Synthesis and biological evaluation of conformationally restricted Gabapentin analogues

  • Bioorg Med Chem Lett. 1999 Aug 16;9(16):2329-34. doi: 10.1016/s0960-894x(99)00383-2.
J M Receveur  1 ,  J S Bryans ,  M J Field ,  L Singh ,  D C Horwell
Affiliations
  • 1. Parke-Davis Neuroscience Research Centre, Cambridge University Forvie Site, UK.
PMID: 10476863 DOI: 10.1016/s0960-894x(99)00383-2
Abstract

A series of conformationally restricted Gabapentin analogues has been synthesised. The pyrrolidine analogue (R)-2-Aza-spiro[4.5]decane-4-carboxylic acid hydrochloride (3a) had an IC50 of 120 nM, similar to that of Gabapentin (IC50 = 140 nM), at the Gabapentin binding site on the alpha2delta subunit of a Calcium Channel. Compound (3a) also reversed carrageenan induced hyperalgesia in rats.

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