3-Hydroxy-4-methyl-5-pentyl-2-iminopyrrolidine: a potent and highly selective inducible nitric oxide synthase inhibitor.
(3S,4S,5R)-2-Imino-4-methyl-5-pentyl-3-pyrrolidinol hydrochloride (1) is a potent inducible nitric oxide synthase (i-NOS) inhibitor that has three times the selectivity of its parent, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine hydrochloride (2).
Tsymbalov
Sofya
S
Department of Discovery Medicinal Chemistry, Pharmacia, Skokie, IL 60077, USA.
Hagen
Timothy J
TJ
Moore
William M
WM
Jerome
Gina M
GM
Connor
Jane R
JR
Manning
Pamela T
PT
Pitzele
Barnett S
BS
Hallinan
E Ann
EA
D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007527:Isoenzymes / Q000187:drug effects; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors*; D052247:Nitric Oxide Synthase Type II; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C475589:3-hydroxy-4-methyl-5-pentyl-2-iminopyrrolidine; C114610:4-methyl-5-pentylpyrrolidin-2-imine; D004791:Enzyme Inhibitors; D007097:Imines; D007527:Isoenzymes; D011759:Pyrrolidines; C496319:NOS2 protein, human; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II