Diastereoselective functionalizations of enecarbamates derived from pipecolic acid towards 5-guanidinopipecolates as arginine mimetics.
Various substituents could be diastereoselectively introduced into the 5-position of pipecolic acid via electrophilic or free-radical-initiated addition to the carbon-carbon double bond of endocyclic enecarbamates derived from pipecolic acid. This study allowed the diastereoselective synthesis of both cis- and trans-5-guanidino pipecolates, which were designed as constrained arginine mimetics and whose potential inhibition of nitric oxide synthase (NOS) was evaluated with three NOS isoforms.
Le Corre
Laurent
L
Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques, (UMR-8601 CNRS) Université Paris Descartes, UFR Biomédicale, 45, rue des Saints-Pères, 75270, Paris 06, France.
Kizirian
Jean-Claude
JC
Levraud
Camille
C
Boucher
Jean-Luc
JL
Bonnet
Véronique
V
Dhimane
Hamid
H
D000588:Amines / Q000737:chemistry; D001120:Arginine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry; D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019791:Guanidine / Q000737:chemistry*; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors / Q000378:metabolism; D010084:Oxidation-Reduction; D010875:Pipecolic Acids / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D001386:Azides; D002219:Carbamates; D004791:Enzyme Inhibitors; D007659:Ketones; D010875:Pipecolic Acids; D001120:Arginine; D019001:Nitric Oxide Synthase; C031345:pipecolic acid; D019791:Guanidine