Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold

Schröder J (2001)
Bielefeld (Germany): Bielefeld University.

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Bielefeld Dissertation | English
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Tschesche, Harald (Prof. em. Dr.)
Abstract
The discovery and optimization of a series of heterocyclic non-peptide matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold is described. A screening effort was utilized to identify some chiral 6-methyl-1,3,4-thiadiazines that are weak inhibitors of the catalytic domain of human neutrophil collagenase (cdMMP-8). Further optimization of the lead compounds produced the selective inhibitor (2R)-N-[5-(4-bromophenyl)-6H-1,3,4-thiadiazine-2-yl]-2-[(phenylsulfonyl)amino]propanamide with high affinity for MMP-9 (Ki = 40 nM). X-ray crystallographic data obtained for cdMMP-8 cocrystallized with N-allyl-5-(4-chlorophenyl)-6H-1,3,4-thiadiazine-2-amine hydrobromide gave detailed design information on binding interactions for thiadiazine-based MMP inhibitors.
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Schröder J. Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. Bielefeld (Germany): Bielefeld University; 2001.
Schröder, J. (2001). Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. Bielefeld (Germany): Bielefeld University.
Schröder, J. (2001). Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. Bielefeld (Germany): Bielefeld University.
Schröder, J., 2001. Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold, Bielefeld (Germany): Bielefeld University.
J. Schröder, Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold, Bielefeld (Germany): Bielefeld University, 2001.
Schröder, J.: Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. Bielefeld University, Bielefeld (Germany) (2001).
Schröder, Jörg. Design and synthesis of matrix metalloproteinase inhibitors derived from a 6H-1,3,4-thiadiazine scaffold. Bielefeld (Germany): Bielefeld University, 2001.
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