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Title

Versatile synthesis of chiral 2-substituted-5-oxo-1,2,3,4-tetrahydro-5H-1,4-benzodiazepines as novel scaffolds for peptidomimetic building

AuthorsHerrero, Susana; García-López, M. Teresa CSIC ; Cenarruzabeitia, Edurne CSIC; Río, Joaquín del CSIC; Herranz, Rosario CSIC ORCID
Keywords5-oxo-1,2,3,4-tetrahydro-5H-1,4-benzodiazepines
1,4-benzodiazepine derivatives
Amino acid-derived amino nitriles
Peptidomimetics
Strecker synthesis
Reduction
Lactamization
Issue Date16-Jun-2003
PublisherElsevier
CitationTetrahedron 59(25): 4491-4499 (2003)
AbstractThe stereocontrolled synthesis of phenylalanine and tryptophan derived 5-oxo-1,2,3,4-tetrahydro-5H-1,4-benzodiazepine derivatives is described. This new methodology involves a modified Strecker reaction of N-Boc protected amino aldehydes and methyl anthranilate, reduction of the resulting α-amino nitriles, and lactamization. The resulting 2-substituted-5-oxo-1,2,3,4-tetrahydro-5H-1,4-benzodiazepines were further functionalized at position 4 by alkylation or acylation reactions. One of these new tryptophan-derived 1,4-benzodiazepines showed significant selective binding affinity at cholecystokinin CCK1 receptors (IC50=156.5±33.2 nM).
Publisher version (URL)http://dx.doi.org/10.1016/S0040-4020(03)00681-1
URIhttp://hdl.handle.net/10261/337052
DOI10.1016/S0040-4020(03)00681-1
Identifiersissn: 0040-4020
e-issn: 1464-5416
Appears in Collections:(IQM) Artículos




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