Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity
- 28 January 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 2 (4), 625-635
- https://doi.org/10.1039/b312682j
Abstract
Novel 3-acetoacetylaminobenzo[b]furan derivatives having a modified triene system at the 3-position were synthesized starting with 3-aminobenzo[b]furans. The enol isomers, 3-[(3-hydroxybut-2-enonyl)amino]benzo[b]furans (1), of the 3-acetoacetylaminobenzo[b]furans were obtained as stable isomers owing to formation of a hydrogen bonding between the enol hydroxyl group and the amidocarbonyl group. The planarity of the C-2 substituent through the C-3 side chain suggested the existence of a modified conjugational triene system in the enol compound. Cysteinyl leukotriene 1 and 2 receptor antagonistic activities for these compounds were evaluated. 2-(4-Cyanobenzoyl or ethoxycarbonyl)-3-[(2-cyano-3-hydroxybut-2-enonyl)amino]benzo[b]furans (15g, 15o, 15u) were moderately active.This publication has 26 references indexed in Scilit:
- Cysteinyl leukotriene receptorsProstaglandins & Other Lipid Mediators, 2002
- Benzofuro[3,2-b]pyridines as mixed ETAETB and selective ETB endothelin receptor antagonistsBioorganic & Medicinal Chemistry Letters, 1999
- Carboxy-Substituted Cinnamides: A Novel Series of Potent, Orally Active LTB4 Receptor AntagonistsJournal of Medicinal Chemistry, 1998
- Leflunomide < Rec INN >Drugs of the Future, 1998
- Synthesis and aldose reductase-inhibitory activity of benzo(b)furan derivatives possessing a carboxymethylsulfamoyl group.CHEMICAL & PHARMACEUTICAL BULLETIN, 1989
- Elimination of 3-hydroxy-2-nitro-2,3-dihydrobenzo[b]furans to 2-nitrobenzo[b]furans.CHEMICAL & PHARMACEUTICAL BULLETIN, 1988
- A typical ElcB process in the elimination of 3-hydroxy-2-nitro-2,3-dihydrobenzo(b)furans to 2-nitrobenzo(b)furans.CHEMICAL & PHARMACEUTICAL BULLETIN, 1985
- Reactions of salicylaldehydes with bromonitromethane.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984
- Reaction of epichlorohydrin with hydroxybenzo(b)furan.CHEMICAL & PHARMACEUTICAL BULLETIN, 1983
- Studies on Analgesics of Aniline Series. III. Preparation and Properties of N, N-Dialkyl 3-(Substituted anilino) butyramide SeriesCHEMICAL & PHARMACEUTICAL BULLETIN, 1965