Abstract
Parallel synthesis of the C-terminal-modified DAPT (1) derivatives was accomplished utilizing our novel resin 7. Condensation reaction of the N-acylamino acid 10 with the amines 11a-o proceeded smoothly to give the corresponding amides 6a-o without any epimerization. Among the analogues, the benzophenonemethyl amide derivative 6o showed 30 times more potent activity than the original DAPT (1).
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amides / chemical synthesis
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Amides / pharmacology
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Amyloid Precursor Protein Secretases
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Benzophenones / chemical synthesis
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Benzophenones / pharmacology
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Dipeptides / chemical synthesis*
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Dipeptides / pharmacology*
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Endopeptidases / drug effects*
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Endopeptidases / metabolism
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Molecular Structure
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Protease Inhibitors / chemical synthesis*
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Protease Inhibitors / pharmacology*
Substances
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Amides
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Benzophenones
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Dipeptides
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N-(N-(3,5-difluorophenacetyl)alanyl)phenylglycine tert-butyl ester
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N-(N-(3,5-difluorophenylacetyl)alanyl)phenylglycine 4-benzoylbenzyl amide
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Protease Inhibitors
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Amyloid Precursor Protein Secretases
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Endopeptidases