Substituted (pyridylmethoxy) naphthalenes as potent and orally active 5-lipoxygenase inhibitors: Synthesis, biological profile, and pharmacokinetics of L-739,010

…, D Dubé, Y Ducharme, D Ethier, E Grimm…

Index: Hamel, Pierre; Riendeau, Denis; Brideau, Christine; Chan, Chi-Chung; Desmarais, Sylvie; Delorme, Daniel; Dube, Daniel; Ducharme, Yves; Ethier, Diane; Grimm, Erich; Falgueyret, Jean-Pierre; Guay, Jocelyne; Jones, Tom R.; Kwong, Elizabeth; McAuliffe, Malia; McFarlane, Cyril S.; Piechuta, Hanna; Roumi, Marie; Tagari, Philip; Young, Robert N.; Girard, Yves Journal of Medicinal Chemistry, 1997 , vol. 40, # 18 p. 2866 - 2875

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Citation Number: 33

Abstract

Dioxabicyclooctanyl naphthalenenitriles have been reported as a class of potent and nonredox 5-lipoxygenase (5-LO) inhibitors. These bicyclo derivatives were shown to be metabolically more stable than their tetrahydropyranyl counterparts but were not well orally absorbed. Replacement of the phenyl ring in the naphthalenenitrile 1 by a pyridine ring leads to the potent and orally absorbed inhibitor 3g (L-739,010, 2-cyano-4-(3-furyl)-7-[[6-[3 ...