Hydrogenation in the Pyridine Series. II. Catalytic Reduction of 2-Monoalkyl- and 2-Dialkylaminopyridines

Freifelder, Morris; Mattoon, Richard W.; Ng, Yew Hay

doi:10.1021/jo01035a529

Cited by 7 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A number of synthetic approaches to the 2-iminopiperidine class of NOS inhibitors were pursued. There is precedence in the literature for the partial reduction of 2-aminopyridines to 2-iminopiperidines under acidic conditions . The protonated amidino group does not undergo reduction under the conditions of catalytic hydrogenation as shown in Scheme .…”

Section: Chemistrymentioning

confidence: 99%

“…There is precedence in the literature for the partial reduction of 2-aminopyridines to 2-iminopiperidines under acidic conditions. 12 The protonated amidino group does not undergo reduction under the conditions of catalytic hydrogenation as shown in Scheme 1. This method proved to be a facile route to 2-iminopiperidines with various substitutions at positions 3-6.…”

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Substituted 2-Iminopiperidines as Inhibitors of Human Nitric Oxide Synthase Isoforms

et al. 1998

View full text Add to dashboard Cite

A series of analogues of 2-iminopiperidine have been prepared and shown to be potent inhibitors of the human nitric oxide synthase (NOS) isoforms. Methyl substitutions on the 4-position (3) or 4- and 6-positions (8) afforded the most potent analogues. These compounds exhibited IC50 values of 0.1 and 0.08 microM, respectively, for hiNOS inhibition. Substitution with cyclohexylmethyl at the 6-position (13) afforded an inhibitor that showed the best selectivity for hiNOS versus heNOS (heNOS IC50/hiNOS IC50 = 64). Following oral administration, inhibitors were found to decrease serum nitrite/nitrate levels in an in vivo rat endotoxin assay. This series of 2-iminopiperidines were prepared via the described synthetic methodologies. The effect of ring substitutions on potency and selectivity for this class of cyclic amidines as NOS inhibitors is described.

show abstract

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%