzoates Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Drug Discovery Sterol esterase Anthranilic acid Animals Chymotrypsin Humans Physical and Theoretical Chemistry Enzyme Inhibitors Heterocyclisation Cathepsin biology Molecular Structure Organic Chemistry Thiourea 1-Benzothiazin-4-ones 4H-3 Sterol Esterase Cathepsins Cysteine Endopeptidases chemistry Chemistry (miscellaneous) 4H-3 1-Benzothiazin-4-ones biology.protein Molecular Medicine Cattle Leukocyte Elastase |
| Zdroj: | Molecules; Volume 14; Issue 1; Pages: 378-402 Molecules, Vol 14, Iss 1, Pp 378-402 (2009) Molecules |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules14010378 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|