Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity
| Autor: | Kumiko Ando, Jun-ichi Kunitomo, Shunsaku Ohta, Masayuki Yamashita, Noriko Kuwata, Yuko Ando, Eriko Tsuji, Yoshitaka Ohishi, Shigekatsu Kohno |
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| Rok vydání: | 2004 |
| Předmět: |
Models
Molecular Receptors Leukotriene Molecular Structure Hydrogen bond Stereochemistry Organic Chemistry Substituent Biochemistry Enol Cell Line Structure-Activity Relationship chemistry.chemical_compound chemistry Cricetinae Furan Side chain Animals Humans Structure–activity relationship Molecule Physical and Theoretical Chemistry Receptor Benzofurans |
| Zdroj: | Org. Biomol. Chem.. 2:625-635 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/b312682j |
| Popis: | 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 (), 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 (, ) were moderately active. |
| Databáze: | OpenAIRE |
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