title: Applications of organocatalytic asymmetric synthesis to drug prototypes--dual action and selective inhibitors of n-nitric oxide synthase with activity against the 5-HT1D/1B subreceptors.
abstract: The scope of MacMillan's organocatalytic asymmetric conjugate addition reaction of indoles and electron-rich aromatics to α,β-unsaturated aldehydes has been extended to the use of 3-amino crotonaldehydes as substrates. The aromatics used include indoles as well as an aniline and a furan. The scope and effect of the groups on nitrogen (R, R') has also been studied. The method has been applied to the concise synthesis of an advanced precursor to S-(+)-1, a drug prototype for the treatment of migraine headaches.
authors.affiliation: Department of Chemistry, Université de Montréal, Montreal, QC, Canada. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Eli
authors.initials: E
authors.lastname: Stoffman
authors.forename: Xueling
authors.initials: X
authors.lastname: Mi
authors.forename: Paul
authors.initials: P
authors.lastname: Renton
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors*; D044282:Receptor, Serotonin, 5-HT1A / Q000187:drug effects*; D044346:Receptor, Serotonin, 5-HT1D / Q000187:drug effects*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000814:Aniline Compounds; D005663:Furans; D007211:Indoles; D044346:Receptor, Serotonin, 5-HT1D; D044282:Receptor, Serotonin, 5-HT1A; D019001:Nitric Oxide Synthase; C023650:aniline; C039281:furan