title: Synthesis and pharmacology of 8-amino-3-[(tetrahydro-2-furanyl)methyl] benzomorphan.
abstract: OBJECTIVE
  To design and synthesize new chiral 8-(substituted) amino-analogues of 3-[(tetrahydro-2-furanyl)methyl] benzomorphans, to expand knowledge of the structure-activity relationship (SAR) for 8-aminobenzomorphan.
  
  
  METHODS
  Target compounds were synthesized from the 8-triflate of the optically active 3-[(tetrahydro-2-furanyl)methyl]-2,6-methano-benzomorphans using Pd-catalyzed aminations. Opioid receptor binding experiments were performed to evaluate their biological activities.
  
  
  RESULTS
  Both 8-amino and 8-phenylamino analogues showed lower binding affinity for mu, delta and kappa receptors than corresponding 8-hydroxy-3-[(tetrahydro-2-furanyl)methyl]-2,6-methano-benzomorphan in vitro.
  
  
  CONCLUSIONS
  The relative poor binding affinity of the target compounds did not warrant conducting the in vivo studies to determine if they have the profile(kappa agonist/mu antagonist) that will be potentially useful in the treatment of drug addiction. Further study is in progress.
authors.affiliation: Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, USA. zhouqun08@hotmail.com
authors.forename: Qun
authors.initials: Q
authors.lastname: Zhou
authors.forename: Wen-hu
authors.initials: WH
authors.lastname: Duan
authors.forename: Dana J
authors.initials: DJ
authors.lastname: Cohen
authors.forename: Jean M
authors.initials: JM
authors.lastname: Bidlack
authors.forename: Mark P
authors.initials: MP
authors.lastname: Wentland
mesh_terms: D000818:Animals; D001575:Benzomorphans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001921:Brain / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006168:Guinea Pigs; D015394:Molecular Structure; D009292:Narcotic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D011957:Receptors, Opioid / Q000378:metabolism*; D017465:Receptors, Opioid, delta / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: C488554:8-amino-3-((tetrahydro-2-furanyl)methyl) benzomorphan; D001575:Benzomorphans; D005663:Furans; D009292:Narcotic Antagonists; D011957:Receptors, Opioid; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu