3-Carboxamido analogues of morphine and naltrexone. synthesis and opioid receptor binding properties

  • Bioorg Med Chem Lett. 2001 Jul 9;11(13):1717-21. doi: 10.1016/s0960-894x(01)00278-5.
M P Wentland  1 ,  R Lou ,  C M Dehnhardt ,  W Duan ,  D J Cohen ,  J M Bidlack
Affiliations
  • 1. Department of Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, 12180, Troy, NY, USA. [email protected]
PMID: 11425545 DOI: 10.1016/s0960-894x(01)00278-5
Abstract

In response to the unexpectedly high affinity for opioid receptors observed in a novel series of cyclazocine analogues where the prototypic 8-OH was replaced by a carboxamido group, we have prepared the corresponding 3-CONH(2) analogues of morphine and naltrexone. High affinity (K(i)=34 and 1.7nM) for mu opioid receptors was seen, however, the new targets were 39- and 11-fold less potent than morphine and naltrexone, respectively.

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