Cyclic nitrone free radical traps: Isolation, Identification, and synthesis of 3, 3-dimethyl-3, 4-dihydroisoquinolin-4-ol N-oxide, a metabolite with reduced side effects

…, SF Chaney, D Friedrich, DA Janowick…

Index: Thomas, Craig E.; Bernardelli, Patrick; Bowen, S. Marc; Chaney, Stephen F.; Friedrich, Dirk; Janowick, David A.; Jones, Bryan K.; Keeley, Frederick J.; Kehne, John H.; Ketteler, Bert; Ohlweiler, David F.; Paquette, Leo A.; Robke, David J.; Fevig, Thomas L. Journal of Medicinal Chemistry, 1996 , vol. 39, # 25 p. 4997 - 5004

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Citation Number: 18

Abstract

A C-4 hydroxylated metabolite (2, 3, 3-dimethyl-3, 4-dihydroisoquinolin-4-ol N-oxide) of the previously described cyclic nitrone free radical trap 1 (3, 3-dimethyl-3, 4-dihydroisoquinoline N-oxide, a cyclic analog of phenyl-tert-butylnitrone (PBN)) was isolated, identified, and synthesized. The metabolite (2), though a less potent antioxidant than 1 in an in vitro lipid peroxidation assay, showed greatly reduced acute toxicity and sedative properties. ...