title: Synthesis of oxazolo[4,5-c]quinoline TRPV1 antagonists.
abstract: An efficient synthesis of 2-amino-oxazolo[4,5-c]quinoline TRPV1 antagonists is described via a thiourea formation/carbodiimide cyclization sequence. Synthetic route optimization eliminates intermediate isolations and facilitates the rapid preparation of a series of novel pentacyclic TRPV1 antagonists. From this series, compound (S)-4 was identified as a potent and selective ligand for the TRPV1 ion channel.
authors.affiliation: Global Pharmaceutical Research and Development, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, Illinois 60064, United States. eric.a.voight@abbott.com
authors.forename: Eric A
authors.initials: EA
authors.lastname: Voight
authors.forename: Jerome F
authors.initials: JF
authors.lastname: Daanen
authors.forename: Michael E
authors.initials: ME
authors.lastname: Kort
mesh_terms: D002211:Capsaicin / Q000737:chemistry; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D050916:TRPV Cation Channels / Q000037:antagonists & inhibitors* / Q000737:chemistry; D013890:Thiourea / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D010080:Oxazoles; D011804:Quinolines; D050916:TRPV Cation Channels; D013890:Thiourea; D002211:Capsaicin