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Bioorg Med Chem Lett. 2001 Mar 12;11(5):623-6.

8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines.

Author information

1
Department of Chemistry, Rensselaer Polytechnic Institute, Troy, NY 12180, USA. wentmp@rpi.edu

Abstract

Unexpectedly high affinity for opioid receptors has been observed for a novel series of cyclazocine analogues where the prototypic 8-OH was replaced by a carboxamido group. For mu and kappa opioid receptors, the primary carboxamido derivative of cyclazocine ((+/-)-15) displayed high affinity (Ki=0.41 and 0.53 nM, respectively) nearly comparable to cyclazocine. A high enantiopreference ((2R,6R,11R)-) for binding was also observed. Compound (+/-)-15 also displayed potent antinociception activity in mice when administered icv.

PMID:
11266156
DOI:
10.1016/s0960-894x(01)00014-2
[Indexed for MEDLINE]

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