title: SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region).
abstract: Certain derivatives and analogues of capsazepine are potent in vitro inhibitors of bronchoconstriction in human small airways. During an investigation of the dependency of the potency on the structural features of the capsazepinoids in the thiourea moiety (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region), it was revealed that capsazepinoids with a thiourea or an amide link between the B-ring and the C-region in general have a good bronchorelaxing activity, while urea is a less attractive choice. Further, it was shown that 1,2,3,4-tetrahydroisoquinolines with a 2-(phenyl)ethyl derivative as the C-region are considerably more potent than those with an octyl group, while 2,3,4,5-tetrahydro-1H-2-benzazepines were found to be more insensitive to the nature of the C-region.
authors.affiliation: Division of Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
authors.forename: Magnus
authors.initials: M
authors.lastname: Berglund
authors.forename: María F
authors.initials: MF
authors.lastname: Dalence-Guzmán
authors.forename: Staffan
authors.initials: S
authors.lastname: Skogvall
authors.forename: Olov
authors.initials: O
authors.lastname: Sterner
mesh_terms: D001993:Bronchodilator Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002211:Capsaicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D017606:Chlorine Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D008055:Lipids / Q000737:chemistry; D015394:Molecular Structure; D012119:Respiration / Q000187:drug effects; D013329:Structure-Activity Relationship; D013890:Thiourea / Q000737:chemistry*
chemical_list: D001993:Bronchodilator Agents; D017606:Chlorine Compounds; D008055:Lipids; D013890:Thiourea; C071423:capsazepine; D002211:Capsaicin