title: N-heterocyclic dipeptide aldehyde calpain inhibitors.
abstract: A series of Val-Leu based peptidic aldehydes containing either a furan or thiophene at the N-terminus was prepared and assayed against ovine m-calpain. In general, potency is favoured by a 2-substituted (rather than 3-substituted) heterocycle, a thiophene rather than a furan, and a shorter chain length at the N-terminus. Molecular docking experiments provide some rationale for these observations.
authors.affiliation: School of Chemistry & Physics, University of Adelaide, North Terrace, Adelaide, SA 5005, Australia.
authors.forename: Seth A
authors.initials: SA
authors.lastname: Jones
authors.forename: Matthew A
authors.initials: MA
authors.lastname: Jones
authors.forename: Stephen B
authors.initials: SB
authors.lastname: McNabb
authors.forename: Steven G
authors.initials: SG
authors.lastname: Aitken
authors.forename: James M
authors.initials: JM
authors.lastname: Coxon
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D002154:Calpain / Q000037:antagonists & inhibitors*; D004151:Dipeptides / Q000737:chemistry / Q000494:pharmacology*; D005663:Furans / Q000737:chemistry; D006023:Glycoproteins / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000494:pharmacology*; D011487:Protein Conformation; D012756:Sheep; D013876:Thiophenes / Q000737:chemistry
chemical_list: D000447:Aldehydes; D004151:Dipeptides; D005663:Furans; D006023:Glycoproteins; D010456:Peptides, Cyclic; D013876:Thiophenes; C039304:calpain inhibitors; C041390:valylleucine; D002154:Calpain; C449000:m-calpain; C039281:furan