title: Synthesis and pharmacological evaluation of 6,7-indolo/thiazolo-morphinans--further SAR of levorphanol.
abstract: To further extend the structure-activity relationships of levorphanol, two series of novel morphinans were prepared by incorporation of an indole or aminothiazole fragment to the hexyl ring (ring C) in levorphanol. Such morphinans differed from previously reported ligands in that such indole- or aminothiazole-containing morphinans displayed enhanced binding affinity to the delta opioid receptor, while the affinity to kappa and micro receptors was slightly reduced.
authors.affiliation: Bioorganic and Medicinal Chemistry Laboratory, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China. aozhang@mail.shcnc.ac.cn
authors.forename: Ao
authors.initials: A
authors.lastname: Zhang
authors.forename: Fuying
authors.initials: F
authors.lastname: Li
authors.forename: Chunyong
authors.initials: C
authors.lastname: Ding
authors.forename: Qizhen
authors.initials: Q
authors.lastname: Yao
authors.forename: Brian I
authors.initials: BI
authors.lastname: Knapp
authors.forename: Jean M
authors.initials: JM
authors.lastname: Bidlack
authors.forename: John L
authors.initials: JL
authors.lastname: Neumeyer
mesh_terms: D000701:Analgesics, Opioid / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D007211:Indoles / Q000138:chemical synthesis* / Q000494:pharmacology; D007981:Levorphanol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D011869:Radioligand Assay; D013329:Structure-Activity Relationship; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000701:Analgesics, Opioid; D007211:Indoles; D013844:Thiazoles; D007981:Levorphanol