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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 

Alpha-methylation at benzylic fragment of N-aryl-N'-benzyl ureas provides TRPV1 antagonists with better pharmacokinetic properties and higher efficacy in inflammatory pain model.

SAR studies for N-aryl-N'-benzyl urea class of TRPV1 antagonists have been extended to cover alpha-benzyl alkylation. Alkylated compounds showed weaker in vitro potencies in blocking capsaicin activation of TRPV1 receptor, but possessed improved pharmacokinetic properties. Further structural manipulations that included replacement of isoquinoline core with indazole and isolation of single enantiomer led to TRPV1 antagonists like (R)-16a with superior pharmacokinetic properties and greater potency in animal model of inflammatory pain.[1]

References

  1. Alpha-methylation at benzylic fragment of N-aryl-N'-benzyl ureas provides TRPV1 antagonists with better pharmacokinetic properties and higher efficacy in inflammatory pain model. Gomtsyan, A., Bayburt, E.K., Keddy, R., Turner, S.C., Jinkerson, T.K., Didomenico, S., Perner, R.J., Koenig, J.R., Drizin, I., McDonald, H.A., Surowy, C.S., Honore, P., Mikusa, J., Marsh, K.C., Wetter, J.M., Faltynek, C.R., Lee, C.H. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
 
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